Reagent Guide. Synthetic Organic Chemistry & Materials Chemistry

Reagent Guide Synthetic Organic Chemistry & Materials Chemistry We have reviewed our line of reagents and organized them according to various fields...
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Reagent Guide

Synthetic Organic Chemistry & Materials Chemistry

We have reviewed our line of reagents and organized them according to various fields such as synthetic organic chemistry, materials chemistry and their individual basic structures. We hope that this reagent guide will be of assistance to your research and development laboratories. However, this guide is not an all inclusive list of all the reagents we deal in. Please be sure to look up our catalog and visit our website as well to remain updated on the latest information in the various fields of your interest.

Contents Synthetic Organic Chemistry Environmentally-Friendly Oxidation .........................1 Ionic Liquids ................................................................5 Fluorous Chemistry ................................................. 13 Amphiphilic Polymer-assembled Pd Complex Catalyst .......................................... 21 Stable Lewis Acids in Aqueous Media ................ 22 Polymer-Supported Reagents ................................ 24 Asymmetric Organocatalysts ................................. 26 Asymmetric Synthesis............................................. 31 Chiral Building Blocks ............................................ 40 Optical Resolution ................................................... 60 Enantiomer Excess & Absolute Configuration Determination ....................................................... 67 Chiral Columns for HPLC....................................... 74 Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds ................ 76 Halogenation ............................................................ 85 New Oxidation of Primary & Secondary Alcohols ..... 90 Oxidation ................................................................... 93 Reduction .................................................................. 99 Mitsunobu Reaction ..............................................105 Condensation & Active Esterification .................108 Glycosylation ..........................................................113 Phosphorylation .....................................................123 Amination ................................................................124 Wittig & Horner-Emmons Reaction .....................126 Titanium-mediated Carbonyl Olefination ............131 Suzuki-Miyaura Cross-Coupling Reaction .........135 Iron-Catalyzed Organic Synthesis .......................141 Metal Catalysts for Organic Synthesis ...............144 Grignard Reagents & Alkyl Metals ......................151 Protection & Derivatization ..................................155 Silicon Compounds for Organic Synthesis ........162 Sulfur Compounds for Organic Synthesis ..........169 Phosphines for Organic Synthesis ......................178 Hypervalent Iodine Compounds ..........................182 Phase-Transfer Catalysts .....................................185 Combinatorial Chemistry ......................................188 Gas Cylinders .........................................................191 Precursors for Preparation of Highly Reactive Reagents ................................193

Materials Chemistry C60 & C70 The Third Form of Carbon ................196 Carbon Nanotube ..................................................197 Building Blocks for Dendrimers ...........................199 Organic Semiconducting Materials .....................202 Charge Transfer Complexes for Organic Metals ...205 Reagents for Conducting Polymer Research ....210 Electroluminescence .............................................218 Reagents for Solar Cell Research ......................240 Photochromic Compounds ...................................247 Liquid Crystals & Related Compounds ..............250 Building Blocks for Liquid Crystals .....................257 Organic Nonlinear Optical Materials ..................269 Phthalonitriles & Naphthalonitriles .....................271

Macrocycles for Host-Guest Chemistry .............275 Diacetylene Monocarboxylic Acids for LB Films ...281 Reagents for High-Performance Polymer Research ...282 Metal-Organic Frameworks (MOFs / PCPs) .....299 Photopolymerization Initiators..............................302 Silane Coupling Agents ........................................305 Pressure & Heat Sensitive Recording Materials ...310

Chemicals by Class Ethylene Glycols & Monofunctional Ethylene Glycols................315 Monoprotected Diaminoalkanes ..........................317 3-Aminopyrrolidines ...............................................318 -Substituted Maleimides, Succinimides & Phthalimides ...................................................321 1,4-Disubstituted Cyclohexanes .........................327 Monofunctional & α,ω-Bifunctional Alkanes ......333 ω-Functional Alkanols, Carboxylic Acids, Amines & Halides ..............................................334 Quaternary Ammonium Compounds ...................337 Imidazolium Compounds.......................................342 Pyridinium Compounds .........................................345 Phosphonium Compounds....................................350 Iodonium, Sulfonium & Oxonium Compounds ...354 Classes of Boron Compounds .............................357 Metallocenes ..........................................................374 Classes of Metal Compounds..............................378 Non-benzenoid Aromatic Compounds ................394 NMR Spectrometry ................................................396 Standards for Mass Spectrometry & Matrix Materials .............................................398 TLC Stains ..............................................................400 Abbreviations ..........................................................402 Pressure-Temperature Nomograph .....................403 The physical properties of the typical organic solvents / Freezing mixtures............................404 Periodic Table of the Elements ...........................405 TCI International Offices .......................................406 TCI Distributors ......................................................407 If you are looking for products in the field of Bioscience & Analytical Science, please see below.

Reagent Guide Bioscience & Analytical Science Bioscience Example : Antibody / Sugars / Nucleosides / Amino Acids / Lipids and Related Compounds / Terpenes / Steroids etc. Analytical Science Example : Reagent for Protein Analysis DAABD-Cl / GC Derivatizing Reagents / Labeling Reagents for HPLC / Chromatography Columns for HPLC etc.

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Environmentally-Friendly Oxidation

Environmentally-Friendly Oxidation In recent years, organic synthesis has improved to the point of being environmentally-friendly. Many excellent methodologies have been devised for green chemistry and environmentally-friendly manufacturing. Oxidation reactions employing atmospheric oxygen or molecular oxygen as an oxidant is one of the methodologies of green chemistry. The earth is filled with air, and about 20% of air is oxygen. If oxygen could be utilized as the oxidant, this would provide a method that is not only economically prudent, but also environmentally clean. However, the oxidation capability of atmospheric oxygen and molecular oxygen is not powerful enough when used alone. Therefore, there is much active R&D underway to make improvements in the oxidation capability with the presence of transition metal complex catalysts and radical producing catalysts.1) For example, Markó and co-workers have reported that tetrapropylammonium perruthenate (TPAP) can be used for the oxidation of alcohols to aldehydes and ketones using molecular oxygen as the oxidant.2) Similarly, Uemura and co-workers have demonstrated that palladium(II) diacetate is also a catalyst for the same type of oxidations.3) Katsuki and co-workers reported the oxidation method of alcohols using (nitrosyl) Ru-Salen complex as a catalyst.4) This catalyst is activated by photo-irradiation and can be used to oxidize primary alcohols to aldehydes selectively. Fukuzumi and co-workers reported the oxygenation using 9-aromatic substituted acridinium derivatives as effective electron-transfer photocatalysts.5) Ishii and his group have reported a catalytic carbon radical formation method using -hydroxyphthalimide (NHPI).6) In this method, the hydrogen atom of the hydroxyimino group in NHPI is pulled off by molecular oxygen, thereby producing a phthalimide -oxyl (PINO) radical. The PINO radical then pulls hydrogen atoms from carbon-hydrogen bonds such as alkanes and alcohols to furnish the corresponding carbon radicals. The resulting carbon radicals readily react with different types of molecules, thereby producing oxygen-containing compounds such as carboxylic acids under an oxygen atmosphere. A porous metal-organic framework (MOF) (porous coordination polymers (PCP)) pre-ELM-11 is also utilized as a catalyst in organic synthesis for molecular oxygen-derived oxidation.7) Typical transition metal complex catalysts and carbon radical producing catalysts for oxidation using molecular oxygen are as follows.

C0373

B2681 CH3

CH3 Co

T0746

O

O

Co

V O O

O CH3

. xH2O

2

S0318

CH3

O Co

Mn

O CH3

2

C1944

CF3

CH3

. 2H2O

O CH3

V0016

CH3 O

O

Transition Metal Complexes

M0042

O CH3

2

A1424

H3C CH3 H3C CH3 N NO N Ru O C(CH3)3 (CH3)3C O Cl C(CH3)3 (CH3)3C

2

P1870

O

O CH3 C O

Pd2

CF3

2

O

Pd2 2

2

T1559

I0079

D1997 CH3

N

Pr

Co O

Pr

N O

N Pr

O RuO4 CH3

Product No. Product Name C0373 B2681 M0042 V0016

P

Fe 3

O

Pr

Bis(2,4-pentanedionato)cobalt(II) Dihydrate Bis(2,4-pentanedionato)cobalt(II) Bis(2,4-pentanedionato)manganese(II) Dihydrate Bis(2,4-pentanedionato)vanadium(IV) Oxide

Rh

Cl Cl

3

3

Unit Size 25g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500g 25g 500g 25g

1

Environmentally-Friendly Oxidation

Product No. Product Name T0746 C1944

Unit Size

Bis(trifluoro-2,4-pentanedionato)cobalt(II) Hydrate Chloronitrosyl[N,N '-bis(3,5-di-tert-butylsalicylidene)-1,1,2,2-tetramethylethylenediaminato]ruthenium(IV) Palladium(II) Acetate Palladium(II) Trifluoroacetate Salcomine Tetrapropylammonium Perruthenate Tris(2,4-pentanedionato)iron(III) Tris(triphenylphosphine)ruthenium(II) Dichloride

A1424 P1870 S0318 T1559 I0079 D1997

B2897

5g

25g

D3428

1g 1g 100g 1g 25g 1g

100mg 5g 5g 500g 5g 500g 5g

D3429

CH3

CH3

CH3

CH3

Radical Producing Catalysts N

N ClO4

CH3

H1036

H0395

M1774

CH3

M2072

O

N OH

ClO4 CH3

CH3

CH3

CH3

CH3

O

N CH3

CH3

N

N CH3

ClO4

CH3

Product No. Product Name B2897 D3428 D3429 H1036 H0395 M1774 M2072 M1775

ClO4

M1775

O

O2N N OH

CH3

CH3

CH3

O

N

ClO4

ClO4

Unit Size

9-(2-Biphenylyl)-10-methylacridinium Perchlorate 9-(2,5-Dimethylphenyl)-10-methylacridinium Perchlorate 9-(2,6-Dimethylphenyl)-10-methylacridinium Perchlorate N-Hydroxy-4-nitrophthalimide N-Hydroxyphthalimide 9-Mesityl-10-methylacridinium Perchlorate 9-Mesityl-2,7,10-trimethylacridinium Perchlorate 10-Methyl-9-phenylacridinium Perchlorate

H0186

1g 1g 1g 25g 1g 1g

5g 5g 5g 5g 500g 5g 1g 5g

T1560 OH CH3

Redox Catalysts

CH3 OH

Product No. Product Name H0186 T1560

2

Hydroquinone 2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical

CH3 N

CH3

O

Unit Size 25g 5g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

500g 25g

Environmentally-Friendly Oxidation

P0052

A0869

B0989 NaO3S

O

Ligands

CH3

B1733

D1678

O

O

C CH2

C

CH3

P1297

CH3

CH3

T1438 O

CH3

CH3

CH3

Cl

N

P0160 N

O

. H2O

O

CH3 C CH2 C

CH3

T0434

T0519

Cl

Cl

Cl NH N

N

NH N

HN

Cl

O

N HN

Cl Cl

N

N

CH3

T1359

O CH3

O

CH3

OCH3

. xH2O

O

P0221 P0879 O

O

CH3

C CH3

CH3

M1132 O

CH3O

SO3Na

O

O

O P

CF3

CH3

Cl

Product No. Product Name

Unit Size

P0052 A0869 B0989 B1733 D1678 M1132 P0221 P0879 P0160 P1297 T1438 T1359 T0434 T0519

25ml

Acetylacetone 2-Acetylcyclopentanone Bathophenanthrolinedisulfonic Acid Disodium Salt Hydrate [for Determination of Ferrous Ion] 1,3-Bis(4-methoxyphenyl)-1,3-propanedione Dipivaloylmethane 3-Methyl-2,4-pentanedione 1,10-Phenanthroline Monohydrate 1,10-Phenanthroline Monohydrate 1-Phenyl-1,3-butanedione 3-Phenyl-2,4-pentanedione 5,10,15,20-Tetrakis(2,6-dichlorophenyl)porphyrin Tetraphenylporphyrin (Chlorin free) Trifluoroacetylacetone Triphenylphosphine

1g 5g 5g 5ml 1g 25g 1g

25g 25g

500ml 25ml 5g 25g 25g 25ml 25g 25g 500g 5g 100mg 1g 100g 500g

C2409

MOF / PCP

[Cu(bpy)(BF4)2(H2O)2]bpy

Product No. Product Name C2409

Unit Size

pre-ELM-11

5g

Metal-Organic Frameworks (MOFs/PCPs) (see p.299)

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

3

Environmentally-Friendly Oxidation

References 1) Review: C. N. Cornell, M. S. Sigman, in , ed. by W. B. Tolman, Wiley-VCH, Weinheim, 2006, pp.159-186; T. Punniyamurthy, S. Velusamy, J. Iqbal, . 2005, , 2329; I. W. C. E. Arends, R. A. Sheldon, in , ed. by J.-E. Bäckwall, Wiley-VCH, Weinheim, 2004, pp.83-118. 2) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, . 1997, , 12661. 3) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, . 1998, , 6011. 2004, number 4) A. Miyata, M. Murakami, R. Irie, T. Katsuki, . 2001, , 7067; T. Katsuki, , 2. 5) S. Fukuzumi, H. Kotani, K. Ohkubo, N. V. Tkachenko, H. Lemmetyinen, . 2004, , 1600; H. Kotani, K. Ohkubo, S. Fukuzumi, . 2004, , 15999. 6) Y. Ishii, T. Iwahama, S. Sakaguchi, K. Nakayama, Y. Nishiyama, . 1996, , 4520; Y. Ishii, S. Sakaguchi, 2002, number 2001, , 2; Y. Ishii, , 2. 7) T. Arai, H. Takasugi, T. Sato, H. Noguchi, H. Kanoh, K. Kaneko, A. Yanagisawa, . 2005, , 1590; T. Arai, T. Sato, H. Noguchi, H. Kanoh, K. Kaneko, A. Yanagisawa, . 2006, , 1094; D. Jiang, T. Mallat, F. Krumeich, A. Baiker, . 2008, , 390.

4

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Ionic Liquids

Ionic Liquids Ionic liquids are salts composed of cations such as imidazolium ions, pyridinium ions and anions such as BF4‒, PF6‒ and are liquid at relatively low temperatures. Their characteristic properties include; (1) essentially no vapor pressure, (2) non-flammability, (3) high thermal stability, (4) relatively low viscosity, (5) liquid state over extended temperature ranges, (6) high ionic conductivity. Applications of ionic liquids with these features are being vigorously explored in various fields. When an ionic liquid is used as a reaction solvent, the solute is solvated by ions only. Thus, the reaction proceeds in an environment totally different from that when water or ordinary organic solvents are used and therefore, high selectivity is possible. To date application in the Friedel-Crafts reaction, the Diels-Alder reaction, metal-catalyzed asymmetric synthesis and so forth, have been reported.1) Furthermore, some ionic liquids have low solubility in water and low polar organic solvents. By using this property, ionic liquids can be recovered and reused after reaction product is extracted with organic solvents. Recently, methods are being studied which reduce the load on the environment from the viewpoint of green chemistry. Ionic liquids are receiving much attention as a superb solvent from the point of safety, separation/purification procedures, and recyclability.2) Ionic liquids are used not only as a reaction solvent but also electrochemically, for example, as electrolytes of rechargeable batteries.3) Watanabe and co-workers have developed a novel solid electrolyte in which an ionic liquid is confined in a network polymer called“ion gel”.4) This ion gel is expected to contribute to solidification of various electrochemical systems and safety improvement as it exhibits exceedingly high ion-conductivity compared with conventional solid polymer electrolytes. Hamaguchi and co-workers reported that 1-butyl-3-methylimidazolium tetrachloroferrate is magnetic ionic liquid.5) The new magnetic ionic liquid overcomes various problems of traditional magnetic fluids, and is expected to be applied to many fields including the use as a sealing agent for the motor axis. Below shows the major ionic liquids. The melting points are shown as the reference value. These are not specification value. The salts that form liquid state at room temperature are given the description“liquid” .

D3341

D3240 CH3

N

CH3 CH3O

Cl

N

Imidazolium & Pyrrolidinium Salts

N

E0490

N

CH3

CH3O

N

E0755

CH3 Br

N

I

N

CH2CH3

N

mp 74 ℃

N

CH3 HSO4

N CH2CH3

N

N

Liquid

N

N

(CF3SO2)2N

CH2CH3

N

BF4

N

N

mp 61 ℃ B2193

N N

CH3 Cl

(CH2)3CH3

Liquid

PF6

CH2CH3

Liquid

CH3 I

CH3

N

CH2CH3

CH2CH2CH3

Liquid

N

B2194

N

FeCl4

CH3

Liquid

CH3

CH2CH3

Liquid

N

M1440

CH3

N

N

(NC)2N

Liquid E0493

CH3

Liquid E0706

E0599

Liquid

CH2CH3

CH2CH3

CF3BF3

N CH2CH3

E0496

CH3 CH3CH2OSO3

CF3SO3

N

CH3

N

Liquid E0680

N

CH3

CH2CH3

mp 79 ℃ E0650

E0754

CH3SO3

mp 84 ℃ E0836

N

CH2CH3

CH2CH3

Liquid

CH3

N

Cl

N CH2CH3

E0494

CH3

N

P O

CH3

mp 125 ℃ E0556

E0543

CH3

N

O

N

CH3

N

Br

(CH2)3CH3

mp 41 ℃

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

Liquid

5

Ionic Liquids

B2708

B2337

B3542

CH3

N

N

CH3

N

N

Liquid B2672

B2477

(CF3SO2)2N

N

N

FeCl4

N

N

CH3

N

Cl

B2473

N N

N

I N

CH3

N

CH3

CH2CH2CH3

Liquid

CH2CH3

N N

Solid

N

(CF3SO2)2N N

CH3

CH3

(CH2)3CH3

Liquid

B2851

N

(CF3SO2)2N

(CH2)3CH3

CH3

N

(CH2)3CH3

Solid

Product No. Product Name D3341 D3240 E0490 E0543 E0556 E0755 E0494 E0836 E0754 E0650 E0680 E0496 E0493 E0599

1,3-Dimethylimidazolium Chloride 1,3-Dimethylimidazolium Dimethyl Phosphate 1-Ethyl-3-methylimidazolium Chloride 1-Ethyl-3-methylimidazolium Bromide 1-Ethyl-3-methylimidazolium Iodide 1-Ethyl-3-methylimidazolium Methanesulfonate 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate 1-Ethyl-3-methylimidazolium Trifluoro(trifluoromethyl)borate 1-Ethyl-3-methylimidazolium Hydrogen Sulfate 1-Ethyl-3-methylimidazolium Ethyl Sulfate 1-Ethyl-3-methylimidazolium Dicyanamide 1-Ethyl-3-methylimidazolium Tetrafluoroborate 1-Ethyl-3-methylimidazolium Hexafluorophosphate 1-Ethyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)imide (This product is only

E0706 M1440 B2194 B2193 B2708 B2337 B3542 B2195

1-Ethyl-3-methylimidazolium Tetrachloroferrate 1-Methyl-3-propylimidazolium Iodide 1-Butyl-3-methylimidazolium Chloride 1-Butyl-3-methylimidazolium Bromide 1-Butyl-3-methylimidazolium Iodide 1-Butyl-3-methylimidazolium Trifluoromethanesulfonate 1-Butyl-3-methylimidazolium Trifluoro(trifluoromethyl)borate 1-Butyl-3-methylimidazolium Tetrafluoroborate

Liquid

Unit Size 5g

5g 5g 25g 5g 5g 5g 5g 5g 5g 1g 5g 5g 5g

available for selling domestically in Japan)

6

CH3

PF6

mp 38 ℃

Br CH3

CH3

(CH2)3CH3

fp 32 ℃

(CH2)3CH3

Liquid B3159

BF4

(CH2)3CH3

Cl N

CH3

Liquid

CH3

B3427

(CF3SO2)2N

N

(CH2)7CH3

CH3

mp 99 ℃ B3358

M2098

CH3

N

CH3 (CF3SO2)2N

PF6

B2474

CH3

(CH2)3CH3

Solid

N

Liquid

Cl

CH3

CH3

N

B2475

CH3

CH2CH2CH3

N

Br

Liquid

Liquid E0753

N

(CH2)7CH3

Liquid D3903

Liquid

CH3

N

BF4

N

(CH2)5CH3

M2063

N

(CH2)7CH3

(CH2)5CH3

Br

N

CH3

N

Liquid

CH3

N

CH3

(CH2)5CH3

M1904

PF6

N

Cl

Liquid M2062

H1098

N

(CH2)5CH3

Liquid

Liquid H1099

CH3

N

(CH2)3CH3

(CH2)3CH3

Liquid H1227

CH3

N

PF6

N (CH2)3CH3

Liquid H1097

CH3

BF4

(CH2)3CH3

Liquid

CH3

N

N

(CH2)3CH3

(CH2)3CH3

CH3

N CF3BF3

N

N

(CH2)3CH3

N

CH3

CF3SO3

I

B2320

B2195

5g

5g 25g 5g 5g 5g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

25g 25g 250g 25g 25g 25g 25g 5g 25g 25g 5g 25g 25g 25g 5g 25g 100g 5g 25g 25g 5g 25g

Ionic Liquids

Product No. Product Name

Unit Size

B2320 B2477

1-Butyl-3-methylimidazolium Hexafluorophosphate 1-Butyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)imide (This product is only

5g

25g

available for selling domestically in Japan)

B2672 H1097 H1227 H1099 H1098 M2062 M1904 M2063 E0753

1-Butyl-3-methylimidazolium Tetrachloroferrate 1-Hexyl-3-methylimidazolium Chloride 1-Hexyl-3-methylimidazolium Bromide 1-Hexyl-3-methylimidazolium Tetrafluoroborate 1-Hexyl-3-methylimidazolium Hexafluorophosphate 1-Methyl-3-n-octylimidazolium Chloride 1-Methyl-3-n-octylimidazolium Bromide 1-Methyl-3-n-octylimidazolium Hexafluorophosphate 1-Ethyl-2,3-dimethylimidazolium Bis(trifluoromethanesulfonyl)imide (This product is

5g 5g 5g 5g 5g 5g 5g 5g 5g

25g 25g 25g 25g 25g 25g 25g 25g 25g

D3903 B2473 B2475 B2474 B3159

1,2-Dimethyl-3-propylimidazolium Iodide 1-Butyl-2,3-dimethylimidazolium Chloride 1-Butyl-2,3-dimethylimidazolium Tetrafluoroborate 1-Butyl-2,3-dimethylimidazolium Hexafluorophosphate 1-Butyl-2,3-dimethylimidazolium Bis(trifluoromethanesulfonyl)imide (This product is

5g 5g 5g 5g 5g

25g 25g 25g 25g 25g

M2098 B3358 B3427 B2851

1-Methyl-1-propylpyrrolidinium Bis(trifluoromethanesulfonyl)imide 1-Butyl-1-methylpyrrolidinium Chloride 1-Butyl-1-methylpyrrolidinium Bromide 1-Butyl-1-methylpyrrolidinium Bis(trifluoromethanesulfonyl)imide

5g 5g 5g 5g 5g

25g 25g 25g 25g 25g

only available for selling domestically in Japan)

only available for selling domestically in Japan)

B3424

Br

Piperidinium Salts

N

CH3

(CH2)3CH3

mp 230 ℃

Product No. Product Name B3424

Unit Size

1-Butyl-1-methylpiperidinium Bromide

5g

E0544

E0171

Cl

N

Pyridinium Salts

B1329

N

Solid B3232

B1743

Br

B2196

(CH2)3CH3

mp 120 ℃ B3425

Solid B3104

CH3 Br N

BF4

N (CH2)3CH3

(CH2)3CH3

mp 104 ℃

Liquid

CH3 N

CH2CH3

N

Liquid

N

Solid

CH3 Br

Cl N

(CH2)3CH3

mp 160 ℃

Solid B2701

CH3

N

Br

(CH2)3CH3

B2700

CH3CH2OSO3

Liquid

Cl

mp 75 ℃

CH3

CH2CH3

CH3

(CH2)3CH3

B3426 CH2OH

CH3CH2OSO3

N

(CH2)3CH3

E0682

E0681

PF6

N

Cl

N

CH2CH3

CH2CH3

25g

PF6 N

(CH2)3CH3

(CH2)3CH3

mp 137 ℃

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

mp 42 ℃

7

Ionic Liquids

Product No. Product Name E0544 E0171 B1329 B1743 B3232 B2196 B3425 B3104 E0681 E0682 B3426 B2700 B2701

Unit Size

1-Ethylpyridinium Chloride 1-Ethylpyridinium Bromide 1-Butylpyridinium Chloride 1-Butylpyridinium Bromide 1-Butylpyridinium Tetrafluoroborate 1-Butylpyridinium Hexafluorophosphate 1-Butyl-3-methylpyridinium Chloride 1-Butyl-3-methylpyridinium Bromide 1-Ethyl-3-methylpyridinium Ethyl Sulfate 1-Ethyl-3-(hydroxymethyl)pyridinium Ethyl Sulfate 1-Butyl-4-methylpyridinium Chloride 1-Butyl-4-methylpyridinium Bromide 1-Butyl-4-methylpyridinium Hexafluorophosphate

5g 10g 5g 5g 5g 1g 5g 5g 5g 5g 5g

A2274

T2679

CH3 N

(CF3SO2)2N

CH3(CH2)3 N

C1966

(CH2)3CH3 Br

CH3 N

CH3

H1047

T2564

T2680

(CH2)3CH3 CH3(CH2)3 P

(CH2)3CH3 Br

(CH2)3CH3

(CF3SO2)2N

Liquid

mp 70 ℃

(CH2)3CH3

N CH3

(CF3SO2)2N

mp 103 ℃

Liquid

CH3

(CH2)7CH3

(CH2)3CH3

(CH2)3CH3 Cl

(CH2)3CH3

T1124

(CH2)7CH3

(CH2)3CH3 CH3(CH2)3 N

(CF3SO2)2N

Liquid

(CH2)7CH3

(CH2)3CH3

(CH2)3CH3

(CH2)3CH3

CH2CH3

M1660

T0054

T0055 (CH2)3CH3

CH2CH3 CH3(CH2)4 N CH2CH3

Ammonium, Phosphonium, Sulfonium Salts

25g 25g 25g 25g 25g 25g 5g 25g 25g 5g 25g 25g 25g

CH3

P

(CH2)3CH3

(CH2)3CH3 (CF3SO2)2N

Solid

mp 104 ℃

Liquid

T2314

(CH2)3CH3 CH3OCH2CH2 P

(CH2)3CH3

(CH2)3CH3

(CH2)3CH3

CH3(CH2)3 P

CH2CH3

(CH2)15CH3 Br

(CH2)3CH3

CH3CH2

S

(CF3SO2)2N CH2CH3

(CF3SO2)2N

Liquid

mp 61 ℃

Liquid

Product No. Product Name A2274 T2679 T0055 T0054 M1660 C1966 T1124 T2680 T2564 H1047 T2314

Amyltriethylammonium Bis(trifluoromethanesulfonyl)imide Tributylmethylammonium Bis(trifluoromethanesulfonyl)imide Tetrabutylammonium Chloride Tetrabutylammonium Bromide Methyltri-n-octylammonium Bis(trifluoromethanesulfonyl)imide Cyclohexyltrimethylammonium Bis(trifluoromethanesulfonyl)imide Tetrabutylphosphonium Bromide Tributylmethylphosphonium Bis(trifluoromethanesulfonyl)imide Tributyl(2-methoxyethyl)phosphonium Bis(trifluoromethanesulfonyl)imide Tributylhexadecylphosphonium Bromide Triethylsulfonium Bis(trifluoromethanesulfonyl)imide

Unit Size 5g 5g 25g

25g

Pyridinium Compounds (see also p.345) Quaternary Ammonium Compounds (see also p.337) Phosphonium Compounds (see also p.350)

8

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

5g 25g 25g 500g 5g 5g 500g 5g 5g 25g 5g

Ionic Liquids

References 1) T. Welton, . 1999, , 2071; J. D. Holbrey, K. R. Seddon, . 1999, , 223; P. Wasserscheid, W. 2001, Keim, . 2000, , 3772; T. Kitazume, , 5; T. Kitazume, 2001, 2002, , 15; R. Sheldon, . 2001, 2399; D. Zhao, M. Wu, Y. Kou, E. Min, , 157. 2000, 2) M. Freemantle, , 37. 3) R. T. Carlin, H. C. De Long, J. Fuller, P. C. Trulove, . 1994, , L73; A. B. McEwen, S. F. McDevitt, V. R. Koch, . 1997, , L84. 2001, 4) M. Watanabe, A. Noda, T. Kaneko, R. Kawano, , 281; A. Noda, M. Watanabe, 2000, , 1265. 2005, , 29. 5) S. Hayashi, H. Hamaguchi, . 2004, , 1590; H. Hamaguchi,

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

9

Ionic Liquids

Physical Physical Properties Properties of Ionic of Ionic Liquids Liquids (contd.) Elec. Window / V

Cathode Limit / V

Anode Limit / V

Conductivity / S/m

Dynamic Viscosity / cp

Decomposition Point /

℃ Melting Point /

Refractive Index nD20

Specific Gravity

Anion

Cation

Name

Product Code



4.1

-2.2

1.9

IMIDAZOLIUM SALTS D3341 1,3-Dimethylimidazolium Chloride

C1MI

Cl

1,3-Dimethylimidazolium D3240 Dimethyl Phosphate

C1MI

Me2PO4 1.26

E0490

1-Ethyl-3-methylimidazolium Chloride

EMI

Cl

84

281

0.3-3.7

E0543

1-Ethyl-3-methylimidazolium Bromide

EMI

Br

74

311

1.4

E0556

1-Ethyl-3-methylimidazolium Iodide

EMI

I

79

303

E0755

1-Ethyl-3-methylimidazolium Methanesulfonate

EMI

MsO

1.25

1.50

5

80

E0494

1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate

EMI

TfO

1.39

1.43

-9

45

0.92

E0836

1-Ethyl-3-methylimidazolium Trifluoro(trifluoromethyl)borate

EMI

CF3BF3

1.35

26

1.48

E0754

1-Ethyl-3-methylimidazolium Hydrogen Sulfate

EMI

HSO4

1.38

1.50

Liquid

E0650

1-Ethyl-3-methylimidazolium Ethyl Sulfate

EMI

EtSO4

1.24

1.48

Liquid

E0680

1-Ethyl-3-methylimidazolium Dicyanamide

EMI

(NC)2N

1.11

1.52

-21

240

21

2.2

E0496

1-Ethyl-3-methylimidazolium Tetrafluoroborate

EMI

BF4

1.29

15

391

38

1.4

E0493

1-Ethyl-3-methylimidazolium Hexafluorophosphate

EMI

PF6

61

375

E0599

1-Ethyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)imide

EMI

TFSI

-15

453

33

E0706

1-Ethyl-3-methylimidazolium Tetrachloroferrate

EMI

FeCl4

Liquid

M1440 1-Methyl-3-propylimidazolium Iodide

C3MI

I

Liquid

B2194

1-Butyl-3-methylimidazolium Chloride

BMI

Cl

254

280

B2193

1-Butyl-3-methylimidazolium Bromide

BMI

Br

B2708

1-Butyl-3-methylimidazolium Iodide

BMI

I

1.44 1.57d

-72

B2337

1-Butyl-3-methylimidazolium Trifluoromethanesulfonate

BMI

TfO

1.31

13

B3542

1-Butyl-3-methylimidazolium Trifluoro(trifluoromethyl)borate

BMI

CF3BF3

1.27

B2195

1-Butyl-3-methylimidazolium Tetrafluoroborate

BMI

BF4

1.21

1.42

-81

403

219

B2320

1-Butyl-3-methylimidazolium Hexafluorophosphate

BMI

PF6

1.37

1.41

10

349

450

0.15

5

-2

3

B2477

1-Butyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)imide

BMI

TFSI

1.44 1.43d

-2

402

52

0.39

4.62

-2.5

2.12

B2672

1-Butyl-3-methylimidazolium Tetrachloroferrate

BMI

FeCl4

H1097 1-Hexyl-3-methylimidazolium Chloride

C6MI

Cl

253

716

H1227 1-Hexyl-3-methylimidazolium Bromide

C6MI

Br

10

125 1.49

Liquid

-20

1.53

11.9

41

246

4.63 -2.49 2.14

98 3.0

-1.6

1.4

4.55 -2.45 2.10

0.52 0.83

4.6

-2.5

2.1

Liquid

1.44

265 1110

Liquid 238

90

0.37b

49

0.59 4.68 -2.55 2.13

Liquid 1.03

1.52

-75

1.54

Liquid

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Ionic Liquids

Physical Properties of Ionic Liquids (contd.) Dynamic Viscosity / cp

Conductivity / S/m

1.43

-82

409

310

0.12

H1098

1-Hexyl-3-methylimidazolium Hexafluorophosphate

C6MI

PF6

1.29

1.42

-61

M2062 1-Methyl-3-n-octylimidazolium Chloride

C8MI

Cl

M1904 1-Methyl-3-n-octylimidazolium Bromide

C8MI

Br

M2063

1-Methyl-3-n-octylimidazolium Hexafluorophosphate

C8MI

PF6

1.24

1.42

E0753

1-Ethyl-2,3-dimethylimidazolium Bis(trifluoromethanesulfonyl)imide

EDMI

TFSI

1.50

1.43

DMPI

I

D3903 1,2-Dimethyl-3-propylimidazolium Iodide

1.51

12

Anion

Anode Limit / V

Decomposition Point /

1.15

Cathode Limit / V

Melting Point /

BF4



Elec. Window / V

Refractive Index nD20

C6MI

Cation

1-Hexyl-3-methylimidazolium Tetrafluoroborate

Name

H1099

Product Code

Specific Gravity



6

-3

3

560 243

337

-70

376

682

27

456

88

Liquid

0.32b

Solid

B2473

1-Butyl-2,3-dimethylimidazolium Chloride BDMI

Cl

B2475

1-Butyl-2,3-dimethylimidazolium Tetrafluoroborate

99

BDMI

BF4

1.20

37

B2474

1-Butyl-2,3-dimethylimidazolium Hexafluorophosphate

BDMI

PF6

1.24

38

B3159

1-Butyl-2,3-dimethylimidazolium Bis(trifluoromethanesulfonyl)imide

BDMI

TFSI

1.43

1.44

1.43

780

Liquid

PYRROLIDINIUM SALTS M2098

1-Methyl-1-propylpyrrolidinium Bis(trifluoromethanesulfonyl)imide

P13

TFSI

B3358

1-Butyl-1-methylpyrrolidinium Chloride

P14

Cl

Solid

B3427

1-Butyl-1-methylpyrrolidinium Bromide

P14

Br

214

B2851

1-Butyl-1-methylpyrrolidinium Bis(trifluoromethanesulfonyl)imide

P14

TFSI

PP14

Br

230

1.40

12

1.42

340

-18

61

0.14

85

0.22

PIPERIDINIUM SALTS B3424

1-Butyl-1-methylpiperidinium Bromide

E0544

1-Ethylpyridinium Chloride

Epy

Cl

Solid

E0171

1-Ethylpyridinium Bromide

Epy

Br

120

B1329

1-Butylpyridinium Chloride

Bpy

Cl

Solid

B1743

1-Butylpyridinium Bromide

Bpy

Br

B3232

1-Butylpyridinium Tetrafluoroborate

Bpy

BF4

PYRIDINIUM SALTS

104 1.22

1.45

-1

342

75

B2196

1-Butylpyridinium Hexafluorophosphate

Bpy

PF6

B3425

1-Butyl-3-methylpyridinium Chloride

C4Mpy

Cl

B3104

1-Butyl-3-methylpyridinium Bromide

C4Mpy

Br

Solid

E0681

1-Ethyl-3-methylpyridinium Ethyl Sulfate

C2Mpy

EtSO4

Liquid

E0682

1-Ethyl-3-(hydroxymethyl)pyridinium Ethyl Sulfate

C2HMpy EtSO4

B3426

1-Butyl-4-methylpyridinium Chloride

C4M'py Cl

160

B2700

1-Butyl-4-methylpyridinium Bromide

C4M'py Br

137

B2701

1-Butyl-4-methylpyridinium Hexafluorophosphate

C4M'py PF6

Solid

1.51

199

Liquid

42

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

11

Ionic Liquids

Physical Properties of Ionic Liquids (contd.)

T2679

Tributylmethylammonium Bis(trifluoromethanesulfonyl)imide

N1444

TFSI

1.27

1.43

Liquid

T0055

Tetrabutylammonium Chloride

N4444

Cl

70

T0054

Tetrabutylammonium Bromide

N4444

Br

103

N1888

TFSI

-

TFSI

Solid

104

Melting Point /

Anion

Anode Limit / V

Liquid

Cathode Limit / V

1.43

Elec. Window / V

1.32

Conductivity / S/m

TFSI



Dynamic Viscosity / cp

Refractive Index nD20

N5222

Cation

Amyltriethylammonium Bis(trifluoromethanesulfonyl)imide

Name

A2274

Product Code

Specific Gravity

Decomposition Point /



AMMONIUM SALTS

Methyltri- -octylammonium M1660 Bis(trifluoromethanesulfonyl)imide C1966

Cyclohexyltrimethylammonium Bis(trifluoromethanesulfonyl)imide

1.11

1.44

-39

386

367

589

PHOSPHONIUM SALTS T1124

Tetrabutylphosphonium Bromide

P4444

Br

T2680

Tributylmethylphosphonium Bis(trifluoromethanesulfonyl)imide

P4441

TFSI

1.26

1.44

16

T2564

Tributyl(2-methoxyethyl)phosphonium Bis(trifluoromethanesulfonyl)imide

P444,2O1 TFSI

1.25

1.44

10

H1047 Tributylhexadecylphosphonium Bromide

P444,16 Br

0.042

61

SULFONIUM SALTS T2314

Triethylsulfonium Bis(trifluoromethanesulfonyl)imide

S222

TFSI

1.47

1.43

-36

30

The values of physical properties are based on literatures except those of refractive index unless otherwise noted. Please note that those values are not specification details which could vary with lot number of each product. References: 1) S. Zhang, X. Lu, Q, Zhou, X. Li, X. Zhang, S. Li, in       2) S. Zhang, N. Sun, X. He, X. Lu, X. Zhang, Notes: a 25 ℃ , b 20 ℃ , c 64.9 ℃ , d ref. 1, e 30 ℃

12

, Elsevier, Oxford, 2009. 2006,

, 1475.

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Fluorous Chemistry

Fluorous Chemistry In recent years, fluorous chemistry has emerged as one of the promising fields of green chemistry. The term“fluorous”is a coined word meaning having affinity with fluorocarbons. Highly fluorinated compounds, in another words fluorous compounds, are insoluble in general organic solvents or water. However they are highly soluble with fluorous solvents such as perfluoroalkane. Fluorous chemistry is the technique of making use of this property, and it is applied to many organic reactions. Although fluorous solvents are generally immiscible with common organic solvents and water, certain fluorous solvents are able to form homogeneous solutions with some organic solvents at elevated temperatures. The characteristic features of these fluorous solvents is that they have boiling points properties that are almost equal to those of the corresponding hydrocarbons, regardless of their molecular weight, and these solvents have a high solubility of many gases and incombustible property. Taking the advantage of these properties, Horváth . accomplished the hydroformylation of olefins using a fluorous rhodium catalyst in perfluoromethylcyclohexane and toluene in 1994.1) This was regarded as the origin of the fluorous chemistry. This reaction uses perfluoromethylcyclo hexane and toluene as solvents, which exist as a biphasic system at room temperature. In this system the fluorous catalyst exists in the fluorous phase and the olefins in the organic phase. However, the two phases form a homogeneous solution when heated. The reaction then proceeds by introduction of carbon monoxide and hydrogen gases. When the reaction is complete and the system is cooled, the two phases reappears, where the resulting product is found in the organic phase and the fluorous catalyst is in the fluorous phase; thus, the catalyst and the product are easily separated. The biphasic system using a fluorous solvent and an organic solvent is called Fluorous Biphase System (FBS), and the multiple phase system is called Fluorous Multiphase System (FMS). The advantages of FBS and FMS are that the resulting product and the catalyst can be easily separated simply by separating the fluorous phase from the other phase after the reaction. After separation, the fluorous phase containing the fluorous catalyst can be reused. room temp.

room temp. Heat

Cool

Substrate

Product

Catalyst

Catalyst

organic solvent fluorous solvent

Homogeneous

1)

Rh(CO)2(acac) P[(CH2)2(CF2)5CF3]3 CO / H2 (1:1, 150 psi)

C8H17

CH3 CHO

C8H17

CF3C6F11 / Toluene 100 °C, 2 h

C8H17

CHO

Y. 85%

Curran . have introduced the use of fluorous substituents (fluorous tags) into non-fluorous substrates for the synthesis of isoxazoline.2) After the reaction, the fluorous product was separated by fractional extraction with dichloromethane, water, and perfluorohexane. Following this report, numerous applications of fluorous chemistry have been made in combinatorial chemistry3) and oligosaccharide syntheses4). D2669

E0485

P0074

(CF2)3CF3

H0946

CF3(CF2)7CF3

CF3CHFCHFCF2CF3

Fluorous Solvents

H0085

P0837 F F

F

F

F

CF3(CF2)7Br F

F

O0268 F

F F F

F

F

F

F F

F

F F F

F

F

(CF2)3CF3

O0292

F

F

N

CF3(CF2)3

CF3(CF2)6CF3

F

F

F

F

F

F F

F

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

13

Fluorous Chemistry

P0856

P1420 CF3 F

F

F

F

P0851

F

F F

F

CF3

F

F

F

CF3(CF2)5CF3

C5F11 C5F11 N C5F11

F

F

F

F F

F

CF3CF2CF2CF

CF3 CF3

F

Product No. Product Name

Unit Size

2H,3H-Decafluoropentane Eicosafluorononane Heptacosafluorotributylamine Heptadecafluoro-n-octyl Bromide Hexafluorobenzene Octadecafluorodecahydronaphthalene Octadecafluorooctane Octafluorocyclopentene Octafluorotoluene Perfluoro(2-butyltetrahydrofuran) (so called) Perfluoro(1,3-dimethylcyclohexane) Perfluoroheptane (mixture of isomers) Perfluorotriamylamine (so called) Perfluorotriethylamine Tetradecafluorohexane Tetradecafluoromethylcyclohexane Tetradecafluoro-2-methylpentane

25g

5g 25g

5g

10g

Fluorous Alkanes, Fluorous Alkenes

Fluorous Compounds

T2496

14

CF3(CF2)7CH CH2

500g 10g 25g 25g 250g 25g 10g 50g 25g 25g 25g 25g 25g 25g 250g 25g 25ml

N0601

CF3(CF2)3CH CH2

U0076

CF3(CF2)4CHF2

Product No. Product Name H0846 N0601 P1102 T2496 U0076

5g 25g

10g

H0846

CF3(CF2)5CH CH2

CF2CF3

CF3 F

F F

P1102

N

T1012 F

D2669 E0485 P0074 H0946 H0085 P0837 O0268 O0292 P0856 P0867 P1420 P0851 P1051 P1348 P0839 P0846 T1012

CF2CF3 CF3CF2

F

P0846

CF3(CF2)4CF3

P1348

CF3

F F

P0839

F

P1051

1H,1H,2H-Heptadecafluoro-1-decene 3,3,4,4,5,5,6,6,6-Nonafluoro-1-hexene (Perfluorohexyl)ethylene 1H-Tridecafluorohexane 1H-Undecafluoropentane

CF3(CF2)3CHF2

Unit Size 5g 5g 10g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

25g 25g 25g 5g 5g

Fluorous Chemistry

D1101

Fluorous Alcohols

H1232

H(CF2)6CH2OH

H0548

D2891

HOCH2(CF2)6CH2OH

H1233

E0239

H0845

H(CF2)10CH2OH

H1035

CF3(CF2)7CH2CH2OH

H1279

F3C CF3 CF3(CF2)7CH2OH

CF3CF2CF2CH2OH

HOCH2(CF2)8CH2OH

H(CF2)8CH2OH

HO C C OH F3C CF3

H0649

H0746

CF3CHFCF2CH2OH

O0294

HOCH2(CF2)3CH2OH

O0114

HOCH2(CF2)4CH2OH

CHF2(CF2)3CH2OH

N0814

CF3(CF2)8CH2OH

P0904

CF3(CF2)6CH2OH

N0600

CF3(CF2)3CH2CH2OH

P0845

N0810

CF3(CF2)3CH2OH

T1701

CF3CF2CH2OH

CF3(CF2)5CH2OH

T2528

CF3(CF2)5CH2CH2OH

Product No. Product Name D1101 D2891 E0239 H0845 H1232 H0548 H1233 H1035 H1279 H0649 H0746 N0814 N0600 N0810 O0294 O0114 P0904 P0845 T1701 T2528

1H,1H,7H-Dodecafluoro-1-heptanol 2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-1,8-octanediol 1H,1H,11H-Eicosafluoro-1-undecanol 1H,1H,2H,2H-Heptadecafluoro-1-decanol 1H,1H-Heptadecafluoro-1-nonanol 2,2,3,3,4,4,4-Heptafluoro-1-butanol 1H,1H,10H,10H-Hexadecafluoro-1,10-decanediol 1H,1H,9H-Hexadecafluoro-1-nonanol Hexafluoro-2,3-bis(trifluoromethyl)-2,3-butanediol 2,2,3,4,4,4-Hexafluoro-1-butanol 2,2,3,3,4,4-Hexafluoro-1,5-pentanediol 1H,1H-Nonadecafluoro-1-decanol 1H,1H,2H,2H-Nonafluoro-1-hexanol 1H,1H-Nonafluoro-1-pentanol 2,2,3,3,4,4,5,5-Octafluoro-1,6-hexanediol 2,2,3,3,4,4,5,5-Octafluoro-1-pentanol 1H,1H-Pentadecafluoro-1-octanol 2,2,3,3,3-Pentafluoro-1-propanol 1H,1H-Tridecafluoro-1-heptanol 1H,1H,2H,2H-Tridecafluoro-1-n-octanol

Unit Size 25g

25g 5g 1g 5g 1g 5g 5g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

250g 5g 10g 250g 5g 25g 5g 25g 25g 25g 5g 5g 25g 1g 25g 500g 5g 25g 5g 25g

15

Fluorous Chemistry

P1449

Fluorous Carboxylic Acids, Anhydrides and Halides H0024

B1698

O

O

H0743

C

CF3CF2CF2

T2492

O (CF2)8

O HO C

O CF3(CF2)3 C F

O HO C

O

Unit Size

D3589

D3590

O

16

CH3O C

O

CF3(CF2)4 C F

Ammonium Pentadecafluorooctanoate 2,5-Bis(trifluoromethyl)-3,6-dioxaundecafluorononanoyl Fluoride Dodecafluorosuberic Acid Heptadecafluorononanoic Acid Heptafluorobutyric Acid Heptafluorobutyric Anhydride Heptafluorobutyryl Chloride [for Heptafluorobutyration] Hexadecafluorosebacic Acid Hexafluoroglutaric Acid 2,2,3,3,4,4-Hexafluoropentanedioyl Dichloride Nonadecafluorodecanoic Acid Nonafluorovaleric Acid Nonafluorovaleryl Fluoride Octafluoroadipic Acid Pentadecafluorooctanoic Acid Hydrate Tricosafluorododecanoic Acid Tridecafluoroheptanoic Acid Undecafluorohexanoic Acid Undecafluorohexanoyl Fluoride

Fluorous Esters

C OH

(CF2)4 C OH

O

Product No. Product Name P1449 B1698 D2465 H0843 H0024 H0337 H0508 H0892 H0658 H0743 N0607 N0605 N0809 O0260 P0764 T2492 T1545 U0067 U0075

O (CF2)3

U0075

CF3(CF2)4 C OH

CF3(CF2)5 C OH

C OH

O0260

O

CF3(CF2)10 C OH

C OH

U0067

O

. xH2O

O HO C

CF3(CF2)3 C OH

T1545

O CF3(CF2)6 C OH

CF3(CF2)7

H0658

O

CF3(CF2)8 C OH

O

O (CF2)6 C OH

N0809

O

P0764

C Cl

N0605

O (CF2)3 C Cl

HO C

O

N0607

O

C F

H0892

O

CF3CF2CF2 C O C CF2CF2CF3

H0843

O

CF3 O

CF3(CF2)2O CF CF2O CF

H0508

O

Cl

CF3

CF3(CF2)6 C O NH4

H0337

CF3CF2CF2 C OH

D2465

O (CF2)3 C OCH3

5g 5g 25g 5g 5g 1g 5g 5g 10g 1g 5g 5g

H1038

O CH3O C

25g 5g 25g 25g 100g 10g 25g 25g 10g 5g 5g 25g 5g 25g 25g 5g 25g 25g 5g

H0594

O

O

(CF2)4 C OCH3

CF3(CF2)7 C OCH2CH3

O CF3CF2CF2 C OCH2CH3

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Fluorous Chemistry

N0689

H0744

O

M1915

O

CF3(CF2)3 C OCH2CH3

M1916

CH3CH2O C

M1912

CF3(CF2)7 C OCH3

P1453

O

CF3(CF2)3 C OCH3

CF3(CF2)2 C OCH3

M1917

O

O

CF3(CF2)8 C OCH3

M2022

O

O

O (CF2)3 C OCH2CH3

H1033

CF3(CF2)6 C OCH3

O (CF3)2CF C OCH3

M1914

O CF3(CF2)10 C OCH3

O CF3(CF2)5 C OCH3

M1913

O CF3(CF2)4 C OCH3

Product No. Product Name D3589 D3590 H1038 H0594 N0689 H0744 M1915 H1033 M2022 M1916 M1912 P1453 M1917 M1914 M1913

D3572

D3573

Br(CF2)6Br

Fluorohalides

H0844

H1084

CF3(CF2)9I

Unit Size

Dimethyl Hexafluoroglutarate Dimethyl Octafluoroadipate Ethyl Heptadecafluorononanoate Ethyl Heptafluorobutyrate Ethyl Nonafluorovalerate 2,2,3,3,4,4-Hexafluoropentanedioic Acid Diethyl Ester Methyl Heptadecafluorononanoate Methyl Heptafluorobutyrate Methyl Heptafluoroisobutyrate Methyl Nonadecafluorodecanoate Methyl Nonafluorovalerate Methyl Pentadecafluorooctanoate Methyl Tricosafluorododecanoate Methyl Tridecafluoroheptanoate Methyl Undecafluorohexanoate

CF3(CF2)7CH2CH2I

1g 1g 5g

5g 5g 5g

5g 5g

D2804

Br(CF2)4Br

H0946

D2333

Cl(CF2)8Cl

P1084

CF3(CF2)7Br

5g 5g 5g 25g 5g 1g 25g 25g 25g 25g 5g 5g 25g 25g 5g

I(CF2)6I

H0689

CF3(CF2)7I

CF3CF2CF2Br

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

17

Fluorous Chemistry

H0596

N0808

N0499

CF3(CF2)8Br

CF3CF2CF2I

P1753

T2479

CF3(CF2)6Br

P1155

CF3CF2CF2CF2I

T1098

I(CF2)4I

CF3(CF2)3CH2CH2I

T2482

CF3(CF2)4CF2I

CF3(CF2)5Br

D2329

T2074

CF3(CF2)5CH2I

CF3(CF2)5CH2CH2I

U0081

CF3(CF2)4I

Product No. Product Name D3572 D3573 D2804 D2333 H0844 H1084 H0946 P1084 H0689 H0596 N0808 N0499 P1155 D2329 P1753 T2479 T1098 T2482 T2074 U0081

Unit Size

1,6-Dibromododecafluorohexane 1,4-Dibromooctafluorobutane 1,8-Dichlorohexadecafluorooctane Dodecafluoro-1,6-diiodohexane Heneicosafluorodecyl Iodide 1H,1H,2H,2H-Heptadecafluorodecyl Iodide Heptadecafluoro-n-octyl Bromide Heptadecafluoro-n-octyl Iodide Heptafluoropropyl Bromide Heptafluoropropyl Iodide (stabilized with Copper chip) Nonadecafluorononyl Bromide Nonafluorobutyl Iodide 1H,1H,2H,2H-Nonafluorohexyl Iodide Octafluoro-1,4-diiodobutane Pentadecafluoroheptyl Bromide Tridecafluorohexyl Bromide Tridecafluorohexyl Iodide 1H,1H-Tridecafluoro-1-iodoheptane 1H,1H,2H,2H-Tridecafluoro-n-octyl Iodide Undecafluoropentyl Iodide

H0781

Fluorous Sulfonic Acids & their derivatives N0710

O O

5g 5g 5g

5g 25g 5g

5g

5g 5g

H1281

O CF3(CF2)7 S

N0677

O CF3(CF2)3 S OH O

H1055

O

F

CH3

S OCH O

O

O

N0709

CF3(CF2)3 S OLi

18

S OH

P1098

O CF3(CF2)3 S OCH2CF3 O

5g 5g 25g 10g 25g 25g 25g 25g 5g 25g 5g 500g 25g 10g 5g 25g 25g 1g 25g 25g

5g

H1176

O CF3(CF2)7

1g

CF3 CF3

O CF3(CF2)7 S OLi O

H0729

O

O CF3(CF2)3 S

F

CF3(CF2)7 S OK

O

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

O

Fluorous Chemistry

N0711

O CF3(CF2)3 S OK O

Product No. Product Name H0781 H1176 H1281 H1055 N0710 N0709 N0677 P1098 H0729 N0711

Unit Size

Heptadecafluorooctanesulfonic Acid Heptadecafluoro-1-octanesulfonyl Fluoride 1,1,1,3,3,3-Hexafluoroisopropyl p-Toluenesulfonate Lithium Heptadecafluoro-1-octanesulfonate Lithium Nonafluoro-1-butanesulfonate Nonafluoro-1-butanesulfonic Acid Nonafluorobutanesulfonic Acid 2,2,2-Trifluoroethyl Ester Perfluorobutanesulfonyl Fluoride Potassium Heptadecafluoro-1-octanesulfonate Potassium Nonafluoro-1-butanesulfonate

B2340

E0462

O

Other Fluorous Compounds H0926

C CF2CF2CF3

O

O

U0071

N0645

F

F F O S

F F S O N H O

F

O

F F S O N Li O

P1080

CH2 CH

O

C OCH2(CF2)4H

P1081

CH2 CH C OCH2(CF2)6CF3

H1058

O

F

O S CF3

P1163

O CH2CH2CH3

I

O S CF3 O

T2037

CH3CH2CH2

CF3(CF2)7 S N CH2CHCH2OH O

OH

CH2 O

O

CF3(CF2)3SO2 CF3(CF2)3SO2

NK

T1770 O

O N S

CH3

O CF3(CF2)7

O

F F F S O N O K

I

O

P1162

F F O S

CF3(CF2)5

CH2 C C OCH2(CF2)4H

N0712

O CH2O(CH2)2(CF2)5CF3

O CF3(CF2)6 C CH3

M1433

O

P1106

CH C OCH2CH2(CF2)7CF3

F

O0318

CF3(CF2)3CH2NH2

CF3(CF2)3 C CH3

O

O CH2

P1452

O

CF3(CF2)4 C CH3

P1754

F

N0872

O

O

H1057

F F O S

N

CF3CF2CF2 C NH2

A1330

CF3(CF2)4 C CH2CH3

H1056 N

O

25g

CH2(CF2)7CF3 O

25g 250g 25g 25g 25g 25g 5g 250g 25g 25g

5g

P1363

O

CH2 CH C OCH2(CF2)4CH2O C CH CH2

H0467

1g 25g 5g

(CF2)7CF3

CH2

C

(CF2)6CF3

C

(CF2)6CF3

OCH2CH3 CF3(CF2)5CH2CH2 Si OCH2CH3 OCH2CH3

O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

19

Fluorous Chemistry

T2720

T0859

T0829

P1134 (CF2)8CF3

CF2CF2CF3

OCH3 CF3CH2CH2 Si OCH3 OCH3

N CF3CF2CF2

N

N N

CF2CF2CF3 CF3(CF2)8

N N

T0828 (CF2)6CF3

O

N

H(CF2)4CH2O P OCH2(CF2)4H

(CF2)8CF3

OCH2(CF2)4H

CF3(CF2)6

N N

(CF2)6CF3

U0083

CF3(CF2)4CH2NH2

Product No. Product Name B2340 E0462 P1363 A1330 H0926 H0467 H1056 H1057 P1452 U0071 N0645 N0872 O0318 M1433 P1754 P1106 P1080 P1081 N0712 H1058 P1162 P1163 T2037 T1770 T2720 T0859 T0829 P1134 T0828 U0083

1,6-Bis(acryloyloxy)-2,2,3,3,4,4,5,5-octafluorohexane 1,2-Epoxy-1H,1H,2H,3H,3H-heptadecafluoroundecane Ethyl Perfluoroamyl Ketone 1H,1H,2H,2H-Heptadecafluorodecyl Acrylate (stabilized with MEHQ) Heptafluorobutyramide 1-(Heptafluorobutyryl)imidazole [Acylating Agent] 1,1,2,2,3,3-Hexafluoropropane-1,3-disulfonimide Lithium 1,1,2,2,3,3-Hexafluoropropane-1,3-disulfonimide Methyl Pentadecafluoroheptyl Ketone Methyl Perfluoroamyl Ketone Methyl Perfluorobutyl Ketone 1H,1H-Nonafluoropentylamine 1H,1H,5H-Octafluoropentyl Acrylate (stabilized with MEHQ) 1H,1H,5H-Octafluoropentyl Methacrylate (stabilized with TBC) 1H,1H-Pentadecafluoro-n-octyl Acrylate (stabilized with MEHQ) 3-[2-(Perfluorohexyl)ethoxy]-1,2-epoxypropane (Perfluorohexyl)phenyliodonium Trifluoromethanesulfonate (Perfluoro-n-octyl)phenyliodonium Trifluoromethanesulfonate Potassium Bisnonafluoro-1-butanesulfonimidate Potassium 1,1,2,2,3,3-Hexafluoropropane-1,3-disulfonimide N-Propyl-N-(2,3-dihydroxypropyl)perfluoro-n-octylsulfonamide N-Propyl-N-(2,3-epoxypropyl)perfluoro-n-octylsulfonamide 9H,9H-Triacontafluoro-8,10-heptadecanedione Triethoxy-1H,1H,2H,2H-tridecafluoro-n-octylsilane Trimethoxy(3,3,3-trifluoropropyl)silane 2,4,6-Tris(heptafluoropropyl)-1,3,5-triazine [for Mass spectrometry] 2,4,6-Tris(nonadecafluorononyl)-1,3,5-triazine [for Mass spectrometry] Tris(1H,1H,5H-octafluoropentyl) Phosphate 2,4,6-Tris(pentadecafluoroheptyl)-1,3,5-triazine [for Mass spectrometry] 1H,1H-Undecafluorohexylamine

Unit Size 1g

5g 1g 1g

1g

5g 1g 5g 5g 5g 1g 1g 1g

5g 5g

1g

5g 10g 5g 10g 25g 25g 5g 5g 5g 5g 25g 5g 25g 25g 25g 25g 5g 1g 5g 5g 25g 25g 100mg 25g 25g 0.1ml 100mg 10g 100mg 5g

References 1994, 1) I. T. Horváth, J. Rábai, , 72. 1997, 2) A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf, D. P. Curran, , 823. 3) D. P. Curran, S. Hadida, . 1996, , 2531; D. P. Curran, M. Hoshino, . 1996, , 6480; D. P. Curran, . 1998, , 1174; D. P. Curran, Z. Luo, . 1999, , 9069; Q. Zhang, 2001, Z. Luo, D. P. Curran, . 2000, , 8866; Z. Luo, Q. Zhang, Y. Oderaotoshi, D. P. Curran, , 1766; S. Darses, M. Pucheault, J.-P. Genêt, . 2001, 1121. 4) T. Miura, Y. Hirose, M. Ohmae, T. Inazu, . 2001, , 3947; T. Miura, T. Inazu, . 2003, , 1819. 2001, 5) Reviews: K. Ishihara, H. Yamamoto, , 1061; K. Ishihara, 2002, 2002, , 865; I. Ryu, H. Matsubara, , 20; S. Takeuchi, Y. Nakamura, 2002, 2002, , 16; K. Mikami, H. Matsuzawa, , 22; K. Ishihara, H. Yamamoto, 2002, , 30.

20

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Amphiphilic Polymer-assembled Pd Complex Catalyst

Amphiphilic Polymer-assembled Pd Complex Catalyst Product No. Product Name

P1425

Unit Size

Poly[N-isopropylacrylamide-co-4-(diphenylphosphino)styrene] Palladium(II) Dichloride (ratio, acrylamide:phosphine=20:2) 1

100mg

1g

Palladium is one of the most useful catalysts in organic syntheses. Many types of palladium complex catalysts have been developed and utilized in various reactions. Furthermore,“Environmentally-friendly organic syntheses”are desired these days, so there have been many developmental studies of palladium complex catalysts with respect to green chemistry in recent years. Palladium complex catalyst 1 developed recently by Ikegami . is one of those catalysts with excellent properties. Catalyst 1 is solid-phase catalyst which consists of amphiphilic copolymer ligands and palladium. It uptakes substrates and reagents of both hydrophilic and hydrophobic nature in the vicinity of palladium to smoothly promote the reaction. The palladium complex catalyst forms a networked supermolecular complex, which is insoluble in water and organic solvents, and is easily recovered from reaction system. Since the palladium is firmly held in place by the phosphino group of copolymer ligand, it is not lost during the reaction or upon work up; therefore, the catalyst can be recovered and reused multiple times. Ph P Ph

O HN 20

B(OH)2

X + R'

R'' (1.1 mol eq.)

PdCl2 2

1 (5.0 X 10-4- 5.0 X 10-5 mol eq.) Na2CO3 (1.11 mol eq.), H2O, 100 oC

n

R'

R''

X=I, R'=H, R''=H

1st Y. 95% 10th Y. 93% 1st-10th consecutive use av: 95%

X=Br, R'=4-Me, R''=H Y. 95% X=Br, R'=4-Me, R''=4-MeS Y. 95% X=Br, R7=4-Cl, R''=H Y. 94%

Ikegami . have demonstrated an application of 1 for the Suzuki-Miyaura coupling reaction in water, as this reaction does not require any organic solvents.1) This method requires as little as 5×10‒4∼5×10‒5 mol equiv. of 1 to effectively catalyze the reaction. After the reaction, 1 can be recovered by simple filtration. The recovered catalyst 1 can be reused, and it maintains its catalytic activity even after being reused ten times.

As shown in the figure, in the presence of sodium carbonate and catalyst 1, halobenzene and 1.1 mol equiv. of phenylboronic acid react to form product in water as the solvent. The reaction vessel is fitted with glass filter, and after the reaction is completed, the mixture is filtered while it is still hot and then washed with hot water. The catalyst 1 remains in the reaction vessel, while the filtrate contains the biphenyls, as well as sodium carbonate and residual phenylboronic acid. When the filtrate is cooled, the biphenyls crystallize out of the aqueous phase. Upon filtration, the biphenyls are easily obtained. 1 that remains in the reaction vessel can be reused right away. An application of this catalyst for the Heck reaction has been reported as one example of a reaction in an organic solvent.2) References 1) Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, . 2002, , 3371; Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, . 2003, , 7733; Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2003 236388, 2003. 2) Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, . 2003, , 2379.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

21

Stable Lewis Acids in Aqueous Media

Stable Lewis Acids in Aqueous Media 1)

OTMS

O

Yb(OTf)3 (20 mol%)

+

HCHO aq.

H2O – THF

Ph

Ph

OH

Y. 1st run 2nd run 3rd run

94% 91% 93%

2)

CHO

Yb(OTf)3 (20 mol%)

+

CHO

CH2Cl2, 0 °C

Y. 1st run 2nd run

77% (exo : endo = 93 : 7) 75% (exo : endo = 92 : 8)

The Lewis acid-catalyzed C-C bond forming reactions have been of great interest in organic synthesis. While various kinds of Lewis acid-promoted reactions have been developed, these reactions must be carried out under strict anhydrous conditions. The presence of even a small amount of water stops the reaction, because most Lewis acid immediately react with water rather than the substrates and decompose or deactivate. Recently, Kobayashi and co-worker have found that certain metal triflates are stable Lewis acids in aqueous media. The reaction of silyl enol ethers with commercial formaldehyde solution smoothly proceeds in aqueous media by the certain metal triflates, especially Yb(OTf)3 to give the corresponding aldol adducts in high yields. Moreover, the triflates can also be used in organic solvents in many reactions. In all cases, the reaction is completed by only a catalytic amount of the triflate, and the catalyst can be easily recovered after the reaction was completed and can be reused. On the other hand, in asymmetric synthesis, chiral Lewis acid which was prepared by Sc(OTf)3, chiral binaphthol and an amine affords chiral Diels-Alder adduct in the reactions of dienophiles and dienes. Then, the certain metal triflates, especially Yb(OTf)3, Sc(OTf)3, etc. are expected to be useful as new types of Lewis acid catalysts in many organic reactions. From the view points of green chemistry, these are also remarkably effective Lewis Acids as non-toxic and nonflammable water can be used as reaction solvent.

T1918

T1292

O CF3

CF3

CF3

T1921

S OAg

O

O

3

CF3

3

CF3

O Tm3

S O O

3

CF3

Yb3

S O O

Zn2

S O O

3

T1610

O Y3

S O O

22

T1920

CF3

La3

S O O

4

O Sc3

S O

CF3

InCl3

T1294

O CF3

O

T1331

O

3

O Hf4

S O

O Nd3

S O O

CF3

2

T1663

O

T1293

O Cu2

S O O

3

T1919

CF3

I0778

O Ce3

S O O

T1708

2

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

3

. xH2O

Stable Lewis Acids in Aqueous Media

Product No. Product Name T1918 T1292 T1708 I0778 T1293 T1919 T1663 T1331 T1920 T1610 T1921 T1294

Cerium(III) Trifluoromethanesulfonate Copper(II) Trifluoromethanesulfonate Hafnium(IV) Trifluoromethanesulfonate Indium(III) Chloride Anhydrous Lanthanum(III) Trifluoromethanesulfonate Neodymium(III) Trifluoromethanesulfonate Scandium(III) Trifluoromethanesulfonate Silver Trifluoromethanesulfonate Thulium(III) Trifluoromethanesulfonate Ytterbium(III) Trifluoromethanesulfonate Hydrate Yttrium(III) Trifluoromethanesulfonate Zinc(II) Trifluoromethanesulfonate

Unit Size 5g 1g 5g 5g 5g 1g 10g 5g 5g

5g 25g 5g 25g 25g 25g 5g 25g 5g 25g 25g 25g

References 1) Aldol reactions in aqueous media S. Kobayashi, . 1991, 2187; S. Kobayashi, I. Hachiya, . 1992, , 1625. 2) Reusable catalysts for Michael and Diels-Alder reactions S. Kobayashi, I. Hachiya, T. Takahori, M. Araki, H. Ishitani, . 1992, , 6815. 1994, 689; S. Kobayashi, I. Hachiya, 3) Reviews: S. Kobayashi, 1995, , 370; T. Ogino, T. Onozawa, 2000, number Ishikawa, , 2; S. Kobayashi, T. Hamada, S. Nagayama, K. Manabe, , 627; S. Kobayashi, . 2007, , 235.

, 1998,

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

, 71; K. . 2001,

23

Polymer-Supported Reagents

Polymer-Supported Reagents In recent years, the trend in synthetic organic chemistry has been to put special emphasis on harmonization with the environment and reaction efficiency. Much R&D is taking place to address these issues. Polymer-supported synthetic reagents and catalysts are drawing much attention due to the ease of recovery of the reagent after reaction. For this reason, many polymer-supported reagents and catalysts with excellent properties have been reported. One of the most common hypervalent iodine compounds, diacetoxyiodobenzene, has been supported on polystyrene by Togo and co-workers, and they have reported the oxidation of various functional groups. For example, they have reported the oxidation of alcohols in the presence of this polymer-supported reagent and TEMPO.1) Ishikawa and co-workers have developed 1,3-dimethylimidazolidinone supported on polystyrene. The derived 2-chloro-1,3-dimethylimidazolidium, using oxalyl chloride, is used for the esterification as a polymer-supported dehydrating and condensation reagent.2) On the other hand, active research for development of the polymer-supported catalysts has also been carried out. Yao has developed a polyethylene glycol-bound Grubbs catalyst analog for olefin metathesis reactions.3) After the reaction, this catalyst was precipitated by the addition of diethyl ether as a poor solvent. It can be recovered and reused. Ishihara and his group have developed a polystyrene-bound 4-bis(triflyl)methyl2,3,5,6-tetrafluorobenzene and demonstrated its applications as a solid super Brønsted acid catalyst.4) This solid catalyst swells effectively in organic solvents, and shows excellent activity with various acid-catalyzed reactions. This catalyst has been used in esterification, Friedel-Crafts reaction, Michael addition, acetalization, Sakurai-Hosomi allylation and Mukaiyama aldol reaction. Its catalytic activity was superior even to that of Nafion, which is well known as a solid strong acid. After reaction, the solid catalyst was quantitatively recovered by simple filtration and reused. It was also packed in a syringe as a reaction column, and various acid-promoted reactions were performed to afford the desired products by passing a solution of reactants through the syringe. Ikegami and co-workers have developed the Pd complex catalyst, one of the most utilized catalyst in the organic synthesis, to support the polymer, and reported its usefulness.5) This catalyst is a solid-phase catalyst which consists of an amphiphilic copolymer ligands, chloride and palladium. It takes up substrates and reagents of both hydrophilic and hydrophobic nature in the vicinity of palladium to smoothly promote the reaction. It forms a networked supermolecular complex, which is insoluble in water and organic solvents, and is easily recovered from reaction system. Since palladium is firmly held by the phosphine group of copolymer ligand, it is not lost during the reaction or upon work up; therefore, the catalyst can be recovered and reused multiple times. Ikegami and co-workers have demonstrated the uses of this catalyst for a Suzuki-Miyaura coupling reaction in water, and a Heck reaction in organic solvent. This amphiphilic polymer-supported Pd complex catalyst possesses high catalytic efficiency, and can be used in either water or organic solvents. It is now attracting attention as it has fulfilled harmonization with the environment and reaction efficiency. A2006

B2372

B2370

B2371

CH2NHCH2CH2NH P

P

CH2O

C NH(CH2)4NHO2S

P

CH2O

C NH(CH2)2NHO2S

O 2N

B2292

C2141 F

CH2O

C NH(CH2)3NHO2S

D3525

O 2N

D2766

F CH

P F

SO2CF3 SO2CF3

CH3

CH2N C N P

CH2 N (CH2)3N C NCH2CH3

P

CH3

I0680

O CH2NH C

N

N N

M1452

CH2

O P

CH2

N

N

CH3

CH2 N P

OH

24

P

M1857

CH2NCO P

P

Cl

F

H1208

P

P

O 2N

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

O

Polymer-Supported Reagents

P1415

P1427 O

P1697

CH3

O

PEG O C (CH2)2 C O

O C CH3 P

P1425

O

O Ru

I

(CH2 CH)12 (CH2 CH)1

CH CH3 Cl Cl

C O CH3

CH3

P

CH3 2

20

n

O

S0545

NH

CH3 N CH3 C12H25 n

NH2

N

SO2Cl

(CH2)3

P

CH3 CH3 N CH3 n

C12H25 RuO4 n

P

N H

N NH2

Product No. Product Name A2006

N-(2-Aminoethyl)aminomethyl Polystyrene Resin cross-linked with 1% DVB (50-100mesh)

B2372

N-(4-Benzyloxytrityl)-N '-(2-nitrobenzenesulfonyl)-1,4-diaminobutane Resin cross-linked with

B2370

N-(4-Benzyloxytrityl)-N '-(2-nitrobenzenesulfonyl)-1,2-diaminoethane Resin cross-linked with

(3.1-3.5mmol/g)

Unit Size 5g

1g

1% DVB (200-400mesh) (0.9-1.1mmol/g)

B2371

N-(4-Benzyloxytrityl)-N '-(2-nitrobenzenesulfonyl)-1,3-diaminopropane Resin cross-linked with

B2292 C2141

Bis(trifluoromethanesulfonyl)methyltetrafluorophenyl Polystyrene Resin N-Cyclohexylcarbodiimidomethyl Polystyrene Resin cross-linked with 1% DVB (50-100mesh)

D3525

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide Resin cross-linked with 1% DVB (50-100mesh)

D2766 H1208

4-Diphenylphosphinomethyl Polystyrene Resin cross-linked with 2% DVB (200-400mesh) (0.5-1.0mmol/g) 1-Hydroxybenzotriazole-6-carboxamidomethyl Polystyrene Resin cross-linked with 1% DVB

I0680 M1452 M1857 P1415 P1427 P1425

Isocyanatomethyl Polystyrene Resin cross-linked with 1% DVB (50-100mesh) (2.0-2.5mmol/g) 3-Methyl-2-oxoimidazolidin-1-ylmethyl Polystyrene Resin cross-linked with 1% DVB Morpholinomethyl Polystyrene Resin cross-linked with 1% DVB (50-100mesh) (2.9-3.5mmol/g) Poly[4-(diacetoxyiodo)styrene] Polyethylene Glycol-bound Ruthenium Carbene Complex Poly[N-isopropylacrylamide-co-4-(diphenylphosphino)styrene] Palladium(II) Dichloride

P1697

Poly[[N-isopropylacrylamide-co-[N-[3-(dodecyldimethylammonio)propyl]acrylamide]]phosphotungstate] Poly[[N-isopropylacrylamide-co-[N-[3-(dodecyldimethylammonio)propyl]acrylamide]co-(1,3,5-triacryloylhexahydro-1,3,5-triazine)]perruthenate] Sulfonyl Chloride Polystyrene Resin cross-linked with 1% DVB (50-100mesh) (4.5-4.8mmol/g) Tris(2-aminoethyl)amine Polystyrene Resin cross-linked with 1% DVB (50-100mesh)

1g 100mg

1% DVB (200-400mesh) (0.9-1.1mmol/g)

(1.4-1.6mmol/g) (1.0-1.3mmol/g)

(50-100mesh) (1.3-1.5mmol/g)

(ratio, acrylamide:phosphine=20:2)

S0545 T2715

(0.4-0.8mmol/g)

25g 1g

1% DVB (200-400mesh) (0.9-1.1mmol/g)

P1698

n/3

T2715

(CH2 CH)x (CH2 CH)y (CH2 CH)z C O C O C O CH CH3

(CH2)3

PW12O403

P1698

NH

NH

CH CH3

PdCl2

P

O C CH3

C O

NH

O

NH

5g

25g

5g

25g 5g

5g 5g

25g 25g 1g 5g 25g 1g 5g 100mg 100mg

1g

200mg

1g

200mg 5g

1g 25g

5g

25g

References 1) 2) 3) 4) 5)

2002, 1966; Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2003 113131, 2003. H. Togo, K. Sakuratani, 2003, 115. W. Disadee, T. Watanabe, T. Ishikawa, Q. Yao, . 2000, , 3896. K. Ishihara, A. Hasegawa, H. Yamamoto, . 2001, , 4077. Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, . 2002, , 3371; Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, . 2003, , 2379; Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, . 2003, , 7733; Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2003 236388, 2003.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25

Asymmetric Organocatalysts

Asymmetric Organocatalysts Eder . and Hajos . separately reported an intramolecular asymmetric aldol reaction which employed proline as the only asymmetric catalyst at the beginning of the 1970s.1) This reaction was considered to be a special case at that time. Later in 2000, List . reported an intermolecular asymmetric aldol reaction which used proline as a catalyst.2) List’ s report received broad attention and served as a trigger to make research active for asymmetric organic catalysts. Therefore, varieties of asymmetric organic catalysts have been developed and the research has been applied to many areas.3) The proline derivative 1, having the heterocyclic ring was developed by Nakamura . It shows high TON as an asymmetric catalyst for obtaining a chiral aldol adduct.4) O Br O Br

N H

N H

Br

C NH S

S 1 O O . CF3CO2H (0.5 mol%)

HO

O

Br

Acetone, H2O

N H

O

O

Y. 70%, 92% e.e.

Compared with conventional metal complex catalysts, asymmetric organic catalysts are considered to be environmentally friendly and are expected to be further developed because they are stable, easy to handle and free of harmful metals.

A1301

A0945

A1043 O

N

Prolines and its analogs

B3440

D3803

H3C

D3804

N H

H3C C Si O

N H

N H

NH

D3185

N H

D2735

N H

H0784

OH

H0768 OH

OH

C

N H

M1169

N

C

M1097

N CH2OCH3

C

CH3

M1161

N H

D3186

N H

C OH

D2365

N H

OH

CH2NH

O

H3C

26

CH2NH2

CH2CH3

N H

CH2OCH3

CH3

I0395 OH

N

C

CH3

OH

N H

M1183

O

M2077

CH3

CH2NH N CH3

CH2 N

N H

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

C OH O

Asymmetric Organocatalysts

M1995

O0370

P1830

P1404

P0994

H N

N H H

CH3

. 2HCl P0481

O

O

N

N H

C OH

P1241

O

C OH

P1784

N H

O

CH2 N

N H

N H

N H

N

O

O

C NH S

HO C S

Unit Size

(S)-(-)-2-Aminomethyl-1-ethylpyrrolidine (S)-(+)-2-(Anilinomethyl)pyrrolidine L-Azetidine-2-carboxylic Acid trans-4-(tert-Butyldiphenylsilyloxy)-L-proline (R)-(+)-2-(Diphenylmethyl)pyrrolidine (S)-(-)-2-(Diphenylmethyl)pyrrolidine (2R,5R)-2,5-Diphenylpyrrolidine (2S,5S)-2,5-Diphenylpyrrolidine (R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol (R)-(-)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine (S)-(+)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine (S)-(-)-Indoline-2-carboxylic Acid (R)-2-(Methoxymethyl)pyrrolidine (S)-2-(Methoxymethyl)pyrrolidine (S)-(-)-1-Methyl-2-(1-naphthylaminomethyl)pyrrolidine (S)-(-)-1-Methyl-2-(1-piperidinomethyl)pyrrolidine α-Methyl-L-proline (S)-2-[(1-Methyl-2-pyrrolidinyl)methyl]isoindoline Dihydrochloride (2S,3aS,7aS)-Octahydro-1H-indole-2-carboxylic Acid D-Pipecolic Acid L-Pipecolic Acid D-Proline L-Proline (S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine (S)-5-(Pyrrolidin-2-yl)-1H-tetrazole N-(2-Thiophenesulfonyl)-L-prolinamide Trifluoroacetate L-Thioproline

A0177

1g 1g 100mg 1g

1g 1g 1g 1g 5g 1g 5g 25g 1g 100mg 25g

Other Amino Acids

O

OH

OH NH2

O

OH NH2

O OH

OH NH2

CH3

T0541

O

CH3

O

(CH3)3CO OH

NH2

T0539 OH

O

CH3

CH3

NH2

T0230

5g 5g 1g 5g 1g 1g 100mg 100mg 5g 5g 5g 5g 5g 5g 5g 1g 5g 5g 5g 5g 25g 5g 25g 250g 5g 500mg 100mg 500g

B3398

O OH

1g 1g 1g 1g 1g 1g 1g

100mg

A0179

CH3

T0228

NH

S

O

. x CF3CO2H

Product No. Product Name A1301 A0945 A1043 B3440 D3803 D3804 D3185 D3186 D2365 D2735 H0784 H0768 I0395 M1169 M1161 M1097 M1183 M2077 M1995 O0370 P1830 P1404 P0994 P0481 P1241 P1784 T2637 T0219

O

T0219 O

N

N

OH

N H

C OH

T2637

OH

N H

N H

N H

NH2

OH N H

NH2

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

27

Asymmetric Organocatalysts

Product No. Product Name A0177 A0179 B3398 T0228 T0230 T0539 T0541

Unit Size

D-Alanine L-Alanine

5g 25g 1g 25g 25g 5g

O-tert-Butyl-L-threonine D-(+)-Threonine L-(-)-Threonine D-Tryptophan L-Tryptophan

B1683

B1689

CH2

CH

B1684 H

H

CH2

H

CH

H

N

N HO

CH2

Cinchona Alkaloids

C0347 CH2

CH

CH

Cl N

CH2

HO

H

CH2

H

CH3O

N

B1685

CH2

Cl

Cl HO

25g 250g 5g 500g 500g 25g 25g

C0348 CH2 CH

H

N

N

C0349

H

CH2 CH

H

C0350 CH2 CH

H

H CH2

CH

Cl H

HO

N

H

HO

N

HO

H

N

CH2

N

N

C0351

N

HO

H

H

Q0006

O

H

N HO

. H2SO4 . 2H2O

H

N

28

CH2

HO

H

CH3O

N

HO

H

CH

H

N-Benzylcinchonidinium Chloride N-Benzylcinchoninium Chloride N-Benzylquinidinium Chloride N-Benzylquininium Chloride Cinchonidine Cinchonidine Dihydrochloride Cinchonidine Sulfate Cinchonine Cinchonine Hydrochloride Hydrate Hydroquinidine Hydrochloride β-Isocupreidine Quincoridine Quincorine Quinidine

N

N

. HCl . 2H2O

CH3O

2

Product No. Product Name B1683 B1689 B1684 B1685 C0347 C0348 C0349 C0350 C0351 H0752 I0728 Q0076 Q0074 Q0006

H

CH

N

N

N

Q0030 CH2 CH

CH3O

CH3O

N

HOCH2

CH2OH

H CH2

H

Q0028

H

CH2 CH

N

Q0010 CH2 CH

Q0074 CH2 CH

HO

N

N

N

Q0076

N

. HCl

H

CH3CH2

H

N

CH3O

. HCl . xH2O

HO

HO

N

I0728 CH3CH2

N

N

. 2H2SO4 . 2H2O

N

H0752 H CH

HO

H

. 2HCl

CH3O

CH2

HO

N

Unit Size

25g 25g 25g 25g 100mg 100mg 5g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

10g 5g 5g 5g 250g 25g 500g 200g 25g 250g 1g 1g 1g 25g

Asymmetric Organocatalysts

Product No. Product Name Q0010 Q0028 Q0030

Unit Size

Quinidine Sulfate Dihydrate Quinine Quinine Hydrochloride Dihydrate

5g 25g

B1143

B1144

O

O

Chiral Phosphoric Acids

O

P OH

O

O

O P OH

Product No. Product Name B1143 B1144

25g 500g 25g

Unit Size

(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate (S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate

100mg

B1142

B1100

Chiral Diols

1g 100mg

5g 1g

B2048

OH

OH

OH

OH

OH

HO

O

O

H3C CH3

B1614

B1615 OH

HO

O

O

OH

HO

O

O

H3C

H3C CH3

Product No. Product Name B1142 B1100 B2048 B1614 B1615

Unit Size

(R)-(+)-1,1'-Bi-2-naphthol (S)-(-)-1,1'-Bi-2-naphthol (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane (-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2-methyl-2-phenyl-1,3-dioxolane B1683

5g 5g 1g

B1689

CH2

CH

B1684 H

H

CH2

H

CH

H

N

N HO

CH2

Chiral Phase-Transfer Catalysts

D3475 CH2

CH

H

N CH2

CH3O

Cl N

CH2

HO

H

CH2

H

N

N

D3476

H Cl

HO

CH

CH3O

N

B1685

CH2

Cl

Cl HO

25g 25g 5g 5g 1g

CH3 CH2Ph CH2 N CH2 O O CH2 N CH2 CH2Ph CH3

CH3 CH3 2BF4

2

2

CH3 CH2Ph CH2 N CH2 O O CH2 N CH2 CH2Ph CH3

CH3 CH3

2

2

2BF4

N

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

29

Asymmetric Organocatalysts

Product No. Product Name

Unit Size

N-Benzylcinchonidinium Chloride N-Benzylcinchoninium Chloride N-Benzylquinidinium Chloride N-Benzylquininium Chloride 6,10-Dibenzyl-N,N '-dimethyl-N,N,N ',N '-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane(2R,3R)-diylbis(methylammonium) Tetrafluoroborate [=(R,R)-TaDiAS-2nd] 6,10-Dibenzyl-N,N '-dimethyl-N,N,N ',N '-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane(2S,3S)-diylbis(methylammonium) Tetrafluoroborate [=(S,S)-TaDiAS-2nd]

B1683 B1689 B1684 B1685 D3475 D3476

B3296

B3549

10g 5g 5g 5g 200mg

1g

200mg

1g

D3983 CH3

N S

Other Catalysts

N

S

N

H

N N

CH3

N Cl

H

D3984

CH3

N

O

. H2O

T1215 CH3

H

H

CH3

N

N N O

CH3

N

N

S

. HCl

Cl

. H2O

Product No. Product Name B3296 B3549 D3983 D3984 T1215

(+)-Benzotetramisole (-)-Benzotetramisole (+)-(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride Monohydrate (-)-(5aS,10bR)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride Monohydrate Levamisole Hydrochloride

Unit Size 200mg

1g 1g 100mg

10g

100mg 25g

References 1) U. Eder, G. Sauer, R. Wiechert, . 1971, , 496; Z. G. Hajos, D. R. Parrish, , 1615. 2) B. List, R. A. Lerner, C. F. Barbas III, . 2000, , 2395. 3) Review: . 2004, , 487-631,“Asymmetric Organocatalysis”(special edition); H. Pellissier, 2007, , 9267; A. Berkessel, H. Gröger, in , Wiley-VCH, Weinheim, 2005. 4) S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, T. Toru, . 2008, , 8079.

30

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

. 1974,

Asymmetric Synthesis

Asymmetric Synthesis In the research and development of pharmaceuticals, agricultural chemicals or functional materials starting with ferroelectrical liquid crystals, the demand for optically active compounds has increased more than ever. In order to obtain the desired optically active compounds through synthesis, diastereoselective and enantioselective reactions have employed chiral auxiliaries or asymmetric catalysts. In order to achieve even higher optical purity and yield, new chiral auxiliaries and asymmetric catalysts are being developed and a considerable number of successful results have been reported. For instance, camphorsultam and oxazolidinone derivatives are utilized as chiral auxiliaries. BINAP-Rh complexes and oxazaborolidine derivatives are excellent asymmetric catalysts. All of these new developments produce products of high optical purity and good reaction yields. Optically active cobalt(II) complex catalyst, MPAC, developed by Yamada and co-workers is one of these catalysts, and is utilized for a pro-chiral ketone and imine asymmetric reduction.1) Through this asymmetric reduction using MPAC, secondary alcohols and amines of high optical purity can be obtained in good yields. The reaction proceeds under relatively moderate temperatures and utilize sodium borohydride, which has been traditionally employed as a reducing agent of ketones and imines. For this reason, this method is receiving much attention as a route to useful optically active alcohols and amines.

A1534

A1535

A1138

CH3 SO2

CH3 Ph

N O

CH3 Ph

CH3

SO2

CH3

Ph

N O

CH3 Ph

O

CH3

A1548

O

O CH3

OH

A2316

A2317

NH2

NH SO2

O

A1337

OH NH2

NH2

NH2

OH

OH

NH O

CH3

NH2

A1699

NH2

CH2

A0179

O

O

A2095

H2N

CO Ph Ph P CH3 Fe C

CH3

CH3 CH3

A0177

CH3

A1335

NH SO2

CH3

A1301

A1521

A0945 OH

N

CH2OCH3

N

NH2

CH2OCH3

N

NH2

A1043

OH

CH2NH2

B3296

B3549

B1683

N OH

CH

N

S

H

H

CH2

CH

Cl

Cl

N

S

CH2NH

B1689

CH2

O

N H

NH2

CH2CH3

HO

N

H

N

N HO

CH2

CH2

H

NH N

B2103

B2104 CH3

P1371

CH3

SO2 N CH3

Bn

OH

CH3

SO2 CH3

N Bn

B1786 CH3 CH3

CH3

CH3 Ph

P1372 CH3

CH3 CH3

N

Ph

CH3

SO2 N CH3

Bn

CH3

Ph O

CH3

OH O

SO2 CH3

Bn

CH2

Ph

N O

NH CH3

O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

O

O

31

Asymmetric Synthesis

B1754

B1528

B1529 H N

CH3

CH2

B2165 H N

CH3

O

O

B1685

B1142

H CH2

CH2

CH

CH

HO

N O

O

B1100

O

B2230

H

Cl N

C CH2CH3

CH2

N

O

B1684

O

C CH2CH3

CH2

NH O

B2166

O Cl

CH2

HO

H

H

N

OH

OH

CH2

OH

OH

CH3O

CH3O

O S CF3 O O O S CF3 O

N

N

B2231

B1143

B1144

B2314

B2315

CH3

O O S CF3 O O O S CF3 O

B2090

O

O

P OH

O

O

CH3

N

CH3

N

O

O

CH3

O

N

B2653

CH3

N

CH3

O

CH3

O

CH3

CH3

B3449

CH3

B1406

PPh2 Rh

(CH3)3C

CH3

P

OH

(CH3)3C

P

N

N HO

C(CH3)3

(CH3)3C

C(CH3)3 (CH3)3C

PPh2

N

OH

HO

O

Co CH3

O

CH3

N

BF4

CH3

CH3 CH3

Co CH3

B2652

CH3

O

O

P OH

O

CH3

CH3 CH3

C(CH3)3

PPh2

PPh2

C(CH3)3 (CH3)3C

C(CH3)3

CH3

B1405

B2704

B1113

CH3

PPh2

H

P 2

PPh2

P

B1112

CH3 O CH3 O

CH3

H

2

B2048

CH2 P

CH3 O

CH2

P

CH2 P

CH3 O

CH2

P

OH

HO

O

O

H3C CH3

B1614

B1615 OH

B2409 OH

HO

B2217 O

HO N

CH3

N

C O

O

Mn

O

O

O

O Ph

O

O Ph

CH3

B3036 OCH3

B2034

CH3

B2220

O CH3

Co O

O CH3

O

N N

N

N

CH3

O N

CH3

O

N N

CH3

CH3

CH3

CH3

CH3 Ph

Ph

CH3

CH3 N

N Co

CH3

D2520

O

CH3

B1844

. HCl

CH3 Ph

CH3

N H

. HCl

B2219

CH3

CH3

CH3

N H

CH3O

B1845

32

CH3

PCH2CH2P

CH3O

CH3

N N

B2035

OCH3

PCH2CH2P

N

O

N

H3C

B3035

Ph

O

N N

H3C CH3

CH3

B2218

O

CH3

O

O

CH3

O CH3

D2521

F3CO2SHN

F3CO2SHN

N

CH3 O

O CH3

NHSO2CF3

NHSO2CF3

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Asymmetric Synthesis

B2907

B2908

B3398

C1324

C1325 CH3

O (CH3)3C S NH2

(CH3)3C S NH2

CH3

C1327

CH3

NH S

S

O

C1614 CH3

CH3

C0347 CH2 CH

CH3

B Cl

O

S O O

CH3

HO

H

CH3

CH2 CH

N

H

HO

CH2

CH

CH CH3 CH2Ph CH2 N CH2 O

N

N

N

HO

H

. 2H2SO4 . 2H2O

D2240

D2810

O CH2 N CH2 CH2Ph CH3

CH3

OH

2

OH

O

CH3

O

O

O

OH

2

OH

OH

OH

OH

OH

2BF4

D2729

D2730

D2801

OH OH

Br

D2802

D2128

Br

Br

Br

Br

OH

OCH3

OCH3

OH

OCH3

OCH3

Br

Br

CH3 Bu

N Bu

Br

Br

D2129

T1195

T0003

D3444

OH CH3

O

O

O

N O

OH

D3715

OH CH3

CH3

N C CH(C6H5)2

N C CH(C6H5)2

N C CH(C6H5)2

OH O

OH O

T0621

O

O CH3 O

CH3 O

CH3

OH CH3

O

O CH3 O

OH

D2538

N CH2CH2C(CH3)3

CH3 O

CH3

N CH2CH2C(CH3)3

OH

D2535

CH3

N CH2CH2C(CH3)3

D3808

CH3

D2537

CH3

OH

OH CH3

CH3

NH2

CH3

CH3

OH O

N C CH(C6H5)2

N CH2CH2C(CH3)3

O O

H2N

H2N

T1387

OH O

D3809

O

OH

D3716

O

OH

D3445 NH2

CH3

Bu

2

2BF4

Br

Br

Bu

2

D2811 Br

CH3 CH2Ph CH2 N CH2 O

CH3

N

N

D2239

CH3

O CH2 N CH2 CH2Ph CH3

H

. HCl . xH2O

N

D3476

D3475 H

H CH2

. 2HCl

N

2

C0351

H

HO

N

N

CH3

2

C0350

H

H

CH3

C0349 CH2 CH

HO

B Cl

O S O O

C0348

H

CH3

N

N

O

O

O

C2023 C1615

CH3

CH3

HN

OH NH2

C1326

CH3

CH3

O

(CH3)3CO

O

N(CH3)2 PPh2

CH3

(CH3)2N Ph2P

Fe

N(CH3)2 PPh2 Fe

PPh2

D2536

CH3

CH3 (CH3)2N Ph2P

Fe

Fe

Ph2P

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

33

Asymmetric Synthesis

D2176

D2175

D2130

NH2

D2131

D3803

NH2 N H

NH2

NH2

O

N

O

N

B

B

CH3

D3804

D3822

D2774 CH

N N H

D2775

D3185

CH3 CH3

OCH3

Fe PPh2 O

D3186

CH3

OCH3 P(C6H5)2

P(C6H5)2

D2365

D2735

D2702

N H

D2686 O

OH N H

N H

OH

C

N H

O

(CH3)3C

C

O

O

(CH3)3C

HO

OH O

O

OH O

C(CH3)3

O

O

HO

O

O

H0784

H0768

H0862

OH N

H0863

OH

C

N

CH3

HO CH3 O

O

CH3

I0728

I0480

CH3

CH3

CH3

CH3

I0476

CH3CH2 N

OH

HO

CH3

CH3 CH

HN

CH

CH3

O

I0762 CH3

CH3 H

OH

N H

I0761

CH3 O

I0395

HO CH3

C

C(CH3)3

O

CH2OH

NH O

NHCH(CH3)2

CH3 CH

NH

O

O

O

CH3 N

I0567

D2823

I0582 CH3

CH3 O

C

N

CH3

O

O

O

O

N

N

N

O

CH3

CH3 CH3

N

CH3

N O

CH3

NH S

O

M1066

CH3 O

O

T1215 N

CH3 COOH

N

S

. HCl

S

M1070

NH O

O

K0028 CH3

O

CH3

O

M1044

I0575

CH3

NH O

O

O

CH3

CH3

N

C(CH3)3

I0573

CH3

I0451

CH3

CH3

I0594

M0803

M1169

CH3

CH3 O

O

O S

O S

CH3 HO

CH3

CH3 CH3

34

C

N

C(CH3)3

CH3

I0572 CH3

CH3

C

CH3

CH3 CH2SH

CH3OCH2

N O

CH3

N H

CH2OCH3

CH3

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Asymmetric Synthesis

M1161

M1170

M1162

M1401

M1402 O

CH2OCH3

N N H

CH2OCH3

M1097

C H

C H

O

O

M1183

N

N

N

CH2 N

CH3

NH2

OH

OH

P1294

NH2

N

T1491

CH3

P1201 CH3

O N

N

. 2HCl

P0793

O

N

T1490

CH3

P0794

N

M1995

CH2NH

CH3

O

CH2OCH3

N

P1307

NH2

NH2 OH

OH NH O

P1308

P1374

P1375

P1830

N

P1404

N

O

NH CH3 O

N H

CH3

O

OH

P0994

O

C OH

P1241

P1784

Q0076

OH

N H

O

Q0074

N H

O

Q0006

CH2 N

H

HO

OO

Rh

O

R

O

O

Rh

O O O

Rh N

R=

R

O O

H

H

R

O

. 2 CH3

R'

Rh

R

H R'

Rh Rh O O O H R

O

R

O

O F

R=

R'=

N

R=

CH2

F O

. 2 CH3

O

F

C OCH2CH3

O O O

R H

R

O

H R

O

. CH3

O

O C OCH2CH3

F

N F

. 2 CH3

O

O

F

C OCH2CH3

R

O

H R

O

O

Cl O

. 2 CH3

O

Cl

H OO

O O O

R H

R

C OCH2CH3

R

O

R=

N

O

Rh Rh

N

R=

O H

Cl Cl

T0219

Cl Cl Cl

O H

. 2 CH3

O

O

Cl

C OCH2CH3

N H

T0228

O

O

C NH S

HO C

F

O H

. 2 CH3

C OCH2CH3

O R R=

O O O

R

H OO

Rh Rh

N

O H

F

O H

R

H OO

Rh Rh

R

O

O N

R=

O

H

R

O

O

H

H OO

R O

T2659 H

R O

T2637

R O

Rh

N

H R' OO

O

H

OO

Rh O O O

R

. HCl . 2H2O

CH3O

H

O

R

T2661 H

N

2

N

O O O

C OCH2CH3

T2660

R

. H2SO4 . 2H2O

H

H

HO

T2658 R' H

H

O

R

R

T1551 R H

H H

CH3O

N

N

T2054 CH

CH2

N

N

CH3O

HOCH2

CH

CH2OH

T2055

N H

H CH2

HO

N

Q0030

H

CH2 CH

N

N H

Q0010 CH2 CH

CH2 CH

N

N N H

C OH

N H

OH

P0481

OH

O

O

. x CF3CO2H

OH NH

S S

O

CH3

OH NH2

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

35

Asymmetric Synthesis

T0230

T2545 OH

T1380 O

O

CH3

T1381 CH3

NH2

T2223 CH3

Ph

NH2

CH2O Si CH3

S

CH3

CH2

N N

OH

Fe

t

Bu

Ph

H NH SO2

i

iPr

Pr

NH2 CH3

T2578

T2579

CH3

T1499

T1482 OH

CH3

CH3

iPr

T0539 O

OH

OH CH3

S

CH3

CH3

T0541

V0077 O

NH2

NH2

X0049 CH3

CH3 OH

NH2

N H

OH

V0058

CH3

Product No. Product Name A1534 A1535 A1138 A0177 A0179 A2095 A1548 A1699 A2316 A2317 A1337 A1335 A1301 A1521 A0945 A1043 B3296 B3549 B1683 B1689 B2103 B2104 P1371 P1372 B1786 B1754 B1528 B1529 B2165 B2166 B1684 B1685 B1142 B1100 B2230 B2231 B1143 B1144 B2314 B2315

OH

CH3 OH

N H

36

S

CH3

CH3

OH NH2

N H

CH2NH CH3

Unit Size

Acetic Acid (1R,2S)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Ester 1g Acetic Acid (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Ester 1g 5 100mg (R)-(-)-Acetylcarbonyl(η -2,4-cyclopentadien-1-yl)(triphenylphosphine)iron 5g 25g D-Alanine 25g 250g L-Alanine (S)-4-(4-Aminobenzyl)-2-oxazolidinone 1g 5g (R,R)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide 1g (S,S)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide 1g (R)-(+)-2-Amino-2'-hydroxy-1,1'-binaphthyl 100mg (S)-(-)-2-Amino-2'-hydroxy-1,1'-binaphthyl 100mg (R)-(+)-1-Amino-2-(methoxymethyl)pyrrolidine 1g (S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidine 1g 5g (S)-(-)-2-Aminomethyl-1-ethylpyrrolidine 1g 5g (1R,2R)-(-)-2-Amino-1-phenyl-1,3-propanediol Price on request (S)-(+)-2-(Anilinomethyl)pyrrolidine 1g 5g 100mg 1g L-Azetidine-2-carboxylic Acid (+)-Benzotetramisole 200mg 1g (-)-Benzotetramisole 1g N-Benzylcinchonidinium Chloride 10g N-Benzylcinchoninium Chloride 5g (1R,2S)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenyl-1-propanol 1g 5g (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenyl-1-propanol 1g 5g (1R,2S)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Propionate 1g (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Propionate 1g (R)-4-Benzyl-2-oxazolidinone 5g 25g (S)-4-Benzyl-2-oxazolidinone 5g 25g (R)-(+)-N-Benzyl-1-phenylethylamine 5ml 25ml (S)-(-)-N-Benzyl-1-phenylethylamine 5ml 25ml (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone 1g 5g 25g (S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone 1g 5g N-Benzylquinidinium Chloride 5g N-Benzylquininium Chloride 5g (R)-(+)-1,1'-Bi-2-naphthol 5g 25g (S)-(-)-1,1'-Bi-2-naphthol 5g 25g (R)-(-)-1,1'-Binaphthyl-2,2'-diyl Bis(trifluoromethanesulfonate) 1g 5g (S)-(+)-1,1'-Binaphthyl-2,2'-diyl Bis(trifluoromethanesulfonate) 1g 5g (R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate 100mg 1g 5g (S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate 100mg 1g (1R,2R)-N,N '-Bis(2-acetyl-3-oxo-2-butenylidene)-1,2-dimesitylethylenediaminato Cobalt(II) 100mg (1S,2S)-N,N '-Bis(2-acetyl-3-oxo-2-butenylidene)-1,2-dimesitylethylenediaminato Cobalt(II) 100mg

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Asymmetric Synthesis

Product No. Product Name B2090 B2652 B2653 B3449 B1406 B1405 B2704 B1113 B1112 B2048 B1614 B1615 B2409 B2217 B2218 B3035 B3036 B2034 B2035 B1844 B1845 B2219 B2220 D2520 D2521 B2907 B2908 B3398 C1324 C1325 C1326 C1327 C1614 C2023 C1615 C0347 C0348 C0349 C0350 C0351 D3475

(S,S)-1,2-Bis[(tert-butyl)methylphosphino]ethane[η-(2,5-norbornadiene)]rhodium(I) Tetrafluoroborate (1R,2R,4R,5R)-2,5-Bis(3,5-di-tert-butyl-2-hydroxybenzylideneamino)bicyclo[2.2.1]heptane (1S,2S,4S,5S)-2,5-Bis(3,5-di-tert-butyl-2-hydroxybenzylideneamino)bicyclo[2.2.1]heptane (2R,3R)-(-)-2,3-Bis(diphenylphosphino)bicyclo[2.2.1]hept-5-ene (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (2S,3S)-(-)-Bis(diphenylphosphino)butane (2R,3R)-(-)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol (2S,3S)-(+)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane (-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2-methyl-2-phenyl-1,3-dioxolane (1S,2S)-N,N '-Bis[(R)-2-hydroxy-2'-phenyl-1,1'-binaphthyl-3-ylmethylene]1,2-diphenylethylenediaminato Manganese(III) Acetate (R,R)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridine (S,S)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridine (R,R)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane (S,S)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane (R,R)-(+)-Bis(α-methylbenzyl)amine Hydrochloride (S,S)-(-)-Bis(α-methylbenzyl)amine Hydrochloride (1R,2R)-N,N '-Bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]1,2-diphenylethylenediaminato Cobalt(II) (1S,2S)-N,N '-Bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]1,2-diphenylethylenediaminato Cobalt(II) (R,R)-2,6-Bis(4-phenyl-2-oxazolin-2-yl)pyridine (S,S)-2,6-Bis(4-phenyl-2-oxazolin-2-yl)pyridine (R,R)-N,N '-Bis(trifluoromethanesulfonyl)-1,2-diphenylethylenediamine (S,S)-N,N '-Bis(trifluoromethanesulfonyl)-1,2-diphenylethylenediamine (R)-(+)-tert-Butylsulfinamide (S)-(-)-tert-Butylsulfinamide O-tert-Butyl-L-threonine (+)-10,2-Camphorsultam (-)-10,2-Camphorsultam (2R,8aS)-(+)-(Camphorylsulfonyl)oxaziridine (2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine (+)-B-Chlorodiisopinocampheylborane (58% in Hexane, ca. 1.6mol/L) (-)-B-Chlorodiisopinocampheylborane (60% in Heptane, ca. 1.7mol/L) (-)-B-Chlorodiisopinocampheylborane (60% in Hexane, ca. 1.7mol/L) Cinchonidine Cinchonidine Dihydrochloride Cinchonidine Sulfate Cinchonine Cinchonine Hydrochloride Hydrate 6,10-Dibenzyl-N,N '-dimethyl-N,N,N ',N '-tetrakis(4-methylbenzyl)1,4-dioxaspiro[4.5]decane-(2R,3R)-diylbis(methylammonium) Tetrafluoroborate [=(R,R)-TaDiAS-2nd]

D3476

6,10-Dibenzyl-N,N '-dimethyl-N,N,N ',N '-tetrakis(4-methylbenzyl)1,4-dioxaspiro[4.5]decane-(2S,3S)-diylbis(methylammonium) Tetrafluoroborate

D2239 D2240 D2810 D2811 D2729 D2730 D2801 D2802 D2128 D2129 T1195 T0003 D3444 D3445 D3715 D3716 T1387 T0621

(+)-1,4-Di-O-benzyl-D-threitol (-)-1,4-Di-O-benzyl-L-threitol (R)-3,3'-Dibromo-1,1'-bi-2-naphthol (S)-3,3'-Dibromo-1,1'-bi-2-naphthol (R)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol (contains 5% Dichloromethane at maximum) (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol (R)-3,3'-Dibromo-2,2'-dimethoxy-1,1'-binaphthyl (S)-3,3'-Dibromo-2,2'-dimethoxy-1,1'-binaphthyl (1R,2S)-2-(Dibutylamino)-1-phenyl-1-propanol (1S,2R)-2-(Dibutylamino)-1-phenyl-1-propanol Diethyl D-(-)-Tartrate Diethyl L-(+)-Tartrate (11R,12R)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine (11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine (1R,2R)-N,N '-Dihydroxy-N,N '-bis(diphenylacetyl)cyclohexane-1,2-diamine (1S,2S)-N,N '-Dihydroxy-N,N '-bis(diphenylacetyl)cyclohexane-1,2-diamine Diisopropyl D-(-)-Tartrate Diisopropyl L-(+)-Tartrate

[=(S,S)-TaDiAS-2nd]

Unit Size 50mg 100mg

1g 1g 100mg

1g

250mg

1g 500mg 100mg 100mg

100mg 100mg 5g 5g 1g 1g 1g 5g 5g 1g 100mg 5g 5g 1g 1g 5g 5g 100mg

250mg

1g 1g 1g 1g 1g

25g 25g 25g

100mg 1g 250mg 1g 1g 1g 1g 5g 5g 5g 5g 5g 100ml 100ml 100ml 250g 25g 500g 200g 25g

200mg

1g

200mg

1g 1g 1g 5g 1g 1g 5g 1g 1g 5g 5g 250g 500g 1g 1g 100mg 100mg 250g 500g

1g

1g 200mg 200mg 1g 1g 25g 25g 100mg 100mg

25g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

37

Asymmetric Synthesis

Product No. Product Name D3808 D3809 D2537 D2538 D2535 D2536 D2176 D2175 D2130 D2131 D3803 D3804 D3822 D2774 D2775 D3185 D3186 D2365 D2735 D2702 D2686 H0784 H0768 H0862 H0863 I0395 I0728 I0480 I0476 I0761 I0762 I0567 D2823 I0582 I0572 I0451 I0594 I0573 I0575 K0028 T1215 M1044 M1066 M1070 M0803 M1169 M1161 M1170 M1162 M1401 M1402 M1097 M1183 M1995 T1490 T1491 P0794 P0793 P1201 P1294 P1307 P1308 P1374 P1375 P1830 P1404 P0994 P0481

38

(1R,2R)-N,N '-Dimethyl-N,N '-bis(3,3-dimethylbutyl)cyclohexane-1,2-diamine (1S,2S)-N,N '-Dimethyl-N,N '-bis(3,3-dimethylbutyl)cyclohexane-1,2-diamine (R)-N,N-Dimethyl-1-[(S)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine (S)-N,N-Dimethyl-1-[(R)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine (R)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine (S)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (1R,2R)-(+)-1,2-Diphenylethylenediamine (1S,2S)-(-)-1,2-Diphenylethylenediamine (R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (R)-(+)-2-(Diphenylmethyl)pyrrolidine (S)-(-)-2-(Diphenylmethyl)pyrrolidine (S)-1-(Diphenylphosphino)-2-[(S)-4-isopropyloxazolin-2-yl]ferrocene (R)-(+)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl (S)-(-)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl (2R,5R)-2,5-Diphenylpyrrolidine (2S,5S)-2,5-Diphenylpyrrolidine (R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol (+)-Dipivaloyl-D-tartaric Acid (-)-Dipivaloyl-L-tartaric Acid (R)-(-)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine (S)-(+)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine (1R,2R,5R)-(+)-2-Hydroxy-3-pinanone (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone (S)-(-)-Indoline-2-carboxylic Acid β-Isocupreidine (S)-2-Isopropylamino-3-methyl-1-butanol (R)-2-Isopropylamino-2-phenylethanol (4R)-(+)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone (4S)-(-)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone (S,S)-(-)-2,2'-Isopropylidenebis(4-tert-butyl-2-oxazoline) (R,R)-2,2'-Isopropylidenebis(4-phenyl-2-oxazoline) (S,S)-2,2'-Isopropylidenebis(4-phenyl-2-oxazoline) (R)-4-Isopropyl-2-oxazolidinone (S)-4-Isopropyl-2-oxazolidinone (R)-(-)-4-Isopropyl-3-propionyl-2-oxazolidinone (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone (S)-4-Isopropylthiazolidine-2-thione (S)-(+)-Ketopinic Acid Levamisole Hydrochloride (1R,2S,5R)-(-)-Menthyl (S)-p-Toluenesulfinate (1S,2R,5S)-(+)-Menthyl (R)-p-Toluenesulfinate (1S)-(-)-10-Mercaptoisoborneol (4S,5S)-(-)-4-Methoxymethyl-2-methyl-5-phenyl-2-oxazoline (R)-2-(Methoxymethyl)pyrrolidine (S)-2-(Methoxymethyl)pyrrolidine (R)-(+)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde (S)-(-)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (S)-(-)-1-Methyl-2-(1-naphthylaminomethyl)pyrrolidine (S)-(-)-1-Methyl-2-(1-piperidinomethyl)pyrrolidine (S)-2-[(1-Methyl-2-pyrrolidinyl)methyl]isoindoline Dihydrochloride (1R,2S)-(-)-trans-2-Phenyl-1-cyclohexanol (1S,2R)-(+)-trans-2-Phenyl-1-cyclohexanol (R)-(+)-1-Phenylethylamine (S)-(-)-1-Phenylethylamine (R)-(-)-2-Phenylglycinol (S)-(+)-2-Phenylglycinol (R)-(-)-4-Phenyl-2-oxazolidinone (S)-(+)-4-Phenyl-2-oxazolidinone (1R,2S)-1-Phenyl-2-(1-pyrrolidinyl)propan-1-ol (1S,2R)-1-Phenyl-2-(1-pyrrolidinyl)propan-1-ol D-Pipecolic Acid L-Pipecolic Acid D-Proline L-Proline

Unit Size

1g 1g 1g 1g

200mg 100mg 100mg

100mg

1g 1g 1g 5g 1g 1g 1g 1g 1g

5g 1g 1g 100mg 250mg 1g 250mg 1g 5g 1g 5g 1g 1g 1g 10g 5g 1g

1g 1g 1g 500mg 500mg 1g 1g 100mg 100mg 25ml 25ml 5g 5g 5g 5g 1g 1g 5g 1g 5g 25g

1g 1g 100mg 100mg 100mg 100mg 5g 5g 5g 5g 1g 1g 1g 1g 1g 100mg 100mg 5g 5g 5g 25g 5g 5g 5g 5g 5g 1g 5g 25g 5g 5g 1g 5g 1g 25g 25g 5g 5g 1g 5g 25g 25g 5g 1g 1g 5g 5g 1g 5g 1g 1g 1g 5g 5g 1g 1g 500ml 500ml 25g 25g 25g 25g 5g 5g 25g 5g 25g 250g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Asymmetric Synthesis

Product No. Product Name P1241 P1784 Q0076 Q0074 Q0006 Q0010 Q0030 T2054 T2055 T1551 T2658 T2659 T2660 T2661 T2637 T0219 T0228 T0230 T2545 T1380 T1381 T2223 T2578 T2579 T1499 T1482 T0539 T0541 V0077 V0058 X0049

(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine (S)-5-(Pyrrolidin-2-yl)-1H-tetrazole Quincoridine Quincorine Quinidine Quinidine Sulfate Dihydrate Quinine Hydrochloride Dihydrate Tetrakis[N-phthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-phthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-phthaloyl-(S)-phenylalaninato]dirhodium Ethyl Acetate Adduct Tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-tetrafluorophthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct N-(2-Thiophenesulfonyl)-L-prolinamide Trifluoroacetate L-Thioproline D-(+)-Threonine L-(-)-Threonine (R)-(p-Toluenesulfinyl)ferrocene (R)-(+)-1-(p-Tolyl)ethylamine (S)-(-)-1-(p-Tolyl)ethylamine Nα-(2,4,6-Triisopropylbenzenesulfonyl)-O-(tert-butyldiphenylsilyl)-π-methyl-L-histidinol (1R,4R,5R)-4,7,7-Trimethyl-6-thiabicyclo[3.2.1]octane (1S,4S,5S)-4,7,7-Trimethyl-6-thiabicyclo[3.2.1]octane (R)-(+)-1,1,2-Triphenyl-1,2-ethanediol (S)-(-)-1,1,2-Triphenyl-1,2-ethanediol D-Tryptophan L-Tryptophan D-Valinol L-Valinol (S)-(+)-2-(2,6-Xylidinomethyl)pyrrolidine

Unit Size 1g 5g 100mg 500mg 100mg 1g 100mg 1g 5g 25g 5g 25g 25g 100mg 100mg 100mg 50mg 100mg 50mg 100mg 100mg 25g 500g 25g 500g 25g 500g 1g 5g 1ml 5ml 1ml 5ml 100mg 1g 5g 1g 5g 1g 5g 1g 5g 25g 25g 1g 5g 5g 25g 1g 5g

References 1) T. Yamada, T. Nagata, Y. Ohtsuka, T. Ikeno, T. Mukaiyama, 2003, , 843; T. Yamada, T. Nagata, K. D. Sugi, K. Yorozu, T. Ikeno, Y. Ohtsuka, D. Miyazaki, T. Mukaiyama, 2003, , 4485.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

39

Chiral Building Blocks

Chiral Building Blocks

A1299

A1334 O

O CH3

Carboxylic Acids

A1450

OH

OH

CH3

CH3 NH2

A1043

B1121 O

B1757

B3177

N

OH Br

N

O

O

OH

C2109

NH2

CH3

O

Cl

OH Cl

C1954

D2636

O

O

C OH

C OH

O CH3

O

O

HO

CH3

D0083

CH3

OH CH3

OH O HO

OH Cl

O OH

O

CH3

. HCl

C1655

O

CH3

C1953

HO

O OH

Cl

Cl

O

D1386

OH Br

C1371 CH3

O

CH3

Cl

C

O

C OH

C OC(CH3)3

C1200

OH

O CH3

C1612

Cl

C1373

NH

C OC(CH3)3

CH3 OH

CH3

O

C1372

O

Cl

B1756

O

C OH

C1365

CH3

NH2

C OH

O

C1377

NH2

F

O CH3

C OH

O

B3178

F

O

C OH

O

NH C

NH

O

C OH OH

OH OH

Cl CH3

B1120 O

O H2N

S

OH

NH2

A1438

CH3

A1689

O OH

NH2

OH

A1688

O

. HBr

O

O

O S CH3

A0826

O

CH3

CH3

O

A1377

Br

O

A1620

C OH

C OH

O

O

D1573

OH O

CH3

O O

D1377

D3490

O CH3

O

O

HO

O OH

O

O

CH3

H2N

O OH

NH2

. 2HCl

H2N

OH NH2

O

O

. HCl

H2N

OH NH2

. HCl

HOOC

O C

OCH3

HOOC

O C

OCH3

O

O

40

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

D3491

D1398 D3826

D1354 D3492

O

O

O HOOC

O C

OCH3

HOOC

O C

OCH3

D2539

O

Ph

O

HO

OH . H2O O

O

HO O

D1417

O

(CH3)3C

HO O

HN

O

L0026

O O N

OH NH2

L0144

I0395

O

CH3

HO

NH

O

OH

NH2

C Cl

p-Tol

O

H0933

HO

O OH

O

H C O OH

O

H0758

O

HO

p-Tol

O

O

O

H0937

O

O

O O

HO

OH

O

G0265

p-Tol

O

HO

C(CH3)3

O

O

F0721 O

O

p-Tol

O OH

O

C(CH3)3

O

O

HO

OH

O

D1387 O

O O

Ph

O

C OH

NH2

O

D2686 O

OH

OH . H2O

Ph

O

CH3

O

O

(CH3)3C

CH3

O Ph

O

D2702

D3677

O

M0021

OH

N H

OH

O

OH

M0022

M0662 O

O CH3

CH3

OH CH3

O

O

OH

HO

OLi

M0661

M1366

OH

M1021 CH3

C OH

OH

M0830

M0829 O

CH3

C OH

M1229

HO

M1226 O

O OH

N0654

M1227

O

HO

HO

N0678 O

C OH

C OH

HO

O OH

O

CH3

O0370

O

CH3O

O0281

OH O

CH3

H

N H H

N H

P1288

O

O

C OH

P1168

O

O

C OH

P1219

O

O

NH2

OH

OH

OH NH2

CH3

C OH

P0936 O

O

O

O

CH3

O0276

O

P0820

C OH

O OH

O

CH3

N H

CH3O

C1461

O OH

CH3

O

C OH

O

CH3O

O

CH3O OH

CH3O

M1228

C OH

OH O

O

O HO

HO

OH O

OH

HO

O

C OH

O HO

OH O

OH

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

41

Chiral Building Blocks

P1830

P1404

Q0009

T0026

T0025

O HO C OH O N H

O

C OH

N H

OH

C OH HO

OH O

OH

OH

O

HO

O

HO

OH

OH O

OH

OH

T1740

T1741

T1515

T0219 O

O O O

O

C OH

O

C OH

C OH

T1900 O

HO C

NH

CF3

NH

OH

HO CH3

S

T1901 O CF3

OH

HO CH3

Product No. Product Name A1299 A1334 A1620 A1450 A1377 A0826 A1688 A1689 A1438 A1043 B1121 B1120 B1756 B1757 B3177 B3178 C1612 C2109 C1377 C1365 C1372 C1371 C1655 C1373 C1200 C1953 C1954 D2636 D1386 D0083 D1573 D1377 D3490 D3491 D1398 D3826 D1354 D3492 D2539 D3677

42

(S)-(-)-2-Acetoxypropionic Acid (S)-(-)-3-(Acetylthio)isobutyric Acid (R)-3-(Acetylthio)isobutyryl Chloride (S)-(+)-2-Amino-4-bromobutyric Acid Hydrobromide (R)-(-)-2-Aminobutyric Acid (S)-(+)-2-Aminobutyric Acid (1R,2R)-2-Aminocyclohexanecarboxylic Acid (1S,2S)-2-Aminocyclohexanecarboxylic Acid (S)-(-)-4-Amino-2-hydroxybutyric Acid L-Azetidine-2-carboxylic Acid [Antagonist of L-Proline] (+)-cis-2-Benzamidocyclohexanecarboxylic Acid (-)-cis-2-Benzamidocyclohexanecarboxylic Acid (R)-(+)-2-Bromopropionic Acid (S)-(-)-2-Bromopropionic Acid (2S,4R)-1-(tert-Butoxycarbonyl)-4-fluoro-2-pyrrolidinecarboxylic Acid (2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoro-2-pyrrolidinecarboxylic Acid 3-Chloro-L-alanine Hydrochloride (R)-2-Chlorobutyric Acid (S)-2-Chlorobutyric Acid (S)-2-Chloro-3-methylbutyric Acid (2S,3S)-2-Chloro-3-methylvaleric Acid (S)-2-Chloro-4-methylvaleric Acid (R)-(+)-2-Chloropropionic Acid (S)-(-)-2-Chloropropionic Acid D-(-)-Citramalic Acid (1R,2R)-1,2-Cyclohexanedicarboxylic Acid (1S,2S)-1,2-Cyclohexanedicarboxylic Acid (+)-Diacetyl-D-tartaric Acid (-)-Diacetyl-L-tartaric Acid (S)-(+)-2,4-Diaminobutyric Acid Dihydrochloride (R)-(-)-2,3-Diaminopropionic Acid Hydrochloride (S)-(+)-2,3-Diaminopropionic Acid Hydrochloride (+)-Di-p-anisoyl-D-tartaric Acid (-)-Di-p-anisoyl-L-tartaric Acid (+)-Dibenzoyl-D-tartaric Acid Monohydrate (+)-Dibenzoyl-D-tartaric Acid (-)-Dibenzoyl-L-tartaric Acid Monohydrate (-)-Dibenzoyl-L-tartaric Acid D-(-)-2-(2,5-Dihydrophenyl)glycine (S)-(+)-2,2-Dimethylcyclopropanecarboxylic Acid

Unit Size 1g

5g

1g 1g 1g

5g 100mg

5g 5g 200mg 200mg 1g 1g 1g 1g 1g 1g 1g 5g 1g 5g

100mg 100mg

25g 25g 25g 25g 5g 1g

25g 25ml 25g 5g 5g 5g 100mg 100mg 25g 1g 5g 5g 25g 25g 1g 1g 5g 5g 5g 5g 5g 5g 25g 25g 1g 1g 1g 5g 25g 1g 1g 1g 25g 25g 500g 250g 500g 250g 25g 5g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

Product No. Product Name D2702 D2686 D1417 D1387 F0721 G0265 H0937 H0758 H0933 I0395 L0026 L0144 M0021 M0022 M0662 M0661 M1366 M1021 M0830 M0829 M1228 M1229 M1226 M1227 C1461 N0654 N0678 O0370 O0281 O0276 P0820 P1288 P1168 P1219 P0936 P1830 P1404 Q0009 T0026 T0025 T1740 T1741 T1515 T0219 T1900 T1901

Unit Size

(+)-Dipivaloyl-D-tartaric Acid (-)-Dipivaloyl-L-tartaric Acid (+)-Di-p-toluoyl-D-tartaric Acid (-)-Di-p-toluoyl-L-tartaric Acid O-Formyl-D-mandeloyl Chloride (S)-(-)-2-Guanidinoglutaric Acid (R)-(+)-2-(4-Hydroxyphenoxy)propionic Acid D-(-)-2-(4-Hydroxyphenyl)glycine (S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid (S)-(-)-Indoline-2-carboxylic Acid L-Leucic Acid Lithium L-Lactate D-(+)-Malic Acid L-(-)-Malic Acid D-(-)-Mandelic Acid L-(+)-Mandelic Acid (R)-(-)-2-Methoxy-2-(1-naphthyl)propionic Acid (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic Acid (R)-(-)-α-Methoxyphenylacetic Acid (S)-(+)-α-Methoxyphenylacetic Acid (R)-(-)-2-Methylglutaric Acid (S)-(+)-2-Methylglutaric Acid (R)-(+)-Methylsuccinic Acid (S)-(-)-Methylsuccinic Acid 1-Monomethyl (R)-(+)-3-Methylsuccinate (R)-(-)-Nipecotic Acid (S)-(+)-Nipecotic Acid (2S,3aS,7aS)-Octahydro-1H-indole-2-carboxylic Acid (R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid (S)-(+)-5-Oxotetrahydrofuran-2-carboxylic Acid D-2-Phenylglycine L-2-Phenylglycine (S)-(-)-3-Phenyllactic Acid (R)-(-)-2-Phenylpropionic Acid (S)-(+)-Phenylsuccinic Acid D-Pipecolic Acid L-Pipecolic Acid D-(-)-Quinic Acid D-(-)-Tartaric Acid L-(+)-Tartaric Acid (R)-(+)-Tetrahydrofuran-2-carboxylic Acid (S)-(-)-Tetrahydrofuran-2-carboxylic Acid (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid L-Thioproline (R)-3,3,3-Trifluoro-2-hydroxy-2-methylpropionic Acid (S)-3,3,3-Trifluoro-2-hydroxy-2-methylpropionic Acid

A2124

1g 5g 25g 25g

25g 1g 1g 5g 25g 25g 25g

5g 5g 1g 1g 1g 1g 1g 25g 25g 1g 1g 5g 1g

A1383 O

C CH3

O

O

O

C CH3 CH3

Esters

O

L0161

M1354 O

O

O

M1355

O

O

OH

O

O N

O OH

OCH3 CH3

T1671

CH3O C

O

S

O

B1755 O

O O

OH

25g 25g 5g 5g 5g 25g

1g

O

CH3

25g 1g 1g

100mg

A1101

O

5g 25g 250g 250g 25g 100mg 5g 500g 5g 5g 25g 25g 25g 500g 500g 250g 100mg 500g 5g 5g 5g 5g 25g 25g 1g 5g 5g 5g 5g 5g 500g 500g 5g 5g 1g 25g 5g 25g 500g 500g 25g 25g 25g 500g 1g 1g

O

CH3

C O C CH3 CH3 CH3

CH3

OH

O

O

O O

OH

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

43

Chiral Building Blocks

T0005

D3898

OH

OH

O

CH3(CH2)3O

O(CH2)3CH3 O

M1351

T1195

O

CH3

T1387

CH3

O O

OH

O

CH3

O O

OH

T0621

CH3

OH

O

O

O O

CH3

CH3

O

CH3

OH CH3

O

CH3 O

M1343

OCH3 O

CH3O

OCH3 O

OH

T1659 OH

OH OCH3

O

OH

O

O OH

C1634

CH3

O

O

O

CH3 CH3

OH

CH3

O

HO

O Br

O CH3

OCH3 CH3

OCH3 Cl

H0956 O

O OCH3

HO

CH3

CH3

HO

M1350

P0011 O

OCH3 OH

OCH3

OCH3 CH3

O

CH3

C1633

H0702

OCH3 OH

SO3 CH3

B2140

OCH3

CH3

O CH3

N H

M1349 O

OCH3

O

O

L0163

CH3

C OCH2CH3

O O O

L0136

O

H0703

OCH3

CH3

T1241

C OCH2CH3

CH3

D2562

Cl

44

O

CH3O C

CH3

OH

O

Br

O

OCH2CH3

N

O

CH3

O

CH3

OCH3 O

L0162

N0679

B2139

O

CH3

CH3CH2 O

N H

L0115

O

OCH3 O

CH3O

CH3

OH

H0904

OCH2CH3

N0655

CH3

OH

O

E0450

N

O O

CH3

OCH3

CH3CH2 O

M1273

O

M1232

O OCH3

O

CH3 CH3

O

CH3O

OH

M1344

CH3O

O

O

E0469

O

CH3O

CH3

CH3O

CH3

T0006

O

O

OH

C OCH3

O

O

M1231

O

O

O CH3O

CH3

O

C OCH3 CH3O C

CH3O C

CH3

M1230

O OH

O

O

CH3

M1347

O

O

I0447

OH

CH3 O

OH

O

CH3

O

I0474

CH3

O CH3 O

OH

O

CH3

OH

O OH

OH

O

O

OC(CH3)3 O

T0003

O

(CH3)3CO

OH

M1348

CH3 OCH3

OH

OH

CH3 O

O

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

P1189

R0063 O

O

CH3O C

C OCH3 O

HO O

O

O

CH3

OH

OH

Product No. Product Name A2124 A1101 A1383 L0161 M1354 M1355 B1755 T1671 T0005 D3898 M1351 M1348 T1195 T0003 T1387 T0621 I0474 I0447 M1347 M1343 M1230 M1231 M1232 T1659 T0006 E0469 E0450 L0162 M1344 M1273 N0655 N0679 T1241 H0904 L0115 B2139 B2140 C1633 C1634 D2562 H0703 H0702 H0956 L0136 L0163 M1349 M1350 P0011 P1189 R0063

(+)-O-Acetyl-D-malic Anhydride (-)-O-Acetyl-L-malic Anhydride (R)-(+)-3-(Acetylthio)isobutyric Acid Methyl Ester Benzyl (S)-(-)-Lactate Benzyl D-(-)-Mandelate Benzyl L-(+)-Mandelate (S)-(-)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine Dibenzyl L-Tartrate Dibutyl L-(+)-Tartrate Di-tert-butyl L-(+)-Tartrate Diethyl D-(+)-Malate Diethyl L-(-)-Malate Diethyl D-(-)-Tartrate Diethyl L-(+)-Tartrate Diisopropyl D-(-)-Tartrate Diisopropyl L-(+)-Tartrate Dimethyl (+)-2,3-O-Isopropylidene-D-tartrate Dimethyl (-)-2,3-O-Isopropylidene-L-tartrate Dimethyl D-(+)-Malate Dimethyl L-(-)-Malate Dimethyl (S)-(+)-2-Methylglutarate Dimethyl (R)-(+)-Methylsuccinate Dimethyl (S)-(-)-Methylsuccinate Dimethyl D-(-)-Tartrate Dimethyl L-(+)-Tartrate Ethyl (R)-(+)-1-Ethyl-2-pyrrolidinecarboxylate Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylate Ethyl L-(-)-Lactate Ethyl D-(-)-Mandelate Ethyl L-(+)-Mandelate Ethyl (R)-(-)-Nipecotate Ethyl (S)-(+)-Nipecotate Ethyl L-(-)-O-Tosyllactate (R)-2-Hydroxy-4-phenylbutyric Acid Ethyl Ester L-(-)-Lactide Methyl (R)-(+)-3-Bromoisobutyrate Methyl (S)-(-)-3-Bromoisobutyrate Methyl (R)-(+)-2-Chloropropionate Methyl (S)-(-)-2-Chloropropionate Methyl (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxylate Methyl (R)-(-)-3-Hydroxyisobutyrate Methyl (S)-(+)-3-Hydroxyisobutyrate Methyl (R)-(+)-2-(4-Hydroxyphenoxy)propionate Methyl D-(+)-Lactate Methyl L-(-)-Lactate Methyl D-(-)-Mandelate Methyl L-(+)-Mandelate D-(-)-Pantolactone (2R,3R)-2,3-O-(1-Phenylethylidene)-L-tartaric Acid Dimethyl Ester D-(+)-Ribono-1,4-lactone

Unit Size 1g 5g

1g

5g 5g 5g 5g 25g 5g 5g 25g 25g 25g 25g 5g 5g 5g

5g 5g 1g 1g 25g 5g 5g 5g 5g 1g 25g 1g 1g

5g 5g 5g 5g 25g 1g 1g 25g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 25g 25ml 25g 25g 25g 25g 25g 500g 1g 25g 25g 250g 500g 250g 500g 5g 25g 25g 25g 5g 5g 25g 25g 25g 5g 5g 500g 25g 25g 25g 25g 25g 5g 250g 5g 5g 5g 5g 25g 25g 25g 25g 25g 500g 5g 5g 500g 5g 5g

45

Chiral Building Blocks

A1169

Amides

A1170

A1342

O NH C CH3

CH3

H NH2

N

. HCl

NH2

D3676

O

H

H H H

O O C CH3

NH

D1539

CH3 CH3

CH3

C NH C CH3 CH3

NH

CH3 C

Si

CH3 CH3

O

CH3

CH3

CO2H

OH

H N

CH2

O

O

OH

CH2

N H

NH

H

E0468

Si O H 3C CH3

O

B1776

NH2

CH2CH3

(CH3)3C

N H

B3410

O

CH3

O NH C CH3 N H

A2252

A1124

O

E0452

H1241

H0867

CH3 O

CH3 N C NH2

O

C NH2

N

CH2CH3

O

L0167

T1702 O

CH3

C NH2

HOCH2

CH2CH3

T1369 OH

H N

OH O

OH

O

HOCH2

O

O

NH C CF3

NH C CF3

. HCl

N H

N H

Unit Size

(3R)-(+)-3-Acetamidopyrrolidine (3S)-(-)-3-Acetamidopyrrolidine (3R,4R)-4-Acetoxy-3-[(R)-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone (S)-2-Aminobutyramide Hydrochloride (R)-(+)-2-Aminomethyl-1-ethylpyrrolidine (S)-N-tert-Butyldecahydroisoquinoline-3-carboxamide (3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone (+)-N,N '-Diallyl-L-tartardiamide (S)-(+)-2,2-Dimethylcyclopropanecarboxamide (R)-(+)-1-Ethyl-2-pyrrolidinecarboxamide (S)-(-)-1-Ethyl-2-pyrrolidinecarboxamide (R)-5-(Hydroxymethyl)-2-pyrrolidinone (S)-5-(Hydroxymethyl)-2-pyrrolidinone (R)-(+)-Lactamide (2R,3R)-Tartranilic Acid [for optical resolution] (3R)-(+)-3-(Trifluoroacetamido)pyrrolidine Hydrochloride (3S)-(-)-3-(Trifluoroacetamido)pyrrolidine Hydrochloride

I0468

I0469

O

Isocyanates

46

O

. HCl

Product No. Product Name A1169 A1170 A1124 A2252 A1342 B3410 B1776 D1539 D3676 E0468 E0452 H1241 H0867 L0167 T1702 T1369 T1366

N H

T1366

O

NH2 OH

N H

CH3

O NCO

5g 1g 1g 1g 1g 5g 1g 1g 1g

I0471 O

O

O

5g 5g 1g 5g

CH3

5g 5g 25g 25g 5g 25g 1g 25g 25g 5g 5g 5g 5g 25g 5g 25g 25g

CH3S

CH3 O OCH3

NCO

CH3

OCH3 NCO

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

I0334

I0335 CH3

I0473 CH3

NCO

I0466

NCO

I0467

O OCH3

CH3

OCH3

I0465

I0336

O OCH3 NCO

CH3

NCO

CH3

NCO

NCO

OCH3 NCO

Product No. Product Name I0468 I0469 I0471 I0334 I0335 I0473 I0466 I0467 I0472 I0465 I0336 I0398

OCH3 CH3

I0398

O CH3

CH3

NCO

NCO

I0472

O

CH3 O

tBu

Unit Size

Diethyl (S)-(-)-2-Isocyanatoglutarate (S)-(-)-2-Isocyanato-4-(methylthio)butyric Acid Methyl Ester (2S,3S)-2-Isocyanato-3-methylvaleric Acid Methyl Ester (R)-(+)-α-Methylbenzyl Isocyanate (S)-(-)-α-Methylbenzyl Isocyanate Methyl (S)-(+)-2-Isocyanato-3-tert-butoxypropionate Methyl (S)-(-)-2-Isocyanato-3-methylbutyrate Methyl (S)-(-)-2-Isocyanato-4-methylvalerate Methyl (S)-2-Isocyanato-3-phenylpropionate Methyl (S)-(-)-2-Isocyanatopropionate (R)-(-)-1-(1-Naphthyl)ethyl Isocyanate (S)-(+)-1-(1-Naphthyl)ethyl Isocyanate

A0972

1g 1g 1g

5g 5g 5g 25g 5g 1g 5g 25g 5g 5g 5g 5g

5g 1g 1g 5g 1g 1g 1g

A0973

A1230 NH2

CH3

Amino Alcohols

A1231

OH

CH3

NH2

OH NH2 OH

A2306

A1623

A1624

A2307

NH2 OH OH

OH

NH2

A1017

A1521

A1085

OH

D2129

I0462

CH3 Bu

N Bu

OH

I0476

CH3

OH

N Bu

OH

NHCH2

L0137

CH3

CH3 Bu

OH NH2

NH2

NH2

CH2OH

CH3

OH

OH

NH2

D2128

B1119

OH CH3

O2N

NH2

NH2

A2002

OH

OH

OH

NH2

NH2

OH CH3

NH

CH3

OH CH3

NH2

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

47

Chiral Building Blocks

L0160

M0929

N0608

N0631

P1289

CH3 (CH3)3C

HO

CH3S

OH

CH3

NH2

OH

HO

P1028

P1294

P1274

NH2 OH

P1087

NH2 OH

OH N H

NH2

T1537

V0077

NH2

CH2OH

CH3

CH3

OH

CH3

OH NH2

NH2

Product No. Product Name

Unit Size

(R)-(-)-2-Amino-1-butanol (S)-(+)-2-Amino-1-butanol (1R,2S)-(-)-2-Amino-1,2-diphenylethanol (1S,2R)-(+)-2-Amino-1,2-diphenylethanol (1R,2R)-(-)-1-Amino-2-indanol (1R,2S)-(+)-1-Amino-2-indanol (1S,2R)-(-)-1-Amino-2-indanol (1S,2S)-(+)-1-Amino-2-indanol D-(-)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol (1R,2R)-(-)-2-Amino-1-phenyl-1,3-propanediol (R)-(-)-2-Amino-1-propanol (S)-(+)-2-Amino-1-propanol (+)-cis-2-Benzylaminocyclohexanemethanol (1R,2S)-2-(Dibutylamino)-1-phenyl-1-propanol (1S,2R)-2-(Dibutylamino)-1-phenyl-1-propanol L-Isoleucinol (R)-2-Isopropylamino-2-phenylethanol L-(+)-Leucinol L-tert-Leucinol L-(-)-Methioninol (1R,2S)-(-)-Norephedrine (1S,2R)-(+)-Norephedrine D-Phenylalaninol L-Phenylalaninol (R)-(-)-2-Phenylglycinol (S)-(+)-2-Phenylglycinol D-Prolinol L-Prolinol L-(-)-Tryptophanol D-Valinol L-Valinol

B1953

-Protected Amino Alcohols

5ml 1ml 5ml 1g 5g 1g 5g 1g 5g 1g 5g 1g 5g 1g 5g 25g 500g Price on request 5ml 25ml 1ml 5ml 25ml 1g 5g 1g 5g 1g 5g 1g 5g 5g 25g 5ml 25ml 1g 5g 100mg 1g 25g 25g 5g 25g 5g 25g 5g 25g 5g 25g 1g 5g 25g 5g 25g 1g 1g 5g 5g 25g

B2174

CH3

48

N H

CH2OH

V0058 CH3

OH

A0972 A0973 A1230 A1231 A2306 A1623 A1624 A2307 A1017 A1521 A2002 A1085 B1119 D2128 D2129 I0462 I0476 L0137 L0160 M0929 N0608 N0631 P1289 P1028 P1201 P1294 P1274 P1087 T1537 V0077 V0058

OH NH2

P1201

N H

NH2

NH2

NH2

B2123 OH

OH OC(CH3)3

HN O

N

OC(CH3)3 O

OH N

OC(CH3)3 O

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

B1966

B2604

B3270

OH HN

B3272

B3076

OH

OC(CH3)3

HN

OH

OC(CH3)3

O

OH

OC(CH3)3

HN

O

O O

B3077

C1609

O

OC(CH3)3

O

C1610

OH

OH

OH

N

HN

HN

O

O O

O

OC(CH3)3

Product No. Product Name

Unit Size

N-(tert-Butoxycarbonyl)-L-alaninol (R)-1-(tert-Butoxycarbonyl)-2-azetidinemethanol (S)-1-(tert-Butoxycarbonyl)-2-azetidinemethanol N-(tert-Butoxycarbonyl)-D-phenylalaninol N-(tert-Butoxycarbonyl)-L-phenylalaninol N-(tert-Butoxycarbonyl)-D-2-phenylglycinol N-(tert-Butoxycarbonyl)-L-2-phenylglycinol N-(tert-Butoxycarbonyl)-D-prolinol N-(tert-Butoxycarbonyl)-L-prolinol N-Carbobenzoxy-D-phenylalaninol N-Carbobenzoxy-L-phenylalaninol

B1953 B2174 B2123 B1966 B2604 B3270 B3272 B3076 B3077 C1609 C1610

OH

N

OC(CH3)3

HN

1g 100mg 100mg 1g

5g 1g 1g 5g 5g 5g 5g 5g 25g 5g 5g

1g 1g 1g 5g 1g 1g

A2049

A1979

A1980

OH H2N

N

Simple Alcohols

OH

H2N

OH

OH

C CH3

OH

O

A0974

A0975

H1200

B2899

HO CH3

H2N

H2N

O

N

OH

B2901

CH2OH

CH3

OH

B2900

B2902

O

OH

CH2

OH

OH

B2141

OH

B2142

B1532 OH

OH O

OH O

OH

B1533

O

OH N

OH

OH

OH

B1159

O

OH

CH2

B1160

B1161

B1343

OH OH N CH2

CH3

OH

CH3

OH

OH

OH OH

CH3

CH3 OH

CH3

CH3

OH

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

49

Chiral Building Blocks

B2404

B0926

B0925

B3054

B3055 OH

HO

OH

CH3

CH3

OH

CH3

B2909

(CH3)3CHN

B2910

CH3

HC C

D1589

O

O

NC

CH3

H0950

CH3

O

CH3

H0951

O

O

M1788

N CH3

OH

OH

50

CH3

O

OH

O OCH3

O OCH3

CH3

N0784

N0785 OH

OH

CH3 O

CH3

O0235

OH CH3

CH3

O

O0144

OH CH3

CH3

HO CH3

O0145

CH3

O CH3

H0704

OH OCH3

M1374

CH3

OH

T1716

CH3

O

Cl

OH

O0293

O

OH

M1938

N

CH3

CH3

OH

H0705

OH

OH

OH

CH3

HO

OH

M1937

OH CH3

OH

O

O

OH

CH3

H0969

H0887

M1483

CH3O O

CH3

O O

OH O

O

M1790

CH3O

CH3

Cl

HO

OH

O

O

O

H0939

OH

OH

H1032

CH3

O OH

O

OH

OH

O

O

C1717

OH

H0975

OH O

O

HO

H1029

OH

OH

Cl

OH

C1474

OH

SH

OH

CH3

D2239

C1733

OH HS

O

O

CH3

OH

E0455

OH

CH3

O

OH

OH

D2240

N

C O C CH3

Cl

HC C

OH

CH3

C O C CH3

M0967

CH3

OH

O

N OH

OH

B1987

OH

CH3

CH3

CH3

P1411

C OH

CH

CH3

CH3 OH

OH

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

P1412

P0744

CH3

P0743

CH3 OH

T1491

OH

OH CH3

CH3

OH

T1490

CH3

CH3

OH

P1150

P1151 OH

HO

P0795 OH

HO

P0796 CH3

P1417 CH3

OH

OH

OH OH CH3

P1780

P1152

P1129

CH3

OH

OH

P1140

OH

OH OH

S0038

P1667 OH

CH3

OH

CH3

P1608

N H

T2359

N H

T2360

T1499

O C OH

OH

OH

OH

OH

. HCl

N H

HO

OH

OH OH

T1482 OH

OH

Product No. Product Name A2049 A1979 A1980 A0974 A0975 H1200 B2899 B2900 B2901 B2902 B2141 B2142 B1532 B1533 B1159 B1160 B1161 B1343 B2404 B0926 B0925 B3054 B3055 B1987

(R)-1-Acetyl-3-pyrrolidinol (R)-3-Amino-1,2-propanediol (S)-3-Amino-1,2-propanediol (R)-(-)-1-Amino-2-propanol (S)-(+)-1-Amino-2-propanol (3R,4R)-1-Benzyl-4-hydroxy-3-pyrrolidinemethanol (R)-4-Benzyloxy-1,2-butanediol (S)-4-Benzyloxy-1,2-butanediol (R)-4-Benzyloxy-1,3-butanediol (S)-4-Benzyloxy-1,3-butanediol (R)-(+)-3-Benzyloxy-1,2-propanediol (S)-(-)-3-Benzyloxy-1,2-propanediol (R)-1-Benzyl-3-pyrrolidinol (S)-1-Benzyl-3-pyrrolidinol (R)-(-)-1,3-Butanediol (S)-(+)-1,3-Butanediol (R,R)-(-)-2,3-Butanediol (S,S)-(+)-2,3-Butanediol (S)-1,2,4-Butanetriol (R)-(-)-2-Butanol (S)-(+)-2-Butanol (R)-1-(tert-Butoxycarbonyl)-3-pyrrolidinol (S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinol (S)-(-)-3-tert-Butylamino-1,2-propanediol

Unit Size

1g

1g 1g 5g 1g 200mg 200mg

100mg 100mg 1g 5g 1g 1g 1g 100mg 5g 1ml 1ml 1g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

1g 5g 5g 25g 5g 200mg 1g 1g 1g 1g 1g 1g 5g 25g 5g 5g 5g 1g 25g 5ml 5ml 5g 5g 5g

51

Chiral Building Blocks

Product No. Product Name B2909 B2910 M0967 D2239 D2240 D1589 E0455 C1733 C1717 C1474 H1029 H0975 H1032 H0969 H0950 H0951 H0939 H0887 T1716 M1788 M1790 M1483 H0705 H0704 M1937 M1938 M1374 N0784 N0785 O0293 O0145 O0144 O0235 P1411 P1412 P0744 P0743 T1490 T1491 P1150 P1151 P0795 P0796 P1417 P1780 P1152 P1129 P1608 P1667 P1140 S0038 T2359 T2360 T1499 T1482

Unit Size

(R)-(+)-3-Butyn-2-ol (S)-(-)-3-Butyn-2-ol (R)-(-)-3-Chloro-1,2-propanediol (+)-1,4-Di-O-benzyl-D-threitol (-)-1,4-Di-O-benzyl-L-threitol L-Dithiothreitol D-Erythronolactone Ethyl (R)-4-Chloro-3-hydroxybutyrate Ethyl (S)-4-Chloro-3-hydroxybutyrate Ethyl (R)-(-)-4-Cyano-3-hydroxybutyrate Ethyl (R)-(-)-3-Hydroxybutyrate Ethyl (S)-(+)-3-Hydroxybutyrate (2R,5R)-2,5-Hexanediol (2S,5S)-2,5-Hexanediol (R)-(+)-α-Hydroxy-γ-butyrolactone (S)-(-)-α-Hydroxy-γ-butyrolactone (S)-3-Hydroxy-γ-butyrolactone (S)-(+)-3-Hydroxy-2,2-dimethylcyclohexanone (S)-3-Hydroxytetrahydrofuran (R)-4-(4-Methoxybenzyloxy)-1,2-butanediol (S)-4-(4-Methoxybenzyloxy)-1,3-butanediol Methyl (R)-4-Chloro-3-hydroxybutyrate Methyl (R)-(-)-3-Hydroxybutyrate Methyl (S)-(+)-3-Hydroxybutyrate (R)-1-Methyl-3-pyrrolidinol (S)-1-Methyl-3-pyrrolidinol D-Mevalonolactone (R)-(+)-1-(2-Naphthyl)ethanol (S)-(-)-1-(2-Naphthyl)ethanol (3R,6R)-3,6-Octanediol (R)-(-)-2-Octanol (S)-(+)-2-Octanol (S)-1-Octyn-3-ol [ω Side-Chain Unit for PG Synthesis] (2R,4R)-(-)-2,4-Pentanediol (2S,4S)-(+)-2,4-Pentanediol (R)-(-)-2-Pentanol (S)-(+)-2-Pentanol (1R,2S)-(-)-trans-2-Phenyl-1-cyclohexanol (1S,2R)-(+)-trans-2-Phenyl-1-cyclohexanol (R)-(-)-1-Phenylethane-1,2-diol (S)-(+)-1-Phenylethane-1,2-diol (R)-(+)-1-Phenylethyl Alcohol (S)-(-)-1-Phenylethyl Alcohol (R)-1-Phenyl-2-propanol (S)-1-Phenyl-2-propanol (R)-(-)-1,2-Propanediol (S)-(+)-1,2-Propanediol (R)-3-Pyrrolidinol (S)-3-Pyrrolidinol (R)-(-)-3-Pyrrolidinol Hydrochloride Shikimic Acid (R)-(-)-1,2,3,4-Tetrahydro-1-naphthol (S)-(+)-1,2,3,4-Tetrahydro-1-naphthol (R)-(+)-1,1,2-Triphenyl-1,2-ethanediol (S)-(-)-1,1,2-Triphenyl-1,2-ethanediol

10g

1g

1g 100mg 100mg 1g 1g

10ml 5ml 1g 1g

5ml 5ml 1g

1ml 1ml 100mg 100mg 1g 5g 1g 1g 5g 1g 5g

5g 1g 5g 5g 100mg 1g 100mg 100mg 1g 1g

A1445

A2323

A2324 NH2

NH2

Amines

52

O

O

1g 5g 5g 5g 5g 1g 5g

1g

. HCl

1g 1g 25g 1g 1g 5g 25g 25g 25g 25g 5g 25g 1g 5g 1g 1g 5g 100mg 5g 500mg 500mg 5g 25ml 25ml 5g 5g 1g 1g 1g 500mg 25ml 25ml 5g 1g 1g 5ml 5ml 1g 1g 25g 5g 25g 25g 1ml 1ml 25g 5g 5g 25g 25g 5g 1g 1g 5g 1g

N

NH2

. HCl

. HCl

N

C OCH2

C OCH2

O

O

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

A1342

A1301

A1167

A1053

NH2

H

NH2

N

N

CH2CH3

A1174

CH3

CH2

CH2

B1583

NHCH2CH3

N

N

CH2

B1582

NHCH2CH3

NH C O C CH3

N

CH2

B1581

B1580 CH3

O

NH2

N

B2775

NHCH3

B2776 CH3

NHCH3

CH3

NH2

N

N

CH2

NH2

CH3

N

CH2

CH3 NH2

CH2

CH3

CH3 NH2

. xH3PO4

CH3

B3225

B2316 OCH3

NH2

NH2

CH3O

B2317

CH3

CH3

B2920

CH3 NH2

CH3

CH3 CH3

NH2

CH3

B2921

CH3

CH3

CH3

N

C O C CH3 O

CH3

C O C CH3

CH3

O

C1575

CH3

C O C CH3

CH3

CH3

CH3

N H

N H

B2917

B2918

O

CH2O C HN O

C1189

D2459

CH3

CH3

CH3

CH3

NH2

O

C1541

NH2

NH2

NH2

D2828

CH3

NH

O

CH3

NH2

D2827

O

O

CH3 C O C HN

C1448

O

O

NH

NH2

CH3

C1447

H 2N

O

CH3

C O C CH3

NH2 CH3

N

O NH

B1995

NH2

A1172

CH3

NH2

. xH3PO4

CH3

A1171 CH3 NH2

. 2HCl

N H

B1932

NH2

NH2

NH2

N H

N H

A1173

. 2HCl

NH2

CH2NH2

CH2CH3

A1054

N H

A1168

NH2

NH2

D2460

NHCH3

NHCH3

NHCH3

NH2

. 2HCl

NH2

NH2

CH3

CH3

N CH3

N CH3

N H

N H

D2175 NH2

CH3

D2193

NH2

NH2

D2176

NHCH3

CH3

D2149

CH3

. 2HCl

C1531

E0433 NHCH2CH3

NH2

NH2

N H

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

53

Chiral Building Blocks

E0434

M1511

M1512 CH3

NH2

M1107 CH3

M1108

NH2

NHCH2CH3

NHCH3

N H

N H OCH3

M1746 CH2NH2

M2091

CH3

CH2NH2

N0482

N0726 NH2

CH3

P0793 CH3

CH3

NH2

NH2

P1118 CH3

NH2

CH3 NH2

CH3

T1380

T1381 CH3

NH2

CH3

CH3

NH2

CH3

Product No. Product Name A1445 A2323 A2324 A1342 A1301 A1167 A1168 A1053 A1054 A1173 A1174 B1932 B1580 B1581 B1582 B1583 B2775 B2776 B3225 B2316 B2317 A1171 A1172 B2920 B2921 B1995 B2917 B2918 C1575 C1447 C1448 C1541

54

NH2

CH3

P0794

NH2

N0481 CH3

H N N H

N0724

N H

OCH3

M1747

CH3

NHCH3

(S)-(-)-α-Amino-γ-butyrolactone Hydrochloride (R)-3-Amino-1-carbobenzoxypyrrolidine Hydrochloride (S)-3-Amino-1-carbobenzoxypyrrolidine Hydrochloride (R)-(+)-2-Aminomethyl-1-ethylpyrrolidine (S)-(-)-2-Aminomethyl-1-ethylpyrrolidine (3R)-(+)-3-Aminopyrrolidine (3S)-(-)-3-Aminopyrrolidine (3R)-(-)-3-Aminopyrrolidine Dihydrochloride (3S)-(+)-3-Aminopyrrolidine Dihydrochloride (3R)-(-)-1-Benzyl-3-aminopyrrolidine (3S)-(+)-1-Benzyl-3-aminopyrrolidine (3R)-(+)-1-Benzyl-3-(tert-butoxycarbonylamino)pyrrolidine (3R)-(-)-1-Benzyl-3-(ethylamino)pyrrolidine (3S)-(+)-1-Benzyl-3-(ethylamino)pyrrolidine (3R)-(-)-1-Benzyl-3-(methylamino)pyrrolidine (3S)-(+)-1-Benzyl-3-(methylamino)pyrrolidine (1R,2R)-1,2-Bis(3,5-dimethylphenyl)-1,2-ethylenediamine Phosphate (1S,2S)-1,2-Bis(3,5-dimethylphenyl)-1,2-ethylenediamine Phosphate (1R,2R)-1,2-Bis(4-methoxyphenyl)ethylenediamine (1R,2R)-1,2-Bis(2,4,6-trimethylphenyl)ethylenediamine (1S,2S)-1,2-Bis(2,4,6-trimethylphenyl)ethylenediamine (3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine (3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine (3R)-(+)-1-(tert-Butoxycarbonyl)-3-aminopyrrolidine (3S)-(-)-1-(tert-Butoxycarbonyl)-3-aminopyrrolidine N-(tert-Butoxycarbonyl)-L-serine β-Lactone (R)-(-)-sec-Butylamine (S)-(+)-sec-Butylamine N-Carbobenzoxy-L-serine β-Lactone (1R,2R)-(-)-1,2-Cyclohexanediamine (1S,2S)-(+)-1,2-Cyclohexanediamine (R)-(-)-1-Cyclohexylethylamine

Unit Size 1g 1g 1g 1g 5g 5g 5g 5g 10g 10g

5g 5g

100mg 100mg 5g 5g 1g 1g 1g 100mg 1g 5g 5g 5g

1g 5g 5g 5g 5g 25g 25g 25g 25g 25g 25g 5g 5g 5g 25g 25g 100mg 100mg 1g 500mg 500mg 25g 25g 5g 5g 5g 1g 5g 1g 25g 25g 25g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

Product No. Product Name C1531 C1189 D2827 D2828 D2149 D2193 D2459 D2460 D2176 D2175 E0433 E0434 M1511 M1512 M1107 M1108 M1746 M1747 M2091 N0482 N0481 N0724 N0726 P0794 P0793 P1118 T1380 T1381

Unit Size

(S)-(+)-1-Cyclohexylethylamine D-(+)-Cycloserine (R)-1,2-Diaminopropane Dihydrochloride (S)-1,2-Diaminopropane Dihydrochloride (3R)-(+)-3-(Dimethylamino)pyrrolidine (3S)-(-)-3-(Dimethylamino)pyrrolidine (1R,2R)-(-)-N,N '-Dimethylcyclohexane-1,2-diamine (1S,2S)-(+)-N,N '-Dimethylcyclohexane-1,2-diamine (1R,2R)-(+)-1,2-Diphenylethylenediamine (1S,2S)-(-)-1,2-Diphenylethylenediamine (3R)-(+)-3-(Ethylamino)pyrrolidine (3S)-(-)-3-(Ethylamino)pyrrolidine (R)-(+)-1-(4-Methoxyphenyl)ethylamine (S)-(-)-1-(4-Methoxyphenyl)ethylamine (3R)-(+)-3-(Methylamino)pyrrolidine (3S)-(-)-3-(Methylamino)pyrrolidine (R)-(+)-β-Methylphenethylamine (S)-(-)-β-Methylphenethylamine (R)-(-)-2-Methylpiperazine (R)-(+)-1-(1-Naphthyl)ethylamine (S)-(-)-1-(1-Naphthyl)ethylamine (R)-1-(2-Naphthyl)ethylamine (S)-1-(2-Naphthyl)ethylamine (R)-(+)-1-Phenylethylamine (S)-(-)-1-Phenylethylamine (S)-1-Phenyl-2-(p-tolyl)ethylamine (R)-(+)-1-(p-Tolyl)ethylamine (S)-(-)-1-(p-Tolyl)ethylamine

5g 1g

1g 1g 100mg 100mg 1g 1g 1g

5g 5g 1g 1g 5g 5g 5g 1g 1g 1g 1g 25ml 25ml 5g 1ml 1ml

D2265

D3758 O

CH3

CH3

O

O O

D1949 O

CH3

O

O O

I0507

CH3 COOH

CH3

CH3

O

CH3 O

O

CH3

CH3 CH3

O

H3C CH3

O

O

CH3

O O

O

O

CH3

O O

OH

I0688

CH3 CH3

O

HO

O

O

H3C

CH3

I0489 O

OH

OH

OH

HO

O

CH2OH

O

OH

O

I0400

O

HOH2C

O

O O

CH3 CH3

I0375

O

CH3

D2616

2

O

I0376

O

CH3

O

CH3

O

CH3

CH3

HO

OH

HOCH2

O

CH3

O

CH3

OH

O

OH O

CH3 O

.HO

CH3

O

HO

O

OH

I0454 O

CH3 CH3

D2447

O

O

CH3 CH3

O

CH3 CH3

O O

O

O

O

CH3

CH3

D2024

OH

CH3

O

O O

HO

D2191

CH3

D2555

CH3

Isopropylidene Sugars

25g 5g 1g 1g 5g 5g 1g 5g 5g 5g 1g 1g 25g 25g 5g 5g 25g 25g 25g 5g 5g 5g 5g 500ml 500ml 25g 5ml 5ml

O O

CH2OH O

CH3

O

CH3 CH3

CH3

I0721 CH2OH

HOCH2 O

HO

OH O

O

CH3 CH3

O O

CH3 CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

55

Chiral Building Blocks

Product No. Product Name

Unit Size

1,2:5,6-Di-O-isopropylidene-α-D-allofuranose 2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose 1,2:3,4-Di-O-isopropylidene-α-D-galactopyranose 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (-)-2,3:4,6-Di-O-isopropylidene-2-keto-L-gulonic Acid Monohydrate 1,2:5,6-Di-O-isopropylidene-D-mannitol 2,3:5,6-Di-O-isopropylidene-D-mannofuranose 1,2:3,5-Di-O-isopropylidene-α-D-xylofuranose (+)-5,6-O-Isopropylidene-L-ascorbic Acid 2,3-O-Isopropylidene-D-erythronolactone 1,2-O-Isopropylidene-α-D-glucofuranose 1,2-O-Isopropylidene-α-D-glucurono-6,3-lactone 3,4-O-Isopropylidene-D-mannitol (+)-2,3-O-Isopropylidene-L-threitol (-)-2,3-O-Isopropylidene-D-threitol 1,2-O-Isopropylidene-α-D-xylofuranose

D2265 D3758 D2555 D1949 D2191 D2024 D2447 D2616 I0507 I0454 I0400 I0688 I0489 I0376 I0375 I0721

B2136

1g 5g 5g 10g 5g

1g 1g 1g 5g

B2137

C2265

CH2OCH2

Protected 1,2-Diols

C1796

O

D1705

O

CH3 CH3

D1691

O

O

CH3

H1188

O

O

CH3 CH3

HOCH2CH2

O

O CH3

M1451

HOCH2CH2

O

CH3 CH3

O

O

CH3 CH3

H1189

O

CH3

O CH2O

O

CH3OCH2 CH3

O

O

O

CH2O O

CH3

O

CH3

S O

CH3

CH3

P1485

CH3OCH2

O

CH3

O CH3

S O

M1456

CH3

CH3 O

D2550

CH2OH

O CH3

O

CH3

D2549

CH2OH

ClCH2

ClCH2

CH2OCH2 O

5g 25g 25g 25g 25g 25g 5g 5g 5g 1g 25g 1g 5g 5g 5g 25g

CH3

O O

O O

O

O

P1486

CH3

O O

O

Product No. Product Name B2136 B2137 C2265 C1796 D1705 D1691

56

(R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane (S)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane (R)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolane (S)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolane (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol

Unit Size 5g 1g 1g

5g 5g

1g 1g 25g 5g 25g 25g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

Product No. Product Name D2549 D2550 H1188 H1189 M1451 M1456 P1485 P1486

Unit Size

(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate (R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (S)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (R)-(+)-4-(Methoxymethyl)-1,3-dioxolan-2-one (S)-(-)-4-(Methoxymethyl)-1,3-dioxolan-2-one (R)-Propylene Carbonate (S)-Propylene Carbonate

B2238

1g 1g

5g 5g 5g 5g

B2239

CH2OCH2

Glycidyl Compounds

E0533

G0363

E0581

CH2Cl

CH2OCH2 O

O

O

G0364

G0282

G0283 O

CH2OH

CH2Cl

CH2OH

O

O

CH2O C

O

G0286

O

G0287

G0327

O

CH2O S

CH2O S

O

O

O

G0328

T1611

N CH2

O

O

O

T1612

O

NO2

NO2 O

CH2OCH3

O

(CH2)2CH3

O

G0281

CH2OCH3

CH2O C

(CH2)2CH3

O

G0280

5g 5g 1g 1g 25g 25g 25g 25g

O

G0284

G0285

O O

N CH2

O

O CH3

CH2O S O

O

O

O

P1396

CH3

CH2O

CH2O

C

C

O

O

O

P0951

CH3

CH3 O

O

Product No. Product Name B2238 B2239 E0581 E0533 G0363 G0364

CH2O S

Benzyl (R)-(-)-Glycidyl Ether Benzyl (S)-(+)-Glycidyl Ether (R)-Epichlorohydrin (S)-Epichlorohydrin (R)-(+)-Glycidol (S)-(-)-Glycidol

Unit Size 1g 1g

5g 5g 5g 5g 5g 5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 25g 25g 25g 25g 25g

57

Chiral Building Blocks

Product No. Product Name G0282 G0283 G0280 G0281 G0286 G0287 G0327 G0328 T1611 T1612 G0284 G0285 P1396 P0951

Unit Size

(R)-Glycidyl Butyrate (S)-Glycidyl Butyrate (R)-Glycidyl Methyl Ether (S)-Glycidyl Methyl Ether (R)-Glycidyl 3-Nitrobenzenesulfonate (S)-Glycidyl 3-Nitrobenzenesulfonate (R)-N-Glycidylphthalimide (S)-N-Glycidylphthalimide (2R)-(-)-Glycidyl p-Toluenesulfonate (2S)-(+)-Glycidyl p-Toluenesulfonate (R)-Glycidyl Trityl Ether (S)-Glycidyl Trityl Ether (R)-(+)-Propylene Oxide (S)-(-)-Propylene Oxide

1ml

A1576

B2420

CN

OH

Others

O

N

CH3

C1188

N

C

H

B1759

25g 25g 25g 25g 25g 25g 25g 25g 25g 25g 25g 25g 25ml 25ml

B3299 H

O

H2N

B2779

5g 5g 5g 5g 5g 5g 5g 5g 5g 5g 5g 5g 5ml 5ml

CH2

C1363

D3259

CH3 O

Si C(CH3)3

O

O

H C

CH3

N

CH3 BrHC

O

Si C(CH3)3

O

CH3

CN

C O C CH3 CH3

CH3

Cl

CH3

N

N

CH3

CH3

CH3 CH3

O

CH3

D3257

M0803 OCH3

N CH3O

N

CH

M1622

CH3OCH2

CH3

M0824 O OH H N

CH3 O

M0170

HO

M1233

HO

OH H N

OH CH3

CH3

M1234

OH

CH3

OH CH3

M0963

CH3

O

M0965

CH3

P1499

CH3

M0964

CH3

M0966

CH3

CH3

OH

P1500

CH3

P1504

OH CH3

CH3

OH

O

O

O

N O

O

P1509

O

CH3 CH3

OH O

T2551

T2552

T2636

H3C O

CH2NH2

O

O

O

CH2NH2 O

58

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Chiral Building Blocks

Product No. Product Name A1576 B2420 B3299 B2779 B1759 C1188 C1363 D3259 D3257 M0803 M1622 M0824 M1233 M1234 M0170 M0965 M0964 M0966 M0963 P1499 P1500 P1504 P1509 T2551 T2552 T2636

(R)-4-Amino-2-methyl-1-butanol (4aS,8aR)-2-Benzoyloctahydro-6(2H)-isoquinolinone (R)-1-Benzyl-3-pyrrolidinecarbonitrile (1R,3R)-5-(Bromomethylene)-1,3-bis(tert-butyldimethylsilyloxy)cyclohexane (S)-(-)-3-(tert-Butoxycarbonyl)-4-formyl-2,2-dimethyl-1,3-oxazolidine (S)-(+)-1-Chloro-2-methylbutane (-)-2-Cyano-6-phenyloxazolopiperidine (5S)-5,6-Dihydro-6,6-dimethyl-5-phenyl-2H-1,4-oxazin-2-one (2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazine (4S,5S)-(-)-4-Methoxymethyl-2-methyl-5-phenyl-2-oxazoline (R)-(+)-N-(α-Methylbenzyl)phthalamic Acid (S)-(-)-N-(α-Methylbenzyl)phthalamic Acid (R)-(+)-2-Methyl-1,4-butanediol (S)-(-)-2-Methyl-1,4-butanediol (S)-(-)-2-Methyl-1-butanol (S)-(+)-5-Methyl-1-heptanol (S)-(+)-4-Methyl-1-hexanol (S)-(+)-6-Methyl-1-octanol (S)-(+)-3-Methyl-1-pentanol (R)-3-Phenylcyclohexanone (S)-3-Phenylcyclohexanone (R)-3-Phenylcyclopentanone (S)-3-Phenylcyclopentanone (R)-(-)-Tetrahydrofurfurylamine (S)-(+)-Tetrahydrofurfurylamine (R)-(-)-2,3,7,7a-Tetrahydro-7a-methyl-1H-indene-1,5(6H)-dione

Unit Size 1g 1g 1g 10ml

5g

1ml 1ml 1ml 100mg 100mg 100mg 100mg 200mg 200mg 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 50mg 5g 100mg 5g 25ml 1g 1g 1g 1g 5g 1g 5g 25g 25ml 1ml 5ml 5ml 5ml 1g 1g 1g 1g 1g 1g 5g

59

Optical Resolution

Optical Resolution The optical resolution is the method of separating enantiomers from racemates. There are currently many methods to obtain optically active compounds. These methods include asymmetric synthesis, use of chiral building blocks, and optical resolution. In recent years, there has been rapid improvements in asymmetric synthesis, with many reports of success. Optical resolution is widely used, as it is an easy and practical method. One of the most common optical resolution methods utilizes diastereomer which are obtained from the reaction of racemic compounds and an optical resolving agents. The differences of physical properties between diastereomers are utilized in this method. The optical resolving agents are often easily obtained from natural products. For example, alkaloids are used for the optical resolution of racemic acids and tartaric acid is used for the optical resolution of racemic bases. In both cases, diastereomeric salts are formed. When alcohols are to be resolved, the alcohols are reacted with phthalic anhydride to form half ester. The resulting carboxylic acid (half ester) is often then reacted with alkaloids to form diastereomeric salts, which are then resolved. Recently, Ikegami and co-workers have reported a new resolution method for alcohols using amino acid derivatives.1) According to their report, racemic 1-octyn-3-ol is reacted with ( )- - toluenesulfonylphenylalanyl chloride (1), to produce diastereomeric ester. This diastereomeric ester is recrystallized four times from mixed solution of ethanol and hexane, giving the resolved ester with a theoretical yield of 64% (>99% d.e.). Finally, ( )-1-octyn-3-ol is obtained by hydrolysis of pure diastereomeric ester (>99% e.e.). This method is drawing attention as an easy and accurate way to optically resolve alcohols. O

O PhCH2

C Cl

i)

NHTs

PhCH2

C O NHTs

1

ii) recrystallization

OH

Y.64% ( >99% d.e.)

40% KOH aq.

OH

On the other hand, it has been reported that optical resolution is achieved by catalytic amount of chiral source. Ishihara and co-workers have studied minimal artificial enzymes to overcome various problems of enzymatic reactions and to use optical resolution. One reagent that has been developed is α-(2,4,6triisopropylbenzenesulfonyl)- -( -butyldimethylsilyl)-π-methyl-L-histidinol (2). They reported that this reagent was a very effective catalyst for kinetic resolution of racemic alcohols by selective acylation2). This reagent can also be used as catalyst for the kinetic resolution of 1,2-diols, β-hydroxycarboxylic acids, and 2-amino alcohols after the suitable derivatization. H3C N

OTBDPS HN

N

SO2

i-Pr

i-Pr

2 O O C N

(5 mol%)

i-Pr

O

O

O C N

O C N

(i-PrCO)2O (0.5 eq.)

OH syn, racemic

60

i-Pr2NEt (0.5 eq.) nonpolar solvent (49% conv.)

+ O C 94% e.e.

O

i-Pr

OH 90% e.e.

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Optical Resolution

Shiina and co-workers developed the kinetic resolution of racemic alcohols and racemic carboxylic acids using 4-methoxybenzoic anhydride (PMBA) (3) and a Birman-type asymmetric catalyst3) [(+)-benzotetramisole, (+)-BTM].4) For example, in the reaction of racemic alcohols with achiral carboxylic acids, first the mixed anhydrides are formed from PMBA and the carboxylic acids. Subsequently the mixed anhydrides and one enantiomer of racemic alcohol react preferentially to form optically active esters and optically active alcohols using catalyst (+)-BTM. If this reaction is performed replacing the reactive substrates with racemic carboxylic acids and achiral alcohols, the kinetic resolution proceeds efficiently and optically active esters and optically active carboxylic acids can be obtained. The optical resolution of an anti-inflammatory agent, ibuprofen, has been achieved as an example of this reaction. O

O O O

OH

R2

O CH3O

R1

+ R2CO2H

3

OH

R1

O

3

+ R3OH

R1

+

(+)-BTM (cat.), iPr2NEt, CH2Cl2, rt

O

OH

OCH3

O OR

i

(+)-BTM (cat.), Pr2NEt, CH2Cl2, rt

CH3

+

3

OH

CH3

CH3

BTM=(+)-Benzotetramisole

A1230

A1231

A1017

OH

for Resolution of Acids

A1521

A0526

NH

OH

H2N

NH2

B3549

OH

OH

A1029 OH

OH

NH2

NH2

O

N H

OH H2N

B1119

O

B3296

N H

OH

H

H

CH2OH

CH3O

N H

S

N

NHCH2

CH3O

NHCH2

N

H

C0348 CH2 CH

HO

H

N

H

C0349 CH2 CH

HO

H

H

N

HO

H

N

CH3O

N

CH2

H

O

O

H O H . HCl . H2O

H

H CH2

CH

CH N

N

N

H

. 2H2SO4 . 2H2O N

N H

C0351

H

HO

. 2HCl N

H

C0350 CH2 CH

CH3O

H

O

C0347

N

B0671

B0946 B0670

CH2OH

N

S

. HCl

NH2

NH2

B1118

N

O

NH

OH H2N

N H

NH2

O2N

A0528

NH

NH2

HO

H

. HCl . xH2O N

N

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

61

Optical Resolution

C0791

D1588

H0752

CH2

L0129 CH3CH2

CH3

H

L0131

H

CH

HO

. H2SO4 . 2H2O

H

CH3

N

H2N

H

M0826

H2N

H2N

OH

M0545

OH

. HCl

NH2

N0543 CH3

CH3

OH

. HCl

NH2

CH3

N0482

N0481

CH3

CH3

CH3

P0794 CH3

NH2

P1118

Q0006

Q0010

Q0028

H

NH2

NH2

CH3

H

N

N HO

S0249

. HCl . 2H2O

N O

N

S0093

S0094

H

H H

O

O

H

H

H N

H H

N

N

H N

O

. HCl . xH2O

O

N

H

H H

O

. HNO3

O

H

H H

O

NH2

CH3

CH3

NH2

CH3

Product No. Product Name A1230 A1231 A1017 A1521 A1029 A0526 A0528 B3296 B3549 B1119 B1118 B0946 B0670 B0671

(1R,2S)-(-)-2-Amino-1,2-diphenylethanol (1S,2R)-(+)-2-Amino-1,2-diphenylethanol D-(-)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol (1R,2R)-(-)-2-Amino-1-phenyl-1,3-propanediol D-(-)-Arginine L-(+)-Arginine L-(+)-Arginine Hydrochloride (+)-Benzotetramisole (-)-Benzotetramisole (+)-cis-2-Benzylaminocyclohexanemethanol (-)-cis-2-Benzylaminocyclohexanemethanol Brucine Anhydrous Brucine Dihydrate Brucine Hydrochloride

2

. H2SO4 . 5H2O

T1381 CH3

62

N

CH3O N

N

H

N

T1380

H

2

N

S0257

HO

H

N HO

. H2SO4 . 2H2O

H

CH3O

CH3O

H

CH

N

CH

CH2 CH

H CH2

HO

NH2

OH NH2

CH2 CH

Q0030

NO2

P1028

NH2

P0793

. HCl

CH3

OH

CH3O

NH2

OH

P1289

NH2

H

. 2HCl

O

O

CH2

OH NH2

NH2

CH3

CH3

H2N

N

L0071

CH3

O

OH

. HCl

NH2

L0128

H

CH3O

2

N

O

CH3

CH3

N HO

Unit Size 1g 5g 1g 5g 25g 500g Price on request 1g 5g 25g 500g 25g 500g 200mg 1g 1g 1g 5g 1g 5g 25g 25g 5g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Optical Resolution

Product No. Product Name C0347 C0348 C0349 C0350 C0351 C0791 D1588 H0752 L0129 L0131 L0128 L0071 M0826 M0545 N0543 N0482 N0481 P1289 P1028 P0794 P0793 P1118 Q0006 Q0010 Q0028 Q0030 S0249 S0257 S0093 S0094 T1380 T1381

Unit Size

Cinchonidine Cinchonidine Dihydrochloride Cinchonidine Sulfate Cinchonine Cinchonine Hydrochloride Hydrate Cinchonine Sulfate Dihydrate (+)-Dehydroabietylamine Hydroquinidine Hydrochloride L-(+)-Lysine L-(+)-Lysine Dihydrochloride D-(-)-Lysine Monohydrochloride L-(+)-Lysine Monohydrochloride (+)-Menthol (-)-Menthol (S)-α-Methyl-4-nitrobenzylamine Hydrochloride (R)-(+)-1-(1-Naphthyl)ethylamine (S)-(-)-1-(1-Naphthyl)ethylamine D-Phenylalaninol L-Phenylalaninol (R)-(+)-1-Phenylethylamine (S)-(-)-1-Phenylethylamine (S)-1-Phenyl-2-(p-tolyl)ethylamine Quinidine Quinidine Sulfate Dihydrate Quinine Quinine Hydrochloride Dihydrate Strychnine Strychnine Hydrochloride Hydrate Strychnine Nitrate Strychnine Sulfate Pentahydrate (R)-(+)-1-(p-Tolyl)ethylamine (S)-(-)-1-(p-Tolyl)ethylamine

25g

250g 25g 500g 200g 25g 500g 25g 250g 25g 25g 25g 500g 500g 500g 1g 5g 5g 25g 25g 500ml 500ml 25g 25g 25g 500g 25g 25g 25g 25g 25g 5ml 5ml

25g 25g 25g 5g 25g 5g 5g 25g 25g 25g 1g 1g 5g 5g 25ml 25ml 5g 5g 5g 25g

1ml 1ml

A1454

A1453 O

O

CH3 C O

A0545 O

C OH

O

CH3 C O

O

C OH HO

for Resolution of Bases

A0546

B1121

HO

OH O

B1120

C OH

C OH

O

O NH

NH C

NH2

C0012

C0015

CH3

CH3 CH3 COOH COOH

CH3 O

B1143

NH2

B1144

O

O

O

OH O

O O

O

P OH

O

O P OH

C

C0972 CH3 CH2SO3H

O

C0998

CH3 HO3SCH2

CH3 O

C1308

CH3

CH3 CH2SO2Cl

O

CH3 ClSO2CH2

CH3 O

H

C1417

C1418

D2636

D1386

H

O

H

O

O H

O

O CH3

H

O

CH3

O

HO

OH O

D1911 O

O

CH3

O

O O

O O

CH3 C O

O

HO

O

OH O

O

CH3 O

O

CH3 C O

O

O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

63

Optical Resolution

D2645

D1398

D3826

D1354

O

O O

CH3 C O

O CH3 C O

Ph

O

O

HO O

O

D3492

O

O

O

HOOC

COOH

Ph

O

O

HO

OH . H2O

C O

Ph

O

O C O

O

O

O

D1853

D1387 O

p-Tol

OH

NO2

M0021

p-Tol

O

O

OH O

O OH

O

OH

NH2

M0661

HO

O HO

OH

NH2

M1221 CH3

O

O

OH

O

HO

O

M0662

O

O

HO

p-Tol

O

O

M0022

HO

O

G0059

O

O

HO

OH O

O2N

O

G0057

p-Tol

O

HO

O

Ph

COOH O C

O

O

HN

C O

O

D1417 O

HOOC

OH . H2O

HO

C OH

C OH O

OH O

O C Cl

OH CH3

M0990

M1021

I0334

CH3

CH3

CH3

M1622 CH3

NCO

O

NCO

OH H N

OH

O O C Cl

O

CH3O

CH3

I0335

O

CH3

M0824

I0336 O

I0398 CH3

NCO

P1354 CH3

P0573

O

N H

OH

O

O

T0026

T0025

T1702

O

T1163 NO2

O HO C OH

OH

HO

OH

OH

O

HO

OH O

OH

O

HO

OH

H N

OH

OH O

OH

O

NO2

O O2N

NO2 N

OH

O OH

CH3

OH

O

Product No. Product Name

64

OH

N H

CH3

Q0009

A1454 A1453 A0545 A0546 B1121 B1120 B1143 B1144 C0012 C0015 C0972 C0998 C1308 C1417

CH3

NCO

OH H N O

CH3

(+)-O-Acetyl-L-mandelic Acid (-)-O-Acetyl-D-mandelic Acid D-Aspartic Acid L-Aspartic Acid (+)-cis-2-Benzamidocyclohexanecarboxylic Acid (-)-cis-2-Benzamidocyclohexanecarboxylic Acid (R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate (S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate (+)-Camphoric Acid (+)-10-Camphorsulfonic Acid (-)-10-Camphorsulfonic Acid (+)-10-Camphorsulfonyl Chloride (-)-10-Camphorsulfonyl Chloride (+)-trans-1,2-Cyclohexanedicarboxylic Anhydride

Unit Size 5g 5g 25g

100mg

1g 100mg 25g 25g 25g 5g

25g 25g 25g 500g 5g 5g 5g 1g 500g 500g 500g 10g 25g 100mg

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Optical Resolution

Product No. Product Name C1418 D2636 D1386 D1911 D2645 D1398 D3826 D1354 D3492 D1853 D1417 D1387 G0057 G0059 M0021 M0022 M0662 M0661 M1221 M0990 M1021 I0334 I0335 M1622 M0824 I0336 I0398 P1354 P0573 Q0009 T0026 T0025 T1702 T1163

Unit Size

(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride (+)-Diacetyl-D-tartaric Acid (-)-Diacetyl-L-tartaric Acid (+)-Diacetyl-L-tartaric Anhydride (-)-Diacetyl-D-tartaric Anhydride (+)-Dibenzoyl-D-tartaric Acid Monohydrate (+)-Dibenzoyl-D-tartaric Acid (-)-Dibenzoyl-L-tartaric Acid Monohydrate (-)-Dibenzoyl-L-tartaric Acid (R)-(-)-N-(3,5-Dinitrobenzoyl)-α-phenylglycine (+)-Di-p-toluoyl-D-tartaric Acid (-)-Di-p-toluoyl-L-tartaric Acid D-Glutamic Acid L-Glutamic Acid D-(+)-Malic Acid L-(-)-Malic Acid D-(-)-Mandelic Acid L-(+)-Mandelic Acid (+)-Menthyl Chloroformate (-)-Menthyl Chloroformate (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic Acid (R)-(+)-α-Methylbenzyl Isocyanate (S)-(-)-α-Methylbenzyl Isocyanate (R)-(+)-N-(α-Methylbenzyl)phthalamic Acid (S)-(-)-N-(α-Methylbenzyl)phthalamic Acid (R)-(-)-1-(1-Naphthyl)ethyl Isocyanate (S)-(+)-1-(1-Naphthyl)ethyl Isocyanate D-Pyroglutamic Acid L-Pyroglutamic Acid D-(-)-Quinic Acid D-(-)-Tartaric Acid L-(+)-Tartaric Acid (2R,3R)-Tartranilic Acid (+)-α-(2,4,5,7-Tetranitro-9-fluorenylideneaminoxy)propionic Acid

A1454

1g

25g 25g 1g

O

CH3 C O

A2128 O

C OH

O

CH3 C O

O

C OH

for Resolution of Alcohols & Thiols

A1984

B3296

CH2 CH CH2

B3549

B1219

N

O S

CH3

N N

S

CH3

CH3 COCl O

CH3

O

CH3

CH3 O

C1308 CH3 CH2SO2Cl

CH3

CH3

CH3

CH3 CH3

CH3

CH3

N CH3

C0998

B1220

CH3

CH2 CH CH2

C1022

5g 25g 25g 25g 25g 1g 25g 25g 25g 25g 5g 25g 25g 25g 5ml 5ml 25g 5g 1g

1g 1g 5g 25g

A1453 O

100mg 5g 25g 25g 25g 500g 250g 500g 250g 5g 250g 250g 250g 500g 25g 500g 500g 250g 25ml 25ml 500g 25g 5g 5g 1g 5g 5g 25g 500g 25g 500g 500g 5g 1g

CH3 ClSO2CH2

O

O

C1417 CH3

O

O

O

O

CH3

C1418 H

O

H

O

O H

O

O O

H

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

O

65

Optical Resolution

M0573

M0571

M1221

OCH2 C Cl

OCH2 C OH CH3

CH3

I0335

CH3

CH3

N0581

I0334 CH3

O

O

CH3

M0990 CH3

CH3

CH3

CH3

O

O

O C Cl

O C Cl

CH3

CH3

I0336

NCO

CH3

I0398

N0582

O

CH3

NCO

CH3

Cl HN

T1444

NCO

CH3

NCO

O Cl

SO2

HN

SO2

NO2

T2223 O HN

N

Cl HN

Ph

CH3 N

O

i

SO2

Si

tBu

Ph

SO2 iPr

Pr

CH3 iPr

Product No. Product Name A1454 A1453 A2128 A1984 B3296 B3549 B1219 B1220 C1022 C0998 C1308 C1417 C1418 M0573 M0571 M1221 M0990 I0334 I0335 N0581 I0336 I0398 N0582 T1444 T2223

(+)-O-Acetyl-L-mandelic Acid (-)-O-Acetyl-D-mandelic Acid (R)-5-Allyl-2-oxabicyclo[3.3.0]oct-8-ene (S)-5-Allyl-2-oxabicyclo[3.3.0]oct-8-ene (+)-Benzotetramisole (-)-Benzotetramisole Bis[(2R,3aS,4R,7aS)-octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl] Ether Bis[(2S,3aR,4S,7aR)-octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl] Ether (-)-Camphanic Chloride (+)-10-Camphorsulfonyl Chloride (-)-10-Camphorsulfonyl Chloride (+)-trans-1,2-Cyclohexanedicarboxylic Anhydride (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride (-)-Menthoxyacetic Acid (-)-Menthoxyacetyl Chloride (+)-Menthyl Chloroformate (-)-Menthyl Chloroformate (R)-(+)-α-Methylbenzyl Isocyanate (S)-(-)-α-Methylbenzyl Isocyanate N-(1-Naphthalenesulfonyl)-L-phenylalanyl Chloride (R)-(-)-1-(1-Naphthyl)ethyl Isocyanate (S)-(+)-1-(1-Naphthyl)ethyl Isocyanate N-(4-Nitrophenylsulfonyl)-L-phenylalanyl Chloride N-(p-Toluenesulfonyl)-L-phenylalanyl Chloride Nα-(2,4,6-Triisopropylbenzenesulfonyl)-O-(tert-butyldiphenylsilyl)-π-methyl-L-histidinol

Unit Size 5g 5g 1g 200mg 100mg 100mg 1g 5g 5g

5ml

1g

5ml 5ml 5g 1g 1g 1g

25g 25g 5g 1g 1g 1g 1g 1g 25g 10g 25g 100mg 100mg 25ml 10g 25ml 25ml 25g 5g 5g 5g 5g 5g 5g 100mg

References 1) S. Hashimoto, S. Kase, A. Suzuki, Y. Yanagiya, S. Ikegami, . 1991, , 833; Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 04 273835, 1992. 2) K. Ishihara, Y. Kosugi, M. Akakura, . 2004, , 12212. 3) V. B. Birman, X. Li, . 2006, , 1351. 4) I. Shiina, K. Nakata, . 2007, 48, 8314; I. Shiina, K. Nakata, Y. Onda, . 2008, 5887.

66

Availability, price or specification of the listed products are subject to change without prior notice.

Enantiomer Excess & Absolute Configuration Determination

Enantiomer Excess & Absolute Configuration Determination Most biologically active compounds including pharmaceuticals have chiral molecular structures with one or more stereogenic centers. The absolute configuration of pharmaceuticals is very important for biological activity. Generally one enantiomer has medicinal activity while the other enantiomer has no activity. In some cases the opposite enantiomer gives rise to adverse and harmful effects. For this reason it is of great significance to obtain enantiopure compounds and to develop chiral auxiliaries for the determination of their absolute configurations and enantiomeric excess. Various kinds of reagents have been developed to determine their absolute configurations and enantiomeric excess by NMR1), HPLC2) and CD exciton chirality method3). A chiral shift reagent, Chirabite-AR (1), developed by Ema . is also one of the such reagents, and the optical purity can be easily measured using NMR.4) HN O

N

O HN

O

NO2

O HN N

O

O

HN

C2184 Chirabite-AR 1 Chirabite-AR (1) is a macrocyclic compound and has a very unique cavity where the hydrogen-bond donor and acceptor sites are well organized to enable the binding of a wide range of compounds as guest molecules. The incorporated guest molecules experience a strong anisotropic ring-current effect arising from the BINOL moiety, which is a chiral source, resulting in the chemical-shift nonequivalence between the two enantiomers.

(S)

(R)(S) (R)(S) (R)(R)(S)(S)

(R)

HO CO2H

5.1

5.0

4.9

S O

7

6.5

2.5

2

Chirabite-AR (7mg) in CDCl3 at 22℃ When conventional europium complexes are used on high-field NMR spectrometers, which are widely spread nowadays, signal broadening occurs, and as a result, satisfactory NMR spectra cannot be obtained. Because 1 contains no paramagnetic metals, which cause signal broadening, it can be used for both high- and low-field NMR spectrometers. Using 1, therefore, the enantiomeric purities of various compounds such as carboxylic acids, oxazolidinones, carbonates, lactones, alcohols, sulfoxides, sulfoximines, sulfinamides, isocyanates and epoxides can be determined. Moreover, a protocol for its determination is extremely easy; NMR spectra showing chemical-shift nonequivalences can be obtained just by adding 1 to the NMR tube containing a target sample in CDCl3. The reagent 1 is characterized by its facile use, versatility, and applicability to the low- and high-field NMR spectrometers. Thus, 1 has been shown to possess a highly effective capacity superior to that of the conventional chiral shift reagents.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

67

Enantiomer Excess & Absolute Configuration Determination

A1657

A1658

B1720

O O

O O

C OH

C OH

O N

for NMR

N

O

B1721

B1143

O

CH2

O

Si CH2 C OH

B1161

O

O

P OH

O

CH3

B1343

P OH

OH

OH

O

CH3

CH3

CH3

CH3

OH

OH

CH3

C1021

Si CH2 C OH

O

B1144

O

CH2

C2184

D2459

D2460

D1852 NO2

CH3 CO2H O

CH3

CH3

N H

O

N

N H

N

H N

H N

O

O

D1853

NHCH3

NHCH3

NHCH3

NHCH3

CH3

NH

C

NO2

O

O

O

O

O

D2176

D2175

M0662

NO2

M0661

O

O

O

C OH

NO2

NH2

NH2

HO

HO

C OH

C OH

HN C NH2

O

NH2

NO2

M1366

M1367

M0830

CH3

CH3

C OH

I0334

C OH

CH3O

O

O

C OH

CH3O

C OH

M0831 CH3

NCO

M0832

NCO

CF3

N0713 O

C Cl

CF3

O

C OH

C Cl

N0481 CH3

C OH

CF3 CH3O

N0482 O

OCH3

O

C OH

CH3O

N0714

CF3

O

O

C OH

O

O

O

M1103

O CH3O

M1104

CF3 CH3O

I0335

CF3

M1339

O

CH3O

CH3O

CH3

M0829

O

O

CH3

NH2

NH2

CH3O N

N

O

I0336

I0398 CH3

68

O

NCO

P0794 CH3

NCO

P0793 CH3

NH2

P1219 CH3

NH2

Availability, price or specification of the listed products are subject to change without prior notice.

O CH3

C OH

Enantiomer Excess & Absolute Configuration Determination

P1220

S0473

S0474

T1520

O CH3

C OH

O Na

O

O Sm3

O O

N

O

CH3

O N

O O

. xH2O

Na

HO

O Sm3

O O

N

O

CH3

T1521 CF3

HO

N

O O

Product No. Product Name A1657 A1658 B1720 B1721 B1143 B1144 B1161 B1343 C1021 C2184 D2459 D2460 D1852 D1853 D2176 D2175 M0662 M0661 M1366 M1367 M0830 M0829 M1339 I0334 I0335 M0831 M0832 M1103 M1104 N0713 N0714 N0482 N0481 I0336 I0398 P0794 P0793 P1219 P1220 S0473 S0474 T1520 T1521

CF3

O

Unit Size

(1R,2R)-2-(Anthracene-2,3-dicarboximido)cyclohexanecarboxylic Acid (1S,2S)-2-(Anthracene-2,3-dicarboximido)cyclohexanecarboxylic Acid (+)-Benzylmethylphenylsilylacetic Acid (-)-Benzylmethylphenylsilylacetic Acid (R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate (S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate (R,R)-(-)-2,3-Butanediol (S,S)-(+)-2,3-Butanediol (-)-Camphanic Acid Chirabite-AR (1R,2R)-(-)-N,N '-Dimethylcyclohexane-1,2-diamine (1S,2S)-(+)-N,N '-Dimethylcyclohexane-1,2-diamine (R)-(-)-N-(3,5-Dinitrobenzoyl)-α-phenylethylamine (R)-(-)-N-(3,5-Dinitrobenzoyl)-α-phenylglycine (1R,2R)-(+)-1,2-Diphenylethylenediamine (1S,2S)-(-)-1,2-Diphenylethylenediamine D-(-)-Mandelic Acid L-(+)-Mandelic Acid (R)-(-)-2-Methoxy-2-(1-naphthyl)propionic Acid (S)-(+)-2-Methoxy-2-(1-naphthyl)propionic Acid (R)-(-)-α-Methoxyphenylacetic Acid (S)-(+)-α-Methoxyphenylacetic Acid (+)-α-Methoxy-α-(trifluoromethyl)phenylacetic Anhydride (R)-(+)-α-Methylbenzyl Isocyanate (S)-(-)-α-Methylbenzyl Isocyanate (+)-MTPA (-)-MTPA (+)-MTPA-Cl (-)-MTPA-Cl (1R,2R)-2-(Naphthalene-2,3-dicarboximido)cyclohexanecarboxylic Acid (1S,2S)-2-(Naphthalene-2,3-dicarboximido)cyclohexanecarboxylic Acid (R)-(+)-1-(1-Naphthyl)ethylamine (S)-(-)-1-(1-Naphthyl)ethylamine (R)-(-)-1-(1-Naphthyl)ethyl Isocyanate (S)-(+)-1-(1-Naphthyl)ethyl Isocyanate (R)-(+)-1-Phenylethylamine (S)-(-)-1-Phenylethylamine (R)-(-)-2-Phenylpropionic Acid (S)-(+)-2-Phenylpropionic Acid Sodium [(R)-1,2-Diaminopropane-N,N,N ',N '-tetraacetato]samarate(III) Hydrate Sodium [(S)-1,2-Diaminopropane-N,N,N ',N '-tetraacetato]samarate(III) (R)-(-)-2,2,2-Trifluoro-1-(9-anthryl)ethanol (S)-(+)-2,2,2-Trifluoro-1-(9-anthryl)ethanol

A1657

100mg

100mg

100mg 100mg 100mg 100mg 5g 1g 5g 1g 5g 100mg 1g 5g 1g 5g 5g 5g 500g 250g 100mg 100mg 5g 5g 100mg 25g 5g 5g 5g 1g 1g 100mg 100mg 5g 5g 5g 5g 500ml 500ml 5g 5g 100mg 100mg 1g 1g

1g 100mg 1g 100mg 1g 100mg 1g 1g 1g 1g 25g 25g

100mg

1g 1g

1g

5g 1g 1g 1g 100mg 100mg

1g 1g 1g 1g 25ml 25ml 1g 1g

100mg 100mg

A1658

A5561 NH2

O O

for HPLC

N O

C OH

O O

C OH

N N

N O

SO2N

O N CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

CH3

69

Enantiomer Excess & Absolute Configuration Determination

A5560

A5565

A5564

NH2

A5568

N

N

O N CH3 SO2N CH3

SO2N

D2259

N

C Cl

N

O N CH3

O N CH3 SO2N CH3

CH3

A5524

A5523 O

C NH2

C NH2

NH

iPrCH 2

N0713 CH3

N0714

I0336

O

NCO

O

O O

C OH

N

A5563

A5566 O

NCO

N

N

O

N

A5577

A5578

N N

N

O

N

NO2

N

O

N

NO2

A5515

O

AcO AcO

OAc O NCS

BzO BzO

AcO

OBz O NCS BzO

NO2

Unit Size

(1R,2R)-2-(Anthracene-2,3-dicarboximido)cyclohexanecarboxylic Acid (1S,2S)-2-(Anthracene-2,3-dicarboximido)cyclohexanecarboxylic Acid (R)-(-)-DBD-APy [=(R)-(-)-4-(N,N-Dimethylaminosulfonyl)-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole] (S)-(+)-DBD-APy [=(S)-(+)-4-(N,N-Dimethylaminosulfonyl)-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole] (R)-(+)-DBD-Pro-COCl [=(R)-(+)-4-(N,N-Dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl)-

100mg 100mg 100mg 100mg

2,1,3-benzoxadiazole]

100mg

A5564

(S)-(-)-DBD-Pro-COCl [=(S)-(-)-4-(N,N-Dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl)-

A5568

(R)-(-)-DBD-Py-NCS [=(R)-(-)-4-(N,N-Dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)-

A5569

(S)-(+)-DBD-Py-NCS [=(S)-(+)-4-(N,N-Dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)-

D2259 A5524 A5523 M1366 M1367 I0334 I0335 N0713 N0714 I0336 I0398 A5563

Nα-(5-Fluoro-2,4-dinitrophenyl)-L-alaninamide Nα-(5-Fluoro-2,4-dinitrophenyl)-D-leucinamide Nα-(5-Fluoro-2,4-dinitrophenyl)-L-leucinamide (R)-(-)-2-Methoxy-2-(1-naphthyl)propionic Acid (S)-(+)-2-Methoxy-2-(1-naphthyl)propionic Acid (R)-(+)-α-Methylbenzyl Isocyanate (S)-(-)-α-Methylbenzyl Isocyanate (1R,2R)-2-(Naphthalene-2,3-dicarboximido)cyclohexanecarboxylic Acid (1S,2S)-2-(Naphthalene-2,3-dicarboximido)cyclohexanecarboxylic Acid (R)-(-)-1-(1-Naphthyl)ethyl Isocyanate (S)-(+)-1-(1-Naphthyl)ethyl Isocyanate (R)-(-)-NBD-APy [=(R)-(-)-4-Nitro-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole]

100mg

2,1,3-benzoxadiazole]

100mg

2,1,3-benzoxadiazole] 2,1,3-benzoxadiazole]

70

O

NO2

Product No. Product Name A1657 A1658 A5561 A5560 A5565

C Cl

NCS

N

N

N

A5514

NCS

N

N

O

NO2

NO2

O

C Cl

N

N N

A5567

NH2

N

NCO

O

A5562 NH2

CH3

C OH

N

O

CH3

C OH

CH3O

NO2

I0335

I0398

O CH3

C OH

F NO2

NCO

CH3

CH3O

NO2

F NO2

I0334

O N CH3 SO2N CH3

M1367 CH3

NO2

F

N

O N CH3

O

NH

NH NO2

N N

M1366

O

C NH2

iPrCH 2

N C S

N

SO2N

O CH3

CH3

C Cl

N

N

A5569 N C S

O

O

Availability, price or specification of the listed products are subject to change without prior notice.

100mg 100mg

1g

5g 1g

1g 1g

100mg 1g 1g 100mg 100mg 100mg 25g 5g 100mg 100mg 5g 5g 100mg

Enantiomer Excess & Absolute Configuration Determination

Product No. Product Name A5562 A5566 A5567 A5577 A5578 A5514 A5515

Unit Size

(S)-(+)-NBD-APy [=(S)-(+)-4-Nitro-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole] (R)-(+)-NBD-Pro-COCl [=(R)-(+)-4-Nitro-7-(2-chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadiazole] (S)-(-)-NBD-Pro-COCl [=(S)-(-)-4-Nitro-7-(2-chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadiazole] (R)-(-)-NBD-Py-NCS [=(R)-(-)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole] (S)-(+)-NBD-Py-NCS [=(S)-(+)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole] 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl Isothiocyanate 2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranosyl Isothiocyanate

C1766

C1682 CH3

O HO C

for X-ray Crystallography

CH3

CH3

100mg 100mg 100mg 100mg 100mg 100mg 1g 100mg 1g

C1767

CH3

O

O

C

C N

CH3

O

O

HO C

C OH

C N

N S O

O

O

S

Cl

S O

CH3

O

O

Cl

O

C1683 CH3

CH3 O O

C OH

C N S O

Cl

O Cl

Product No. Product Name

Unit Size

N-(2-Carboxybenzoyl)-(+)-10,2-camphorsultam N-(2-Carboxybenzoyl)-(-)-10,2-camphorsultam N-(2-Carboxy-4,5-dichlorobenzoyl)-(+)-10,2-camphorsultam N-(2-Carboxy-4,5-dichlorobenzoyl)-(-)-10,2-camphorsultam

C1766 C1682 C1767 C1683

500mg 500mg 500mg 500mg

A0482

A1150 COOH O C OH

for Exciton Chirality CD Method

A0690

B0062

for Hydroxy Groups B0105

OCH3

B0553

O

O

O

C OH

C OH

C Cl

B0558 O

COOH

C Cl

Br

C0134

C0141

C0445

O

O

C OH

C Cl

Cl

Cl

C1182

Br

D0724 O

CN

CN

COOH

COCl

C OH

N

CH3 CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

71

Enantiomer Excess & Absolute Configuration Determination

M0721

M1338

M0576

N0025

N0048

O C Cl

O NH

O OH

C OCH3

N

O

O

N HN

OH

Cl

CH3O OCH3

N0156

N0176

P0961

O

O

C OH

C Cl

P1079

O

O

C OH

C Cl

NO2

NO2

Product No. Product Name A0482 A1150 A0690 B0062 B0105 B0553 B0558 C0134 C0141 C0445 C1182 D0724 M0721 M1338 M0576 N0025 N0048 N0156 N0176 P0961 P1079

Unit Size

p-Anisic Acid 2-Anthracenecarboxylic Acid 9-Anthracenecarboxylic Acid Benzoic Acid Zone Refined (number of passes:20) Benzoyl Chloride 4-Bromobenzoic Acid 4-Bromobenzoyl Chloride 4-Chlorobenzoic Acid 4-Chlorobenzoyl Chloride 4-Cyanobenzoic Acid 4-Cyanobenzoyl Chloride 4-Dimethylaminobenzoic Acid 4-Methoxybenzoyl Chloride 5-(4-Methoxycarbonylphenyl)-10,15,20-triphenylporphyrin 4-Methoxycinnamic Acid 2-Naphthoic Acid 2-Naphthoyl Chloride 4-Nitrobenzoic Acid 4-Nitrobenzoyl Chloride 4-Phenylbenzoic Acid 4-Phenylbenzoyl Chloride

D0648

D0645 D1495

25g 1g 5g

500g 5g 25g 1sample 25ml 500ml 25g 500g 25g 250g 25g 500g 25g 500g 5g 25g 250g 5g 25g 25g 500g 25g 500g 100mg 1g 25g 25g 25g 25g 500g 25g 500g 25g 500g 5g 25g

N0530

O

O

C H CH3

for Primary Amino Groups

CH3

N

O N

CH

CH

O

C H

CH3

O

CH3

Product No. Product Name D0645 D1495 D0648 N0530

Unit Size

4-Dimethylaminobenzaldehyde 4-Dimethylaminobenzaldehyde 4-Dimethylaminocinnamaldehyde 2,3-Naphthalenedicarboxylic Anhydride

B3515

A1371

72

N CH3CH2 CH3CH2

N Zn N

CH3

H2NCH2CH2NH C O C CH3

CH2 CH2CH3 CH2CH3

O

CH3

Boc

500g 500g 25g 250g

B2124 O

CH2CH3 N

B1185

CH2CH3

CH3CH2 CH3CH2

for Monoalcohols, Monoamines

25g 25g 5g 25g

H N

CH2NH

O

CH3

C OC CH3 CH3

OH

2

Availability, price or specification of the listed products are subject to change without prior notice.

O N

C OH

Enantiomer Excess & Absolute Configuration Determination

P1364

N N

N Zn N

O C

N N

(CH2)5

N Zn N

C O

Product No. Product Name B3515 A1371 B1185 B2124 P1364

Bis(Zinc Porphyrin) (ca. 5μmol/L in Dichloromethane) N-Boc-1,2-diaminoethane Boc-Gly-OH 4-[(tert-Butoxycarbonylamino)methyl]pyridine-2-carboxylic Acid Pentamethylene Bis[4-(10,15,20-triphenylporphin-5-yl)benzoate]dizinc(II)

Unit Size 1g

5ml 25ml 5g 25g 5g 25g 100mg 1g 10mg 100mg

References 1) J. A. Dale, H. S. Mosher, . 1973, , 512; I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, . 1991, , 4092; N. Harada, M. Watanabe, S. Kuwahara, A. Sugio, Y. Kasai, A. Ichikawa, : 2000, , 1249; Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2001 261613, 2001. 2002, 2) T. Toyo’oka, , 25; K. Fujii, Y. Ikai, H. Oka, M. Suzuki, K. Harada, 1997, , 5146; K. Fujii, Y. Ikai, T. Mayumi, H. Oka, M. Suzuki, K. Harada, , 3346. 2001, 3) T. Kurtan, N. Nesnas, F. E. Koehn, Y.-Q. Li, K. Nakanishi, N. Berova, , 5974. 2006, , 3773; T. Ema, D. Tanida, T. Sakai, 2007, 4) T. Ema, D. Tanida, T. Sakai,

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

1997,

, 10591.

73

Chiral Columns for HPLC

Chiral Columns for HPLC ●Chiral Columns“TCI Chiral” New type of chiral separation with synthetic organic polymer phase systems “ - TCI Chiral” 1. A unique new stationary phase Polymaleimide helical polymer bearing chiral side groups coated on silica gel 2. Suitable for separation of a wide range of compounds Carbonyls (Ketones, Esters, Carboxylic acids, -Protected amino acids), Alcohols and others 3. Applicable to both normal and reversed phase modes 4. High column load capacity 5. Superior column longevity Maximum pressure: 2900 psi (20 MPa) 6. High throughput analysis 7. Affordable prices

Product Line Column

Retention Power (Normal Phase)

TCI Chiral MB-S

High

TCI Chiral BP-S

Medium

TCI Chiral CH-S

Weak

Analytes Low Polarity

Carbonyls (Amides, Esters, Ketones, Lactones, Moderate Polarity Carboxylic acids, -Protected amino acids), Alcohols, Diols, Sulfonyls and others High Polarity

Normal and Reversed Phase Applications <Normal Phase> n-Hexane / 2-Propanol = 70 / 30(TCI Chiral MB-S) 90 / 10(TCI Chiral BP-S and TCI Chiral CH-S)

TCI Chiral MB-S(3μm) TCI Chiral BP-S(3μm) TCI Chiral CH-S(3μm)

Column Size Detection Flow Rate Temperature Sample

: : : :

4.6 mm I.D. × 250 mm UV 210 nm 1.0 mL/min 40 ℃

: Butyl Lactate

0.0

2.5

5.0

7.5

Time(min)

0.0

2.5

5.0

7.5

Time(min)

0.0

2.5

5.0

7.5

Time(min)

O O OH

<Reversed Phase> Acetonitrile / Water = 10 / 90

TCI Chiral MB-S(5μm) TCI Chiral BP-S(5μm) TCI Chiral CH-S(5μm)

0

74

5

10

15

Time(min)

0

5

10

15

Time(min)

Availability, price or specification of the listed products are subject to change without prior notice.

0

5

10

15

Time(min)

Chiral Columns for HPLC

Column Particle Size

TCI Chiral MB-S

TCI Chiral BP-S

TCI Chiral CH-S

3μm

5μm

3μm

5μm

3μm

5μm

2.0mmI.D.×50mm

S3816

S3846

S3826

S3856

S3836

S3866

2.0mmI.D.×150mm

S3812

S3842

S3822

S3852

S3832

S3862

2.0mmI.D.×250mm

S3813

S3843

S3823

S3853

S3833

S3863

4.6mmI.D.×50mm

S3815

S3845

S3825

S3855

S3835

S3865

4.6mmI.D.×150mm

S3810

S3840

S3820

S3850

S3830

S3860

4.6mmI.D.×250mm

S3811

S3841

S3821

S3851

S3831

S3861

10.0mmI.D.×250mm



S3870



S3880



S3890

20.0mmI.D.×250mm



S3871



S3881



S3891

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

75

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds Introduction of fluorine into a certain position of bioactive compound such as a pharmaceutical and an agricultural chemical may remarkably reduce the toxicity of the compound, or improve the efficiency of medicine. This is due to the mimic and blocking effect characterized by fluorine. Many compounds, such as 5-fluorouracil, have been reported as success case. Attempts to efficiently synthesize fluorine-containing compounds are performed in many fields. Methods to introduce fluorine into a certain position through the use of fluorinating agents or the use of fluorinecontaining building blocks have been reported. 4-Butyl-2,6-dimethylphenylsulfur trifluoride (1) (FLUOLEAD™), which was first reported by Umemoto ., is a novel nucleophilic fluorinating reagent. Differing from other existing fluorinating reagents, such as DAST, 1 is a crystalline solid with high thermal stability and has less fuming character, which makes it easier to handle. 1 fluorinates a hydroxy or carbonyl group to afford the corresponding fluorinated compounds in good yields.1) Furthermore, 1 even fluorinates thioketones or thioesters. CH3 CH3 CH3

SF3 CH3

S

CH3 OCH3

CF2OCH3

1 (1.5 eq.) CH2Cl2, rt, 26 h

Y. 75%

Triethyl 2-fluoro-2-phosphonoacetate (2) has increasingly been utilized as a useful bifunctional fluorine-containing intermediate.2) This compound is very useful in the generation of physiologically active compounds because it can generate α-fluoro-α,β-unsaturated ester from the reaction with carbonyl compounds in the presence of a base. A subsequent reduction of the above ester leads to the corresponding aldehyde or alcohol. As examples, vitamin A derivatives,3) pheromone of insect origin,4) synthesis of Pyrethroide5) having insecticidal efficacy, etc., can be given.

Me

EtO

Me

Me

CHO Me

EtO

O

F

P CH

CO2Et ,BuLi

Me

Me

Me

Me

Me

Me

F

2 -78 °C ~ 0 °C

Me

CO2Et

CO2Et + Me

F

Y. 95% (2E : 2Z = 5 : 2)

[(Oxido)phenyl(trifluoromethyl)-λ4-sulfanylidene]dimethylammonium tetrafluoroborate (3) is a novel electrophilic trifluoromethylating reagent which was developed by Shibata . 3 trifluoromethylates various substrates under mild conditions to afford the corresponding trifluoromethylated compounds in high yields.6) BF4+ S N(CH3)2

O

CF3 O

3 (1.5 eq.) DBU (1.2 eq.)

C OR O

CH2Cl2, rt, 1 h

O CF3 C OR O R = CH3; Y. 93% R = Bn; Y. 90%

76

Availability, price or specification of the listed products are subject to change without prior notice.

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds

F0342

Cl

Electrophilic Fluorinating Reagents F0358

Cl

CF3SO3

N

O O S N S O F O

N

F

F 2BF4

F0334

F0343

F0327

F 2BF4

N

Cl

N

CH2Cl

BF4

Cl

B2F7

N

N

F

F0346

N

BF4

F

CF3SO3

N F

F

F0328 CH3

CH3 BF4

CH3

N

F0335

F

F0344

N

D3812

N

CH3

CF3SO3 CH3

N

CH3

F

F

Product No. Product Name F0342 D3812 F0335 F0358 F0344 F0334 F0343 F0327 F0346 F0328

Unit Size

2,6-Dichloro-1-fluoropyridinium Trifluoromethanesulfonate 1,1'-Difluoro-2,2'-bipyridinium Bis(tetrafluoroborate) N-Fluorobenzenesulfonimide N-Fluoro-N '-(chloromethyl)triethylenediamine Bis(tetrafluoroborate) 1-Fluoro-2,6-dichloropyridinium Tetrafluoroborate 1-Fluoropyridinium Pyridine Heptafluorodiborate 1-Fluoropyridinium Tetrafluoroborate 1-Fluoropyridinium Trifluoromethanesulfonate 1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate

B2440

5g

25g 1g 25g 25g 25g 5g 25g 25g 5g 25g

5g 5g 5g 5g 5g 5g

B3664

D1868 SF3

CH3OCH2CH2

Nucleophilic Fluorinating Reagents D2831

N

CH3 F

Et

T1909

F Ph

Bu

. (HF)x

F

Bu

F

Ph

N Bu Bu

Bu

HF2

T2027

Bu

H2F3

N Bu Bu

T1339 T1338 T1037 T1125

Bu

Ph

Sn

Bu

N

O

T1635

Ph

F

F

T1295

SF3

F Bu4N

CH3 C CH3

CF3

F Ph Si

Et

N

T1592

Ph

N S

P0999

F

N F

CH3

F

Et

F

M1573 Et

F

CH3

F

CH3

H0598 N

Bu4N

CH3OCH2CH2

CH3

F N S

N Bu

F

(CH3CH2)4NF

. 4HF

Bu

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

77

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds

T2026

T2023

(CH3CH2)4NF

. 3HF

(CH3CH2)3N

T2022

. 5HF

(CH3CH2)3N

. 3HF

Product No. Product Name B2440 B3664 D1868 D2831 H0598 M1573 P0999 T1295 T1909 T1592 T1635 T1339 T1338 T1125 T1037 T2027 T2026 T2023 T2022

Unit Size

Bis(2-methoxyethyl)aminosulfur Trifluoride 4-tert-Butyl-2,6-dimethylphenylsulfur Trifluoride (Diethylamino)sulfur Trifluoride 2,2-Difluoro-1,3-dimethylimidazolidine Ishikawa's Reagent Morpholinosulfur Trifluoride Pyridinium Poly(hydrogenfluoride) Tetrabutylammonium Bifluoride Tetrabutylammonium Difluorotriphenylsilicate Tetrabutylammonium Difluorotriphenylstannate Tetrabutylammonium Dihydrogen Trifluoride Tetrabutylammonium Fluoride (70-75% in Water) Tetrabutylammonium Fluoride (1mol/L in Tetrahydrofuran) Tetrabutylammonium Fluoride (1mol/L in Tetrahydrofuran) Tetrabutylammonium Fluoride Hydrate Tetraethylammonium Fluoride Tetrahydrofluoride Tetraethylammonium Fluoride Trihydrofluoride Triethylamine Pentahydrofluoride Triethylamine Trihydrofluoride

5g 5g

25ml

O0367

T2624

S N

Trifluoromethylating Reagents

CF3

CH3 CH3

I

O

BF4

CH3 CF3

CH3

Unit Size

P1080

P1659 O

CF3(CF2)5

I

O S CF3

CF3 CF3

I

OSO2CF3

O

O S CF3 O

78

5g

1g 1g 25g

O CF

O I

200mg

P1081

P1082

CF3CF2CF2

Si CH3 CH3

[(Oxido)phenyl(trifluoromethyl)-λ4-sulfanylidene]dimethylammonium Tetrafluoroborate 1-Trifluoromethyl-3,3-dimethyl-1,2-benziodoxole (Trifluoromethyl)trimethylsilane

Fits Reagents

25g 1g 25g 5g 5g 1g 5g 25g 100ml 25ml 25g

CH3

Product No. Product Name O0367 T2624 T1570

25g

T1570

CF3

O

25g 5g 100g 10g 500g 5g 100g 25g 25g 5g 25g 500g 500ml 100ml 250g 10g 10g 10g 10g

Availability, price or specification of the listed products are subject to change without prior notice.

CF3(CF2)7

I

O S CF3 O

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds

Product No. Product Name P1080 P1659 P1081 P1082

Unit Size

(Perfluorohexyl)phenyliodonium Trifluoromethanesulfonate (Perfluoroisopropyl)phenyliodonium Trifluoromethanesulfonate (Perfluoro-n-octyl)phenyliodonium Trifluoromethanesulfonate (Perfluoropropyl)phenyliodonium Trifluoromethanesulfonate

1g

B3498

5g 500mg 1g 1g

B1801 O C H Br

Br

Aliphatic & Aromatic Compounds

Fluorinated Building Blocks

C0990

C1503

CH2 CF3

F

C2381

F0283

D2523

O O

O

F F

F

OH

F

Cl

O

Cl

O

C H F

O

Cl

CH3

F

Cl

CH3

O

O

O

F

O

F

OH

CH3

F

F

D1423

D2525

D2524 CH3 C H N CH

O F

OH

C1467

Cl

CH3

E0547

O

CH3

F0030

OH O

CH3

F

F0341

O

CH3

F0518

F

P1894

C0991 F

F

CF3

C O

F F

F

F

CH3

Cl Cl

O

CF3

O

O

O

CH3

O

CF3

OCH3

F0340

CH3CH2O

F

CH3

S CF2 C OCH3

Cl ONa

Cl

O

T1032

O F

O

O

Cl

F0042

O

F

O F

T1245

O OCH3

O

N CH3 F

F0311

F

O

CH3

T0810

CF3

F

O Si CH3

CH3

O CH3

C1586

CH2 C

CH3 O

F

O

CH3

D2782

T0432

F

SO2CH2F

CH3

O F

F

Br

CH3 O

F

CH3

Br

Br

O

O O

O

F

O

F Br

O

D2498

E0663

O

O F

O

F

Cl

B1673

F C H

N CH

F

O O

F

C

D2530

O

CH3

CH3

F

C1458

F

H

F C H

F

F

B1463

CCl3CF3

CH3CH2O

O

O

P

OCH2CH3 F

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

79

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds

T0791

T0433

OH O

CF3

O CF3

CH3

T1604

O

CF3

C N

O

T1516

O CH3

CF3CH2OH

CF3

O S OCH2CF3

CH3

O

T2547 O

OCH3

S OCH2CF3 O

T1512

Cl

S OCH2CF3

M1193

O

T2638

O CF3

T0435

CH2

Cl OH

CF3

C N

CF3

Product No. Product Name B3498 B1801 C0990 C1503 C2381 F0283 D2523 D1423 D2525 D2524 B1463 B1673 C1458 C1467 D2530 D2498 D2782 E0547 F0030 E0663 T0432 T0810 F0341 F0518 C1586 F0311 T1245 P1894 C0991 F0042

2-Bromo-4-fluorobenzaldehyde 2-Bromo-3,3,3-trifluoro-1-propene (stabilized with Copper chip) Chlorodifluoroacetic Acid Chlorodifluoroacetic Anhydride 2-Chloro-5-fluorobenzaldehyde Diethyl Fluoromalonate Difluoroacetaldehyde Ethyl Hemiacetal Difluoroacetic Acid (R)-N-(2,2-Difluoroethylidene)-1-phenylethylamine (S)-N-(2,2-Difluoroethylidene)-1-phenylethylamine Ethyl Bromodifluoroacetate Ethyl Bromofluoroacetate Ethyl Chlorodifluoroacetate Ethyl Chlorofluoroacetate Ethyl Dibromofluoroacetate Ethyl Difluoroacetate Ethyl 3-(Dimethylamino)-3-ethoxy-2,2-difluoropropionate Ethyl 3-Ethoxy-2,2-difluoro-3-hydroxypropionate Ethyl Fluoroacetate Ethyl 2-Fluoropropionate Ethyl Trifluoroacetate Ethyl 4,4,4-Trifluoroacetoacetate Fluoromethyl Phenyl Sulfone (1-Fluorovinyl)methyldiphenylsilane Methyl Chlorodifluoroacetate Methyl Fluorosulfonyldifluoroacetate Methyl 4,4,4-Trifluoroacetoacetate Pentafluorophenyl Trifluoroacetate Sodium Chlorodifluoroacetate Trichlorofluoromethane (in cylinder without valve) [To use this product charged in cylinder,

T1032 F0340 T0791 T0433 T0435 M1193 T1516 T1604 T2638 T1512 T2547

1,1,1-Trichloro-2,2,2-trifluoroethane Triethyl 2-Fluoro-2-phosphonoacetate Trifluoroacetaldehyde Ethyl Hemiacetal (contains ca. 10% Ethanol) Trifluoroacetic Anhydride 2,2,2-Trifluoroethanol 2,2,2-Trifluoroethyl Methanesulfonate 2,2,2-Trifluoroethyl p-Toluenesulfonate 2,2,2-Trifluoroethyl Trifluoromethanesulfonate 2,2,2-Trifluoro-N-(4-methoxyphenyl)acetimidoyl Chloride 2-(Trifluoromethyl)acrylic Acid 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride

Unit Size

1g

5g

5g 5g 25g 10g 5g 5g 5g 5g

25g 5g 25g 5g 5g 5g 1g 25ml 5g 25g 25g 1g 1g 5g 5g 5g 5g 25g

a valve is required which is sold separately (Product Code:V0030)]

80

Availability, price or specification of the listed products are subject to change without prior notice.

1g 20ml 25g 5g 25g 5g 5g

25g 25g 500g 25g 25g 25g 25g 25g 1g 1g 250g 25g 500g 25g 25g 25g 5g 1g 500ml 25g 500g 500g 5g 5g 25g 25g 25g 25g 500g 400g 25g 5g 10g 400ml 500g 25g 500g 25g 5g 25g 5g

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds

A1993

A2125

A1664 NH2

N

Heterocyclic Compounds

F

B2799

F

S

NH2

F

F

N

NH2

B3244

A1546

N

N

OCH3

B2705

NH2

F

B3177

F

N N

Br

N

N

C2113

C2221

F

C2270

N N

F

D3614

N

O

O

C1666 F

N

N H

D3642

Cl

F

D3615

NH2 N

F

N

HO

O

O

F HO

OH

D2057

N N

F0656

Cl N

Cl

N

F

F

F0180

F

NH2

O

N

F

N

NH N

F0534

OCH2CH3

F0556

F

N N

N H

F0369

NH2

NH2 N

Cl

F0647

F

Cl

F

Cl

N

E0684

F Cl

F

F

D1741

Cl F

C OH

O

OH

D3374

N

N

O

Cl

F

OH

F

O

HN

N

O

. xH2O

F

N

D3317

F N

Cl

O

N

O

HO

Cl

D2610

NH2

C OH

C OC(CH3)3

F

N

F

N

C OC(CH3)3

C1549

F

F

O

C OH

Cl Cl

F

F O

Br

Br

N

B3178

F F

F

N

F

F

N

F

N HO

N

N

F

HO

S

O OH

F

O

N

O

OH

OH

OH

F0352

F0555

F0523

F0589

N H

F0693

F

N H

F0547 O C OH

N

F

N

O

F

N

OCH3

F

S

CH3

O

F0533

F

N

N H

O

F0420

NH

O

O N H

F

F0316

F

F0551

F

I F

N H

N H

CH3

N O

CH3

N

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

F

81

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds

F0579

F0581

F0520

CH3

F

F

F0575

F

N

F0382

N

CH3

F0207

NH

HO C

N H

T1778

F

F N

F

F

N

82

F

N

T2061 F

F

F

F N H

. HCl

F F

F N

OH

Product No. Product Name A1993 A2125 A1664 A1546 B2799 B3244 B2705 B3177 B3178 C2113 C2221 C2270 C1549 C1666 D3614 D3642 D3615 D2610 D3317 D3374 D2057 D1741 E0684 F0647 F0656 F0180 F0534 F0556 F0369 F0352 F0555 F0523 F0589 F0551 F0693 F0547 F0316 F0420 F0533 F0579

CH3

. HCl N

T2342

OH

N

. H2O

O

F F

F

F0628

F

F O

N

CH3

O

C OH

F0038

N

F0217

O

F

F0519

F

CH3

N

N

F0300

2-Amino-6-fluorobenzothiazole 4-Amino-5-fluoro-2-methoxypyrimidine 2-Amino-5-fluoropyridine 4-Amino-2,3,5,6-tetrafluoropyridine 2-Bromo-5-fluoropyridine 3-Bromo-5-fluoropyridine 5-Bromo-2-fluoropyridine (2S,4R)-1-(tert-Butoxycarbonyl)-4-fluoro-2-pyrrolidinecarboxylic Acid (2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoro-2-pyrrolidinecarboxylic Acid 5-Chloro-2,3-difluoropyridine 6-Chloro-2-fluoropurine 2-Chloro-5-fluoropyridine 3-Chloro-2,4,5,6-tetrafluoropyridine 5-Chloro-2,4,6-trifluoropyrimidine 2'-Deoxy-2'-fluorocytidine Hydrate 2'-Deoxy-5-fluorocytidine 2'-Deoxy-2'-fluorouridine 2,6-Dichloro-5-fluoronicotinic Acid 3,5-Dichloro-2-fluoropyridine 2,4-Dichloro-5-fluoropyrimidine 3,5-Dichloro-2,4,6-trifluoropyridine 2,6-Difluoropyridine 2-Ethoxy-5-fluoro-4-pyrimidinone 2-Fluoroadenine 2-Fluoroadenosine 2-Fluorobenzothiazole 5-Fluorocytidine 4-Fluoroindole 5-Fluoroindole 6-Fluoroindole 7-Fluoroindole 2-Fluoro-5-iodopyridine 5-Fluoroisatin 7-Fluoroisatin 2-Fluoroisonicotinic Acid 5-Fluoro-2-methoxy-4-pyrimidinone 5-Fluoro-2-methylbenzothiazole 5-Fluoro-2-methylbenzoxazole 2-Fluoro-3-methylpyridine 2-Fluoro-4-methylpyridine

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 5g 1g 5g 1g 5g 200mg 200mg 5g 1g 5g 5g 1g 1g 5g 1g 5g 5g 5g 5g 200mg 200mg 1g 1g 1g 1g 5g 5g 1g 5g 5g 1g 1g 5g

5g 25g 5g 1g 25g 5g 25g 1g 1g 25g 1g 5g 25g 25g 1g 5g 5g 25g 5g 25g 25g 25g 25g 1g 1g 1g 5g 1g 5g 5g 1g 5g 25g 25g 5g 25g 25g 5g 5g 25g

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds

Product No. Product Name F0581 F0520 F0300 F0519 F0575 F0382 F0217 F0207 F0628 F0038 T1778 T2342 T2061

Unit Size

2-Fluoro-5-methylpyridine 2-Fluoro-6-methylpyridine 6-Fluoro-2-methylquinoline 7-Fluoro-2-methylquinoline 2-Fluoronicotinic Acid 5-Fluoroorotic Acid Monohydrate 2-Fluoropyridine 3-Fluoropyridine 4-Fluoropyridine Hydrochloride 5-Fluoro-8-quinolinol 2,3,5,6-Tetrafluoropyridine 3,3,4,4-Tetrafluoropyrrolidine Hydrochloride 3,5,6-Trifluoro-2-hydroxypyridine

1g 1g 1g 1g 100mg

B3165 OH OH CH3

H3C

HO H3C

HO

H3C O

N

O O

OH

E0786

H3C

O

N

F

C OH

N

N

CH3

HN

F0321

HO H3C

O

F

CH2CH2F

CH2CH3

NH2

CH3

F

O

CF3

N

H H

N

. 1 1/2H2O

CF3

N

N

N

F0691

OH CH3

O H3C

O

O

O

N

CH3

CF3

F0437

C OH

C OH

F

H

O

O

O

CH3

NH C N

N

OH

. HCl . H2O

N

E0762

H F

F0646

F

C OH

N

O

OH OH CH3

H3C

HO

O

OH

CH3CH2

F N

O

HN

H

D3773 O

HN

H F

D1961

F

O F

CH3

O

O

HN

HO

H

O OH CH3

H3C

H3C

F

D3579

O

H

O

O

C2227 O

O

D2235

5g 1g 1g 1g 1g 1g

100mg

B1837

Fluorinated Bioactive Compounds

5g 5g 5g 5g 5g 1g 25g 25g 5g 5g 5g 5g 5g

H

O

CHOCH2F

O

N H

F

F0635

F0151

F0636

F0371

O F

HO

N N H

O

HO H3C

CH C OH CH3

L0216

OH

N CH3

O

C OH

P1897

O

F

C OH

N

H

T2506

F

CH2CH3

O

F

O

F

N

O C OH

SO3H

C OH O N

. HCl

N

HN

CH3

O

O

F CH3

N

N

CH3 CH3

F

N0817

O

F O

H F

O O F

S O

O

OH

L0193

N

O

O

O H3C

F O

NH

O

F

HN

N

CH2CH3

HN

N

N

N

N

N CH3

.

F

HN O

F0525

O

O

F

N OH

CH3

NH2

. xH2O F

T2303

T2308 O H3C

HO H3C

O H3C

HO H3C

H F

O

OH OH OH

T2511

H

H

O

O

CF3

HN

CH3 HO

O

N

O F

O

O

OH CH3

H OH

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

83

Fluorinating Reagents, Building Blocks & Fluorinated Bioactive Compounds

Product No. Product Name B1837 B3165 C2227 D2235 D3579 D1961 D3773 E0762 E0786 F0646 F0437 F0321 F0691 F0635 F0151 F0636 F0371 F0525 L0193 L0216 N0817 P1897 T2506 T2303 T2308 T2511

Betamethasone Betamethasone 21-Acetate Ciprofloxacin Hydrochloride Monohydrate 2'-Deoxy-5-fluorouridine 5'-Deoxy-5-fluorouridine Dexamethasone 1,1-Dimethyl-3-[3-(trifluoromethyl)phenyl]urea Enoxacin Sesquihydrate Enrofloxacin Fleroxacin Flunisolide 5-Fluorocytosine Fluoromethyl 1,1,1,3,3,3-Hexafluoroisopropyl Ether 5-Fluoro-1-(tetrahydro-2-furfuryl)uracil 5-Fluorouracil 5-Fluorouridine Flurbiprofen Fluticasone Propionate Levofloxacin Lomefloxacin Hydrochloride Norfloxacin Paliperidone Tosufloxacin p-Toluenesulfonate Hydrate Triamcinolone Triamcinolone Acetonide Trifluorothymidine

Unit Size 1g 1g 5g 100mg 500mg 1g 5g 5g 5g 5g 1g

5g 5g 5g 1g 5g 5g 5g 5g 200mg 5g 1g 100mg

5g 5g 25g 1g 5g 1g 25g 25g 25g 25g 1g 25g 5g 25g 25g 5g 25g 100mg 25g 25g 25g 1g 25g 1g 5g 1g

References 1) T. Umemoto, R. P. Singh, Y. Xu, N. Saito, . 2010, , 18199. 1997, 2) M. Kikuchi, T. Onozawa, , 88. 3) R. S. H. Liu, H. Matsumoto, A. E. Asato, M. Denny, Y. Shichida, T. Yoshizawa, F. W. Dahlquist, , 7195; A. J. Lovey, B. A. Pawson, . 1982, , 71. 1984, 4) F. Camps, J. Coll, G. Fabrias, A. Guerrero, , 2871. 5) Ph. Coutrot, C. Grison, R. Sauvetre, . 1987, , 1. 6) S. Noritake, N. Shibata, S. Nakamura, T. Toru, M. Shiro, . 2008, 3465.

84

Availability, price or specification of the listed products are subject to change without prior notice.

. 1981,

Halogenation

Halogenation Halogenation is a basic and fundamental transformation in organic chemistry, and halogenated compounds are of extreme importance as building blocks in organic synthesis. The development of modern coupling reactions, such as the Suzuki-Miyaura and Mizoroki-Heck reactions, have greatly increased the demand for halogenated compounds as starting materials. In response to this situation, many novel halogenating reagents have been developed. The page below shows some examples of brominating and iodinating reagents, which have been released recently in our lineup of products. Example of brominating products: Dibromoisocyanuric acid (DBI) (1), which was first reported by Gottardi, is a mild and highly effective brominating reagent,1,2) and has superior brominating ability when compared with -bromosuccinimide (NBS), which is frequently used in organic synthesis. For instance, nitrobenzene was converted to the 3-bromonitrobenzene in 88% yield with 1 in conc. sulfuric acid in 5 min at 20ºC, 1a) but in only 70% yield with NBS in 50% sulfuric acid in 3 h at 85ºC. Thus 1 has been widely used as an effective brominating reagent.3) NO2 O

NO2 R O

1a)

Br

HN

Y. 88%

NH2

O

3a)

N

R

NHBr Y. 90-99%

Br N OH

N

O

Br

Br

NO2

Br

N N

O

DBI (1)

1b)

3b)

Y. 68%

Y. 69%

Example of iodinating products: 1,3-Diiodo-5,5’ -dimethylhydantoin (DIH) (2), which was first reported by Ozazi, is an useful iodinating reagent.4) 2 has higher reactivity and selectivity than molecular iodine or -iodosuccinimide (NIS), which are frequently used for iodination reaction. 2 is a pale yellow solid that does not sublime like molecular iodine, and has low toxicity, which makes it easier to handle. In addition, dimethylhydantoin, which is formed after the reaction, can easily be removed by aqueous extraction. 2 reacts smoothly at room temperature with aromatic compounds in the presence of sulfuric acid to give the corresponding iodinated aromatic compounds in a high regioselectivity and a high yield. Moreover, even low-activated substances such as nitrobenzene can easily be iodinated by using sulfuric acid.5) I

O

N

CH3 CH3 OMe

N

O

I

EtOH-conc.H2SO4, 20 °C, 10 min

NO2

OMe

2 (0.5 eq.)

Y. 97%

I

NO2

2 (1 eq.) 90% H2SO4, 0 °C, 60 min

Y. 75%

I COOH F

COOH

2 (1 eq.) 90% H2SO4, 0 °C, 90 min

Y. 75%

F I

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

85

Halogenation

F0342

D1868

D3812

F

Et Cl

Fluorination

F0335

Et

N

F

F F

F0334

F0344

F0225

N

F 2BF4

N

Cl

CH2Cl

F0343

N

Cl

BF4

N

F

F0327

B2F7

N

F0346

F

M1573 Et

F

CH3

CF3SO3 CH3

N

P1888

P1758 P1779

CH3

F

F

N

P0999

. (HF)x

KHF2

KF

CF3 F

N

O

T1909

T1592

Bu N Bu

N

SF3

F

T1295

Bu

CH3 BF4

CH3

F

SO3

F0328

CF3SO3

N

F

H0598

Et

BF4

N

F

CH3

CH3

N

F 2BF4

F0358

O O S N S O F O

CH3

N

N

F

F

CH3

CH3

N

Cl

N S

F

D2831 N

N

CF3SO3

T1635

F

F Ph HF2

Bu4N

Ph

Si

Bu4N

F Ph

Bu

Ph

F

Bu

Ph Bu

Sn

T1339 T1338 T1037 T1125

Ph

N Bu

Bu

H2F3 Bu

Bu

N Bu

F

Bu

T2026

T2027

(CH3CH2)4NF

. 4HF

(CH3CH2)4NF

T2023

. 3HF

(CH3CH2)3N

T2022

. 5HF

(CH3CH2)3N

. 3HF

Product No. Product Name F0342 D1868 D3812 D2831 F0335 F0358 F0344 F0225 F0334 F0343 F0327 F0346 F0328 H0598

86

2,6-Dichloro-1-fluoropyridinium Trifluoromethanesulfonate (Diethylamino)sulfur Trifluoride 1,1'-Difluoro-2,2'-bipyridinium Bis(tetrafluoroborate) 2,2-Difluoro-1,3-dimethylimidazolidine N-Fluorobenzenesulfonimide N-Fluoro-N '-(chloromethyl)triethylenediamine Bis(tetrafluoroborate) 1-Fluoro-2,6-dichloropyridinium Tetrafluoroborate 2-Fluoro-1-methylpyridinium p-Toluenesulfonate 1-Fluoropyridinium Pyridine Heptafluorodiborate 1-Fluoropyridinium Tetrafluoroborate 1-Fluoropyridinium Trifluoromethanesulfonate 1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate Ishikawa's Reagent

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 5g

5g 25g

5g 5g 5g 5g 5g 5g 5g 25g

25g 100g 1g 10g 25g 25g 25g 25g 5g 25g 25g 5g 25g 500g

Halogenation

Product No. Product Name M1573 P1758 P1779 P1888 P0999 T1295 T1909 T1592 T1635 T1339 T1338 T1125 T1037 T2027 T2026 T2023 T2022

Unit Size

Morpholinosulfur Trifluoride Potassium Fluoride Potassium Fluoride Anhydrous (Spray-dried) Potassium Hydrogenfluoride Pyridinium Poly(hydrogenfluoride) Tetrabutylammonium Bifluoride Tetrabutylammonium Difluorotriphenylsilicate Tetrabutylammonium Difluorotriphenylstannate Tetrabutylammonium Dihydrogen Trifluoride Tetrabutylammonium Fluoride (70-75% in Water) Tetrabutylammonium Fluoride (1mol/L in Tetrahydrofuran) Tetrabutylammonium Fluoride (1mol/L in Tetrahydrofuran) Tetrabutylammonium Fluoride Hydrate Tetraethylammonium Fluoride Tetrahydrofluoride Tetraethylammonium Fluoride Trihydrofluoride Triethylamine Pentahydrofluoride Triethylamine Trihydrofluoride

1g

H0362

C0075

CH3 CH2

C0076

CH3

C1374

C0202

SO2NCl

H3C O

N CH3

Chlorination

25g 5g 5g 1g 5g 25g 100ml 25ml 25g

25ml

B1543

5g 300g 25g 500g 100g 25g 25g 5g 25g 500g 500ml 100ml 250g 10g 10g 10g 10g

H3C C C Cl

Na

H3C

ICl4

. xH2O

C0802

C0291

Cl Cl

SO2NNa

O

O

SO2NNa

. 2H2O

. 3H2O

N Cl

N Cl

ClCH2OCH3

CH3

O

O

CH3

C0460

D0318

D1645

M0094

M0970

Cl SO2NCl

Cl

O

Cl N

N

CH3 Cl

Cl

N

OCH3

S Cl O

Cl

O CH3OCH2

C Cl

CH3

O0082

D1003

T0620

T2040 T2048

T0611

O O

Cl Cl

Cl O

O

N

O

N

O

Cl

Cl

Product No. Product Name B1543 H0362 C0075 C0076 C1374 C0202

Cl

O

NNa

Benzyltrimethylammonium Tetrachloroiodate tert-Butyl Hypochlorite Chloramine B Chloramine T Trihydrate o-Chloramine T Chloromethyl Methyl Ether

S

Cl

O

N

N N

O

Cl CCl3 O

S Cl O

Cl

Unit Size 25g 25g 25g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 500g 500g 500g 25g 500g

87

Halogenation

Product No. Product Name

Unit Size

N-Chlorophthalimide N-Chlorosuccinimide Cyanuric Chloride Dichloramine T Dichloromethyl Methyl Ether Methanesulfonyl Chloride Methoxyacetyl Chloride Oxalyl Chloride Sodium Dichloroisocyanurate Thionyl Chloride Thionyl Chloride (ca. 1mol/L in Dichloromethane) Trichloroisocyanuric Acid Trichloromethanesulfonyl Chloride

C0802 C0291 C0460 D0318 D1645 M0094 M0970 O0082 D1003 T2040 T2048 T0620 T0611

25g 25g 25g 25g 25g 25g 25g 25g 25g

25g 5g

T1382

B2414

B0530

CH3 CH2

Bromination

B1016

O

N CH3 CH3

B3311

Br2

CH3

B2152

CH3 N CH3

Br

S

CH3

CH3

N Br

Br

S

D3976

O

D1265

Cl Cl

Br Cl

N

CH3

. HBr3

N

CH3

N

Br O

O

Br Br

O

P0928

CH3 CH3

O O

P0825

NaN

Br3 N H

T1284

O

O N

T1235 O

O

N(CH3)2

Cl Cl

O

Br

B2148

C C Cl

O

O HN

O

N

Br Br Cl

N Br Br

D1710

Br

Br

D1787

N

D3753 O

N

D1987

O

O

Br

O

B0662

Br

B0656

O NC

N H

Br3

B1697

O

500g 500g 500g 500g 250g 500g 500g 500g 500g 500ml 500ml 500g 25g

N N H

Br

Br

. xH2O O

Br

Br3 N H Br

Br

T2725 CH3

Bu Bu

Br

CH3 N CH3 Br3

N Bu Br3 Bu

P Br

Product No. Product Name T1382 B2414 B0530 B1016 B3311 B1697

88

Benzyltrimethylammonium Tribromide Bromine N-Bromoacetamide 2-Bromo-2-cyano-N,N-dimethylacetamide Bromodimethylsulfonium Bromide N-Bromophthalimide

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 5g 5g 5g 5g 5g

25g 500g 25g 25g 25g 25g

Halogenation

Product No. Product Name

Unit Size

N-Bromosaccharin N-Bromosuccinimide Bromotrichloromethane 1,8-Diazabicyclo[5.4.0]-7-undecene Hydrogen Tribromide 1,3-Dibromo-5,5-dimethylhydantoin Dibromoisocyanuric Acid 5,5-Dibromomeldrum's Acid (=5,5-Dibromo-2,2-dimethyl-4,6-dioxy-1,3-dioxane) 1,2-Dibromo-1,1,2,2-tetrachloroethane 4-Dimethylaminopyridinium Bromide Perbromide Monosodium Bromoisocyanurate Hydrate Pyridinium Bromide Perbromide 2,4,4,6-Tetrabromo-2,5-cyclohexadienone Tetrabutylammonium Tribromide Trimethylphenylammonium Tribromide Triphenylphosphine Dibromide

B2152 B0656 B0662 D3976 D1265 D3753 D1710 D1987 D1787 B2148 P0825 T1235 T1284 P0928 T2725

B1604

C1190

Iodination

H1221

N CH3 ICl2

5g 25g 5g 25g 25g 5g D3657 O

N

CH3

ICH2CH2Cl

CH3

CH3

I0604

25g 500g 500g 5g 500g 25g 25g 25g 25g 25g 500g 25g 500g 500g 25g

25g 5g 5g

CH3 CH2

5g 100g 25g

25g

N

I O

I

I0074 O

I2

HI

N

I

O

Product No. Product Name B1604 C1190 D3657 H1221 I0604 I0074

Benzyltrimethylammonium Dichloroiodate 1-Chloro-2-iodoethane (stabilized with Copper chip) 1,3-Diiodo-5,5-dimethylhydantoin Hydriodic Acid (57%) Iodine N-Iodosuccinimide

Unit Size 5g 1g 5g

5g

25g 25g

25g 5g 25g 300ml 500g 100g

References 2002, 83. 1) a) W. Gottardi, . 1968, , 815; b) W. D. Brown, A. H. Gouliaev, 2) S. C. Virgil, in , ed. by L. A. Paquette, John Wiley& Sons, Chichester, 2001, pp. 1560-1561. 3) a) Z. P. Demko, M. Bartsch, K. B. Sharpless, . 2000, , 2221; b) T. R. Walters, W. W. Zajac Jr., J. M. Woods, . 1991, , 316. 4) O. O. Orazi, R. A. Corral, H. E. Bertorello, . 1965, , 1101. 5) V. K. Chaikovskii, V. D. Filimonov, A. A. Funk, V. I. Skorokhodov, V. D. Ogorodnikov, . 2007, , 1291.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

89

New Oxidation of Primary & Secondary Alcohols

New Oxidation of Primary & Secondary Alcohols Oxidation reactions of primary alcohols and secondary alcohols to the corresponding aldehydes and ketones, respectively, are important reactions in organic synthesis. To date, many oxidizing agents utilizing chromium oxides such as Jones reagents, Sarett reagents, Collins reagents, and oxidizing methods using activated DMSO have been reported. Among them, the method to activate DMSO with oxalyl chloride is called Swern oxidation and is widely used as one of the most practical oxidation methods. However, the reaction temperature must be strictly controlled due to the thermal instability of the activated intermediates formed by the reaction of DMSO and oxalyl chloride in the Swern oxidation. Furthermore, because the byproduct, dimethyl sulfide, has a stench, it is considered to be unsuitable for mass production. Ph S Cl t

R

BuN

R1

1

HO R2

1

O

DBU (2.0 eq.), CH2Cl2

R2

Mukaiyama and co-workers have reported oxidation of alcohols using a sulfinimidoyl compound 1.1) According to their method, 1, nearly similar to activated DMSO in structure, oxidizes primary or secondary alcohols to the corresponding aldehydes or ketones in near quantitative yields under mild conditions. The Present Oxidation

Ph S Cl

R1 HO CH R2

tBuN

R1 S O CH tBuN R2

R1 S O CH N R2

Ph

Ph

tBu

R1 S + O C R2 NH

Ph tBu

1

Swern Oxidation

Cl

CH3 S Cl CH3

R1 HO CH R2

Cl

R1 CH3 S O CH R2 CH3

Et3N

R1 CH3 S O CH R2 H2C

R1 CH3 S + O C R2 CH3

+ HCl

1 reacts directly with alcohols without pre-activation to afford the corresponding carbonyl compounds. The oxidation method using 1 can be performed at room temperature without the strict control of reaction temperature required in the Swern oxidation. Moreover, the oxidation reaction is applicable to oxidation of acid-labile compounds since the reaction proceeds under basic conditions. Ph

R2 HO R1

S

t

N H

Bu (5 mol%)

2 NCS (1.1 eq.) K2CO3, MS4A CH2Cl2, 0 oC ~ rt

R2 O R1

Catalytic oxidation of alcohols to aldehydes or ketones has also been explored. To date, the oxidation methods using tetrapropylammonium perruthenate (TPAP) and 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) as a catalyst have been reported and put into practical use. The oxidation method of alcohols reported by Mukaiyama and co-workers using sulfenamide 2 is one of such catalytic oxidation methods.2) In this method -chlorosuccinimide (NCS) can be used as a co-oxidant to yield the corresponding aldehydes and ketones from primary alcohols or secondary alcohols in near quantitative yields without requiring strict temperature control. The method using 2 is receiving much attention as a safe and simple catalytic oxidation method of alcohols. 90

Availability, price or specification of the listed products are subject to change without prior notice.

New Oxidation of Primary & Secondary Alcohols

R1 O R2 R 1 R2

Ph

O S

H

S

Ph

N H 2

t

N Bu

tBu

O

HCl

R1 R2

OH

Ph

Cl S

NtBu

O

N H

O

N Cl

O

Catalytic Cycle of 2

Matano and his group are developing an oxidation method of alcohols using hypervalent organobismuth compounds.3) This reaction progresses as shown below, and yields the desired carbonyl compounds in excellent yields. Cl Ar

Bi Cl

t

Ar

Ar2BiOBiAr2

Ar

H2 O

x2

BuOK H2O

R1 R2

[Ar3Bi=O]

H

O

Ar R1

Bi OH

[Ar2BiOH] Ar Ar

R1 O + ArH

OH R2

R2

R1 R2 Ar3BiCl2 DBU

H

O

Ar

Bi Cl

DBU

Ar Ar2BiCl

Ar

[DBUH] [Cl]

Cl Ar

Bi Cl

Ar [DBUH] [Ar2BiCl2]

Ar

This reaction has fairly high reactivity, and the reactions are completed at room temperature within a short period of time. Matano and co-workers are conducting comparative oxidation studies on the selectivity of the Dess-Martin periodinane and tris(2-methoxyphenyl)bismuth dichloride 3 upon conjugated alcohols and unconjugated alcohols. Ar3BiCl2/DBU

RR'CHOH + EtOH

or Dess-Martin Reagent CDCl3, rt,15 min

Ar=o-MeOC6H5 3

RR'C=O + MeCHO

RR'CHOH Ph Ph

OH OH

Ratio of RR'C=O to MeCHO Dess-Martin Reagent

Ar3BiCl2/DBU 98 : 2

91 : 9

96 : 4

90 : 10

95 : 5

75 : 25

Me Ph

OH

According to their studies, 3 has higher selectivity over Dess-Martin periodinane upon conjugated alcohols. 3 is becoming recognized as a non-explosive, non-toxic, highly reactive and selective oxidizing agent. Recently, Katsuki and co-workers reported that the oxidation method of alcohols using (nitrosyl)Ru-Salen complex as a catalyst. This catalyst is activated by photo-irradiation and can be used to oxidize primary alcohols to aldehydes selectively.4) This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

91

New Oxidation of Primary & Secondary Alcohols

CHO

OH catalyst, hν, air

+

OH

quant.

d6-benzene, rt, 12 h CH3 CH3 CH3 N

O

0%

CH3 NO N Ru

catalyst = (CH3)3C

O

Cl O

C(CH3)3

C(CH3)3 (CH3)3C

B2240

B2188

C1944

CH3 S

CH3

NH C CH3

Cl

H3C CH3 H3C CH3 N NO N Ru O C(CH3)3 (CH3)3C O Cl C(CH3)3 (CH3)3C

S N C CH3

CH3

CH3

T1956

T2038

Bi

Cl

OCH3

CF3

Bi

Bi

T1837 T2507 T1956 T2038 T1957

BF4

Bi

Cl CH3

CH3

Cl CF3

CH3

Product No. Product Name B2240 B2188 C1944

CH3

Cl

CH3 Cl Bi

Cl

Cl OCH3

T2507

T1957 CF3

CH3O Cl

T1837

N-tert-Butylbenzenesulfenamide N-tert-Butylbenzenesulfinimidoyl Chloride Chloronitrosyl[N,N '-bis(3,5-di-tert-butylsalicylidene)-1,1,2,2-tetramethylethylenediaminato]ruthenium(IV) Triphenylbismuth Dichloride Triphenyl-2,6-xylylbismuthonium Tetrafluoroborate Tris(2-methoxyphenyl)bismuth Dichloride Tris(4-trifluoromethylphenyl)bismuth Dichloride Tri-o-tolylbismuth Dichloride

Unit Size 1g

5g 1g

25g 5g

100mg 5g 100mg 1g 1g 5g 1g 1g 5g

References 1) T. Mukaiyama, J. Matsuo, M. Yanagisawa, . 2000, 1072; T. Mukaiyama, J. Matsuo, H. Kitagawa, . 2000, 1250; J. Matsuo, H. Kitagawa, D. Iida, T. Mukaiyama, . 2001, 150; J. Matsuo, D. Iida, K. Tatani, T. Mukaiyama, . 2002, , 223; K. Tahara, 2002, , 708; Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2002 37753, 2002. 2) T. Mukaiyama, J. Matsuo, D. Iida, H. Kitagawa, . 2001, 846; J. Matsuo, D. Iida, H. Yamanaka, T. Mukaiyama, 2003, , 6739; Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2002 026627, 2002. 3) Y. Matano, H. Nomura, . 2002, , 3028; Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2003 113130, 2003; Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2005 023052, 2005. 4) A. Miyata, M. Murakami, R. Irie, T. Katsuki, . 2001, , 7067.

92

Availability, price or specification of the listed products are subject to change without prior notice.

Oxidation

Oxidation Oxidation, making its target substance lose electrons, is one of the most basic reactions in organic chemistry and is exemplified by the combination with oxygen or a dehydrogenation reaction. In particular, it is often used for the transformation of alcohols to the corresponding aldehydes, ketones or carboxylic acids. Heavy metal compounds, such as chromium (VI) oxide and potassium permanganate, have been exploited for many years. Especially, chromium (VI) oxide has been utilized abundantly, based on the report of the control of oxidization powers by Jones or Sarett.1) Furthermore, chromium (VI) oxide have been improved as the Collins reagent2), PCC3) and PDC4) and are used in many fields. On the other hand, the Dess-Martin periodinane5), the Mukaiyama oxidizing agent6) and oxoammonium salts have been developed without containing harmful metals. Moreover, oxidation reactions employing inexpensive sodium hypochlorite or molecular oxygen have also been reported in the presence of oxidation catalysts such as tetrapropylammonium perruthenate (TPAP)7) and TEMPO8). This section shows the typical oxidizers and the catalysts used for oxidation reactions.

B2134

B1375

B1123

O Se

OH

Metal Oxidants

L0021 H3C CH3 H3C CH3 N NO N Ru O C(CH3)3 (CH3)3C O Cl C(CH3)3 (CH3)3C

N H

N

C O

2

L0021

12MoO3 . H3PO4

. xH2O

Q0058

N H

2

N Bu

FCrO3

N H

Cr2O722

Bu

Pr ReO4

Pr

N Pr

RuO4

Pr

Product No. Product Name B2134 B1375 B1123 C1944

2

T1559

Bu Bu

OsO4

Pb

P1088

N H

Cr2O7 2

N Bu

4

Cr2O72

ClCrO3

T1803

Ag2

Bu

P1910

O

P0931

KMnO4

O

OCH3

O0308

CH3 C O

P0930

S0815

Se

Bu

C1944

P1742

Bu

O CH3O

Benzeneseleninic Acid Bis(4-methoxyphenyl) Selenoxide Bis(tetrabutylammonium) Dichromate Chloronitrosyl[N,N '-bis(3,5-di-tert-butylsalicylidene)-1,1,2,2-tetramethylethylenediaminato]ruthenium(IV) Lead Tetraacetate (contains Acetic Acid)

Unit Size 5g 1g

25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 5g 10g 100mg 500g

93

Oxidation

Product No. Product Name O0308 P1910 P1742 P0930 P0931 P1088 Q0058 S0815 T1803 T1559

Unit Size

Osmium Tetroxide (4% in Water) Phosphomolybdic Acid Hydrate Potassium Permanganate Pyridinium Chlorochromate Pyridinium Dichromate Pyridinium Fluorochromate Quinolinium Dichromate Silver(II) Picolinate Tetrabutylammonium Perrhenate Tetrapropylammonium Perruthenate

25g

10ml 100g 300g 500g 500g 5g 10g 1g 5g 5g

100g 25g

1g 1g

B2897

D3428

D3429

CH3

CH3

CH3

CH3

Perchlorates N

N ClO4

CH3

M1774

M2072

M1775

N

ClO4

CH3

T0836

CH3

T0839

CH3

CH3

ClO4

CH2CH3

Bu CH3

ClO4

CH3

CH3

CH3

CH3

Bu

CH3

N Bu

CH3CH2 N CH2CH3 ClO4

ClO4

CH2CH3

Bu N CH3

N

N CH3

ClO4

ClO4

CH3

T0841

CH3 CH3 N CH3

ClO4

CH3

Product No. Product Name B2897 D3428 D3429 M1774 M2072 M1775 T0836 T0839 T0841

Unit Size

9-(2-Biphenylyl)-10-methylacridinium Perchlorate 9-(2,5-Dimethylphenyl)-10-methylacridinium Perchlorate 9-(2,6-Dimethylphenyl)-10-methylacridinium Perchlorate 9-Mesityl-10-methylacridinium Perchlorate 9-Mesityl-2,7,10-trimethylacridinium Perchlorate 10-Methyl-9-phenylacridinium Perchlorate Tetrabutylammonium Perchlorate Tetraethylammonium Perchlorate Tetramethylammonium Perchlorate

B3152

94

1g 25g

B3497

O

Organic Peroxides

1g 1g 1g 1g

B3153

CH3

O

C O O C

CH3

5g 5g 5g 5g 1g 5g 500g 25g 25g

Si CH3

CH3

CH3 O O Si

CH3

CH3

Availability, price or specification of the listed products are subject to change without prior notice.

CH3 C OOH CH3

Oxidation

C2223

C2392 C0357

D3411

M0927

O

O

CH3

CH3

C OOH

CH3

C O Mg2+

CH3 C O O C CH3

C OOH

CH3

CH3

CH3

. 6H2O

C OOH

Cl

2

O

Product No. Product Name B3152 B3497 B3153 C2392 C0357 C2223 D3411 M0927

Unit Size

Benzoyl Peroxide (wetted with ca. 25% Water) Bis(trimethylsilyl) Peroxide (contains Hexamethyldisiloxane) (ca. 30% in Hexane) tert-Butyl Hydroperoxide (70% in Water) 3-Chloroperoxybenzoic Acid (contains min. 17% Water and min. 6% 3-Chlorobenzoic Acid) 3-Chloroperoxybenzoic Acid (contains ca. 30% Water) Cumene Hydroperoxide (contains ca. 20% Aromatic Hydrocarbon) Di-tert-butyl Peroxide Monoperoxyphthalic Acid Magnesium Salt Hexahydrate

B1175

B1616 O

O CF3

C O

I

O C CF3

B2121

C O

Hypervalent Iodine Compounds

100g 25g

25g

O

O CF3

25g

25g 5g 100g 500g 250g 100g 100ml 500g

I

O C CF3

F

F

F

F

CH3 CH3 C OO

I

O

CH3

O

F

D2045

P1015

I0330

I0479

I0072 O

AcO OAc O AcO I

O

O HO

I

CH3

O S

CH3 C O

O

O

O I

O C CH3

CH3 C O

O I

O C CH3

I

O

CH3

CH3

n

CH3

I0073

P1415 HO

I

O

O

O C CH3

O

P

I O C CH3 O

Product No. Product Name B1175 B1616 B2121 D2045 P1015 I0330 I0479 I0072 I0073 P1415

[Bis(trifluoroacetoxy)iodo]benzene [Bis(trifluoroacetoxy)iodo]pentafluorobenzene 1-(tert-Butylperoxy)-1,2-benziodoxol-3(1H)-one Dess-Martin Periodinane [Hydroxy(tosyloxy)iodo]benzene Iodobenzene Diacetate Iodomesitylene Diacetate Iodosobenzene 2-Iodosobenzoic Acid Poly[4-(diacetoxyiodo)styrene]

Unit Size 5g

1g 10g

5g 5g 25g 5g

1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 1g 1g 25g 25g 250g 25g 5g 10g 5g

95

Oxidation

D3219

D3220

L0069 N(CH3)2

Cl

-Oxides

N

Cl

CH3

. xH2O

N O

P0557

T0466

CH3 O

T1362 CH3

N N O

CH3 N CH3

CH3

. 2H2O

CH3

N CH3 O

O

O

Product No. Product Name D3219 D3220 L0069 M0981 P0557 T0466 T1362

Unit Size

2,6-Dichloropyridine N-Oxide 4-(Dimethylamino)pyridine N-Oxide Hydrate 2,6-Lutidine N-Oxide 4-Methylmorpholine N-Oxide (50% in Water, ca. 4.8mol/L) Pyridine N-Oxide Trimethylamine N-Oxide Dihydrate Trimethylamine N-Oxide Anhydrous

A1348

1g 25ml 25g 25g 1g

H0878 O

HN C CH3 CH3 CH3

N

OCH3

O C

CH3

CH3

CH3

CH3

O

5g 5g 25g 500ml 500g 500g 5g

M1197

O

TEMPOs

CH3

O

O

M0981

N

CH3

CH3 N

CH3

CH3

CH3

N

CH3

O

O

T1560

CH3 CH3

CH3 N

CH3

O

Product No. Product Name A1348 H0878 M1197 T1560

Unit Size

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Benzoate Free Radical 4-Methoxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical 2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical

T1837

5g 1g 1g 5g

T2507

T1956 CH3

Cl

Organic Bismuth Compounds

Bi

CH3O Cl BF4

Bi

Cl CH3

96

25g 5g 5g 25g

Availability, price or specification of the listed products are subject to change without prior notice.

Bi Cl OCH3

OCH3

Oxidation

T2038

T1957 CF3

CH3 Cl

Cl CF3

Bi

CH3

Bi

Cl

Cl CF3

CH3

Product No. Product Name T1837 T2507 T1956 T2038 T1957

Unit Size

Triphenylbismuth Dichloride Triphenyl-2,6-xylylbismuthonium Tetrafluoroborate Tris(2-methoxyphenyl)bismuth Dichloride Tris(4-trifluoromethylphenyl)bismuth Dichloride Tri-o-tolylbismuth Dichloride

5g 1g 5g 1g 5g

100mg 1g 1g

A2065

B2151

T0617

O

O

NH C CH3 CH3

CH3

Others

CH3

N O

B0656

B2240

O

N

Bu

Br

2

Br O

BF4

C1326 CH3

CH3

CH3

H3C O

S N C CH3

H3C C C Cl

N

H3C

Br

C1327

C1806 CH3

Br

S2O8 2

N Bu

CH3 Cl

CH3

O

Br

H0362

CH3 NH C CH3

Bu

CH3

B2188

S

Bu

C0076

T0061

T0970

Cl

CH3

S O O O

SO2NNa

O Cl

O Cl

Cl

Cl

Cl

O

(NH4)2Ce(NO3)6

N O S O O

D0318

. 3H2O

Cl

I0074

O0310

Cl

O

CH3

Cl

P0998

T1559

SO2NCl2

O

N I

O

. SO3

2KHSO5 . KHSO4. K2SO4

Pr Pr

N

N Pr

RuO4

Pr

CH3

Product No. Product Name A2065 B2151 T0617 B0656 B2240 B2188 H0362 C1326 C1327 C1806 C0076 T0061 T0970 D0318

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate Bis(tetrabutylammonium) Peroxydisulfate Bromanil N-Bromosuccinimide N-tert-Butylbenzenesulfenamide N-tert-Butylbenzenesulfinimidoyl Chloride tert-Butyl Hypochlorite (2R,8aS)-(+)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent] (2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent] Ceric Ammonium Nitrate Chloramine T Trihydrate Chloranil o-Chloranil Dichloramine T

Unit Size

25g 1g

5g 5g 100g 5g 1g 25g 1g 1g 50g 25g 25g 5g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 25g 25g 500g 25g 5g 500g 5g 5g 500g 500g 500g 25g 500g

97

Oxidation

Product No. Product Name N-Iodosuccinimide Potassium Peroxymonosulfate [>45%(T) as KHSO5] Pyridine - Sulfur Trioxide Complex Tetrapropylammonium Perruthenate

I0074 O0310 P0998 T1559

Unit Size 5g

25g 25g 25g 1g

100g 500g 500g 5g

Many oxidizing agents may cause combustion or explosion upon mixture with flammable materials or upon exposure to heat, shock, and friction etc. Sufficient safety measures, such as using safety shields, wearing protective equipment, and using extreme caution should be taken when working with these reagents as well as disposing of the reagents.

References 1) K. Bowden, I. M. Heilbron, E. R. H. Jones, . 1946, 39; Review: S. V. Ley, A. Madin, 1991, , 253. 2) J. C. Collins, W. W. Hess, F. J. Frank, . 1968, , 3363. 3) E. J. Corey, J. W. Suggs, . 1975, , 2647. 4) E. J. Corey, G. Schmidt, . 1979, , 399. 5) D. B. Dess, J. C. Martin, . 1983, , 4155; R. E. Irekand, L. Liu, . 1993, , 2899. 6) J. Matsuo, D. Iida, K. Tatani, T. Mukaiyama, . 2002, , 223. 7) W. P. Griffith, S. V. Ley, G. P. Whitcombe, A. D. White, . 1987, 1625; Review: S. V. Ley, J. 1994, 639. Norman, W. P. Griffith, S. P. Marsden, 8) O. L. Lebelev, S. N. Kazarnovskii, . 1960, , 1631; Review: A. E. J. de Nooy, A. C. Besemer, H. van 1996, 1153. Bekkum,

98

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Reduction

Reduction Reduction is a chemical reaction in which the target substances receive electrons, and is one of the most fundamental reactions in organic chemistry including the deoxygenation reaction and the hydrogenation reaction. The well-known reducing agents include metal hydrides such as LiAlH41) , boranes used in the hydride reduction, and hydrazine used in the Wolff-Kishner reduction.2) Sodium tris(1,1,1,3,3,3-hexafluoroisopropoxy)borohydride (1) is a selective reducing agent developed by Toshima . Aldehydes are selectively reduced in the presence of ketones and other reducible functions using 1 to afford the corresponding primary alcohols in high yields.3) OCH(CF3)2 1:

H B OCH(CF3)2

Na

OCH(CF3)2 O

OTBS

CH3

O

1 / THF (3 eq.) CHO

Hexafluoroisopropanol, 25 °C, 1.5 h

OTBS OH

CH3 Y. 94%

In addition, the radical reductive reaction using silane compounds tris(trimethylsilyl)silane4) and tetraphenyldisilane (TPDS)5) as radical reducing agents has been developed avoiding the use of highly toxic tin compounds. This section shows the typical reducing agents. Table. Comparison of reactivities of hydride reducing agents for carbonyl compounds and imines Reagents

NaBH(OCOCH3)3 S0394

Reactions

Reactivity :

High

THF・BH3 T2346

NaBH3CN S0396

Middle

NaBH4 S0480

LiBH4 L0186

LiAlH4 L0170, L0203

Me2S・BH3 D1843 PhNEt2・BH3 D2581

Low

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

99

Reduction

D2971 D2972

L0159

LiAlH4

[(CH3)2CHCH2]2AlH

Aluminum Hydrides

Metal Hydrides

L0170 L0203

S0467

OC(CH3)3 Li

H Al

OC(CH3)3

NaAl(OCH2CH2OCH3)2H2

OC(CH3)3

Product No. Product Name D2971 D2972 L0170 L0203 L0159 S0467

Unit Size

Diisobutylaluminum Hydride (19% in Hexane, ca. 1.0mol/L) Diisobutylaluminum Hydride (17% in Toluene, ca. 1.0mol/L) Lithium Aluminum Hydride (10% in Tetrahydrofuran, ca. 2.5mol/L) Lithium Aluminum Hydride (Powder) Lithium Tri-tert-butoxyaluminum Hydride (20% in Tetrahydrofuran, ca. 0.7mol/L) Sodium Bis(2-methoxyethoxy)aluminum Dihydride (70% in Toluene, ca. 3.6mol/L)

T1473

25g 25g

(CH2)7CH3 CH3(CH2)7 Sn

CH3(CH2)3 Sn H

H

(CH2)7CH3

(CH2)3CH3

Product No. Product Name T1473 T1572

Unit Size

Tributyltin Hydride (stabilized with BHT) Tri-n-octyltin Hydride

S0481

25g

H

Zr

Product No. Product Name S0481 Z0010

100

250g 10g

Z0010

NaH

Other Metal Hydrides

500ml 500ml 100ml 100g 100ml 500g

T1572

(CH2)3CH3

Tin Hydrides

100ml 100ml

Sodium Hydride (60%, dispersion in Paraffin Liquid) Zirconocene Chloride Hydride

Cl

Unit Size 1g

5g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

100g 25g

Reduction

B1139

L0186

L0164

P 3

Borohydrides

Cu

CH(CH3)CH2CH3

. BH4

LiBH4

Li

H B CH(CH3)CH2CH3 CH(CH3)CH2CH3

P 3

P1681

P1380

S0480

CH3

KBH4

CH3CH2CH

S0810

3

BH

OCH(CF3)2 Bu

OCH(CF3)2

N Bu

CH3 N CH3

CH3 BH4

OAc

CH3 N CH3 AcO B H CH3

CH3

Bu

NaBH(OCOCH3)3

T1553

CH3 BH4

S0394

NaBH3CN

T0852

Bu Na

H B OCH(CF3)2

NaBH4

K

T0917

S0396

OAc

Product No. Product Name B1139 L0186 L0164 P1681 P1380 S0480 S0396 S0394 S0810 T0917 T0852 T1553

Unit Size

Bis(triphenylphosphine)copper Tetrahydroborate Lithium Borohydride (ca. 3mol/L in Tetrahydrofuran) Lithium Tri-sec-butylborohydride (21% in Tetrahydrofuran, ca. 1.0mol/L) Potassium Borohydride Potassium Tri-sec-butylborohydride (ca. 1.0mol/L in Tetrahydrofuran) Sodium Borohydride Sodium Cyanoborohydride Sodium Triacetoxyborohydride Sodium Tris(1,1,1,3,3,3-hexafluoroisopropoxy)borohydride Tetrabutylammonium Borohydride Tetramethylammonium Borohydride Tetramethylammonium Triacetoxyborohydride

100g 25g 25g 5g 5g 5g

B1827

T2346

CH3

CH3

CH3 C S(CH2)2S

Borane Complexes

Boranes

D2581

5g 100ml 100ml 100g 100ml 500g 250g 100g 5g 25g 25g 25g

CH3

. 2BH3

.

C CH3 CH3

BH3

O

D1843

CH2CH3 N

.

BH3

CH3SCH3

. BH3

CH2CH3

Product No. Product Name B1827 T2346

1,2-Bis(tert-butylthio)ethane Borane Borane - Tetrahydrofuran Complex (8.5% in Tetrahydrofuran, ca. 0.9mol/L)

D2581 D1843

N,N-Diethylaniline Borane Dimethyl Sulfide Borane

(stabilized with Sodium Borohydride)

Unit Size 1g 100ml 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500ml 100g 25ml

101

Reduction

B1264

B3018

CH3

Borane-Amine Complexes D1842

CH3 C NH2

N

CH3

T1180

. BH3

B1569 H N

. BH3

. BH3 CH3

. BH3

. BH3 N

O

T1181

CH2CH3 CH3NHCH3

M0898

CH3

. BH3

CH3CH2 N

CH3 N

. BH3

CH3

CH2CH3

Product No. Product Name B1264 B3018 M0898 B1569 D1842 T1180 T1181

Unit Size

Borane - tert-Butylamine Complex Borane - 2-Methylpyridine Complex Borane - Morpholine Complex Borane - Pyridine Complex Dimethylamine Borane Triethylamine Borane Trimethylamine Borane

C1614

5g 5g 25ml 25g

C2023 C1615 CH3

CH3 B Cl

Other Boranes

CH3

B Cl CH3

CH3

CH3

2

2

Product No. Product Name C1614 C2023 C1615

Unit Size

(+)-B-Chlorodiisopinocampheylborane (58% in Hexane, ca. 1.6mol/L) (-)-B-Chlorodiisopinocampheylborane (60% in Heptane, ca. 1.7mol/L) (-)-B-Chlorodiisopinocampheylborane (60% in Hexane, ca. 1.7mol/L)

C1492

100ml 100ml 100ml

C0778

D2403

CH(CH3)2

Silanes

CH3CH2SiH2CH2CH3

Si H

Si H OCH2CH3

P1291

CH3

H

Si H

Si

SiH2

CH3

CH3

D1825

D2406 D2820

CH3

102

Cl

CH(CH3)2

D2196

OCH2CH3

CH3

H Si Cl

D3761

25g 25g 25g 250ml 500g 25g 25g

SiH3

CH3

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Reduction

T1437

T1896

CH3 CH3

T0398

O Si

H

H

CH3

T1533

H Si Si

Si

H

H

i

(CH2)5CH3 CH3(CH2)5 Si H

CH2CH3

(CH2)5CH3

T1463

Si(CH3)3

Pr

Si

CH3CH2 Si H

Cl

Cl

T0661

T1334

CH2CH3

Cl

CH3

Si

i Pr

T0662

H

Si

H

(CH3)3Si

Si H Si(CH3)3

i Pr

Product No. Product Name C1492 C0778 D2403 D3761 D2196 D2406 D2820 D1825 P1291 T1437 T1896 T0398 T0662 T1334 T1533 T0661 T1463

Unit Size

Chlorodiisopropylsilane Chlorodimethylsilane Diethoxymethylsilane [Hydrosilylating Reagent] Diethylsilane Dimethylphenylsilane Diphenylsilane Diphenylsilane Methyldiphenylsilane Phenylsilane 1,1,3,3-Tetramethyldisiloxane 1,1,2,2-Tetraphenyldisilane Trichlorosilane Triethylsilane Trihexylsilane Triisopropylsilane Triphenylsilane Tris(trimethylsilyl)silane (stabilized with TBBP)

5ml 25ml 5ml 5g 5g

5g

5ml

H0174

H2NNH2 .2HBr

. xH2O

H2NNH2 .2HCl

I0777 SO2NH N C

H2NNH2 . HBr

H0170

H0169

H2NNH2 . H2O

H0173

25ml 5ml

H0172 H0204 H0697

Hydrazines

5ml 25ml 1g 25g 25ml

25ml 250ml 25ml 25ml 25ml 25g 25g 25ml 25ml 250ml 5g 500g 250ml 10g 100ml 25g 25ml

H2NNH2

. HCl

NO2

CH3 CH3

Product No. Product Name

Unit Size

H0172 H0204 H0697 H0169 H0170 H0173

25ml 25g 10g 25g 25g 25g

Hydrazine Monohydrate Hydrazine Monohydrate (79%) Hydrazine Anhydrous Hydrazine Dihydrobromide Hydrazine Dihydrochloride Hydrazine Monohydrobromide

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500ml 500g 100g 500g 500g 500g

103

Reduction

Product No. Product Name H0174 I0777

Unit Size

Hydrazine Monohydrochloride N '-Isopropylidene-2-nitrobenzenesulfonohydrazide

25g

D3775

H1221

S0494

O

O CH3CH2O C

C OCH2CH3

SmI2

HI

Others

CH3

T0430

T0488

500g 5g

N H

CH3

T0519

T1819

CH3 OCH3 O CH3

O

P

CH3O O

P

P

Se

CH3

Product No. Product Name D3775 H1221 S0494 T0430 T0488 T0519 T1819

P

OCH3

Diethyl 1,4-Dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate Hydriodic Acid (57%) Samarium(II) Iodide (ca. 0.1mol/L in Tetrahydrofuran) Triethyl Phosphite Trimethyl Phosphite Triphenylphosphine Triphenylphosphine Selenide

Unit Size 1g

5g

25ml 25ml 25g

25g 300ml 25ml 500ml 500ml 500g 5g

Many reducing agents may spontaneously ignite on contact with air, or may react violently with water to produce flammable gases. Sufficient safety measures, such as using safety shields, wearing protective equipment, and using extreme caution should be taken when working with these reagents as well as disposing of the reagents.

References 1972, 217. 1) Review: J. Malek, M. Cerny, 2) Review: N. Kishner, . 1911, , 582; L. Wolff, . 1912, , 86; R. O. Hutchins, M. K. 1991, , 327. Hutchins, 2008, 3) Y. Kuroiwa, S. Matsumura, K. Toshima, , 2523. 4) C. Chatgilialoglu, D. Griller, M. Lesage, . 1988, , 3641. 5) O. Yamazaki, H. Togo, S. Matsubayashi. M. Yokoyama, . 1998, , 1921.

104

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Mitsunobu Reaction

Mitsunobu Reaction O O O O H H EtO C N N C OEt EtO C N N C OEt O

R1 OH R2

+

O

R1

R3 C OH

O C R3 R2 O PPh3

PPh3

The Mitsunobu reaction is a unique dehydration-condensation reaction between alcohols and various nucleophiles using the redox system comprised of diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP).1) The reactions proceed under mild conditions, and a wide variety of compounds can be used as nucleophiles, for example, carboxylic acids, active methylenes, imides, thiols, etc. The reaction between secondary alcohols and nucleophiles yields products with Walden inversion. The Mitsunobu reaction has been used widely in organic synthesis. Due to its utility, efforts have been made to expand application of the Mitsunobu reaction, and modified reactions have been reported.2) For example, by using azodicarboxamides instead of azodicarboxylates the Mitsunobu reaction is being applied to weak-acidity nucleophiles with a higher p a value.3) Methods have been reported for the easy removal of phosphine oxide, a reaction by-product, by utilizing phosphines which have an intramolecular basic component4) and diphenylphosphino polystyrene resin.5) The modified method using a catalytic amount of DEAD and a stoichiometric amount of PhI(OAc)2 as a reoxidizing reagent has also been reported, which makes it possible to dramatically reduce the hydrazine byproduct.6) Moreover, the DEAD-TPP reaction system is generally not applicable to sterically-hindered tertiary alcohols. Mukaiyama and Kuroda . have reported the modified method using phenoxydiphenylphosphine (1), instead of TPP. In this system, condensation of tertiary alcohols and 2-nitrobenzoic acid affords the corresponding ester with inversion of the configuration as shown below.7) O2N NO2 Me Et

PhOPPh2 1

OH

O

DEAD

+

CO2Bn

COOH Toluene, rt

Me

O

Et

CO2Bn Y. 52%, 96% e.e.

In 1994, Tsunoda and co-workers reported a new Mitsunobu reagent, cyanomethylenetributylphosphora ne (2).8) This reagent alone can achieve the functions of DEAD and TPP. It is shown to be very effective in the reaction of secondary alcohols and active methylene of p a value above 23.4. Accordingly, 2 is a reagent which increases the usefulness of the Mitsunobu reaction. Bu

MeS

SO2Tol

+ OH

Bu P Bu

CH

CN 2

Benzene, 150 °C

pKa 23.4 Tol = Tolyl

MeS

SO2Tol

Y. 88 %

A1458

A1051

O

Azodicarboxylates & Amides

Me2N

O

O

C N N C

A1332

NMe2

O

N C N N C N

O

O

Cl3CH2CO C N N C OCH2CCl3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

105

Mitsunobu Reaction

A0776

D3544

O

A0705

O

O

BnO C N N C OBn

t

O

O

BuO C N N C Ot Bu

A1246

O

A0882

O iPrO

EtO C N N C OEt

O

O

C N N C OiPr

Product No. Product Name A1458 A1051 A1332 A0776 D3544 A0705 A1246 A0882

O

MeO C N N C OMe

Unit Size

1,1'-Azobis(N,N-dimethylformamide) 1,1'-(Azodicarbonyl)dipiperidine Bis(2,2,2-trichloroethyl) Azodicarboxylate Dibenzyl Azodicarboxylate (40% in Dichloromethane, ca. 1.7mol/L) Di-tert-butyl Azodicarboxylate (20% in Toluene) Diethyl Azodicarboxylate (40% in Toluene, ca. 2.2mol/L) Diisopropyl Azodicarboxylate (40% in Toluene, ca. 1.9mol/L) Dimethyl Azodicarboxylate (40% in Toluene, ca. 2.7mol/L)

D2411

1g

5g 5g

25g 25g 5g 25g 25g 250g 250g 25g

25g 25g

D1019

D2478

Et

Phosphines (Mitsunobu Reaction)

D2766

D2471

(CH3)2N

P

P

P

Et

I0583

P1843

T0361

Bu

CH3 CH2

P

P

P

T1165

t t

Bu

P

T0503 (CH2)5CH3

P t Bu

CH3(CH2)5 P (CH2)5CH3

T0519 (CH2)7CH3

CH3(CH2)7 P

P

(CH2)7CH3

Product No. Product Name D2411 D1019 D2478 D2766

P Bu

T1005

Bu

P

Bu

O P

CH3

N

T1912

CH

Dicyclohexylphenylphosphine Diethylphenylphosphine 4-(Dimethylamino)phenyldiphenylphosphine 4-Diphenylphosphinomethyl Polystyrene Resin cross-linked with 2% DVB (200-400mesh)

Unit Size 1g 1ml 1g

(0.5-1.0mmol/g)

D2471 I0583 P1843 T0361 T1912 T1165 T1005 T0503 T0519

106

Diphenyl-2-pyridylphosphine Isopropyldiphenylphosphine Phenoxydiphenylphosphine Tributylphosphine Tri-tert-butylphosphine Tricyclohexylphosphine (contains Tricyclohexylphosphine Oxide) (ca. 18% in Toluene, ca. 0.60mol/L) Trihexylphosphine Tri-n-octylphosphine Triphenylphosphine

1g 5g 25ml 25ml 25ml 25g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

5g 5ml 5g 5g 1g 5g 25g 500ml 5g 500ml 25ml 500ml 500g

Mitsunobu Reaction

C1500

Bu

Modified Mitsunobu Reaction (Tsunoda Reagent) Product No. Product Name C1500

Cyanomethylenetributylphosphorane

Bu

P CH CN Bu

Unit Size 1g

5g

25g

On exposure to heat, impact, friction, etc., azodicarboxylic acid derivatives are prone to highly exothermic reaction or explosive decomposition. Sufficient safety measures, such as usage of safety shield, wearing of protective equipment, and extreme caution should be taken, when using these compounds, from the opening up to the disposal of the reagents.

References 1981, 1. 1) O. Mitsunobu, 2001, 1999, number 2) S. Ito, , 567; T. Onozawa, , 10. 3) T. Tsunoda, Y. Yamamiya, S. Ito, . 1993, , 1639; T. Tsunoda, J. Otsuka, Y. Yamamiya, S. Ito, . 1994, 539; S. Ito, T. Tsunoda, . 1994, , 2071; T. Tsunoda, Y. Yamamiya, Y. Kawamura, S. Ito, 1999, . 1995, , 2529; K. Tahara, T. Onozawa, , 633. 4) L. D. Arnold, H. I. Assil, J. C. Vederas, . 1989, , 3973; A. R. Tunoori, D. Dutta, G. I. Georg, . 1998, , 8751. 5) R. A. Amos, R. W. Emblidge, N. Havens, . 1983, , 3598. 6) T. Y. S. But, P. H. Toy, . 2006, , 9636. 7) K. Kuroda, Y. Maruyama, Y. Hayashi, T. Mukaiyama, . 2008, , 836; K. Kuroda, Y. Maruyama, Y. Hayashi, T. Mukaiyama, . 2009, , 381; T. Mukaiyama, K. Kuroda, Y. Mukaiyama, Y. Hayashi, . 2008, 2010, , 1072; Review: T. Mukaiyama, K. Kuroda, Y. Maruyama, , 63. 8) T. Tsunoda, M. Nagaku, C. Nagino, Y. Kawamura, F. Ozaki, H. Hiroki, S. Ito, . 1995, , 2531; T. Tsunoda, F. Ozaki, N. Shirakata, Y. Tamaoka, H. Yamamoto, S. Ito, . 1996, , 2463.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

107

Condensation & Active Esterification

Condensation & Active Esterification The synthesis of carboxylic esters is one of the most fundamental and important processes for producing useful compounds in organic chemistry. The classical esterification reaction is condensation of a carboxylic acid and an alcohol under acidic conditions. This is an equilibrium reaction, and in order to effectively generate the ester, the equilibrium need to be shift toward the ester. To achieve this equilibrium shift requires adding one of the substrates in large excess and the removal of the generated water by distillation. However, when both carboxylic acid and alcohol are expensive and not easily available, it is not economical to use one of the substrates in large excess. Thus the classical esterification method is not the best method to use in such a case. Furthermore, when the substrate is unstable to heat, the classical method does not always yield the desired results. Since esterification is a basic reaction that is applied to many different types of substrates, there is a need for alternative methods which proceed under mild conditions without the need for using large excess of one of the substrates. Over the years, there has been much research done by many chemists, and many useful methods have been reported. NO2 O

O

NO2

O Me Me 1 (1.1 eq.)

O R1

OH

+

(1.0 eq.)

R2OH

NO2 O

O R1

Et3N (1.1 eq.), DMAP (0.1 eq.), rt

OR2

OR2

+ Me

(1.1 eq.)

Ester A R1COOH Ph(CH2)2 Ph(CH2)2 Ph(CH2)2 Ph(CH2)2

Ester B

R2OH

Y. %

Ester A / Ester B

95 98 92 94

>200 >200 >200 >200

PhCH2 THPO(CH2)5 CH2=CHCH2 C9H19C(CH3)2

Recently, Shiina and co-workers have reported a method using 2-methyl-6-nitrobenzoic anhydride (1). This esterification procedure is quite simple. Triethylamine, a catalytic amount of 4-dimethylaminopyridine, and 1 were dissolved in a solvent. The carboxylic acid was added and stirred, and finally a nearly equimolar amount of alcohol was added and the reaction stirred under room temperature. Through this reaction process, the desired ester (ester A) is obtained in high yields. The nitro group on the condensation reagent 1 promotes and facilitates the esterification under room temperature. The introduction of substituents at the two ortho positions of benzene ring controls the generation of byproduct (ester B). These two effects synergistically act to produce the desired ester in excellent yield and high purity. This reaction can also be applied to intramolecular esterification, and can afford lactones in high yields.

A1861

B1774

B1651 N

N N

N

N

O C

BF4 N(CH3)2

N

N

O

P N

CH3

108

N

N

N(CH3)2

N

N

N

N

O O

CH2 N C N CH2

O

N

PF6

O C

OP[N(CH3)2]3

B1213

O

B1658

PF6

N

B2771

CH3

B1657

CH3

O

F

N

PF6

Cl

N

O C

N(CH3)2

N(CH3)2 N(CH3)2

B1036 F

F

F

F

F

O

N P N O

N(CH3)2

B3604 O

CH3

N

O O

F

O C O F

F

F

N

Br

CH2CH3

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

BF4

BF4

Condensation & Active Esterification

B0832

C1124

C1298

CH3

O

C CH3 ClO4

O

CH2O C O N

CH2O C O N

O

O

Cl O Cl

CH3

CH3

C0119

C1988

O

Cl

N C N

N

O C

C0905

O

C0903

N

N

Cl

N

CH3

C0906

CH3 O

CH3

Cl

O

O

O

CH3

N

CH2O C O N

PF6

N(CH3)2 N(CH3)2

N N

C

C1651

O

N

O

O

C1408 C1639

Cl

N

N

Cl

C1131

N

O O

N

O C O C CH3 CH3

CH3

N

C1362

O

Br

O O

CH3

N

C1574

PF6

Cl

CH3

C1379

C1375

SO3 CH2CH3

N

BF4 O

N

I

Cl

N

CH3

C1957

CH3

N

Cl

CH3

N

N

CH3

C1242

O

CH3

N

SO3

D0254

N

D2919

CH3

N O

N

D1601

F NH2

CH3

CH3

D1450

SO3

CH3

CH3 N C N

N

OCH2CH3

D3293

O OH

OCH2CH3

O P

N

N

D1393

N

O

N C N

O

NC P OCH2CH3 OCH2CH3

BF4

D3262

C N

N

D2039

O

N

C Cl

D0436

CH2CH2N

CH3

P CH CN Bu

Cl

N

PF6

CH3

C0793

Bu Bu

PF6

N

C Cl

CH3

C1500

CH3

Cl

CH3

CH3

D2898

F

F

2

F F

D2899

OCH3 N CH3O

N

CH3

N

CH3CH2 N C N

CH3

N

(CH2)3N

CH3 CH3

N

CH3

CH3

N

CH3

N

H CH2

CH3

N

CH2OH

N C

N

. HCl

Cl

N CH2OH

N C

H CH2

CH3

O

D1771

D3683

D2038

D1720

SO3

CH3

N H

O

O

.

NH2

. CF3SO3

N

D1672

O

C N

P O

O 2

CH3

O

P O N3

S

CH3 OCH3

D2201

C1407

D1114

D2477

T1906

O O

O

O N

S O

O C O

N N

N

S

S

N

S

S

S

N N

O C O

N

O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

109

Condensation & Active Esterification

D1662

D2222

O

E0363

E0219

F0239

O O

O2 N

NO2

N

N O C O N N

O

S S

N

OCH2CH3

F0726

O

H0468

H0528

H0395

CH3

N

CH3

F

CH3

CH3 N

O

CH3

PF6

N

H1304

N

O

O

OH

N

N OH

O

O

M0071

M0670 SO2Cl

CH3 CH3

SO2Cl

N

CH3 O

O

CH3

OH

M1439

NOH

M1186 SO3Na

O

. H2O

N

OH

SO3

H0623 B0249

O

N

F

CH3

CH2O C O N

SO3

O

N

O

CH2CH3

C OCH2CH3

O

F0225

O

N

O

CH3

CH3

SO2Cl

M1116

N

CH3

N0604

T0681

N0477 O

NO2 O

O

NO2

CH3

O

N O

Me Me

O C CF3

O

N

NO2

N

S N

O2N

N H

N

O

N

N

NO2

N0634

O0200

O0195

T0648

P1626 O

O

N CH3

N O

(CH3)2N

CH3 N

N

N C C N

O C BF4

O O

N(CH3)2

(CH3)2N P O P N(CH3)2 (CH3)2N

N CH3

Cl

F

F

Cl

Cl

F

F

CF3SO3

N(CH3)2 2BF4

CH3

P1042

P

O

SO2CH3

OSO2CH3

n

F

Cl

P1768

P1320 P1319 O

CH3SO3

NH3

O C CCl3 Cl

O CH2CH2CH3 P O CH3CH2CH2 O P P O CH2CH2CH3 O

P0939 O

Q0016

O N

C O C

O

N N

SO2Cl

N N

T1513

T1562

T2224 SO2Cl

O Cl

CH3

O

CCl3CHO C O N

T0340

N

N O C

SO2Cl

O

N(CH3)2 N(CH3)2

T1673

BF4

N H

T1413 N

N H

N

N

N

SO2

CH3

N

Cl

T1593 OH

C Cl

Cl

Cl

O CF3

O

C O C

Cl

OH Cl

110

N

T0389 O

N

N

N

O

CH3

N

T1985

O

CH3

CH3

T1017

Cl

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

CF3

Condensation & Active Esterification

T0459 CH3 CH3

T1122 SO2Cl

CH

CH

CH

CH3 CH3

CH3

SO3

CH3

CH3 CH3

N H

CH3 CH3

Product No. Product Name

Unit Size

A1861 B1774 B1651 B1657 B1658 B2771

O-(7-Azabenzotriazol-1-yl)-N,N,N ',N '-tetramethyluronium Tetrafluoroborate 1H-Benzotriazol-1-yloxytripyrrolidinophosphonium Hexafluorophosphate 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate O-(Benzotriazol-1-yl)-N,N,N ',N '-tetramethyluronium Hexafluorophosphate O-(Benzotriazol-1-yl)-N,N,N ',N '-tetramethyluronium Tetrafluoroborate 1,3-Bis(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbodiimide (This product is only

1g 5g 5g 5g 5g

5g 25g 25g 25g 25g

available for selling domestically in Japan)

B1213 B3604 B1036 B0832 C1124 C1298 C1574 C1362 C0119 C1988 C1131 C1408 C1639 C1651 C0905 C0903 C0906 C1379 C1375 C1957 C1500 C0793 D0436 D3262 C1242 D2039 D1393 D0254 D3293 D2919 D1601 D1450 D2898 D2899 D1771 D3683 D2038 D1720 D1672 D2201 C1407 D1114 D2477 T1906 D1662 D2222 E0363 E0219 F0239 F0225 F0726 H0468

Bis(2-oxo-3-oxazolidinyl)phosphinic Chloride Bis(pentafluorophenyl) Carbonate 2-Bromo-1-ethylpyridinium Tetrafluoroborate N-tert-Butyl-5-methylisoxazolium Perchlorate N-Carbobenzoxyoxysuccinimide Carbonic Acid 2-Bromobenzyl Succinimidyl Ester Carbonic Acid tert-Butyl 2,4,5-Trichlorophenyl Ester 2,2'-Carbonylbis(3,5-dioxo-4-methyl-1,2,4-oxadiazolidine) 1,1'-Carbonyldiimidazole O-(6-Chlorobenzotriazol-1-yl)-N,N,N ',N '-tetramethyluronium Hexafluorophosphate N-(2-Chlorobenzyloxycarbonyloxy)succinimide 2-Chloro-1,3-dimethylimidazolinium Chloride 2-Chloro-1,3-dimethylimidazolinium Chloride (ca. 25% in Dichloromethane) 2-Chloro-1,3-dimethylimidazolinium Hexafluorophosphate 2-Chloro-3-ethylbenzoxazolium Tetrafluoroborate 2-Chloro-1-methylpyridinium Iodide 2-Chloro-1-methylpyridinium p-Toluenesulfonate 1-(Chloro-1-pyrrolidinylmethylene)pyrrolidinium Hexafluorophosphate 1-(Chloro-1-pyrrolidinylmethylene)pyrrolidinium Tetrafluoroborate Chloro-N,N,N ',N '-tetramethylformamidinium Hexafluorophosphate Cyanomethylenetributylphosphorane 1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide Metho-p-toluenesulfonate N,N '-Dicyclohexylcarbodiimide 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one Diethyl Cyanophosphonate 3,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine 3,4-Dihydro-2H-pyrido[1,2-a]pyrimidin-2-one N,N '-Diisopropylcarbodiimide Dimesitylammonium Pentafluorobenzenesulfonate 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide Hydrochloride 4-Dimethylaminopyridine (4R,5R)-1,3-Dimethyl-4,5-diphenyl-2-[(S)-1-benzyl-2-hydroxyethylimino]imidazolidine (4S,5S)-1,3-Dimethyl-4,5-diphenyl-2-[(R)-1-benzyl-2-hydroxyethylimino]imidazolidine 2,6-Dimethylpyridinium p-Toluenesulfonate Diphenylammonium Trifluoromethanesulfonate Diphenyl (2,3-Dihydro-2-thioxo-3-benzoxazolyl)phosphonate N,N-Diphenyl-4-methoxybenzamide Diphenylphosphoryl Azide 4,6-Diphenylthieno[3,4-d]-1,3-dioxol-2-one 5,5-Dioxide Di-2-pyridyl Carbonate 2,2'-Dipyridyl Disulfide 4,4'-Dipyridyl Disulfide O,O '-Di-2-pyridyl Thiocarbonate Di(N-succinimidyl) Carbonate 2,2'-Dithiobis(5-nitropyridine) 1-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline N-Ethyl-5-phenylisoxazolium-3'-sulfonate N-[(9H-Fluoren-9-ylmethoxy)carbonyloxy]succinimide 2-Fluoro-1-methylpyridinium p-Toluenesulfonate Fluoro-N,N,N ',N '-tetramethylformamidinium Hexafluorophosphate 1-Hydroxybenzotriazole Monohydrate

1g 5g

5g 25g 5g 25g 5g 250g 10g 5g 5g 250g 5g 10g 25g 25g 25g 25g 500g 25g 25g 5g 5g 25g 25g 500g 5g 25g 25g 25g 250g 5g 25g 250g 500g 100mg 100mg 25g 25g 25g 5g 250g 5g 5g 250g 25g 1g 25g 5g 25g 1g 25g 25g 5g 500g

5g 1g 25g

25g 1g 5g 5g 5g 25g 5g

1g

5g

1g 5g 5g 25g 5g 10g 5g 25g 1g 5g 25g 25g

1g

5g 5g

5g

25g

5g

25g 5g 5g

5g 5g 1g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

111

Condensation & Active Esterification

Product No. Product Name H0528 H0395 H0623 B0249 H1304 M1186 M0071 M0670 M1439 M1116 N0604 T0681 N0477 N0634 O0200 O0195 T0648 P1626 P1042 P1320

N-Hydroxy-5-norbornene-2,3-dicarboximide N-Hydroxyphthalimide N-Hydroxysuccinimide N-Hydroxysuccinimide N-Hydroxysulfosuccinimide Sodium Salt 2,4-Mesitylenedisulfonyl Dichloride 2-Mesitylenesulfonyl Chloride 9-Methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidin-2-one 2-Methyl-6-nitrobenzoic Anhydride 6-Methyl-2H-pyrido[1,2-a]pyrimidin-2-one 1-(4-Nitrobenzenesulfonyl)-1H-1,2,4-triazole 4-Nitrophenyl Trifluoroacetate 3-Nitro-1,2,4-triazole 2-(5-Norbornene-2,3-dicarboximido)-1,1,3,3-tetramethyluronium Tetrafluoroborate 1,1'-Oxalyldiimidazole μ-Oxo-bis[tris(dimethylamino)phosphonium] Bis(tetrafluoroborate) (=Bates' Reagent) Pentachlorophenyl Trichloroacetate Pentafluoroanilinium Trifluoromethanesulfonate Phosphorus Pentoxide - Methanesulfonic Acid Propylphosphonic Acid Anhydride (Cyclic Trimer) (48% in N,N-Dimethylformamide,

Unit Size 25g 25g 25g 200mg 5g 25g 1g

5g

5g 5g 1g

1g

5g 25g

ca. 1.6mol/L)

P1319 P1768 P0939 Q0016 T1513 T1562 T2224 T1017 T1985 T0340 T1673 T1413 T0389 T1593 T0459 T1122

Propylphosphonic Acid Anhydride (Cyclic Trimer) (50% in Ethyl Acetate, ca. 1.7mol/L) 3-Pyridinecarboxylic Anhydride 4-Pyrrolidinopyridine Quinoline-8-sulfonyl Chloride N-(1,2,2,2-Tetrachloroethoxycarbonyloxy)succinimide 2,4,5,6-Tetramethylbenzenedisulfonyl Dichloride N,N,N ',N '-Tetramethyl-O-(N-succinimidyl)uronium Tetrafluoroborate 1H-Tetrazole 1-(p-Toluenesulfonyl)imidazole 1,2,4-Triazole 3H-1,2,3-Triazolo[4,5-b]pyridin-3-ol 2,4,6-Trichlorobenzoyl Chloride 2,4,5-Trichlorophenol 4-Trifluoromethylbenzoic Anhydride 2,4,6-Triisopropylbenzenesulfonyl Chloride 2,4,6-Trimethylpyridinium p-Toluenesulfonate

1g 5g 5g

1g

1g 5g 5g 25g 5g 5g 25g 25g

References 1) 2) 3) 4) 5) 6) 7)

112

I. Shiina, R. Ibuka, M. Kubota, . 2002, 286. I. Shiina, M. Kubota, R. Ibuka, . 2002, , 7535. J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, . 2003, , 3021. I. Shiina, H. Oshiumi, M. Hashizume, Y. Yamai, R. Ibuka, . 2004, 45, 543. I. Shiina, M. Kubota, H. Oshiumi, M. Hashizume, . 2004, , 1822. I. Shiina, . 2007, , 239. Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2003 335731, 2003.

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

250g 500g 500g 25g 1g 25g 500g 25g 25g 5g 5g 25g 5g 25g 5g 1g 25g 25g 500g 25g 25g 5g 25g 25g 10g 5g 5g 25g 25g 500g 25g 25g 500g 10g 500g 25g

Glycosylation

Glycosylation It has been revealed that the oligosaccharide is an important factor in many areas of life processes, embryonic growth, differentiation, aging, immunity and carcinogenesis. Many researches have been conducted to understand the functions in biological systems and structure-activity relationship of oligosaccharides. For the structure-based studies, it is necessary to synthesize oligosaccharides with confirmed structure so as to evaluate their activity. Throughout the synthesis of oligosaccharides, glycosylation, protection and deprotection processes are repeated for every glycosidic linkage formed. Thus, in order to synthesize oligosaccharides effectively, the glycosyl donor and acceptor, as well as the protecting agents are vitally important. For this reason, there is much research activity in finding glycosyl donors and acceptors with suitable properties. The glucose derivative 1, with thioformimidate as a leaving group, was developed by Mukaiyama and his co-workers.1) This reagent is a glycosyl donor with high reactivity and stability. 1 is activated with a catalytic amount of TfOH in the presence of MS5A and reacts with a glycosyl acceptor 2 to provide a disaccharide 3 in a quantitative yield. Furthermore, by choosing the appropriate solvents, αor β-glycosides can be obtained selectively. The glycosyl acceptors with a fluorine atom or an ethylthio group at 1-position were also used and the resulting disaccharides can also be used as glycosyl donors. OH O

R'O OR' BnO BnO

OBn O BnO

X 2

R'O

Acceptor (1.0 eq.)

NR O C SCH2R

1

OBn O

BnO BnO

O BnO R'O OR' 3

TfOH (5 mol%), MS 5A (3 g/mmol), Solvent

R=p-trifluoromethylphenyl

Acceptor

Entry 1 2

R'

X

Benzoyl EtS Benzyl F

O X R'O Yield % (α/β) EtCN

t-BuOMe

95 (98/11) 98 (2/98) 97 (87/13) 81 (2/98)

In addition, the utility of -methoxyphenyl glycosides has been reported.2) The -methoxyphenyl group is a useful anomeric protective group which is stable under most of the conditions used in oligosaccharide synthesis. It is removed selectively by treatment with 2,3-dichloro-5,6-dicyano- -benzoquinone and ammonium cerium(IV) nitrate, to give the corresponding hemiacetals. Also the -methoxyphenyl glycosides are converted in one step into the corresponding glycosyl halides and thiophenyl glycosides in high yields and can be used as glycosyl donors. O

O

phosphite

Br / Cl O O

OCH3

O

O imidate

OH O

O F

SR

The followings are glycosyl donors in which the anomeric position is activated, including 1, -methoxyphenyl glycosides, glycosyl acceptors and activating agents that can be obtained from TCI. TCI is pleased to supply these reagents for your needs in the research of oligosaccharides and related studies.

T2295 AcO

Glycosyl Donors

Imidate Sugars

T2491 OAc O

AcO AcO

NH O C CCl3

AcO AcO

OAc O

NH O C CCl3

OAc

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

113

Glycosylation

T1991

T1999 OBz O

BzO BzO

N

BzO

T2615

OBn O

BnO BnO

CF3

CF3

N

BnO

O S CH2

T2695

AcO

O S CH2

CF3

NH

OAc O

CF3

O C CCl3

OAc O

AcO AcO

NH O C CCl3

O

N

O

OAc

Product No. Product No.

Unit Size

2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl 2,2,2-Trichloroacetimidate 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl 2,2,2-Trichloroacetimidate 2,3,4,6-Tetra-O-benzoyl-α-D-glucopyranosyl p-TrifluoromethylbenzylthioN-(p-trifluoromethylphenyl)formimidate 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl p-TrifluoromethylbenzylthioN-(p-trifluoromethylphenyl)formimidate 2,3,4-Tri-O-acetyl-β-L-arabinopyranosyl 2,2,2-Trichloroacetimidate 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl 2,2,2-Trichloroacetimidate

T2295 T2491 T1991 T1999 T2695 T2615

I0328

M1706

HO

Thioglycosides

M1501

OH O

HO

S

CH3

HO

M1649

AcO

SCH3 N

CH3

Ph

O

O N

SPh Bn

O O HO

SCH3 OAc

O OAc

SPh

CH3 BnO

OH O

SPh HO

P1680

AcO

SPh NH C OCH2CCl3

P1736 AcO

OBn O

BnO

SPh OBn

OAc O

O

AcO SPh

OAc

SCH3

P1660

O

SPh OAc

P1476 OAc O SPh

OAc O

AcO AcO

SPh AcO

OAc

AcO

SPh OBn

AcO

AcO

OBn O

O

OBn

P1642 OAc O

BnO

SCH3 OBn

O

O

P1679

OAc O

AcO AcO

AcO

P1477

HO

O

BnO

O

1g

OAc

P1643 HO

O

COOCH3 O

M1628

AcO

P1475

O

COOCH3

O

SCH3

Ph

O

AcO AcO

200mg

M1682

AcO

M1626

O

P1762

SPh

AcO AcHN

5g 5g

200mg 1g Price on request Price on request

OAc O

AcO AcO

OAc O

AcO AcO

OAc

AcO

CH3

M1759

1g 1g

P1866 OAc O SPh NH C OCH2CCl3

AcO AcO

OAc O SPh NH C OCH2CCl3

O

P1842

CH3 BnO

114

O

SPh OBn

OBn

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

O

Glycosylation

Product No. Product No. I0328 M1706

Unit Size

Isopropyl 1-Thio-β-D-galactopyranoside Methyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glyceroD-galacto-2-nonulopyranosylonate Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-β-D-glucopyranosid)uronate Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-glucopyranoside Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-α-D-mannopyranoside (contains ca. 5% β-isomer) Methyl 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside Methyl 2,3,4-Tri-O-acetyl-1-thio-β-L-fucopyranoside Methyl 2,3,4-Tri-O-benzyl-1-thio-β-L-fucopyranoside Phenyl 3-O-Allyl-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside Phenyl N-Benzyl-2-amino-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-1-thioβ-D-glucopyranoside Phenyl 4,6-O-Benzylidene-1-thio-β-D-glucopyranoside Phenyl 2-Deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-β-D-galactopyranoside Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-galactopyranoside Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-glucopyranoside Phenyl 2,3,4,6-Tetra-O-benzyl-1-thio-β-D-galactopyranoside Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-β-D-galactopyranoside Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)β-D-galactopyranoside Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)β-D-glucopyranoside Phenyl 2,3,4-Tri-O-benzyl-1-thio-β-L-fucopyranoside

M1759 M1682 M1501 M1649 M1626 M1628 P1660 P1762 P1475 P1643 P1477 P1476 P1679 P1680 P1736 P1642 P1866 P1842

A1416

Halogeno Sugars

T1971

BnO BnO

T1961 OAc O

AcO AcO

AcHN

AcO AcO

OBn O BnO

F

OAc O AcO

Cl

T1922

T1995

BnO BnO

BnO

BnO BnO

AcO

1g 1g 1g 5g 5g 1g 5g 1g 5g 1g Price on request 1g 5g Price on request 5g 25g 5g 25g 1g Price on request 1g Price on request

AcO

F

F

OBn O

RO RO F

OR O F O

R=

C C(CH3)3

Unit Size

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl Chloride 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Bromide (stabilized with CaCO3) 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Fluoride 2,3,4,6-Tetra-O-acetyl-D-mannopyranosyl Fluoride 2,3,4,6-Tetra-O-benzyl-D-glucopyranosyl Fluoride 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl Fluoride 2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl Fluoride 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl Fluoride

R0067

R0080

BzO

OAc

OBz OBz

BzO

1g

5g 5g 1g 1g 5g 500mg 500mg 500mg 1g

R0066

OBz OBz O

O

Others

OAc O

AcO AcO

Product No. Product No. A1416 T1961 T1995 T2567 T1971 T1922 T1923 T2568

5g 5g

1g

T2568

BnO

F

OAc O

Br

RO

OBn O

5g

T2567

AcO AcO

T1923

1g

OAc

T2197

AcO

OAc O

BnO BnO

OBn O BnO

O O P N(CH3)2

OAc OAc

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

N(CH3)2

115

Glycosylation

Product No. Product No.

Unit Size

β-D-Ribofuranose 1-Acetate 2,3,5-Tribenzoate β-L-Ribofuranose 1-Acetate 2,3,5-Tribenzoate Tetra-O-acetyl-β-D-ribofuranose 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl N,N,N ',N '-Tetramethylphosphorodiamidate

R0067 R0080 R0066 T2197

5g

25g 1g 25g

5g

5g

(ca. 20% in Benzene)

B0041

B2440

B3664 SF3

SH CH3OCH2CH2

Reagents for Glycosyl Donor Synthesis D1868

N S

F

F

CH3 C CH3

M1573

P1243 SF3

CH3

F

CH3

F

S

N

CH2

HBr

P Cl

OH

O

T1308

T0372

CH3

CH3

CH3

H0182

F

Et

N S

CH3OCH2CH2

D2159

Et

CH3

F

S

S

P

P CH3

T2638

T2547

Cl

CCl3CN

CF3

Cl

C N

CF3

OCH3

C N

CH3 CH3

Product No. Product No. B0041 B2440 B3664 D1868 D2159 H0182 M1573 P1243 T1308 T0372 T2638 T2547

Unit Size

Benzenethiol Bis(2-methoxyethyl)aminosulfur Trifluoride 4-tert-Butyl-2,6-dimethylphenylsulfur Trifluoride (Diethylamino)sulfur Trifluoride [Fluorinating Reagent] Dimethylthiophosphinoyl Chloride Hydrogen Bromide (30% in Acetic Acid, ca. 5.1mol/L) [for Peptide research] Morpholinosulfur Trifluoride 4-Penten-1-ol Tetramethyldiphosphine Disulfide Trichloroacetonitrile 2,2,2-Trifluoro-N-(4-methoxyphenyl)acetimidoyl Chloride 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride

25ml 5g 5g

500ml 25g 5g 100g 5g 500g 5g 250ml 5g 500g 5g 5g

25g 1g 25g 1g 25ml 25g

M1620

M1590 Ph

Ph

O O

O O

Galactose

-Methoxyphenyl Glycosides & Related Reagents M1633

O O

O O

O

OCH3

O

OBn

CH3 O

M1596

M1477

M1588

O CH3 CH3 CH3

O

OBn O

O

CH3 O

OBn

OCH3

CH3

O

AcO

O O

O

O

OCH3

O

BnO

OAc O

AcO

O OAc

OCH3

OBn O

BnO

O

OCH3

OBn

CH3 O

116

OCH3

O

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Glycosylation

Product No. Product No. M1620 M1590 M1633 M1596 M1477 M1588

Unit Size

4-Methoxyphenyl 3-O-Allyl-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 4-Methoxyphenyl 3-O-Allyl-4,6-O-benzylidene-2-O-(4-methylbenzoyl)-β-D-galactopyranoside 4-Methoxyphenyl 2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside 4-Methoxyphenyl 3,4-O-Isopropylidene-2,6-bis-O-(4-methylbenzoyl)-β-D-galactopyranoside 4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside 4-Methoxyphenyl 2,3,4,6-Tetra-O-benzyl-β-D-galactopyranoside

1g 1g 1g 1g 25g 5g

5g

M1643 Ph O O

Galactosamine

O O

O N3

OCH3

Product No. Product No. M1643

Unit Size

4-Methoxyphenyl 3-O-Allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

M1630

Glucose

M1642

OAc O

AcO AcO

1g

O

OCH3

OAc O

AcO BnO

O

OAc

OCH3

OAc

Product No. Product No. M1630 M1642

Unit Size

4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-β-D-glucopyanoside 4-Methoxyphenyl 2,4,6-Tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside

M1834

M1598

OBn O

AcO BnO

Ph

O O

Glucosamine

M1638

N

O

OCH3

Ph

O O

O O

O

OCH3

5g 5g

1g

M1609

O O O O

O O N O

Ph

OCH3

O O BnO

O O O

N

OCH3

O

N3

M1480 OAc O

AcO AcO

O O

N

OCH3

O

Product No. Product No. M1834 M1638 M1598 M1609 M1480

4-Methoxyphenyl 4-O-Acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 4-Methoxyphenyl 3-O-Allyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 4-Methoxyphenyl 3-O-Allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimidoβ-D-glucopyranoside 4-Methoxyphenyl 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Unit Size 1g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 1g 5g 1g 5g

117

Glycosylation

M1647 AcO

OAc O

AcO AcO

Mannose

O

OCH3

Product No. Product No.

Unit Size

4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranoside

M1647

G0330

M1694

5g

G0309

G0311

Ph AcO

O AcO

Disaccharides

OAc O

AcO

O O O

O

OAc

G0299

AcO AcO O

OAc BnO O O N O

AcO OCH3

AcO O

OCH3

OBn

OAc

AcO O AcHN AcO

O OAc AcO

O

OCH3

AcO

O

O O

OAc

OAc

M1763

COOCH3 O BzO BnO

OAc Ph O

AcO

O O N3

OCH3

O OAc

O O

O O O N O

OCH3

O

O OBz

N0816

OAc AcO COOCH3 AcO O O HN BzO AcO O O BnO O OBz

OCH3

OCH3

AcO

OBz O

O OBz

OCH3

Unit Size

Gal[2346Ac]β(1-3)GalN3[46Bzd]-β-MP Gal[2346Ac]β(1-4)Glc[236Ac]-β-MP Gal[2346Ac]β(1-3)GlcN3[46Bzd]-β-MP Gal[2346Ac]β(1-3)GlcNPhth[46Bzd]-β-MP GlcNPhth[346Ac]β(1-3)Gal[246Bn]-β-MP Neu5Ac[1Me,4789Ac]α(2-6)Gal[24Bz,3Bn]-β-MP Neu5GcAc[1Me,4789Ac]α(2-6)Gal[24Bz,3Bn]-β-MP Neu5GcAc[1Me,4789Ac]α(2-3)Gal[246Bz]-β-MP

C1806

BzO OAc CH3OOC AcO O O HN AcO O

AcO

AcO

Product No. Product No. G0330 M1694 G0309 G0311 G0299 M1761 M1763 N0816

OAc Ph O

AcO

OAc O

N3

M1761 OBn O

AcO OAc O

Price on request Price on request Price on request 1g 5g Price on request 200mg 200mg Price on request

D1070 O NC

Deprotecting Reagents

NC

118

Cl O

Product No. Product No. C1806 D1070

Cl

(NH4)2Ce(NO3)6

Ceric Ammonium Nitrate 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Unit Size 50g 25g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

500g 250g

Glycosylation

M1589

M1482

Ph OH

O O

Galactose

Glycosyl Acceptors

OH O

O

O O

O

O

OCH3

O

OCH3

HO

OCH3

HO

M1725

M1710

M1597

HO

O

BnO

O

HO

O HO

O

O

OCH3

HO

CH3 CH3 CH3

O O

CH3

HO

OBn

O

OCH3

HO

O

OBz O

BzO

OCH3

BzO

OBn

OBn

OCH3

Unit Size

4-Methoxyphenyl 3-O-Allyl-4,6-O-benzylidene-β-D-galactopyranoside 4-Methoxyphenyl 3-O-Allyl-β-D-galactopyranoside 4-Methoxyphenyl 3-O-Benzyl-β-D-galactopyranoside 4-Methoxyphenyl 4,6-O-Benzylidene-β-D-galactopyranoside 4-Methoxyphenyl 2,6-Bis-O-(4-methylbenzoyl)-β-D-galactopyranoside 4-Methoxyphenyl 2,6-Di-O-benzyl-β-D-galactopyranoside 4-Methoxyphenyl 3,4-O-Isopropylidene-β-D-galactopyranoside 4-Methoxyphenyl 3,4-O-Isopropylidene-6-O-(4-methylbenzoyl)-β-D-galactopyranoside 4-Methoxyphenyl 2,3,6-Tri-O-benzyl-β-D-galactopyranoside 4-Methoxyphenyl 2,4,6-Tri-O-benzyl-β-D-galactopyranoside Methyl 2,3,6-Tri-O-benzoyl-α-D-galactopyranoside

A1833

A1832

Ph

1g 5g Price on request Price on request 1g 1g 1g 1g Price on request 1g 5g 25g 250g

P1643

Ph O

O

HO

O

O

OH O

O

O

Galactosamine

HO

N3 O

HO

N3 O

O

HO

OC(CH3)3 HN

O

OC(CH3)3

CH3 HN

Fmoc

SPh NH C OCH2CCl3

O

Fmoc

Product No. Product No. A1833 A1832 P1643

Unit Size

O-(2-Azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren9-ylmethoxy)carbonyl]-L-serine tert-Butyl Ester O-(2-Azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren9-ylmethoxy)carbonyl]-L-threonine tert-Butyl Ester Phenyl 2-Deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-β-D-galactopyranoside D1949

I0400

CH3

O

CH3

O

Price on request Price on request Price on request

M1640

M1641

HO HO

OH

OH O

O

Glucose

OH

OH

Product No. Product No. M1589 M1482 M1725 M1710 M1597 M1634 M1593 M1594 M2104 M1592 M1933

O O

M1933

O

O

OCH3

OCH3

CH3

BnO

OBn O

OH

CH3

O OBn

M1592

BnO

O O

OBn O

HO

O

M2104 O

O

OCH3

O

HO

M1594

HO O

OCH3

HO

M1593

CH3 O

OH

O

OH O

M1634

O

Ph

Ph

O

O O

CH3 CH3

O

O O BnO

O O OH

CH3

OCH3

HO BnO

OH O O

OCH3

OH

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

119

Glycosylation

M1125 Ph

M1487

O O HO

O HO

M1488 OH O

BzO BzO

BzO

OCH3

P1475 OH O

BnO BnO

BnO

OCH3

Ph

O O HO

O SPh HO

OCH3

Product No. Product No.

Unit Size

1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 1,2-O-Isopropylidene-α-D-glucofuranose 4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-β-D-glucopyranoside 4-Methoxyphenyl 3-O-Benzyl-β-D-glucopyranoside Methyl 4,6-O-Benzylidene-α-D-glucopyranoside Methyl 2,3,4-Tri-O-benzoyl-α-D-glucopyranoside Methyl 2,3,4-Tri-O-benzyl-α-D-glucopyranoside Phenyl 4,6-O-Benzylidene-1-thio-β-D-glucopyranoside

D1949 I0400 M1640 M1641 M1125 M1487 M1488 P1475

A1811

Ph

O O HO

Glucosamine

N3

M1479 OH O

Ph

O O

O

N

OCH3

O O O

O

Ph

O

OCH3

N

OCH3

O

O O HO

O O

M1617

O O

OCH3

HO BnO

OBn O O

N

O

OCH3

HO HO

OH O

OPh

Product No. Product No.

Unit Size

2-Acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl Azide 4-Methoxyphenyl 2-Amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 4-Methoxyphenyl 2-Azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 4-Methoxyphenyl 2-Azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 4-Methoxyphenyl 3-O-Benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 4-Methoxyphenyl 4,6-O-Benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 4-Methoxyphenyl 3,6-Di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside Phenyl N-Acetyl-α-D-glucosaminide

1g 1g 1g

5g 5g 5g 1g Price on request 5g 1g 100mg

T1459

AcO

Mannose

120

AcO AcO

OCH3

N3

AcHN

A1811 M1616 M1637 M1617 M1610 M1479 M1615 P0130

25g 25g 5g 1g 25g 5g 1g 5g

P0130 OBn O

HO BnO

5g 1g

N3

NH2

M1615

O O HO

1g

M1637

OBn O

HO BnO

NHAc

M1610

HO BnO

M1616

10g

HO O OAc

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Glycosylation

Product No. Product No. T1459

Unit Size

1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose

M1686

HO

Disaccharides

HO

1g

M1726

HO

OBn O O OBn BnO

OBn O O

M1727

BnO

OBn O

BnO

OCH3

OBn

O OBnBnO

OBn O O

HO

OCH3

OBn

OBn O

OBn O

O OBn BnO

O

OCH3

OBn

Product No. Product No.

Unit Size

Gal[26Bn]β(1-4)Glc[236Bn]-β-MP Gal[236Bn]β(1-4)Glc[236Bn]-β-MP Gal[246Bn]β(1-4)Glc[236Bn]-β-MP

M1686 M1726 M1727

5g

Price on request 1g 5g Price on request

B0527

B0656

C0903 O

BF3

Activating Agents

.

CH3

O

N Br

CH3

N

O

T1292

H0914

I0074

Cl

I

CH3

T2029

T1331

O CF3

Cu2

S O O

O

O

O Cl

Hf

N

Cl

I

CF3

CH3O S CF3

S OAg O

O

2

O

T0751

T0871

T1173

O CF3SO3H

CF3

CH3

S O Si CH3 O

Z0007

C

BF4

Product No. Product No. B0527 B0656 C0903 T1292 H0914 I0074 T2029 T1331 T0751 T0871 T1173 Z0007

Cl

Zr

Cl

CH3

Boron Trifluoride - Ethyl Ether Complex N-Bromosuccinimide 2-Chloro-1-methylpyridinium Iodide Copper(II) Trifluoromethanesulfonate Hafnocene Dichloride N-Iodosuccinimide Methyl Trifluoromethanesulfonate Silver Trifluoromethanesulfonate Trifluoromethanesulfonic Acid Trimethylsilyl Trifluoromethanesulfonate [Trimethylsilylating Agent] Triphenylmethylium Tetrafluoroborate Zirconocene Dichloride

Unit Size 25g

1g 5g

10g 5g

25ml 100g 25g 5g 5g 25g 5g 10g 25g 25g 5g 5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500ml 500g 500g 25g 25g 100g 25g 25g 250g 250g 25g 25g

121

Glycosylation

Enzyme-related Reagents Enzyme Product No. Product No.

Unit Size

A1844

endo-α-N-Acetylgalactosaminidase (=Endo-α) Recombinant: from Bifidobacterium longum

A1651

endo-β-N-Acetylglucosaminidase (=Endo-M) Recombinant: from Mucor hiemalis expressed in

1vial

expressed in Escherichia coli

1vial

Candida boidinii [Purity: single band by SDS-PAGE(85KDa)]

A1614 OH O

HO HO

Enzyme Substrates

D3690

AcHN

H N

COOH O

NHBoc

OH OH COOH HO HO O O AcHN O O OH HO HO OH

G0297 OH O

O NHAc HO HO O HO O HO O HO OH HO O OH COOH HO HO OHOH O O AcHN O O O O HO HO OH OH NHAc

O OH O HO O

R=

NHAc O O HO OH H N

OH O

R

NHAc

COOH O NH O S O

Me

N

HO HO

OH O AcHN

HN H

H N

NH H S

O

Me

S0523 HO

OH

HO AcHN

O HO

CO2Na HO O HO

O OH

O HO

OH O O AcHN HO HO HO

O HO O HO

OH

HO AcHN

CO2Na HO O O

HO

HO

HO HO HO HO O O O HO OH AcHN

NH2

Lys O

Val OH O

HO O

O O

NHAc O HO

O OH

OH O

Ala

Asn NHAc Lys Thr COOH

Product No. Product No. A1614 D3690 G0297 S0523

Unit Size

N ω-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-Nα-(tert-butoxycarbonyl)-L-asparagine DNS-SGN N-GlcNAc-Biotin Sialylglycopeptide

100mg 1mg 50mg 10mg

References 1) T. Mukaiyama, H. Chiba, S. Funasaka, . 2002, 392; H. Chiba, S. Funasaka, K. Kiyota, T. Mukaiyama, . 2002, 746; H. Chiba, T. Mukaiyama, . 2003, , 172; H. Chiba, S. Funasaka, T. Mukaiyama, . 2003, , 1629. 2) M. Mori, Y. Ito, T. Ogawa, . 1989, , 131; Y. Matsuzaki, Y. Ito, T. Ogawa, . 1992, , 4025; A. Dan, Y. Ito, T. Ogawa, . 1995, , 4680; C. Murakata, T. Ogawa, . 1992, , 95; H. Kuyama, T. Nukada, Y. Nakahara, T. Ogawa, . 1993, , 2171; Z. Zhang, G. Magnusson, . 1996, , 41; H. Ando, Y. Koike, H. Ishida, M. Kiso, . 2003, , 6883.

122

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Phosphorylation

Phosphorylation The phosphorylation reaction is an important reaction in organic synthesis, especially in DNA or RNA synthesis where nucleotides are made by adding phosphate groups to nucleosides. Various reagents and methods of phosphorylation have been developed. For example, the phosphorylation methods include the DCC method by Khorana ., the phosphotriester method and the phosphite method by Letsinger . and the amidite method by Caruthers . etc. They are utilized depending on each purpose. This section below shows the typical reagents employed for phosphorylation.

C0978

C1210

C1215

NCCH2CH2O P O O

O

Ba2+

O

. xH2O

P

C0977

O

O

P

O

O O

Cl

Cl

C2228 O P

C0976

O

O

O

C1250

D2624

P

O P O

Cl

Cl Cl

Cl

D0624

D0764

Cl Cl

OCH2CH2CN (CH3)2CH (CH3)2CH

N

P

N

BnO

CH(CH3)2

BnO

S

S

CH(CH3)2 P N

CH(CH3)2

Cl CH(CH3)2

CH3O P Cl

P OCH2CH3

OCH3

OCH2CH3

Cl

D1059

D2883

M0905

M0904

P0209 O

O

O

Cl

O P O Cl

O

P O P Cl Cl

Cl

CH3O P

Cl

O

Cl

CH3O P

O P Cl

Cl Cl

Cl

P1223

O

O

CH2O P O P OCH2 2

2

Product No. Product No. C0978 C1210 C1215 C1250 C0976 C0977 C2228 D2624 D0624 D0764 D1059 D2883 M0905 M0904 P0209 P1223

Barium 2-Cyanoethylphosphate Hydrate 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one 2-Chloro-1,3,2-dioxaphospholane 2-Chloro-2-oxo-1,3,2-dioxaphospholane 2-Chlorophenyl Phosphorodichloridate 4-Chlorophenyl Phosphorodichloridate 2-Cyanoethyl N,N,N ',N '-Tetraisopropylphosphordiamidite Dibenzyl N,N-Diisopropylphosphoramidite Diethyl Chlorothiophosphate Dimethyl Chlorothiophosphate Diphenyl Chlorophosphate Diphosphoryl Chloride Methyl Dichlorophosphite Methyl Phosphorodichloridate Phenyl Dichlorophosphate Tetrabenzyl Pyrophosphate

Unit Size 5g 5g 5g 5g 5g 1g 25g 25g 25g

5g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 25g 25g 25g 25g 25g 5g 5g 500g 500g 500g 25g 10g 25g 500g 1g

123

Amination

Amination The Gabriel reagent is widely used as a nucleophilic aminating agent since its reactivity is reliable and its handling is easy.1) A variety of aminating agents analogous to the Gabriel reagent have been reported. The potassium salt of imide 1 reacts with alkyl halide to give imide 2. 2 is treated with base or acid to give either -Boc-amine 3 or -methoxycarbonylamine 4, respectively. Moreover, 1 also serves as an acid nucleophile in the Mitsunobu reaction to allow for the conversion of hydroxy groups to amino groups. Therefore, 1 is a useful reagent to give monoprotected amines.2) O O

NaOH aq. / MeOH

t-BuO C

NH , KOH

MeO C O

R CH2Br

O

1

R CH2N

R CH2N

C Ot-Bu H

C Ot-Bu

3

C OMe O

CF3CO2H

2

R CH2N

H C OMe O

4

Fukuyama and co-workers have demonstrated various reactions using the -substituted sulfonamide 5.3) Smooth reactions of 5 occur with alkyl halides under basic conditions and alcohols under Mitsunobu conditions to provide -nitrobenzenesulfonyl ( -Ns) amines 6. The various -Ns amines (Alloc, Boc, Cbz) 6 obtained from these reactions can be selectively deprotected, under the appropriate conditions, to afford the monoprotected amines 7 and 8. Furthermore, 7 can be converted to the primary amine in high yields via a second deprotection. 8 can be converted to the secondary amine in high yields by repeating the alkylation and deprotection process.4) RS -

R1 SO2NHY a)

NO2

SO2NHR1

NO2

NO2

b)

i) c) ii) RS -

5

6

Y = Alloc 5a Boc 5b Cbz 5c

R1NH2

7

N Y

O2S

b)

R1NHY

R1NHR2

8

a) R1X, K2CO3, DMF or R1OH, DEAD, PPh3

b) When 5a Pd(PPh3)4, pyrrolidine 5b TFA 5c BCl3

c) R2X, K2CO3, DMF or R2OH, DEAD, PPh3

On the other hand, acetoxime -(2,4,6-trimethylphenyl)sulfonate 9 has been reported as a useful electrophilic aminating agent. 9 reacts with Grignard reagents in the presence of a catalytic amount of magnesium chloride to afford primary amines in good yields.5)

Me

R MgBr

A1441

A1137 O

S O N C O CH3

124

R N C

A1632 CH3 O

CH3

Me O Me S O N C Me O Me 9 , MgCl2 (cat.)

CH3 CH3

SO2NH C OCH2CH NO2

CH2

Me

Hydrolysis

R NH2

Me

A1341 N

N N

B2303 S CH2N3

O SO2NH

C OtBu

NO2

NH2

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Amination

B1648

B2857

I0510

C1757

I0497

O O

SO2NH C OtBu O CH3 H P O N C O C CH3

O

O CH3O 2

CH3

O

SO2NH

C OCH2

NO2

CH3O C NH C OtBu

t BuO

O

O

C NH

C Ot Bu

CH3

B1734

D2361

O t

D1899

O

O

BuO C NH P OCH2CH3

H2N P OCH2CH3 OCH2CH3

OCH2CH3

H0093

CH3

H0258

D1672

N H

OCH3

M1182

O

S O N C

CH3

O

N3

H0196

OCH2CH3 CH3

CH3

H0530

M0343 M0886 O

H2N OH

N

. HCl

H2N OH

N

2

. H2SO4

H2N O S OH

CH3ONH2

. HCl

O

P1235

P0403

D2479 O

O

T1184 O

NK

N

CH3

H C

N

O

O

P O

N N

CH3

O

. HCl

N H

NNa H C

O

Si

CH2N3

CH3

O

Product No. Product No. A1441 A1632 A1137 A1341 B2303 B1648 B2857 I0510 C1757 I0497 B1734 D2361 D1899 D1672 M1182 H0093 H0258 H0196 H0530 M0343 M0886 P1235 P0403 D2479 T1184

CH3

Acetoxime O-(2,4,6-Trimethylphenylsulfonate) N-Allyloxycarbonyl-2-nitrobenzenesulfonamide 4-Amino-1,2,4-triazole Azidomethyl Phenyl Sulfide N-(tert-Butoxycarbonyl)-2-nitrobenzenesulfonamide N-(tert-Butoxycarbonyl)-p-toluenesulfonamide tert-Butyl [Bis(4-methoxyphenyl)phosphinyloxy]carbamate tert-Butyl Methyl Iminodicarboxylate N-Carbobenzoxy-2-nitrobenzenesulfonamide Di-tert-butyl Iminodicarboxylate Diethyl N-(tert-Butoxycarbonyl)phosphoramidate Diethyl Phosphoramidate N,O-Dimethylhydroxylamine Hydrochloride Diphenylphosphoryl Azide Ethyl O-Mesitylsulfonylacetohydroxamate Hexamethylenetetramine Hydroxylamine Hydrochloride Hydroxylamine Sulfate Hydroxylamine-O-sulfonic Acid O-Methylhydroxylamine Hydrochloride O-Methylhydroxylamine Hydrochloride (ca. 40% in Water, ca. 5.4mol/L) Phthalimide DBU Salt Phthalimide Potassium Salt Sodium Diformylamide Trimethylsilylmethyl Azide

Unit Size 5g 25g 1g

5g 10g 1g 5g 5g

5g 1g

25g 25g 5g 25g 25g 25g 25g 25g 25ml 25g 1g

25g 5g 250g 5g 25g 25g 5g 5g 25g 25g 5g 25g 500g 250g 25g 500g 500g 500g 500g 500g 500ml 25g 500g 25g 5g

References 1) S. Gabriel, . 1887, , 2224; M. S. Gibson, R. W. Bradshaw, . 1968, , 919; U. Ragnarsson, L. Grehn, . 1991, , 285. 2) J. D. Elliott, J. H. Jones, . 1977, ; C. T. Clarke, J. D. Elliott, J. H. Jones, 1978, 1088; J. M. Chong, S. B. Park, . 1993, , 7300. 1999, 1301. 3) T. Fukuyama, M. Cheung, T. Kan, 2002, 4) T. Kan, A. Fujiwara, H. Kobayashi, T. Fukuyama, , 6267. 5) E. Erdik, M. Ay, . 1989, , 663. This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

125

Wittig & Horner-Emmons Reaction

Wittig & Horner-Emmons Reaction Wittig and Horner-Emmons reactions are useful reactions which react with aldehydes and ketones to form carbon-carbon double bonds and are frequently utilized in organic syntheses.1) Recently, syntheses of α,β-unsaturated esters have increasingly been performed using Wittig and Horner-Emmons reagents. In Horner-Emmons reactions, carbon-carbon double bonds generally lead to the -form. Attempts to selectively obtain -form are being investigated and reaction solvents, temperatures, and new Horner-Emmons reagents are being examined.2, 3) R O P CH2CO2Et

O

, Triton®B

2

Ph

CHO

Ph

THF, -78 °C

CO2Et

When R=Me Y. 100 % (Z : E = 96 : 4)

Ando has developed ethyl (diaryl)phosphonoacetate and found a method for the synthesis of selective -α,β-unsaturated ester.4) This method has received much attention as it utilizes quaternary ammonium hydroxide. The reaction is stable toward water and does not require special reactive technique. The reaction has an exceedingly high selectivity for -α,β-unsaturated ester.

A1305

A1439

A1007

O

O P CH2

Wittig Reaction

A1012

C CH3

P CH

Br

Cl

A0862

P CH2CH CH2

B2025

P

(CH2)4CH3

Cl

B0824

P CH2

B1206

P CH2

P CH2Br

Br

P CH2Cl

Cl

Br Cl

Br

B1208

P CH2CH CH2

C CH3

B0970

C1061

C1759

C1009 Cl

O P CH2CH2CH2Br

P

(CH2)3CH3

(CH2)4 C OH

P

CH2

Br

Br

Br

C1286

P

Cl

C1739

C1378

D2907

D1654 Cl

P CH2CH

CH

P

CH2CN

Cl

P

Br

P CH2

Cl

P CH2CH2N

Br

Cl

126

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Br

CH3 CH3

Wittig & Horner-Emmons Reaction

D1655

D2056

D2164

E0421

O

O P CH2CH2

P CH2CH2

O

O P CH2

O

O

E0407

Br

O

P CH2

Br

Br

Br

E0382

E0549

T1944

C1641

P+ CH2CH3 I -

Br

P

Br

F0331

O

O

P CH2CH3

P CH2 C OCH2CH3

OCH2CH3

O

P C C OCH2CH3

CH C OCH2CH3

P CH2

C H

CH3

H0545

H0540

H1240

Cl

I0552

M1326

HO O P

(CH2)6CH3 Br

P

(CH2)5CH3 Br

P CH(CH3)2 I

P CH2

P CH2

C OCH3 Br

Br

M0828

M0779

M0253

T1363

N0700

O P CH2OCH3

P CH3

P CH3

Br

I

P CH

C OCH3

P CH2

Cl

Cl

N0701

P1182

T2718

O CH2

P

NO2

P CH2

T1458

O

C

O

T1510

(CH2)3CH3 CH2 P

(CH2)3CH3

CH3

CH3

Br

P CH2CH2 Si CH3

P CH2OCH2CH2 Si CH3

(CH2)3CH3

CH3

Br

CH3

Cl

Br

T1498

T2001

I

T1958

T2002

T2565

O

CH3 P CH2C C Si CH3

P CH

O

C H

P

CHCN

P CH

C

P C C O

CH3 Br

P1438

P1200

P

CH2C

CH Br

T1506

P CH2CH2CH3 Br

Product No. Product Name A1305 A1439 A1007 A1012 A0862 B2025

Acetonyltriphenylphosphonium Chloride (Acetylmethylene)triphenylphosphorane Allyltriphenylphosphonium Bromide Allyltriphenylphosphonium Chloride Amyltriphenylphosphonium Bromide Benzyltriphenylphosphonium Bromide

T1644

P

(CH2)13CH3

Br

P CH CH2 Br

Unit Size

25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 25g 25g 25g 25g 250g

127

Wittig & Horner-Emmons Reaction

Product No. Product Name B0824 B1206 B1208 B0970 C1061 C1759 C1009 C1286 C1739 C1378 D2907 D1654 D1655 D2056 D2164 E0421 E0407 E0382 E0549 T1944 C1641 F0331 H0545 H0540 H1240 I0552 M1326 M0828 M0779 M0253 T1363 N0700 N0701 P1182 T2718 T1458 T1510 T1498 T2001 T1958 T2002 T2565 P1438 P1200 T1506 T1644

Unit Size

Benzyltriphenylphosphonium Chloride (Bromomethyl)triphenylphosphonium Bromide 3-Bromopropyltriphenylphosphonium Bromide Butyltriphenylphosphonium Bromide 4-(Carboxybutyl)triphenylphosphonium Bromide (2-Chlorobenzyl)triphenylphosphonium Chloride (Chloromethyl)triphenylphosphonium Chloride Cinnamyltriphenylphosphonium Bromide (Cyanomethyl)triphenylphosphonium Chloride Cyclopropyltriphenylphosphonium Bromide (2,4-Dichlorobenzyl)triphenylphosphonium Chloride 2-Dimethylaminoethyltriphenylphosphonium Bromide 2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium Bromide 2-(1,3-Dioxolan-2-yl)ethyltriphenylphosphonium Bromide (1,3-Dioxolan-2-yl)methyltriphenylphosphonium Bromide 4-Ethoxybenzyltriphenylphosphonium Bromide Ethoxycarbonylmethyl(triphenyl)phosphonium Bromide Ethyltriphenylphosphonium Bromide Ethyltriphenylphosphonium Iodide Ethyl (Triphenylphosphoranylidene)acetate Ethyl 2-(Triphenylphosphoranylidene)propionate (Formylmethyl)triphenylphosphonium Chloride Heptyltriphenylphosphonium Bromide Hexyltriphenylphosphonium Bromide (2-Hydroxybenzyl)triphenylphosphonium Bromide Isopropyltriphenylphosphonium Iodide Methoxycarbonylmethyl(triphenyl)phosphonium Bromide (Methoxymethyl)triphenylphosphonium Chloride Methyltriphenylphosphonium Bromide Methyltriphenylphosphonium Iodide Methyl (Triphenylphosphoranylidene)acetate (1-Naphthylmethyl)triphenylphosphonium Chloride (4-Nitrobenzyl)triphenylphosphonium Bromide Phenacyltriphenylphosphonium Bromide Tributyl(1,3-dioxolan-2-ylmethyl)phosphonium Bromide 2-(Trimethylsilyl)ethoxymethyltriphenylphosphonium Chloride (2-Trimethylsilylethyl)triphenylphosphonium Iodide (3-Trimethylsilyl-2-propynyl)triphenylphosphonium Bromide (Triphenylphosphoranylidene)acetaldehyde (Triphenylphosphoranylidene)acetonitrile 2-(Triphenylphosphoranylidene)acetophenone (Triphenylphosphoranylidene)ketene Triphenylpropargylphosphonium Bromide Triphenylpropylphosphonium Bromide Triphenyl(tetradecyl)phosphonium Bromide Triphenylvinylphosphonium Bromide

B2815

25g 5g 10g 25g 5g

5g 5g 5g 5g 5g 25g 25g 25g 25g

25g 25g 5g 5g 25g 25g 25g 5g

5g 1g 5g 1g 5g 25g

B2801

B1714 O CH2 P

CH3O

Horner‒Emmons Reaction

CH3O

B2814

O CH3CH2O

128

O CH2

P OCH2CH3 OCH2CH3

CH3CH2O CH3CH2O

O CF3CH2O P CH2

O

CH3CH2O P CH2

OCH2CH3

P CH2 C OCH2

CH2 P

B1923

OCH2CH3

O

O

OCH2CH3

O

CH3

P CH2 C O C CH3 CH3

CF3CH2O

OCH2CH3

D3069

O

500g 25g 25g 25g 250g 25g 25g 25g 25g 5g 25g 25g 25g 25g 25g 25g 250g 500g 250g 250g 5g 25g 500g 500g 25g 25g 25g 500g 500g 500g 25g 25g 25g 25g 5g 25g 5g 5g 5g 25g 5g 5g 25g 500g 25g 5g

B1795

O CH2 CHCH2 P

O

OCH2CH3 OCH2CH3

CH3CH2O P CH2 CH3CH2O

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

O C OCH3

Wittig & Horner-Emmons Reaction

D3688

B1781 O

CH2 P

C1595

D3335

D3323 O

OCH2CH3

OCH2CH3

CH2 P

Cl

O

OCH2CH3

O

CH3CH2O P CH2CH2Br

CH2

CH3CH2O

OCH2CH3

O

OCH2CH3

P

NC

CH2 P

OCH2CH3

Br

OCH2CH3 OCH2CH3

Cl

C1430

D2423

E0483

D3324

D3689 O

O

O

CH3CH2O P CH2CN

OCH2CH3

O

CH3CH2O P CH2CH3

CH3CH2O P CH2 OCH2CH3

CH3CH2O

CH3CH2O

CH2 P

O F

CH2 P

CH3CH2O

OCH2CH3 OCH2CH3

OCH2CH3 OCH2CH3

I

D3325

D3326

D3708 O

CH3 CH3

O CH

CH2 P

D3327 O

OCH2CH3

CH2 P

O

O

OCH2CH3

OCH2CH3

D3873

CH3

OCH2CH3

P

N

OCH2CH3

O

OCH2CH3

CH3OCH2 P OCH2CH3

CH2 P

OCH2CH3

OCH2CH3 CH3

OCH2CH3

OCH3 OCH3

D3328

D3336 O

CH2 P

D3827 O

OCH2CH3

M1208

CH2 P

O

OCH2CH3

OCH2CH3

P1193

P

O

C CH2 P

CH3CH2O P CH2SCH3

OCH2CH3

OCH2CH3 OCH2CH3

CH3CH2O

P1258

D3992

M0943

O

O

O

OCH2CH3

CH3

D3174

CH3 C CH2

O

O CH3

CH3

D3339

OCH2CH3

O

P OCH2CH3

N CH2

OCH2CH3

O0208

P

S OCH2CH3 OCH2CH3

O

O C CH3

D2548

M1210

D2547 O

O CH3

CH P O 2

CH3O

CH3O

D3709

Cl

O

CH3O P CH3

OCH3

D3824

CH P O

O

O P OCH3

OCH2CH3

Cl Br

S

CH2 P OCH2CH3

O

D3875

CH3O P CH2

O

N

2

D2873

O

O

P O

N

C OCH2CH3

2

OCH3

D2445

O

O P CH2 2

T1582 O

O

O CH3 O O P CH2

O

CH3OCH2 P

O

O

CH3CH2O P CH2

C OCH2CH3

CH2

P CH3

C OCH3 O

CH3CH2O

2

P OCH2CH3 OCH2CH3

CH2

P OCH2CH3 OCH2CH3

M1319

(CH3)2CHO (CH3)2CHO

F0340

O

O

P CH2 P

OCH(CH3)2 OCH(CH3)2

CH3CH2O CH3CH2O

D1523 O

O

P

O

OCH2CH3 F

T2135

CH3CH2O P CH2 CH3CH2O

O C OCH2CH3

CH3CH2O CH3CH2O

D1524

O CH3 O

O

P CH C OCH2CH3 CH3CH2O P

O (CH2)2

C OCH2CH3

CH3CH2O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

129

Wittig & Horner-Emmons Reaction

P1265

O

O

CH3O P CH2

C OCH3

CH3O

Product No. Product Name B2815 B2801 B1714 B1923 B2814 D3069 B1795 D3688 B1781 C1595 D3335 D3323 C1430 D2423 E0483 D3324 D3689 D3325 D3326 D3708 D3873 D3327 D3328 D3336 D3827 M1208 D3339 D3174 P1193 P1258 D3992 M0943 O0208 D3875 D3824 D3709 D2547 D2548 M1210 D2873 D2445 T1582 M1319 F0340 D1523 T2135 D1524 P1265

Benzyl Dimethylphosphonoacetate 9,10-Bis(diethylphosphonomethyl)anthracene Bis(2,2,2-trifluoroethyl) (Methoxycarbonylmethyl)phosphonate 4,4'-Bis(diethylphosphonomethyl)biphenyl tert-Butyl Diethylphosphonoacetate Diethyl Allylphosphonate Diethyl Benzylphosphonate Diethyl (4-Bromobenzyl)phosphonate Diethyl 2-Bromoethylphosphonate Diethyl (3-Chlorobenzyl)phosphonate Diethyl (4-Chlorobenzyl)phosphonate Diethyl (4-Cyanobenzyl)phosphonate Diethyl Cyanomethylphosphonate Diethyl 2,2-Diethoxyethylphosphonate Diethyl Ethylphosphonate Diethyl (4-Fluorobenzyl)phosphonate Diethyl (4-Iodobenzyl)phosphonate Diethyl (4-Isopropylbenzyl)phosphonate Diethyl (3-Methoxybenzyl)phosphonate Diethyl (N-Methoxy-N-methylcarbamoylmethyl)phosphonate Diethyl (Methoxymethyl)phosphonate Diethyl (2-Methylbenzyl)phosphonate Diethyl (3-Methylbenzyl)phosphonate Diethyl (4-Methylbenzyl)phosphonate Diethyl Methylphosphonate Diethyl (Methylthiomethyl)phosphonate Diethyl (2-Oxo-2-phenylethyl)phosphonate Diethyl (2-Oxopropyl)phosphonate Diethyl (Phthalimidomethyl)phosphonate Diethyl 1-Pyrrolidinemethylphosphonate Dimethyl 1,3-Benzodithiol-2-ylphosphonate Dimethyl Methylphosphonate Dimethyl (2-Oxopropyl)phosphonate Diphenyl 4-Bromo-α-chlorobenzylphosphonate Diphenyl α-Chlorobenzylphosphonate Diphenyl (N-Methoxy-N-methylcarbamoylmethyl)phosphonate Ethyl Diphenylphosphonoacetate Ethyl Di-o-tolylphosphonoacetate Methoxymethyl(diphenyl)phosphine Oxide Methyl Diethylphosphonoacetate Methyl(diphenyl)phosphine Oxide Tetraethyl p-Xylylenediphosphonate Tetraisopropyl Methylenediphosphonate Triethyl 2-Fluoro-2-phosphonoacetate Triethyl Phosphonoacetate Triethyl 2-Phosphonopropionate Triethyl 3-Phosphonopropionate Trimethyl Phosphonoacetate

Unit Size 1g

5g 1g 1g 5g 5g 1g 5g 5g 5g 5g 5g 5g 5g 1g 5g 5g 5g 5g 5g 5g 5g 5g

25g 5g 5g 1g 1g

5g 5g 5g

25g 1g 25g 25g 25g

1g 1g 25g 5g 1g 5g 25g 25g 25g 5g 25g 25g 25g 25g 25g 25g 25g 5g 25g 5g 25g 25g 25g 25g 25g 25g 1g 25g 25g 5g 1g 500g 25g 25g 5g 5g 1g 1g 25g 25g 10g 100g 25g 5g 500g 25g 250g 250g

References 1) H.-J. Altenbach, . 1979, , 940; R. D. Little, G. W. Muller, 1982, 391. Schmidt, N. H. Chishti, T. Breining, 2) S. K. Tompson, C. H. Heathcock, . 1990, , 3386; A. Redjal, J. Seyden-Penne, 1733. 3) W. C. Still, C. Gennari, . 1983, , 4405. 4) K. Ando, . 1995, , 4105; K. Ando, . 1997, , 1934; K. Ando, 2000, , 869; K. Ando, T. Oishi, M. Hirama, H. Ohno, T. Ibuka, Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 10 265486, 1998.

130

. 1981,

, 2744; C. . 1974,

. 2000,

, 4745;

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Titanium-mediated Carbonyl Olefination

Titanium-mediated Carbonyl Olefination Carbonyl olefination is one of the most fundamental conversions in organic synthesis and a variety of synthetic methods have been developed and used. Especially, phosphorus mediated reactions such as Wittig and Horner-Emmons reactions have been widely investigated and several improved synthetic conditions, easy work up procedures and stereoselective Wittig type olefinations have been reported. Among these studies, a number of useful Wittig type reagents were provided and widely used for this transformation. In the 1990s, organotitanium species-promoted carbonyl olefination had been studied and various successful methods were reported.1) The biggest advantage of the use of organotitanium species in carbonyl olefination is that not only aldehydes and ketones, but also esters and lactones can be transformed to the corresponding olefins. Furthermore, the basicities of the organotitanium species are weaker compared to that of Wittig type bases and these chemical properties enable easily enolizable substrates to be used in carbonyl olefination and to produce the desired olefins with high yields.

Titanium-mediated carbonyl olefination

Ester, Lactone, Thiolester, Amide Wittig reaction Horner-Emmons reaction Aldehyde, Ketone

Tebbe2) and Petasis3) reagents are representative organotitanium reagents in carbonyl olefination which have been used for methylenation of various carbonyl compounds. Especially, Petasis reagent is a useful methylenating reagent because it is chemically stable to moisture and air in comparison to the Tebbe reagent.

Ti

Cl

Al

CH3 CH3

or

CH3 Ti CH3

O R1

(Tebbe Reagent)

CH2

(Petasis Reagent)

R1

Y

Y

Y = H, R2, OR2, SR2, NR2R3

Y = H, R2, OR2, SR2, NR2R3

On the other hand, olefination utilizing the RCHX2-TiCl4-Zn system reported by Takai and Utimoto enables alkylidenation of carbonyl groups. In this reaction, the stereochemistry of the double bond is   preferentially.4) R

O R1

Y

RCHX2-TiCl4-Zn-TMEDA

Y = H, R2, OR2, SR2, NR2R3

R1

Y

Y = H, R2, OR2, SR2, NR2R3

Takeda reported more general alkylidenation of carbonyl compounds by the treatment of thioacetals with a titanocene(II) compound.5) Even though the titanocene(II) compound needs to be prepared before use, thioacetals can be easily synthesized from aldehydes and thiophenol. Therefore, this synthetic procedure can be applied to wide range of alkylidenation of carbonyl compounds. Takeda also reported the synthesis of tetrasubstituted olefins by the alkylidenation of carbonyl compounds with an organotitanium species prepared from a titanocene(II) compound and -dihalides.6)

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

131

Titanium-mediated Carbonyl Olefination

O R2 SPh R1

2Cp2Ti[P(OEt)3]2

R

SPh

1

Y R2

R1

TiCp2

Y Cp2Ti=O

Y = H, R3, OR3, SR3

Preparation of low valent titanium species

Cl Ti Cl

= Cp2TiCl2

Mg, 2P(OEt)3

Cp2Ti[P(OEt)3]2 Low valent titanium species

Preparation of thioacetals SPh

2PhSH, BF3 EOEt

O R1

R1

H

BuLi, R1X

H H

SPh

PhS

SPh

Thioacetal

O X X R1

R2

R3

R2

Y

R2

2Cp2Ti[P(OEt)3]2 R1

R3

R1 Y

TiCp2

X = Cl, Br

Y = H, R4, OR4, SR4

Cp2Ti=O

There are several types of organotitanium species-promoted carbonyl olefination and some active intermediates have been proposed. In one of them, it is considered that methylenation performed by Tebbe and Petasis reagents proceeds via a Schrock type titanium-methylidene complex as an active intermediate. Therefore, dependent on structures of substrates and reaction conditions, when the substrate possesses a carbonyl function and a carbon-carbon double bond in the same molecule, olefination and a subsequent ring-closing metathesis (RCM) occurs in one-pot. This sequential process has been applied to the total synthesis of marine natural products having a cyclic polyether structure.7)

Ti CH2 O O O

R

R 6 or 7 menberd cyclic products

Tebbe or Petasis reagent-promoted olefination with a subsequent RCM proceeds only when the substrate is fixed by a cyclic structure, and cyclization of this is limited within 6- and 7-membered cyclic systems.7) On the other hand, olefination-subsequent RCM of acyclic substrates can be performed by the use of the CH3CHBr2-TiCl4-Zn system.8) TiCl4, Zn, TMEDA

O

O

PbCl2, CH3CHBr2

O

6 or 7 menberd cyclic products

It is known that the reactivity of CH3CHBr2-TiCl4-Zn system is higher than that of Tebbe and Petasis reagents. So olefination-subsequent RCM successfully proceeds even when acyclic substrates, the structure-flexibility of which is higher compared to that of cyclic substrates, are employed. Furthermore, CH3CHBr2-TiCl4-Zn system-promoted RCM of dienes has been reported, which was synthetically difficult when using other organotitanium reagents.8) TiCl4, Zn, TMEDA R1 O R2

n

PbCl2, CH3CHBr2

R1 R2 O

n = 0, 1, 2 n

Although organotitanium species-promoted olefination-subsequent RCM is dependent on the structure of the substrate, it is synthetically very available for use in the RCM process. TCI deals in various organotitanium reagents such as Tebbe and Petasis reagents and titanocene dichloride, which is used for preparation of organotitanium species. 132

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Titanium-mediated Carbonyl Olefination

D3956

C1411

CH3

Organotitanium Reagents

Ti

CH3

T2052

Ti

Cl

Al

CH3

TiCl4

CH3

T0616

Cl

Ti

Cl

Product No. Product Name D3956 C1411 T2052 T0616

Unit Size

Dimethyltitanocene (=Petasis Reagent) (5% in Toluene) Tebbe Reagent (ca. 0.5mol/L in Toluene) Titanium(IV) Chloride (14% in Dichloromethane, ca. 1.0mol/L) Titanocene Dichloride

B0041

100g 25ml 100ml 25g

5g

B1444

B0527

SH SCH2S

Others

B0396

D0184

D0192

D1106

D0610

CH3

Br

Cl

N

CH3

CH3 H3C

Cl Cl

CH3 N

CH3

CH3

O CH3

O

Product No. Product Name B0041 B1444 B0527 B0396 D0184 D0192 D1106 D0400 D0610 T0147 T0430

O

T0430 CH3

CH3

CH3

D0400

CH3CH2 C CH3

CH2Br2

T0147

CH2I2

.

Cl

Br Li

CH3

BF3

Benzenethiol Bis(phenylthio)methane Boron Trifluoride - Ethyl Ether Complex Butyllithium (ca. 15% in Hexane, ca. 1.6mol/L) 1,1-Dibromoethane (stabilized with Copper chip) Dibromomethane 2,2-Dichlorobutane 2,2-Dichloropropane Diiodomethane (stabilized with Copper chip) N,N,N ',N '-Tetramethylethylenediamine Triethyl Phosphite

P

O

CH3

Unit Size 25ml 5g 25ml 100ml 25g

25g 25ml 25ml

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500ml 25g 500ml 500ml 5g 500g 10ml 10ml 500g 500ml 500ml

133

Titanium-mediated Carbonyl Olefination

References 1) 2) 3) 4) 5) 6) 7) 8)

134

, ed. by T. Takeda, Wiley-VCH, 2004. F. N. Tebbe, G. W. Parshall, G. S. Reddy, . 1978, , 3611. N. A. Petasis, E. I. Bzowej, . 1990, , 6392. T. Okazoe, K. Takai, K. Oshima, K. Utimoto, . 1987, , 4410. Y. Horikawa, M. Watanabe, T. Fujiwara, T. Takeda, . 1997, , 1127. T. Takeda, R. Sasaki, T. Fujiwara, . 1998, , 7286. K. C. Nicolaou, M. H. D. Postema, C. F. Claiborne, . 1996, , 1565. K. Iyer, J. D. Rainier, . 2007, , 12604.

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Suzuki-Miyaura Cross-Coupling Reaction

Suzuki-Miyaura Cross-Coupling Reaction The Suzuki-Miyaura reaction is a palladium catalyzed cross-coupling reaction between organic boron compounds and organic halides.1) The reaction requires an additional base for the activation of the boron compound and proceeds under mild conditions. This relatively simple and versatile C-C bond formation reaction can be extended to various substrates and therefore finds wide application for the synthesis of pharmaceuticals and total synthesis of complex natural products. R1 BXn +

PdLn

R2 Y

R1 R 2

Base

Xn = (OH)2, (OR)2, R2, F3K

Y = Cl, Br, I, OTf etc.

Ln = Ligand

The usefulness of this reaction has been well documented by the synthesis of biaryl compounds in 1981,3) triggered by the initial synthesis of dienes using the vinyl-type boron compounds initiated in 1979.2) Eventually the reaction also proved applicable to the coupling reaction of alkyl halides and alkylboranes. Organotrifluoroborates also represent an effective alternative to boronic acids and boronate esters being stable towards numerous reagents and allow the manipulation of functional groups within them.4) -Heterocyclic carbenes prepared from imidazolium and imidazolinium salts can also be efficiently employed as ligands in addition to organophosphine compounds.5) Recently, the synthesis of biaryl compounds without the aid of ligands has also been accomplished.6) It has been recently reported that nickel can also catalyze the above reaction with the same efficiency as the expensive palladium catalysts specially in case of difficult substrates like aryl chlorides in which reaction does not proceed easily with conventional palladium as the catalyst. In addition to being inexpensive, nickel catalysts can also be removed much easily from the reaction system.7) Proper choice of metals, ligands, bases and solvents enable the widespread application of the SuzukiMiyaura cross-coupling reaction to various substrates and different synthetic sequences. We provide a wide range of organic boron compounds as coupling partners. In this section, we introduce different varieties of reaction partners in addition to the organoboron compounds, such as metal catalysts and phosphine ligands to explore the versatile applicability of the Suzuki-Miyaura cross-coupling reaction.

A1479

B2029

CH2 HC

Palladium Catalysts

Pd Cl

CH2

P

CH2

Cl Pd

B1676

3

CH CH2

Pd

Cl

(CH3CN)2PdCl2

CH2

P 3

B1668

B3224

CN Pd

B1374 Ph Ph P

Cl

Pd

Cl Ph

Cl Cl

CH CH C CH CH

Fe

B2192

P C(CH ) 3 3 C(CH3)3

B2161

Ph P Ph PdCl2. CH2Cl2 P Ph

Ph Ph P Cl Pd Cl P

Ph

Ph

Ph

Ph Ph P Cl Pd P Cl Ph Ph

PdCl2

Fe

Pd

2

B2064 Ph Ph P Pd P Ph Ph

C(CH3)3 P C(CH3)3 2

Ph

B2031

O

P

CN

B2016

B3160

B2018 CH3

CH3Ph2P Pd CH3Ph2P

O

Cl

Pd

Cl

O CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

2

135

Suzuki-Miyaura Cross-Coupling Reaction

B3161

B2055

B2042

B1667

B2026 CH3

[(CH3)3C]3P [(CH3)3C]3P

P 3

Pd

Cl

3

Pd Cl

P

O

P

O C CH3

Pd

3

P

Cl

Pd

O C CH3

P

3

P 3

CH3

Cl

Cl

Pd

Cl

P

O

3

P

3

3

C2387

C2372 i-Pr

i-Pr

C2406 i-Pr N

N

i-Pr

i-Pr

i-Pr

i-Pr

HN

i-Pr CH3O

Pd Cl

O

CH3O

N CH3 CH3

CH3

P1491 P1785 P1490

CH3O

i-Pr N

N

i-Pr

i-Pr

Pd Pd Cl

Pd Cl N CH3 CH3

P1489

A1424

HN

Cl Cl

O CH3

P1528

P1870

O

O

Pd

N i-Pr

D2604 i-Pr

i-Pr N

N

Pd Cl

C2407 i-Pr

i-Pr

N

CH3 C O

PdCl2

Pd2

Pd(OH)2

CF3

2

P1425

S0540

T1350

O

Pd2 2

T2184 O

CH3

CH3

P

NH

PdCl2

Na2PdCl4

P 3

20

Pd 4

B2192 B2161 B2018 B3161 B2055 B2042 B1667 B2026 C2387 C2372 C2406

C2407 D2604 P1491 P1785 P1490

136

Ph Ph

Pd

Pd O

Ph Ph

2

n

Product No. Product Name A1479 B2029 B1676 B1668 B3224 B1374 B3160 B2031 B2016 B2064

Ph

Ph

O

Allylpalladium(II) Chloride Dimer Benzylbis(triphenylphosphine)palladium(II) Chloride Bis(acetonitrile)palladium(II) Dichloride Bis(benzonitrile)palladium(II) Dichloride Bis[1,2-bis(diphenylphosphino)ethane]palladium(0) Bis(dibenzylideneacetone)palladium(0) [1,1'-Bis(di-tert-butylphosphino)ferrocene]palladium(II) Dichloride [1,4-Bis(diphenylphosphino)butane]palladium(II) Dichloride [1,2-Bis(diphenylphosphino)ethane]palladium(II) Dichloride [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) Dichloride Dichloromethane Adduct [1,3-Bis(diphenylphosphino)propane]palladium(II) Dichloride Bis(methyldiphenylphosphine)palladium(II) Dichloride Bis(2,4-pentanedionato)palladium(II) Bis(tri-tert-butylphosphine)palladium(0) Bis(tricyclohexylphosphine)palladium(II) Dichloride Bis(triphenylphosphine)palladium(II) Diacetate Bis(triphenylphosphine)palladium(II) Dichloride Bis(tri-o-tolylphosphine)palladium(II) Dichloride Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](acetanilide)palladium(II)] (This product is unavailable for selling domestically in U.S.) Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](N,N-dimethylbenzylamine)palladium(II)] (This product is unavailable for selling domestically in U.S.) Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](N,N-dimethyl3,5-dimethoxybenzylamine)palladium(II)] (This product is unavailable for selling domestically in U.S.) Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](4'-methoxyacetanilide)palladium(II)] (This product is unavailable for selling domestically in U.S.) Dichloro(1,5-cyclooctadiene)palladium(II) Palladium 10% on Carbon (wetted with ca. 55% Water) Palladium 10% on Carbon (wetted with ca. 55% Water) [Useful catalyst for coupling reaction, etc.] Palladium 5% on Carbon (wetted with ca. 55% Water)

O

Unit Size 500mg 100mg 1g 1g 1g 1g 1g 1g 1g

1g 1g 5g 5g 5g 5g 5g 5g 5g

5g 1g 1g 1g 250mg 1g 1g 1g 5g

25g 5g 5g 5g 1g 5g 5g 25g 1g

200mg

1g

200mg

1g

200mg

1g

200mg 1g 5g 5g 5g

1g 5g 25g 25g 25g

1g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Suzuki-Miyaura Cross-Coupling Reaction

Product No. Product Name A1424 P1430

Unit Size

Palladium(II) Acetate Palladium Catalyst Set (includes useful 7 Palladium catalysts)

1g

5g

1g 10g 1g

1set 5g 50g 5g

Palladium(II) Acetate Allylpalladium(II) Chloride Dimer Bis(benzonitrile)palladium(II) Dichloride Bis(dibenzylideneacetone)palladium(0) [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) Dichloride Dichloromethane Adduct Bis(triphenylphosphine)palladium(II) Dichloride Tetrakis(triphenylphosphine)palladium(0)

P1489 P1528 P1870 P1425

Palladium(II) Chloride Palladium Hydroxide 20% on Carbon (wetted with ca. 50% Water) Palladium(II) Trifluoroacetate Poly[N-isopropylacrylamide-co-4-(diphenylphosphino)styrene] Palladium(II) Dichloride

S0540 T1350 T2184

Sodium Tetrachloropalladate(II) Tetrakis(triphenylphosphine)palladium(0) Tris(dibenzylideneacetone)dipalladium(0)

100mg

(ratio, acrylamide:phosphine=20:2)

1g

B2225

B2226 Ph

Nickel Catalysts

B3534

Ph

P

O 3

O CH3

Ph

Ph

Ph

3

Cl

Ni

Cl

P Ph

Cl

P

3

3

Unit Size

[1,2-Bis(diphenylphosphino)ethane]nickel(II) Dichloride [1,1'-Bis(diphenylphosphino)ferrocene]nickel(II) Dichloride [1,3-Bis(diphenylphosphino)propane]nickel(II) Dichloride Bis(2,4-pentanedionato)nickel(II) Hydrate Bis(tricyclohexylphosphine)nickel(II) Dichloride Bis(triphenylphosphine)nickel(II) Dichloride Skeletal Nickel Catalyst slurry in Water [Active catalyst for Hydrogenation]

B2711

1g

Fe P

C(CH3)3 C(CH3)3 C(CH3)3 C(CH3)3

5g 1g 5g 25g 10g

B2710

P

Phosphine Ligands

Cl Ni

Cl

Product No. Product Name B2225 B2226 B1313 N0096 B3534 B1571 S0487

Ph P

P

Cl Ni

P 2

Ph P Ph NiCl2 P Ph

B1571

CH3 Ni

Fe

Cl

P Ph

N0096

Cl

Ni

5g 1g

B1313

Ph P

1g 1g 25g 5g

25g 5g 25g 500g 1g 100g 50g

B1406

P Fe P

CH(CH3)2 CH(CH3)2 CH(CH3)2

PPh2 PPh2

CH(CH3)2

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

137

Suzuki-Miyaura Cross-Coupling Reaction

B1405

B1246

B2709

B1137 CH3

CH3

PPh2

PPh2

P (CH2)4

PPh2

P

P CH2CH2 P

O P

B1113

P

CH3 O CH3 O H

B2867 (C6H5)2P

B1982

CH2 P

CH3 O

CH2

P

CH2 P

CH3 O

CH2

P

B1138

PPh2

2

B1112 H

(CH2)6 P

P

P

D3387

(CH2)5 P

D2411

(CH3)3C

C(CH3)3 P CH2CH2CH2

B1960

P CH2

D3940

P(C6H5)2 O

Fe

P

2

B1959

B2027

C(CH3)3 P

P

P

P C(CH3)3

D3388

D3389

D2535

D2536

D2775 CH3

CH3 P N(CH3)2 PPh2

2

P

(CH3)2N Ph2P

Fe

OCH3 P(C6H5)2

Fe

(CH3)2N

D2766

E0519

T0361

T1912

T1165

t Bu

Bu CH2

P

Bu

P CH2CH3

P

t

P

Bu

t Bu

Bu

T1643

T0519

P

P

T1614

T0861

T1024 OCH3

CH3O

O O

P

P

O

CH3O

3

CH3O

T1025

OCH3

CH3

T0862 CH3

CH3

CH3

CH3

CH3

P

P

P

P P CH3

CH3

CH3

Product No. Product Name B2711 B2710 B1406 B1405 B1246 B2709

138

1,1'-Bis(di-tert-butylphosphino)ferrocene 1,1'-Bis(diisopropylphosphino)ferrocene (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 1,4-Bis(diphenylphosphino)butane 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

Unit Size 100mg 100mg 1g 1g 5g 1g

1g 1g 5g 5g 25g 5g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Suzuki-Miyaura Cross-Coupling Reaction

Product No. Product Name

Unit Size

B1137 B2027 B1959 B1113 B1112 B1982 B1960 B2867 B1138 D3940 D3387 D2411 D3388 D3389 D2535 D2536 D2775 D2766

1,2-Bis(diphenylphosphino)ethane 1,1'-Bis(diphenylphosphino)ferrocene 1,6-Bis(diphenylphosphino)hexane (2R,3R)-(-)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol (2S,3S)-(+)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol Bis(diphenylphosphino)methane 1,5-Bis(diphenylphosphino)pentane Bis[2-(diphenylphosphino)phenyl] Ether 1,3-Bis(diphenylphosphino)propane Di-tert-butylphenylphosphine 2-(Di-tert-butylphosphino)biphenyl Dicyclohexylphenylphosphine 2-(Dicyclohexylphosphino)biphenyl 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl (R)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine (S)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (S)-(-)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl 4-Diphenylphosphinomethyl Polystyrene Resin cross-linked with 2% DVB (200-400mesh)

E0519 T0361 T1912 T1165

Ethyldiphenylphosphine Tributylphosphine Tri-tert-butylphosphine Tricyclohexylphosphine (contains Tricyclohexylphosphine Oxide)

T1643 T0519 T1614 T0861 T1024 T1025 T0862

Tri(2-furyl)phosphine Triphenylphosphine Tris(2,6-dimethoxyphenyl)phosphine Tris(4-methoxyphenyl)phosphine Tris(2-methylphenyl)phosphine Tris(3-methylphenyl)phosphine Tris(4-methylphenyl)phosphine

10g 5g 1g

1g

5g

5g

1g 1g 1g

100mg

(0.5-1.0mmol/g)

25ml 25ml 1g 25g

(ca. 18% in Toluene, ca. 0.60mol/L)

5g 5g 5g 5g

B3506

-Heterocyclic Carbene Ligands

B3465

B3158

(CH3)2CH

N

N

CH3 CH CH3

N

CH3 CH CH3

CH3 CH3 CH3 CH CH3

N

CH

CH3

N (CH3)2CH

N CH(CH3)2 CH(CH3)2

CH(CH3)2

N Cl

(CH3)2CH

CH(CH3)2

Cl

D3882

CH3 N

CH3 CH3

C CH3

N

CH3

N

BF4

(CH3)3C

N

N

C(CH3)3

N

Cl

CH3 C CH3

Cl

CH3

CH3

D3446

500ml 5g 500g 25g 25g 25g 25g 25g

(CH3)2CH

D3472

CH3

N N

CH3 CH3 CH3 CH CH3 CH

N

5g 5g 500ml 5g

D3611

CH3 CH CH3

D3711 CH3

CH3 CH CH3

B3157

25g 25g 5g 1g 1g 25g 1g 5g 25g 5g 1g 5g 5g 5g 100mg 100mg 1g

D3870 CH3

CH3

N N CH3

CH3

CH3

CH3 CH3

N

N

Cl CH3

CH3 CH3

CH3

CH3

Product No. Product Name B3506 B3157 D3611 B3465 B3158 D3711

1,3-Bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene 1,3-Bis(2,6-diisopropylphenyl)imidazolinium Chloride 1,3-Bis(2,6-diisopropylphenyl)imidazolium Chloride 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium Chloride 1,3-Di-tert-butylimidazolium Tetrafluoroborate

Unit Size 500mg 500mg 1g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

1g 5g 5g 5g 5g 5g

139

Suzuki-Miyaura Cross-Coupling Reaction

Product No. Product Name D3472 D3882 D3446 D3870

Unit Size

1,3-Di-tert-butylimidazol-2-ylidene 1,3-Dicyclohexylimidazolium Chloride (This product is only available for selling domestically in Japan) 1,3-Dimesitylimidazolium Chloride 1,3-Dimesitylimidazol-2-ylidene

H1176

T1848

1g 1g 1g 1g

5g 5g 5g 5g

T0508 O

CH3 C O

O CF3(CF2)7 S

Others

F

O

Sb

As

CH3 C O O

Product No. Product Name H1176 T1848 T0508

Unit Size

Heptadecafluoro-1-octanesulfonyl Fluoride Triphenylantimony Diacetate Triphenylarsine

25g

250g 1g 5g

Bases & Additives Product No. Product Name D0905 B2695 B0468 B1018 B0709 C2430 C2160 C2204 D0925 D1599 L0204 L0222 M0508 P0221 P0081 P1748 P1758 P1779 S0560 S0485 T0054 T0057 Z0015

Bathophenanthroline Bathophenanthroline (refined product of D0905) 2,2'-Bipyridyl 1,8-Bis(dimethylamino)naphthalene [for Dehydrohalogenation] tert-Butylamine Cesium Acetate Cesium Carbonate Cesium Fluoride Diisopropylamine N,N-Diisopropylethylamine Lithium Chloride Anhydrous Lithium Chloride (2.3% in Tetrahydrofuran, ca. 0.5mol/L) 1-Methylimidazole 1,10-Phenanthroline Monohydrate 1,10-Phenanthroline Hydrochloride Monohydrate Potassium Carbonate Potassium Fluoride Potassium Fluoride Anhydrous (Spray-dried) Sodium Carbonate Sodium Methoxide Tetrabutylammonium Bromide Tetrabutylammonium Iodide Zinc (Powder)

Unit Size 1g

1g

25ml

25g 5g 25ml 25g 25g 25g 25ml 100ml 25g 25g 1g

100g 25g 25g

5g 1g 500g 25g 500ml 100g 100g 100g 500ml 500ml 300g 100ml 500g 25g 25g 300g 300g 25g 300g 500g 500g 500g 300g

References 1) Review: A. Suzuki, . 2005, 4759; A. Suzuki, 2005, 2004, , 312; A. Suzuki, , 359; N. Miyaura, A. Suzuki, . 1995, , 2457. 2) N. Miyaura, K. Yamada, A. Suzuki, . 1979, , 3437. 3) T. Yanagi, N. Miyaura, A. Suzuki, . 1981, , 513. 4) Review: G. A. Molander, N. Ellis, . 2007, , 275. 5) Review: E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, . 2007, , 2768. 6) T. Maegawa, Y. Kitamura, S. Sako, T. Udzu, A. Sakurai, A. Tanaka, Y. Kobayashi, K. Endo, U. Bora, T. Kurita, A. Kozaki, Y. Monguchi, H. Sajiki, . 2007, , 5937. 2006, 7) Review: T. Kamikawa, , 53.

140

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Iron-Catalyzed Organic Synthesis

Iron-Catalyzed Organic Synthesis Including palladium catalysts, which are frequently used for the Suzuki-Miyaura coupling reaction, transition metal catalysts, such as nickel, copper, or rhodium, have been widely used for organic synthesis. However, the percentages of these metals in the earth’s crust are extremely small, and their prices are rather expensive.1) On the other hand, iron is abundant and less expensive, therefore, more and more chemists have focused their attention to organic synthesis using iron compounds as a catalyst. 2) For instance, with regards to the reactions of Grignard reagents with alkyl bromides, Hayashi and 3) Chai have reported the synthetic methods using Fe(acac)3 as a catalyst, Fe(OAc)2 as a catalyst and Xantphos as a ligand, respectively, by which the desired coupling products can be obtained in good yields. Fe(acac)3 (5 mol%)

(CH2)5CH3

MgBr

+

Et2O, reflux, 0.5 h

Br

(CH2)5CH3 Y. 73%

Br 8

Fe(OAc)2 (3 mol%)

O PPh2

PPh2

Xantphos (6 mol%)

MgBr

+

8

Et2O, rt, 15 min

Y. 64%

Furthermore, Nakamura have reported the method using the -heterocyclic carbene generated from SIPr・HCl, which suppresses the generation of the homo-coupling products, thereby leading to an excellent yield of the desired product.4) Cl

iPr

N iPr

FeF3 3H2O (5 mol%) Cl

+ BrMg

iPr

N + iPr

SIPr HCl (15 mol%)

THF, 60 °, 24 h Y. 98%

Thus, synthetic technologies using iron catalysts are being actively developed. It can be expected that iron catalysts will exhibit their own catalytic properties in addition to replacing other metal catalysts in the near future.

D2571

I0765

T1686 Ph

N

N

O

O Fe2

Fe

Iron Catalysts

O

CH3

O

O

Fe O

2

Ph

H0555

I0079

T0750 CH3

CF3 O

CF3 O

O Fe

Fe

Fe

O CF3

O

O 3

3

CH3

3

CH3

3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

141

Iron-Catalyzed Organic Synthesis

Product No. Product Name

Unit Size

N,N '-Bis(salicylidene)ethylenediamine Iron(II) Iron(II) Acetate Tris(dibenzoylmethanato) Iron Tris(hexafluoroacetylacetonato)iron(III) Tris(2,4-pentanedionato)iron(III) Tris(trifluoro-2,4-pentanedionato)iron(III)

D2571 I0765 T1686 H0555 I0079 T0750

5g 5g 5g

25g 25g 25g 1g 500g 5g

25g

B3372

B2709 CH3

CH3

PPh2 PPh2

O

Phosphine Ligands

Ligands

B1137

B1982

P

D3387

P CH2

D2471

(CH3)3C

P

P 2

2

T1912

C(CH3)3 t Bu

P P

P CH2CH2 P

t

Bu

P

N

T1165

t Bu

T0519

P

P

Product No. Product Name B3372 B2709 B1137 B1982 D3387 D2471 T1912 T1165 T0519

Unit Size

1,2-Bis(diphenylphosphino)benzene 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene 1,2-Bis(diphenylphosphino)ethane Bis(diphenylphosphino)methane 2-(Di-tert-butylphosphino)biphenyl Diphenyl-2-pyridylphosphine Tri-tert-butylphosphine Tricyclohexylphosphine (contains Tricyclohexylphosphine Oxide) (ca. 18% in Toluene, ca. 0.60mol/L) Triphenylphosphine

D0905

D0720

CH3

Bidentate Nitrogen Ligands

N

142

N H

H N

25ml 25g

T0147 CH3

N CH3

N

5g 5g 25g 25g 1g 1g 5g 500ml 500g

. H2O

CH3

N

N

CH3

CH3

N

Product No. Product Name D0905 D0720 P0879 T0147

P0879

1g 1g 10g 5g

Bathophenanthroline N,N '-Dimethylethylenediamine 1,10-Phenanthroline Monohydrate N,N,N ',N '-Tetramethylethylenediamine

Unit Size 1g 5ml 25ml

5g 25ml 25g 500ml

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Iron-Catalyzed Organic Synthesis

B3506

B3157 CH3 CH CH3

NHC & Precursors

CH3 CH CH3

B3158

CH3 CH3 CH3

D3621

(CH3)2CH

CH(CH3)2

D3711

N

N

N

CH3 CH3 CH3

CH CH

CH3

C CH3 CH3

N

BF4

Cl

BF4

BF4

(CH3)3C

N

N

C(CH3)3

CH3 C CH3 CH3

CH3

D3882

D3850

D3622

N

D3623

N

N Cl

D3870

CH

D3446

CH3 N

CH3

CH

CH3

CH3

CH3

N

CH3

CH3

N

N

N

BF4

CH

CH3 CH3

BF4

N CH

CH3

BF4

CH3

CH3

CH3

Cl

CH3

P1816 CH3

CH3 N CH3

CH3 CH CH3

D3472

N

N

CH3

N

Cl

N

CH3

CH3

CH3

Cl

CH3

N N

CH(CH3)2

N CH(CH3)2

N

CH3

D3620 CH3

CH(CH3)2

N (CH3)2CH

CH3 CH CH3

N

N

CH CH

B3465

(CH3)2CH

(CH3)2CH

N N

D3611

N

N

CH3 CH3

CH3

N

N CH3

N N

2Br

CH3

Product No. Product Name B3506 B3157 D3611 B3465 B3158 D3620 D3621 D3711 D3472 D3882 D3850 D3622 D3623 D3446 D3870 P1816

1,3-Bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene 1,3-Bis(2,6-diisopropylphenyl)imidazolinium Chloride 1,3-Bis(2,6-diisopropylphenyl)imidazolium Chloride 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium Chloride 1,3-Di(1-adamantyl)imidazolinium Tetrafluoroborate 1,3-Di(1-adamantyl)imidazolium Tetrafluoroborate 1,3-Di-tert-butylimidazolium Tetrafluoroborate 1,3-Di-tert-butylimidazol-2-ylidene 1,3-Dicyclohexylimidazolium Chloride (This product is only available for selling domestically in Japan) 1,3-Dicyclohexylimidazolium Tetrafluoroborate 1,3-Diisopropylimidazolinium Tetrafluoroborate 1,3-Diisopropylimidazolium Tetrafluoroborate 1,3-Dimesitylimidazolium Chloride 1,3-Dimesitylimidazol-2-ylidene 1,1'-(2,6-Pyridinediyl)bis(3-methylimidazolium) Dibromide

Unit Size 500mg 500mg 1g 1g

1g 1g 1g 1g 1g 1g

1g 5g 5g 5g 5g 500mg 1g 5g 5g 5g 5g 5g 1g 5g 5g 1g

References 1) 2) 3) 4)

J. Emsley, in , 3rd ed., Oxford Univ. Press, New York, 1998. 2004, , 1297. T. Nagano, T. Hayashi, 2007, K. G. Dongo, H. Koh, M. Sau, C. L. L. Chai, , 1015. 2007, T. Hatakeyama, M. Nakamura, , 9844.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

143

Metal Catalysts

Metal Catalysts for Organic Synthesis

T1548

T1550

T1304

O

O CF3

Homogeneous Catalysts

A0804

OCH(CH3)2

Al

Al

OC(CH3)3

(CH3)2CHO

CF3

O

M1211

2

A0241 tBu

t

CH3 Bu

O

Cl CH3CH2 Al

OCH(CH3)2

CH3

Cl

Mg2

S O

O

E0648

OC(CH3)3

O

S ONa

O

A0246

(CH3)3CO

CF3

S OLi

O

Al

CH3

O

Al

O

CH3 tBu

tBu

CH3

A1267

T1549

T1663

B1588

3

C1994

CF3 O

O Al

CF3

O CH3

O

S OK

CF3

O

O Sc3

S O O

Ti O

Cl

O

3

Ti

Cl

Cl

3

D2257

I0646

P1651

B0742

T0967

CH3 Cl

CH3

(CH3)2CHO Ti OCH(CH3)2 Cl

Cl

Ti

CH3(CH2)3O Ti

Cl

CH3 Ti CH3 Cl3

Cl

T0978

T0133

T0666

OCH2CH3

O(CH2)3CH3

CH3

O(CH2)3CH3

CH3CH2O Ti OCH2CH3

O(CH2)3CH3

C0336

OCH2CH3

H0557 CF3

CH3 OCH(CH3)2

OCH2CH(CH3)2 (CH3)2CHCH2O Ti OCH2CH(CH3)2

(CH3)2CHO Ti OCH(CH3)2

OCH2CH(CH3)2

O(CH2)17CH3 CH3(CH2)17O Ti O(CH2)17CH3

M0042 O N

N

CH3

T0685

Mn

T1686

CH3

2

N

CF3

CH3

Fe

Fe CH3

CH3

CH3 CH3

O

CH3

N

3

CH3

N

CH3

O

Co

O

O 3

2

O

O

O

O

B2314 CF3

Fe

O

Fe2 O

2

CH3

Fe

O CH3

T0750

O

O

N Fe

O

I0079 CF3

3

2

I0765

Mn O

H0555 Ph

144

. 2H2O

O CH3

Ph

D2571

O

O

Mn O O Ph Ph

CF3

3

CF3

CH3

C O

. xH2O

O

O CH3

B2409

Mn

Cr

O(CH2)17CH3

OCH(CH3)2

O

O

3

CH3

O CH3

CH3

O CH3

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Metal Catalysts

B2315

H0553

CH3

CH3

CH3 CH3

B1844

CF3

CH3

O

N

CH3

N

O

Co CH3

. xH2O

Co

O

O

CH3

O

CH3

CH3

B2681

CF3

O

O

Co CH3

Ph

OC

Fe

Ph

CO

Ph

Ph

Ph

Ni Cl

P

CH3

Cl

O

Cl

O

2

H0554

O

N

N

Cl

N

CF3

Ni N

Br

CH3

CF3

Br

CH3

(CH3)2CH

CH3

N

N N

2

T1292 CH3

CH(CH3)2 Cu Cl CH(CH3)2

. xH2O

Cu O

2

C2422

Cu O

O Ni2

S O O

N

O

CH3

CH3

2

CF3

2

. xH2O

Ni O

N0861

(CH3)2CH

CH3

O

Ni . xH2O

CF3

Ph

3

N0096

CF3

Ph

C2304

O

O

CF3 Cl

Ni

Cu

O

CH3

P

T0752

O

O Co

O

Ni

3

CH3

N Co

CO

P

P

3

C0384

CH3

P 3

2

C0374

N

B3354

Cl

3

CH3

H0558

Ph P Ph NiCl2 P Ph

B1571

P

O

O CH3

CO Co

. 2H2O

Co

O

CH3

B1313

Cl

B3534

O

CO

Co

2

Ph

P

O

CH3

S0318

OC

B2226

Cl

O

Co

CH3

CH3

OC

. xH2O

O

Ni

O

CH3

CH3 N

CO

O

P

CH3

D3213

Co

Ph

Co

CH3

Ph

N

CH3

O

B2225

CH3 Ph CH3

N

CF3

2

CH3

CH3 N

2

O

CH3

C0373

Ph

CH3

O

T0746 CH3

CH3 Ph

O CH3

B1845

O

CH3 Cu Cl CH3

N CH3

CF3

Cu2

S O O

2

2

CH3

T1442

D2542

O CF3

Cu2

S O O

.

2

C1995

Z0002

H3C CH3 N Cu N H3C CH3

H3C CH3 N Cu O N H H3C CH3

Zn

CH3

B1902

Cl

Ru Cl

Ru Cl

O Zr

O

B3067

Cl

CH3 O

CH3

4

CF3SO3

Zr SO3CF3

.

Mo O

O

CH3

4

B3068

C2201

Ph

Ph

P

P

Ph Cl Ru Cl P Ph Ph

3

M0464

CF3

O

Y3

S O O

2

2

Zr

Cl

CF3

Z0009

O Cl

Zn2

S O O

T0747 CH3

Zr

CF3

O CH3

O

O

O 2Cl

Z0006

Cl

T1921

CH3

2

H O

T1294

Ph Cl Ru Cl P Ph Ph

O O

2

D2751 (CH3)2CH

CH3 Cl

Ph3P Ru PPh3 Cl

Cl Ru

Ru Cl Cl

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

CH(CH3)2

145

Metal Catalysts

H1010

P1688

R0074

R0086

T1559

(C6H11)3P Cl Cl

Ru

Pr

Cl

Cl

Ru

Cl

Ru Cl

RuCl3

. H2O

RuCl3NO

Pr

N Pr

(C6H11)3P

T1655

RuO4

Pr

T2183

D1997

B2090

B2091

2

CH3

N N

O

N

P

Ru

2Cl

Ru N

N N

B1692

Cl Cl

3

BF4 Rh

(CH3)3C

3

C2253

2

P

Rh

C(CH3)3

CH3

C1383

BF4

CH3

P

CH3

. 6H2O

Rh

3

O

B1045

N0453

P 3

Cl

CO

Rh

P

CO

Rh

H

Cl

Cl

Rh

Rh

Cl

Cl

Rh

Cl

P

Rh

Rh

Rh Cl

3 3

P1788

R0069

T2054

T2055

CH3 O Cl Cl

Rh Cl

Rh

Cl

CH3

R

H

O

CH3 O O Rh

Rh O O

O

Rh

Rh

O O O

R

O

OO

R O

O H

R

. 2 CH3

H OO

R

O

Rh Rh O O O H R

O

R=

H

O

Cl Cl Cl

. 2 CH3

Rh

N

O O

O

Cl

C OCH2CH3

T1544

R R'

Ph O Rh O O Ph Ph Ph

Rh

Rh

O

O

O

N

R=

O

H

O

. 2 CH3

R

R

O

O

Cl Cl

O H

C OCH2CH3

Cl

N

R=

O

. 2 CH3

O

Cl

C OCH2CH3

T2661

H R' OO

O

R

H R'

R

R O

Rh

O O O

R'=

O O O

R

O

R

O

O

O

. 2 CH3

O

F

H OO

Rh Rh

N

R=

F

H

R

F F

O

H

O

. CH3

OO

Rh Rh

CH2

H

H

O

N

R=

R

H

O

O

H

O O O

R

H

R

C OCH2CH3

H OO

Rh Rh

O

H

O

R

R

O O O

R H

R

C OCH2CH3

R

O

R=

N

O

F F F

O H

. 2 CH3

O

O

F

C OCH2CH3

C OCH2CH3

T0931 Ph Ph O

OO

O O O

R

H

H

O

T2660 R' H

R O

A1479

B2029

B1676

Ph Ph Ph O O Ph Rh

O

CH2

P 3

O Ph Ph

. CH2Cl2

B1668

Rh

Cl

Pd

3

Ph Ph P

Cl

Pd

Cl

3

CH CH2

Pd

Cl

(CH3CN)2PdCl2

CH2

P

B3160 C(CH3)3 P C(CH3)3

CH CH C CH CH 2

Ph

Cl Fe

B2031

O

P Ph

Cl

Pd Cl

B1374

B2192

P C(CH ) 3 3 C(CH3)3

B2161

Ph P Ph PdCl2. CH2Cl2 P Ph

Ph Ph P Cl Pd Cl P

Ph

Ph

Ph

Ph Ph P Cl Pd P Cl Ph Ph

PdCl2

Fe

Pd

2

B2064 Ph Ph P Pd P Ph Ph

P

CH2

Cl Pd

3

CN

B2016

HC CH2

B3224

CN

146

N

R=

T1551 H

R

O

O

H

R

H

H

O

CH3

T2659

T2658

R

B2018 CH3

CH3Ph2P Pd CH3Ph2P

O

Cl

Pd

Cl

O CH3

2

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Metal Catalysts

B3292

B3161

B2055

B2042

O

O S

O C CH3

O

O

B3553

P 3

Pd

N

N N

Cl

Pd Br

i-Pr N

O C

Cl HN

C2407

D3806 i-Pr

i-Pr

i-Pr

i-Pr

N

N OH

Pd Cl O

Cl

CH3

i-Pr

N CH3 CH3

D3807

D2604 OH CH3

HO Pd N OH

CH3

Cl Pd Cl

N

Cl

Pd

Cl

HO

Cl

A1424

i-Pr

Pd Cl

CH3O

N CH3 CH3

CH3 CH3 N Cl Pd Pd Cl N CH3 CH3

HO Cl Pd Pd Cl

N

i-Pr CH3O

Pd Cl

O

i-Pr N

N

i-Pr

D3847 Cl

N

i-Pr

i-Pr N

Cl

i-Pr N

HN

C2406 i-Pr

CH3

3

Cl

P

O

Pd Cl

P

Cl

Pd

3

N

i-Pr

N

P 3

O C CH3

P

C2372 i-Pr

O C

Pd

O C CH3

3

C2387

CH3

P1489

P1870

S0540

T1350

O

O

PdCl2

Pd2

CH3 C O

C2373

Na2PdCl4

Pd2

O

CF3

2

T2184

P

Pd

3

2

T1331

D2466

4

T1194

(CH3)2CH

O Ph

Ph Ph Ph

Cl

3

B2026

CH3

3

Pd P

O

P

Cl

3

Pd

[(CH3)3C]3P

O C CH3

S

P

[(CH3)3C]3P

Pd

CH3O

B1667

Pd

Pd O

Ph Ph

CH(CH3)2 Ag Cl CH(CH3)2

(CH3)2CH

(CH2)3CH3

O

N N

CF3

CF3SO3

S OAg

Sn

SO3CF3

O CF3

(CH2)3CH3

O

Sn2

S O O

2

O

T1918

T1293

T1919

T1920

L0148 CH3

O CF3

O Ce3

S O O

CF3

T1610

La3

S O O

3

O

O CF3

Nd3

S O O

3

T1708

CF3

O Tm3

S O O

3

C1807

La

. xH2O

O

3

CH3

P1763

3

B3115 CH3

O CF3

O Yb3

S O O

3

. xH2O

B3162

[(CH3)3C]3P [(CH3)3C]3P

CF3

Hf4

S O O

Cl

Ir

Cl

Cl

Ir

Ir

Cl

O

Cl

Pt O

4

D3592

Pt

Ir

Cl

CH3

2

T2485

Pt

Cl Cl

P 3

Pt 4

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

147

Metal Catalysts

Product No. Product Name T1548 T1550 T1304 A0804 A0246 E0648 M1211 A0241 A1267 T1549 T1663 B1588 C1994 D2257 I0646 P1651 B0742 T0967 T0978 T0133 T0666 C0336 H0557 B2409 M0042 T0685 D2571 I0765 T1686 H0555 I0079 T0750 B2314 B2315 H0553 B1844 B1845 C0373 B2681 T0746 D3213 S0318 C0374 B2225 B2226 B1313 H0558 N0096 B3534 B1571 B3354 N0861 H0554 C0384 T0752 C2304 C2422 T1292 T1442 D2542 Z0002 T1294 T1921 C1995

148

Lithium Trifluoromethanesulfonate Sodium Trifluoromethanesulfonate Magnesium Trifluoromethanesulfonate Aluminum tert-Butoxide Aluminum Isopropoxide Ethylaluminum Dichloride (17% in Hexane, ca. 1mol/L) Methylaluminum Bis(2,6-di-tert-butyl-4-methylphenoxide) (0.4mol/L in Toluene) Tris(2,4-pentanedionato)aluminum(III) Tris(trifluoro-2,4-pentanedionato)aluminum(III) Potassium Trifluoromethanesulfonate Scandium(III) Trifluoromethanesulfonate [1,2-Benzenediolato(2-)-O,O ']oxotitanium Cyclopentadienyltitanium(IV) Trichloride Dichlorotitanium Diisopropoxide (Indenyl)titanium(IV) Trichloride (Pentamethylcyclopentadienyl)titanium(IV) Trichloride Tetrabutyl Orthotitanate Tetraethyl Orthotitanate Tetraisobutyl Orthotitanate (contains Isopropoxide) Tetraisopropyl Orthotitanate Tetraoctadecyl Orthotitanate Tris(2,4-pentanedionato)chromium(III) Bis(hexafluoroacetylacetonato)manganese(II) Hydrate (1S,2S)-N,N '-Bis[(R)-2-hydroxy-2'-phenyl-1,1'-binaphthyl-3-ylmethylene]-1,2-diphenylethylenediaminato Manganese(III) Acetate Bis(2,4-pentanedionato)manganese(II) Dihydrate Bis(trifluoro-2,4-pentanedionato)manganese(II) N,N '-Bis(salicylidene)ethylenediamine Iron(II) Iron(II) Acetate Tris(dibenzoylmethanato) Iron Tris(hexafluoroacetylacetonato)iron(III) Tris(2,4-pentanedionato)iron(III) Tris(trifluoro-2,4-pentanedionato)iron(III) (1R,2R)-N,N '-Bis(2-acetyl-3-oxo-2-butenylidene)-1,2-dimesitylethylenediaminato Cobalt(II) (1S,2S)-N,N '-Bis(2-acetyl-3-oxo-2-butenylidene)-1,2-dimesitylethylenediaminato Cobalt(II) Bis(hexafluoroacetylacetonato)cobalt(II) Hydrate (1R,2R)-N,N '-Bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-1,2-diphenylethylenediaminato Cobalt(II) (1S,2S)-N,N '-Bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-1,2-diphenylethylenediaminato Cobalt(II) Bis(2,4-pentanedionato)cobalt(II) Dihydrate Bis(2,4-pentanedionato)cobalt(II) Bis(trifluoro-2,4-pentanedionato)cobalt(II) Hydrate Dicobalt Octacarbonyl (stabilized with 1-5% Hexane) Salcomine [=N,N '-Bis(salicylidene)ethylenediiminocobalt(II)] Tris(2,4-pentanedionato)cobalt(III) [1,2-Bis(diphenylphosphino)ethane]nickel(II) Dichloride [1,1'-Bis(diphenylphosphino)ferrocene]nickel(II) Dichloride [1,3-Bis(diphenylphosphino)propane]nickel(II) Dichloride Bis(hexafluoroacetylacetonato)nickel(II) Hydrate Bis(2,4-pentanedionato)nickel(II) Hydrate Bis(tricyclohexylphosphine)nickel(II) Dichloride Bis(triphenylphosphine)nickel(II) Dichloride Bromo[(2,6-pyridinediyl)bis(3-methyl-1-imidazolyl-2-ylidene)]nickel Bromide Nickel(II) Trifluoromethanesulfonate Bis(hexafluoroacetylacetonato)copper(II) Hydrate Bis(2,4-pentanedionato)copper(II) Bis(trifluoro-2,4-pentanedionato)copper(II) Chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I) Chloro(1,3-dimesitylimidazol-2-ylidene)copper(I) Copper(II) Trifluoromethanesulfonate Copper(I) Trifluoromethanesulfonate Benzene Complex Di-μ-hydroxo-bis[(N,N,N ',N '-tetramethylethylenediamine)copper(II)] Chloride Bis(2,4-pentanedionato)zinc(II) Zinc(II) Trifluoromethanesulfonate Yttrium(III) Trifluoromethanesulfonate Cyclopentadienylzirconium(IV) Trichloride

Unit Size 5g 5g 100g

25g 5g 1g 1g 5g

25g 25ml 25g 25g 25g 1g

25g 5g 5g 5g 25g

25g 25g 25g 25g 500g 100ml 50ml 500g 25g 25g 5g 1g 5g 25g 1g 1g 500g 500ml 25ml 500g 500g 500g 5g 100mg 500g 5g 25g 25g 25g 1g 500g 5g 100mg 100mg 5g 100mg

25g

25g 1g

100g 25g 5g 1g 5g 1g 25g 10g 1g 1g 25g 200mg 200mg 5g 1g 5g 25g 5g 1g

100mg 500g 25g 5g 5g 500g 500g 25g 5g 25g 5g 500g 1g 100g 1g 5g 5g 250g 5g 1g 1g 25g 5g 25g 500g 25g 25g 5g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Metal Catalysts

Product No. Product Name Z0006 T0747 Z0009 M0464 B1902 B3067 B3068 C2201 D2751 H1010 P1688

Tetrakis(2,4-pentanedionato)zirconium(IV) Tetrakis(trifluoro-2,4-pentanedionato)zirconium(IV) Zirconocene Bis(trifluoromethanesulfonate) Tetrahydrofuran Adduct Bis(2,4-pentanedionato)molybdenum(VI) Dioxide Benzeneruthenium(II) Chloride Dimer [(R)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II) Dichloride [(S)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II) Dichloride Cyclopentadienylbis(triphenylphosphine)ruthenium(II) Chloride Dichloro(p-cymene)ruthenium(II) Dimer (Hexamethylbenzene)ruthenium(II) Dichloride Dimer (3-Phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(IV) Dichloride

R0074 R0086 T1559 T1655 T2183 D1997 B2090

Ruthenium(III) Chloride Ruthenium(II) Nitrosyl Chloride Monohydrate Tetrapropylammonium Perruthenate Tris(2,2'-bipyridyl)ruthenium(II) Chloride Hexahydrate Tris(2,4-pentanedionato)ruthenium(III) Tris(triphenylphosphine)ruthenium(II) Dichloride (S,S)-1,2-Bis[(tert-butyl)methylphosphino]ethane[η-(2,5-norbornadiene)]rhodium(I) Tetrafluoroborate Bis[η-(2,5-norbornadiene)]rhodium(I) Tetrafluoroborate Carbonylbis(triphenylphosphine)rhodium(I) Chloride Carbonyltris(triphenylphosphine)rhodium(I) Hydride Chlorobis(cyclooctene)rhodium(I) Dimer Chloro(1,5-cyclooctadiene)rhodium(I) Dimer Norbornadiene Rhodium(I) Chloride Dimer (Pentamethylcyclopentadienyl)rhodium(III) Dichloride Dimer Rhodium(II) Acetate Dimer Tetrakis[N-phthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-phthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-phthaloyl-(S)-phenylalaninato]dirhodium Ethyl Acetate Adduct Tetrakis[N-tetrafluorophthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis(triphenylacetato)dirhodium(II) Dichloromethane Adduct Tris(triphenylphosphine)rhodium(I) Chloride Allylpalladium(II) Chloride Dimer Benzylbis(triphenylphosphine)palladium(II) Chloride Bis(acetonitrile)palladium(II) Dichloride Bis(benzonitrile)palladium(II) Dichloride Bis[1,2-bis(diphenylphosphino)ethane]palladium(0) Bis(dibenzylideneacetone)palladium(0) [1,1'-Bis(di-tert-butylphosphino)ferrocene]palladium(II) Dichloride [1,4-Bis(diphenylphosphino)butane]palladium(II) Dichloride [1,2-Bis(diphenylphosphino)ethane]palladium(II) Dichloride [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) Dichloride Dichloromethane Adduct [1,3-Bis(diphenylphosphino)propane]palladium(II) Dichloride Bis(methyldiphenylphosphine)palladium(II) Dichloride Bis(2,4-pentanedionato)palladium(II) 1,2-Bis(phenylsulfinyl)ethane Palladium(II) Diacetate Bis(tri-tert-butylphosphine)palladium(0) Bis(tricyclohexylphosphine)palladium(II) Dichloride Bis(triphenylphosphine)palladium(II) Diacetate Bis(triphenylphosphine)palladium(II) Dichloride Bis(tri-o-tolylphosphine)palladium(II) Dichloride Bromo[[1,3-bis[(4S,5S)-1-benzoyl-4,5-diphenyl-2-imidazolin2-yl]benzene]palladium(II)] Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](acetanilide)palladium(II)] (This product is unavailable for selling domestically in U.S.) Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](N,N-dimethylbenzylamine)palladium(II)] (This product is unavailable for selling domestically in U.S.) Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](N,N-dimethyl3,5-dimethoxybenzylamine)palladium(II)] (This product is unavailable for selling domestically in U.S.) Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](4'-methoxyacetanilide)palladium(II)] (This product is unavailable for selling domestically in U.S.) Di-μ-chlorobis[5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl]palladium(II) Dimer

Unit Size 25g 1g 1g

1g 1g 100mg 1g

Tetrahydrofuran Adduct

B2091 B1692 C1383 C2253 B1045 N0453 P1788 R0069 T2054 T2055 T2658 T2659 T1551 T2660 T2661 T1544 T0931 A1479 B2029 B1676 B1668 B3224 B1374 B3160 B2031 B2016 B2064 B2192 B2161 B2018 B3292 B3161 B2055 B2042 B1667 B2026 B3553 C2387 C2372 C2406

C2407 D3806

1g 1g 1g 1g

100mg 1g 100mg 100mg

100mg

1g 500mg 100mg 1g 1g 1g 1g 1g 1g 1g 1g

5g 1g 1g 1g 200mg 250mg 1g 1g 1g 5g

500g 1g 5g 25g 5g 250mg 250mg 5g 5g 1g 1g 5g 1g 5g 5g 5g 5g 50mg 1g 1g 5g 500mg 1g 100mg 200mg 1g 100mg 100mg 50mg 100mg 100mg 50mg 100mg 100mg 5g 1g 1g 5g 5g 5g 5g 5g 5g 5g 25g 5g 5g 5g 1g 1g 5g 5g 25g 1g 100mg

200mg

1g

200mg

1g

200mg

1g

200mg

1g

250mg

1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

149

Metal Catalysts

Product No. Product Name D3847 D3807 D2604 A1424 P1430

Unit Size

Di-μ-chlorobis[2-[(dimethylamino)methyl]phenyl-C,N]dipalladium(II) Di-μ-chlorobis[5-hydroxy-2-[1-(hydroxyimino)ethyl]phenyl]palladium(II) Dimer Dichloro(1,5-cyclooctadiene)palladium(II) Palladium(II) Acetate Palladium Catalyst Set (includes useful 7 Palladium catalysts) Palladium(II) Acetate Allylpalladium(II) Chloride Dimer Bis(benzonitrile)palladium(II) Dichloride Bis(dibenzylideneacetone)palladium(0) [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) Dichloride Dichloromethane Adduct Bis(triphenylphosphine)palladium(II) Dichloride Tetrakis(triphenylphosphine)palladium(0)

P1489 P1870 S0540 T1350 T2184 C2373 T1331 D2466 T1194 T1918 T1293 T1919 T1920 L0148 T1610 T1708 C1807 P1763 B3115 B3162 D3592 T2485

Palladium(II) Chloride Palladium(II) Trifluoroacetate Sodium Tetrachloropalladate(II) Tetrakis(triphenylphosphine)palladium(0) Tris(dibenzylideneacetone)dipalladium(0) Chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]silver Silver Trifluoromethanesulfonate Dibutyltin Bis(trifluoromethanesulfonate) Tin(II) Trifluoromethanesulfonate Cerium(III) Trifluoromethanesulfonate Lanthanum(III) Trifluoromethanesulfonate Neodymium(III) Trifluoromethanesulfonate Thulium(III) Trifluoromethanesulfonate Tris(2,4-pentanedionato)lanthanum(III) Hydrate Ytterbium(III) Trifluoromethanesulfonate Hydrate Hafnium(IV) Trifluoromethanesulfonate Chloro(1,5-cyclooctadiene)iridium(I) Dimer (Pentamethylcyclopentadienyl)iridium(III) Dichloride Dimer Bis(2,4-pentanedionato)platinum(II) Bis(tri-tert-butylphosphine)platinum(0) Dichloro(1,5-cyclooctadiene)platinum(II) Tetrakis(triphenylphosphine)platinum(0)

1g 1g 5g 5g

250mg 1g 1g

1g 1g 1g

5g 1g 200mg 10g

1g

5g 5g 5g

5g 1g

200mg

1set 5g 5g 1g 25g 5g 1g 25g 5g 25g 5g 25g 25g 5g 25g 25g 5g 1g 1g 1g 250mg 1g 1g

Heterogeneous Catalysts Product No. Product Name P1702 P1703 P1491 P1785 P1490 P1701 P1528 P1786 R0075 R0076 S0487

Palladium 5% on Barium Sulfate Palladium 5% on Calcium Carbonate (poisoned with Lead) Palladium 10% on Carbon (wetted with ca. 55% Water) Palladium 10% on Carbon (wetted with ca. 55% Water) [Useful catalyst for coupling reaction, etc.] Palladium 5% on Carbon (wetted with ca. 55% Water) Palladium 5% on Barium Carbonate Palladium Hydroxide 20% on Carbon (wetted with ca. 50% Water) Palladium on SH Silica Gel (0.1mmol/g) Rhodium 5% on Carbon (wetted with ca. 55% Water) Ruthenium 5% on Carbon (wetted with ca. 50% Water) Skeletal Nickel Catalyst slurry in Water [Active catalyst for Hydrogenation]

Unit Size 5g 5g 5g 5g 5g 10g

5g

25g 25g 25g 25g 25g 10g 50g 1g 1g 25g 50g

Polymer-Supported Reagents (see p.24) References 1) C. Elschenbroich, J. Oliveira, in , 3rd ed., Wiley-VCH, Weinheim, 2006. 2) Y. Murakami, J. Kikuchi, Y. Hisaeda, O. Hayashida, . 1996, , 721.

150

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Grignard Reagents & Alkyl Metals

Grignard Reagents & Alkyl Metals

A0963

A1554

B1883 CH2MgBr

CH2

MgBr

Grignard Reagents

B1933

B1884

CH2

B0726

C1504

B1147 B1148

CH2MgCl

C1505

MgBr

CH3

CH3 CH3

MgCl

CH3

MgBr

C2039

CH3

MgCl

MgCl CH3

D3551

E0135 E0778

E0134 E0497 MgBr

MgBr

MgBr

CH3

CH3

MgBr

CH3

MgCl

CH3

H0821

H0822

I0517

I0518

CH3

CH3

MgBr

CH3

MgBr

M0364

M0785 M0362

P0190

P1381

CH3

CH3

MgBr

P0191

T1700

CH3(CH2)14MgBr

P0880

MgCl

CH3

MgBr

T1698 MgBr

MgI

T1451

CH3

P1177

CH3

T1699

CH3

MgBr

P1251

MgCl

MgBr

CH3

MgBr CH3

O0240

CH3MgI

CH3MgBr

I0542 I0543

MgBr

CH3

V0053

MgBr

MgBr

CH3 CH3 CH3

Si

CH2MgCl

CH2 CHMgBr

CH3 CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

151

Grignard Reagents & Alkyl Metals

Product No. Product Name A0963 A1554 B1883 B1933 B1884 B0726 B1147 B1148 C1504 C1505 C2039 D3551 E0134 E0497 E0135 E0778 H0822 H0821 I0517 I0518 I0542 I0543 M0785 M0362 M0364 O0240 P1251 P1177 P0190 P1381 P0191 P0880 T1698 T1699 T1700 T1451 V0053

Unit Size

Allylmagnesium Bromide (ca. 13% in Ethyl Ether, ca. 0.7mol/L) Allylmagnesium Chloride (ca. 9% in Tetrahydrofuran, ca. 0.8mol/L) Benzylmagnesium Bromide (ca. 12% in Tetrahydrofuran, ca. 0.6mol/L) Benzylmagnesium Chloride (ca. 16% in Tetrahydrofuran, ca. 1mol/L) sec-Butylmagnesium Bromide (16% in Tetrahydrofuran, ca. 1mol/L) Butylmagnesium Chloride (23% in Tetrahydrofuran, ca. 2mol/L) tert-Butylmagnesium Chloride (26% in Ethyl Ether, ca. 2mol/L) tert-Butylmagnesium Chloride (23% in Tetrahydrofuran, ca. 2mol/L) Cyclohexylmagnesium Bromide (ca. 17% in Tetrahydrofuran, ca. 1mol/L) Cyclopentylmagnesium Bromide (18% in Tetrahydrofuran, ca. 1mol/L) Cyclopropylmagnesium Bromide (ca. 10% in Tetrahydrofuran, ca. 0.7mol/L) (2,5-Dimethylphenyl)magnesium Bromide (20% in Tetrahydrofuran, ca. 1mol/L) Ethylmagnesium Bromide (39% in Ethyl Ether, ca. 3mol/L) Ethylmagnesium Bromide (13% in Tetrahydrofuran, ca. 1mol/L) Ethylmagnesium Chloride (18% in Tetrahydrofuran, ca. 2mol/L) Ethylmagnesium Chloride (ca. 1.0mol/L in Tetrahydrofuran) activated with Zinc Chloride (ca. 10mol%) Heptylmagnesium Bromide (21% in Tetrahydrofuran, ca. 1mol/L) Hexylmagnesium Bromide (20% in Tetrahydrofuran, ca. 1mol/L) Isobutylmagnesium Bromide (17% in Tetrahydrofuran, ca. 1mol/L) Isopropylmagnesium Bromide (15% in Tetrahydrofuran, ca. 1mol/L) Isopropylmagnesium Chloride (13% in Ethyl Ether, ca. 1mol/L) Isopropylmagnesium Chloride (ca. 11% in Tetrahydrofuran, ca. 1mol/L) Methylmagnesium Bromide (35% in Ethyl Ether, ca. 3mol/L) Methylmagnesium Bromide (12% in Tetrahydrofuran, ca. 1mol/L) Methylmagnesium Iodide (33% in Ethyl Ether, ca. 2mol/L) n-Octylmagnesium Bromide (ca. 22% in Tetrahydrofuran, ca. 1mol/L) Pentadecylmagnesium Bromide (17% in Tetrahydrofuran, ca. 0.5mol/L) Pentylmagnesium Bromide (18% in Tetrahydrofuran, ca. 1mol/L) Phenylmagnesium Bromide (32% in Tetrahydrofuran, ca. 2mol/L) Phenylmagnesium Chloride (27% in Tetrahydrofuran, ca. 2mol/L) Phenylmagnesium Iodide (42% in Ethyl Ether, ca. 2mol/L) Propylmagnesium Bromide (ca. 27% in Tetrahydrofuran, ca. 2mol/L) o-Tolylmagnesium Bromide (19% in Tetrahydrofuran, ca. 1mol/L) m-Tolylmagnesium Bromide (19% in Tetrahydrofuran, ca. 1mol/L) p-Tolylmagnesium Bromide (19% in Tetrahydrofuran, ca. 1mol/L) Trimethylsilylmethylmagnesium Chloride (20% in Ethyl Ether, ca. 1mol/L) Vinylmagnesium Bromide (14% in Tetrahydrofuran, ca. 1mol/L)

A1479

A1222

CH2 HC

Alkyl Metals

B1975

B1832 (CH2)3CH3

CH3(CH2)3

Sn

CH3(CH2)3 Sn

(CH2)3CH3

(CH2)3CH3

CH3(CH2)3

D0305

152

Sn

(CH2)3CH3 CH

CH3(CH2)3

CH2

B0396

Sn

(CH2)3CH3

Sn CH2CH (CH2)3CH3

B2651

CH3

CH3 C Li

Li

CH3(CH2)3 (CH2)3CH3

CH3

Al Cl

CH3

CH3(CH2)3

D1338

Zn(CH2CH3)2

(CH2)3CH3

(CH2)3CH3 Cl

CH3

D3214 D3902

(CH2)3CH3

D0223

Sn Cl (CH2)3CH3

D1373

Cl CH3

CH3(CH2)3

CH2 CH3(CH2)3 Sn C C Sn (CH2)3CH3

CH3

CH3(CH2)3 (CH2)3CH3 CH3(CH2)3 Sn

D1340

O CH3

Pd Cl

CH2

B1974

CH2

Cl Pd

100ml 100g 100g 250g 100g 250g 250g 250g 100g 100g 100g 100g 250g 250g 250g 250g 250g 250g 250g 250g 250g 250g 250g 250g 100g 250g 250g 250g 250g 250g 250g 250g 100g 100g 100g 100ml 100g

CH3 Sn CH3 Cl

O CH3(CH2)7 Sn (CH2)7CH3

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Grignard Reagents & Alkyl Metals

H0842

M0589

M0258

M0744

T2009

CH2CH CH2

O CH3

T0058

T0919

(CH2)3CH3

Sn CH3

(CH2)3CH3 CH3(CH2)3 Sn H (CH2)3CH3

CH3

CH3

(CH2)3CH3

(CH2)3CH3

CH3

CH3

Si CH2 CH3

Sn

(CH2)3CH3

CH3 CH3

CH3

Cl

(CH2)3CH3 CH3(CH2)3 Sn F

(CH2)3CH3

(CH2)3CH3

T1086 T0783 T0925 (CH2)3CH3

CH3(CH2)3 Sn

(CH2)3CH3

Sn Cl CH3

CH3

CH CH2

Al

CH3

CH3

(CH2)3CH3

(CH2)7CH3 CH3(CH2)7 Sn

H

(CH2)7CH3

CH3

Product No. Product Name A1479 A1222 B1974 B1975 B1832 B0396 B2651 D0223 D0305 D1340 D3214 D3902 D1338 D1373 H0842 M0589 M0258 M0744 T2009 T0058 T0919 T1750 T0363 T0678 T1473 T1865 T1866 T1794 T1086 T0783 T0925 T1330 T0784

(CH2)3CH3

T1572

CH3 CH3

CH2CH CH2

T0678

CH3(CH2)3 Sn

(CH2)3CH3

T0958

Al

OH

T1794

CH3

(CH2)3CH3

Si C C Sn

CH3 Al

CH3

T1866

CH3 CH3

C CH

(CH2)3CH3

T0782 T1575

CH3

CH3(CH2)3 Sn

CH3

T1865

CH2 CHCH2 Sn CH2CH CH2

Sn

T0363

CH3 CH3

(CH2)3CH3

T1473

CH3

T1750

(CH2)3CH3 CH3(CH2)3 Sn (CH2)3CH3

T1330 T0784

CH3HgI

CH3HgCl

Li

Allylpalladium(II) Chloride Dimer Allyltributyltin Bis(tributylstannyl)acetylene trans-1,2-Bis(tributylstannyl)ethylene Bis(tributyltin) Butyllithium (ca. 15% in Hexane, ca. 1.6mol/L) tert-Butyllithium (ca. 16% in Pentane, ca. 1.6mol/L) Dibutyltin Dichloride Dibutyltin Oxide Diethylaluminum Chloride (ca. 15% in Hexane, ca. 0.87mol/L) Diethylzinc (ca. 17% in Hexane, ca. 1mol/L) Diethylzinc (ca. 15% in Toluene, ca. 1mol/L) Dimethyltin Dichloride Di-n-octyltin Oxide Hexyllithium (30% in Hexane, ca. 2.3mol/L) Methylmercuric Chloride Methylmercuric Iodide Monobutyltin Oxide Tetraallyltin Tetrabutyltin Tetramethyltin Tributylethynyltin Tributyltin Chloride Tributyltin Fluoride Tributyltin Hydride (stabilized with BHT) [Reducing Reagent] Tributyl(trimethylsilylethynyl)tin Tributyl(trimethylsilylmethyl)tin Tributylvinyltin Triethylaluminum (15% in Benzene, ca. 1.1mol/L) Triethylaluminum (15% in Hexane, ca. 1.0mol/L) Triethylaluminum (15% in Toluene, ca. 1.1mol/L) Triisobutylaluminum (15% in Heptane, ca. 0.53mol/L) Triisobutylaluminum (15% in Hexane, ca. 0.50mol/L)

Unit Size 500mg 5g 1g 1g 5g 100ml 25g 25g

25g 25g

25g 1g 25g 5g 1g 25g 25g 5g 1g

5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

1g 25g 5g 5g 25g 500ml 100ml 500g 500g 100ml 100ml 100ml 500g 500g 100ml 5g 25g 500g 5g 500g 25g 5g 500g 25g 250g 25g 5g 25g 100ml 100ml 100ml 100ml 100ml

153

Grignard Reagents & Alkyl Metals

Product No. Product Name T0782 T1575 T0958 T1572

Trimethylaluminum (15% in Hexane, ca. 1.4mol/L) Trimethylaluminum (15% in Toluene, ca. 1.8mol/L) Trimethyltin Chloride Tri-n-octyltin Hydride [Reducing Reagent]

Unit Size 5g

100ml 100ml 25g 10g

Many alkyl metals, Grignard reagents may spontaneously ignite on contact with air, or may react violently with water to produce flammable gas. Sufficient safety measures, such as usage of safety shield, wearing of protective equipment, and extreme caution should be taken, when using this compound, from the opening up to the disposal of the reagents.

154

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Protection & Derivatization

Protection & Derivatization In organic synthesis, appropriate use of protecting agents is very important to a synthetic strategy. Useful protecting agents must have the following properties: - the protecting agent must selectively react with the functional group that requires protection. - the protective group must be introduced in high yields, without side reactions. - the protected functional groups should be stable under various reaction conditions. - the protective group should be capable of being selectively deprotected under specific conditions that are not adverse to the integrity of the protected compound. A list shows a wide range of protecting agents, from conventional protective groups (TMS, Boc, trityl etc.) to a new special protecting agent, 1,2-bis(chlorodimethylsilyl)ethane1) (which reacts only with primary amines to generate azadisilacyclopentane derivatives) and Teoc-NT2) developed by Sodeoka and Shimizu in 2007. Particularly, Teoc-NT is a useful protecting agent which is stable and easy to handle. It reacts rapidly with various amines, alcohols, and thiols at room temperature to give the corresponding protected compounds in high yields, respectively. The by-product nitrotriazole (NT) has low solubility in the solvent and precipitates out as a crystalline solid. As a result, NT can be removed by simple filtration. The Teoc group can be removed easily by fluoride ions under a neutral condition. Teoc-NT is applicable to the synthesis of various base-sensitive oligonucleotide derivatives. O N TBSO

O

O

NH

N

N

NH2

N

+ Me3Si

NO2

N

O

N TBSO

Teoc-NT (4 eq.)

OTBS

O N

NH

O

N

Et3N (10 eq.)

TBSO

CH2Cl2, rt, 4 h

O

TBSO

B0643

A2298

N

N

N H

SiMe3

O

N NT (insoluble)

Y. 80%

OTBS

C0274

NO2

+ HN

A1268

A2302 O

CH3 CH3 CH2

Br

CH2 CHCH2

Si

CH2

C CH3

O

O Cl

CH3 CH3

Cl

CH2

O

CH2 CHCH2O C O N O

A2303

A2299

A0480

A1247 CHO

CH2 CHCH2O

C O

CH

CH2CH3

O

CH2 CHCH2

B2379 OCH3 O

OCH3

H

Si CH2CH3 CH2CH3 OCH3

B1128

B1151

B0105

OCH3

B3571

B0411

O

SO2Cl S

SO2Cl S

O

C Cl BF4

N S

CH2Br

C S

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

155

Protection & Derivatization

B0412

B2334

B1257

C0176 B3021

CH2Cl

CH3 CH2

O

Si Cl

CH2O C Cl

B3574

CH3

O

CH2 C O CH2

CH2O C O

CH3

B1483

B3234

B1906

B1688

B1773

tBu

NH

CH3

Si CH3

CH3

CF3

Cl3C C OCH2

N

CH2O C N

Cl

CH3

CH3 C O Si tBu

Si

CH3 CH2CH2

Si

CH3

CH3 CH3

Cl

CH3 N

CH3 CH3

Si CH2CH2 Si CH3

CH3

N CH3

CH3

CH3

B1699

B3563

B1702

B0916

B0988 O

CH3 SiH(CH3)2 (CH3)3SiO

CH3

OSi(CH3)3

B1089

B1969

CH3

B1436

N

CH3

B0995

Cl

CH3

H3C

B3565

O CH3CH3

O

NHNH2

CH3

CH3

O

CH3

B3577

CH3

H3C C O Si

CN

O C O N C

N

C0933

H3C

CH3

C O C CH3

N

CH3

N

N

O C S

CH3

CH3

N

CH3 O

N

O C

Br

SiH(CH3)2

CH3

O

CH3

B1043

B2697

CH3 C

Si O

CH

CH3CH3

OCH3 OCH3

T1525 CH3

CH3 CH3 CH3

CH3 CH3

Si Cl

CH3 C

CH3 CH3

CH3 tBu

Si H

CH3 CH3

B1223

B2898

Si

N

CH3 CH3

O Si C(CH3)3

N

CH3

CH3

CH3

CH3 CH3

C N

B1663

B1496

O

Si O S CF3 O

C1124

Br CH3 H3C

H 3C

H3C C Si

H3C C Si

Cl

H3C

O S CF3

C1573

CH3

CH3

O C OCH2

Cl

CH3 CH3

156

Si

CH3 CH3

Cl

Cl

CH3

C0202

Si CH3

CH3 CH3

CH2CH3 CH Si

O

T0589

CH3

CH3 CH3

CH2O C O N

CH3

C1339

CH C

O O

CH3

O C O C CH3

CH3

T2116

D2262

Cl O

O

CH2O C O N O

C1131 Cl

O

O C O N

O

CH3 CH3

O O2N

O

CH3

Cl3C C O

C1574

CH3

O

NH

C CH3

O

H3C

C1591

CH3O Si

O

C0306

CH3

CH2CH3 CH2CH2OCH2Cl

ClCH2OCH3

Cl

CH2CH3

CH3CH2 Si

Cl

CH2CH3

CH3

Si Cl CH3

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Protection & Derivatization

C2411

D2504

P1277

D2461

Si(CH3)3 (CH3)3Si

O

Si Cl

C Cl

O CH2O

O OCH2

D2334

O

O O

CH2O C OCH2

CH2

O

Cl

D1547 D3878 D3879 D3880

C O C

O

Cl

Si(CH3)3

P1281

CH2

C1600

t

D3135

D2469

O

H3C Cl CH3

O

H3C C Si C

BuO C O C OtBu

O

CH3

CF3

C(CH3)3

D0626

C(CH3)3

CH(CH3)2

(CH3)2HC

O

Cl

O S CF3

S O Si O

H3C Cl CH3

D0555

D1608

O

Si O Si Cl

(CH3)2HC

D1612

CH(CH3)2

D2915

O CH3 Cl

C H

CH3

OCH3

Si O Si Cl CH3

CH3

CH3O

CH3

OCH3

D1594

D2159

D0835

CH3

CH3

Si Cl

CH3

CH3

CH3

D1463

N C

C1415 SCl NO2

NO2

S

O P

P Cl

Cl NO2

NO2

C0683

N

Cl

OCH3

F CH3

CH3

C Cl

O

E0478

E0479

E0471

E0105

O O

CH3

CH3 CH3

CH3CH2O C N

Si

O(CH2)2O Si CH3

CH3

CH3

CH3 CH3

CH3

Si

S(CH2)2S

Si

CH3

O O S S CH2CH2 S S O O

CH3

CH3

CH3

CH3

OH

HO

O

T0872

F0239

F0197

I0060

I0303

O

CF3

O

O

O

CH2O C Cl

CH2O C O N

C SCH2CH3

CH3I

CH2 CH3 C OCH3

O

I0324

M0071

M0802

M0676

SO2Cl CH3

CH3

CH3

CH2 C O Si

M2016

SO2Cl

CH2Cl

CH3

NH

CH3

Cl3C C OCH2

OCH3

CH3 CH3

M0680

OCH3

M0681

M1004

OCH3

M1199

M0790

O C CH2Br

CH2CH3

CH3O(CH2)2OCH2Cl

CH2CH3

CH3 CH3

CH3O(CH2)2OCH2 N CH2CH3 Cl

OCH3

Si O C CHCH3

CH3O

C Cl

CH3 OCH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

157

Protection & Derivatization

M0441

M0536

N0142

N0507

N0181

OH SO2Cl

O CH3 CH3 CH3 C N

SO2F

CH2Br

NO2

NO2

NO2

Si CH3 CH3

SCH3

C1400

N0363

P1782 SCl

O O2N

P1378

P1614

O

O C Cl

O CH3

C CH2Br

NO2

CH3

Si

S

O

CH3 O

P0677

P0763

T1485

T0272

C0795 SO2Cl

O

O

O

O CH3

S O S

CH3

SH

HS

(CH3)3C C Cl

CCl3CH2O C Cl

O

O

CH3

T1606

T1689

T0670

CH2CH3 O

CH2CH3 O

CH3CH2

CH2CH3

BF4

T1588

Si O S CF3

O O S S(CH2)3S S O O

CH3

O

CH3

CH3

C OCH2CH2Si(CH3)3

N

CH3

Si

Cl

i Pr

O O

N

(CH3)3SiCH2CH2O C O N

O C OCH2CH2Si(CH3)3 O

O

T1535

Si

CH3

CH3 N

CH3

Si

T1237

O

O

T1467

CH3

(CH3)3SiO

CH3

C CH3

O

T1526 O Cl

C O

Cl3CO

O

CH3 C CH

O

C S Cl

CH3

Si CH3

T1071

O

S O Si CH3

T1573

N

CH3

T0512

i Pr

N

CHN2

CH3

N N

O

Si CH3

CH3

O

CH2CH3

i Pr

CH3

T2591

CH3 CH3

CH

T2590

T1277

NO2

CF3

CH2CH3

S O Si

O

N

T0871

CF3

C N

T1078

O

N

T1146

T0585

N

CF3

O

T2544

N

O

S CF3

CH2CH3 O

O

iPr

OCCl3

CBr

N

CBr 3

Cl O

3

C0308

C Br

158

O

D2390

iPr iPr

CH3CH2 Si

T1468

C Cl

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Protection & Derivatization

Product No. Product Name B0643 A2298 C0274 A1268 A2302 A2303 A2299 A0480 A1247 B2379 B1128 B1151 B0105 B3571 B0411 B0412 B2334 C0176 B3021 B1257 B3574 B1483 B3234 B1906 B1688 B1773 B1699 B3563 B1702 B0916 B0988 B1089 B1969 B1436 C0933 B3577 B0995 B3565 B1043 B2697 T1525 B1223 B2898 B1663 B1496 C1124 C1591 C1573 C1574 C1131 D2262 T2116 C1339 C0202 T0589 C0306 C2411 D2504 P1277 D2461 C1600 P1281 D1547 D3878 D3879 D3880 D2469 D3135

Allyl Bromide Allyl(tert-butyl)dimethylsilane Allyl Chloride Allyl Chloroformate N-(Allyloxycarbonyloxy)succinimide Allyl Phenyl Carbonate Allyltriethylsilane p-Anisaldehyde p-Anisaldehyde Dimethyl Acetal Benzaldehyde 1,2-Benzenedisulfonyl Dichloride 1,3-Benzodithiolylium Tetrafluoroborate [Hydroxyl-Protecting Agent] Benzoyl Chloride 3-Benzoylthiazolidine-2-thione Benzyl Bromide (stabilized with Propylene Oxide) Benzyl Chloride (stabilized withε-Caprolactam) Benzylchlorodimethylsilane Benzyl Chloroformate (30-35% in Toluene) Benzyl Chloroformate Benzyl Isopropenyl Ether [Hydroxyl-Protecting Agent] Benzyl Phenyl Carbonate Benzyl 2,2,2-Trichloroacetimidate Benzyl 2,2,2-Trifluoro-N-phenylacetimidate N,O-Bis(tert-butyldimethylsilyl)acetamide [tert-Butyldimethylsilylating Agent] 1,2-Bis(chlorodimethylsilyl)ethane [Protecting Reagent for Primary Amines] 1,2-Bis[(dimethylamino)dimethylsilyl]ethane [Protecting Reagent for Aromatic Primary Amines] 1,2-Bis(dimethylsilyl)benzene 1,3-Bis(trimethylsilyloxy)propane 9-Bromo-9-phenylfluorene N-tert-Butoxycarbonylimidazole 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 2-(tert-Butoxycarbonylthio)-4,6-dimethylpyrimidine [Boc Agent for Peptides Synthesis] 1-tert-Butoxycarbonyl-1,2,4-triazole tert-Butoxydiphenylchlorosilane (stabilized with CaCO3) tert-Butyl Carbazate tert-Butyl[4-(dimethoxymethyl)phenoxy]dimethylsilane tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent] tert-Butyldimethylsilane 1-(tert-Butyldimethylsilyl)imidazole [tert-Butyldimethylsilylating Agent] tert-Butyldimethylsilyl N-Phenylbenzimidate tert-Butyldimethylsilyl Trifluoromethanesulfonate tert-Butyldiphenylchlorosilane tert-Butyldiphenylsilyl Trifluoromethanesulfonate tert-Butylmethoxyphenylsilyl Bromide tert-Butyl 2,2,2-Trichloroacetimidate N-Carbobenzoxyoxysuccinimide Carbonic Acid Benzyl 4-Nitrophenyl Ester Carbonic Acid tert-Butyl Phthalimido Ester Carbonic Acid tert-Butyl 2,4,5-Trichlorophenyl Ester N-(2-Chlorobenzyloxycarbonyloxy)succinimide Chlorodiethylisopropylsilane Chloro(dimethyl)thexylsilane 2-(Chloromethoxy)ethyltrimethylsilane (stabilized with Diisopropylethylamine) Chloromethyl Methyl Ether Chlorotriethylsilane Chlorotrimethylsilane Chlorotris(trimethylsilyl)silane 2-Chlorotrityl Chloride Diallyl Pyrocarbonate Dibenzosuberyl Chloride Dibenzyl Carbonate Dibenzyl Pyrocarbonate Di-tert-butyl Dicarbonate [Boc-reagent for Amino Acid] Di-tert-butyl Dicarbonate (ca. 30% in Dioxane) Di-tert-butyl Dicarbonate (ca. 30% in Tetrahydrofuran) Di-tert-butyl Dicarbonate (ca. 30% in Toluene) Di-tert-butyldichlorosilane Di-tert-butylsilyl Bis(trifluoromethanesulfonate)

Unit Size 25g 25ml 25g 5g 5g 25ml 25ml 1g

5g 25ml 1g 25g 25g 25ml 25g 1ml 5g 1g 5g

5g 5g 5g 5g 5g 5ml 25g 5g

25g 1g

5ml

5g 25ml 1g 5ml 25g

1g 5g 5ml 25g 5g 25ml

25g

1g 5g 1g 5g 100g 100g 100g 100g 5g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500g 5g 500ml 500g 25g 25g 5g 500ml 500ml 500g 25g 5g 500ml 5g 500g 500g 5g 500ml 250g 5ml 25g 25g 5g 5g 25g 5g 5ml 25g 25g 10g 25g 25g 25g 25ml 250g 5g 100g 5g 5g 5g 25g 100ml 5g 1g 25ml 250g 5g 5g 5g 10g 5g 25g 25ml 500g 25g 500ml 5g 25g 5g 25g 5g 25g 500g 500g 500g 500g 25g 5g

159

Protection & Derivatization

Product No. Product Name D1608 D2334 D0555 D0626 D1612 D2915

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane [Hydroxyl Protecting Agent] 1,3-Dichloro-1,1,3,3-tetramethyldisiloxane 3,4-Dihydro-2H-pyran 2,4-Dimethoxybenzaldehyde 4,4'-Dimethoxytrityl Chloride [Hydroxyl Protecting Agent] 4-(Dimethylamino)-1-(triphenylmethyl)pyridinium Chloride

D1594 D2159 D0835 D1463 C1415 C0683 E0478 E0479 E0471 E0105 T0872 F0239 F0197 I0060 I0303 I0324 M0071 M0802 M0676 M2016 M0680 M0681 M1004 M1199 M0790 M0441 M0536 N0142 N0507 N0181 C1400 N0363 P1782 P1378 P1614 P0677 P0763 T1485 T0272 C0795 T1606

Dimethylisopropylchlorosilane [Dimethylisopropylsilylating Agent] Dimethylthiophosphinoyl Chloride 2,4-Dinitrofluorobenzene 2,4-Dinitrophenylsulfenyl Chloride Diphenylphosphinic Chloride N-Ethoxycarbonylphthalimide [for Peptide Synthesis] Ethylenedioxybis(trimethylsilane) [Protecting Reagent for Aldehydes and Ketones] Ethylenedithiobis(trimethylsilane) [Protecting Reagent for Aldehydes and Ketones] Ethylene Di(thiotosylate) [Protecting Reagent for Active Methylene] Ethylene Glycol S-Ethyl Trifluorothioacetate [Trifluoroacetylating Agent for Peptides Research] N-[(9H-Fluoren-9-ylmethoxy)carbonyloxy]succinimide 9-Fluorenylmethyl Chloroformate [N-Protecting Agent for Peptides Research] Iodomethane (stabilized with Copper chip) Isopropenyl Methyl Ether Isopropenyloxytrimethylsilane [Trimethylsilylating Agent] 2-Mesitylenesulfonyl Chloride 4-Methoxybenzenesulfonyl Chloride 4-Methoxybenzyl Chloride (stabilized with Amylene) 4-Methoxybenzyl 2,2,2-Trichloroacetimidate 2-Methoxyethoxymethyl Chloride (2-Methoxyethoxymethyl)triethylammonium Chloride 4'-Methoxyphenacyl Bromide 1-Methoxy-1-trimethylsilyloxypropene 4-Methoxytrityl Chloride [Hydroxyl Protecting Agent] 4-(Methylthio)phenol N-Methyl-N-trimethylsilylacetamide [Trimethylsilylating Agent] 2-Nitrobenzenesulfonyl Chloride 4-Nitrobenzenesulfonyl Fluoride 4-Nitrobenzyl Bromide 4-Nitrophenyl Chloroformate 2-Nitrophenylsulfenyl Chloride [N-Protecting Agent for Peptides Research] Phenacyl Bromide (Phenylthio)trimethylsilane Phthalic Anhydride Pivaloyl Chloride 1,3-Propanedithiol p-Toluenesulfonic Anhydride p-Toluenesulfonyl Chloride 2,2,2-Trichloroethyl Chloroformate Triethyloxonium Tetrafluoroborate (15% in Dichloromethane, ca. 1mol/L)

T1689 T0670 T1468 T1078 T1588 D2390 T1146 T2590 T2591 T2544 T0585 T1277 T1535 T1573 T0871 T1237 T1467 T1071 T1526

Triethylsilyl Trifluoromethanesulfonate 1-(Trifluoroacetyl)imidazole Trifluoromethanesulfonic Acid Diethylisopropylsilyl Ester Triisopropylsilyl Chloride Triisopropylsilyl Trifluoromethanesulfonate Trimethylene Di(thiotosylate) [Protecting Reagent for Active Methylene] Trimethylsilyldiazomethane (ca. 10% in Hexane, ca. 0.6mol/L) 1-[2-(Trimethylsilyl)ethoxycarbonyloxy]benzotriazole N-[2-(Trimethylsilyl)ethoxycarbonyloxy]succinimide 2-(Trimethylsilyl)ethyl 3-Nitro-1H-1,2,4-triazole-1-carboxylate N-Trimethylsilylimidazole [Trimethylsilylating Reagent] N-(Trimethylsilyl)morpholine 3-Trimethylsilyl-2-oxazolidinone [Trimethylsilylating Reagent] 4-Trimethylsilyloxy-3-penten-2-one Trimethylsilyl Trifluoromethanesulfonate [Trimethylsilylating Agent] Triphenylmethanesulfenyl Chloride Triphosgene 4,4',4''-Tris(benzoyloxy)trityl Bromide [Hydroxyl Protecting Agent] 4,4',4''-Tris(4,5-dichlorophthalimido)trityl Bromide [Protecting Reagent for Primary Alcohol]

Unit Size 5g 5g 25ml 25g 5g

(contains 5% Dichloromethane at maximum)

5ml 1g 25g 10g 25g

5g 25g 5g 5g 10ml 25ml 5ml 25g 25g

25ml 5g 1g 25g 25g 10g 25g 25g 25g 25g 25g 5g 25ml 5g 25g 25g

[Ethylating Reagent]

160

5ml

10ml

5g

5g 5g 1g 25ml 5g 5g 25ml 1g 1g 1g 25g 5ml

25g 25g 5g

25g 25g 500ml 500g 25g 5g 25ml 5g 500g 5g 25g 500g 25g 5g 25g 500g 5ml 25g 25g 100ml 500ml 25ml 500g 500g 25ml 5g 500ml 5g 25g 5g 250g 250g 25g 500g 1g 500g 250g 100g 500g 25g 500g 500ml 25ml 25g 500g 250g 100ml 25g 25g 5g 250ml 25g 25g 100ml 5g 5g 5g 100g 25ml 5g 25ml 250g 10g 250g 25g 1g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Protection & Derivatization

Product No. Product Name T0512 C0308

Trityl Bromide Trityl Chloride

Unit Size 25g 25g

100g 500g

References 1) S. Djuric, J. Venit, P. Magnus, 1990, 2) M. Shimizu, M. Sodeoka, 3) Review: York, 1999.

. 1981, , 1787; S. Kojima, K. Akiba, , 1040. . 2007, , 5231. 3rd ed., ed. by T. W. Greene, P. G. M. Wuts, John Wiley & Sons, New

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

161

Silicon Compounds for Organic Synthesis

Silicon Compounds for Organic Synthesis Silicon is an element belongs to Group 14 of the Periodic Table and thus has properties similar to carbon. A silicon atom can form a σ-bond to a carbon atom and thereby form a variety of organic silicon compounds. However, as carbon belongs to period II and silicon to period III, the two element’s atoms differ in atomic size, ionization energy, electronegativity, and atomic orbital configuration amongst other things. These differences cause organic silicon compounds to exhibit characteristic reactivities that are not found in carbon compounds. Silylenol ethers, hydrosilanes, Peterson type reagents, silylcyanides, silyldiazomethane and others are increasingly being used in organic syntheses, not only for their protective moieties, but also as reagents of general interest.

A2298

A1326

CH3 CH3 Si

CH3 C

A0927

CH2

ClCH2 Si

CH3 CH3

CH2CH

CH2

CH3

Si

CH2CH3 OCH2CH

CH2

CH3CH2 Si

CH3

CH3

A0729

A1858

CH3

CH3 CH2CH

A2299

B2334

CH(CH3)2

CH2CH

CH2

(CH3)2CH Si

B1856

CH2CH

CH2

CH(CH3)2

CH2CH3

B1728

B1906 t

Bu

CH3 CH3

Si

CH3 CH2CH

CH2

CH2

CH3

CH3

CH3

Si Cl

CH2

CH3

Si

CH2NH

CH3

Si CH3

N

CH3

CH3

Si CH3

CH3

CH3

CH3 C O Si tBu CH3

B1688

B1813

B1699

B2004

B0511 CH3

CH3 Cl

Si

CH2CH2

Si

CH3

SiH(CH3)2

CH3

CH3 Cl

ClCH2 Si CH2Cl

CH3 SiH(CH3)2

CH3

CH3

CH3

CH3 SCH3 Si CH3 SCH3

Si CH3 N

CH3

CH3 C O Si CH3 CH3

B1090

B3047

CH3 CH3

CH3

Si C C Si CH3 CH3

CH3

B1768

B1298

(CH3)3Si

CH3

Si(CH3)3

CF3O2SO

OSO2CF3

B3563

B1302

CH3

B1857

CH3

O

CH3

O

CH3

Si C C C C Si CH3 CH3

CH3

B1245

(CH3)3SiO

OSi(CH3)3

B0830

CH3

Si CH2

Si CH3

CH3

CH3

B1103 CH3

OSi(CH3)3

CH3 (CH3)3SiO

OSi(CH3)3

CH3

CH3

CH3

O

CH3

Si CH3 N

Si O S O Si CH3 CH3

OSi(CH3)3

O

CF3

CH3

C O Si CH3

CH3 CH3

Si

O

CH3

NH C NH

CH3

Si CH3 CH3

CH3

B1695

B1892

CH3 CH3

CH3

162

B1654

CH3

Si CH3

CH2Br

CH3

Si Br CH3

B1769

CH3

CH3

CH3

Br

Si CH2 C CH2

B1087

CH3

Si

CH3 Br C C CH2Br

CH3

Availability, price or specification of the listed products are subject to change without prior notice.

CH3

Si CH3

C CH2

Silicon Compounds for Organic Synthesis

B1436

B3577

H3C

B0995

Cl

CH3 C

Si O

CH

CH3CH3

H3C

B1223

T1525

CH3 CH3

CH3CH3

H3C C O Si

B3565

OCH3

CH3 C

OCH3

CH3 C

CH3 CH3

B2898

CH3 CH3

CH3 CH3

Si Cl

Si H

CH3 C

D2262

O

CH3 CH3

CH3 CH3

B1663

O O S CF3

Si

C1492

Br CH3 H3C

H 3C

H3C C Si H3C

T2116

CH3

CH3

Si Cl

CH3

CH3

C1419

Si

Cl

Si

H3C Cl CH3 CF3

C(CH3)3

O

H3C Cl CH3

D2403

CH3

C(CH3)3

CH3

Si CH3

O

D3761

Cl

CH3

Si

D3386

OCH3

Si Cl

Si CH3

CH3

OCH3

CH3 CH3

CH(CH3)2

Si O Si Cl

(CH3)2HC

Cl

Cl

D3883

Si

Si Cl

CH3 CH3

CH(CH3)2

D1789 OSO2CF3

OCH2CH3 CH3

OCH3

Si H

CH3CH2SiH2CH2CH3

CH3

OCH2CH3

Si(CH3)3

Si CH CH2 OCH3

CH3O OCH3

D2196

D2934

D2935

CH3

CH3

Si H

N

CH3

CH3 Si CH3

T1584

CH3

N

CH3

CH3

Si CH3

O CH2

O Si CH3

CH3

CH3 OCH3

D2406 D2820

Si CH

C OCH2CH3

SiH2

CH2

Si Cl

CH3

F0518

CH3

CH3 O(CH2)2O Si

D1390

CH3 CH3

CH3 H

CH3

E0478

CH3

Si

CH3

H0638

H0089

CH3 CH3

F CH2 C

Si CH3

CH3

D2144

(CH3)2HC

Cl CH3

CH3

C1982

D1608

O

OCH

CH3

C0306

ClCH2

O S CF3

S O Si

ClCH2 Si

Cl

D0358

O

CH3

CH3

Si CH2Cl

CH3

CH3

D3135

CH(CH3)2

C1370

CH3

OCH2CH3

D2469

CH2CH3

CH3

OCH2CH3

H Si Cl

Cl CH2CH2OCH2Cl

OCH2CH3 ClCH2 Si

Cl

C1358

C0862

CH3

H3C C Si C

CH3

CH3 CH3

CH3

CH Si

CH3

CH3 CH3 CH C

CH(CH3)2

CH2CH3

CH3 CH3

C1339

C1402

Si CH2Cl

C CH3 CH3

O

H3C

D1147

CH3O Si

O O S CF3

H3C C Si

Cl

CH3

Si

Si CH3

CH3 CH3

CH3 CH3

CH3

Si NH Si CH3 CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

CH3

163

Silicon Compounds for Organic Synthesis

H0091

I0449 CH3

CH3

I0324

CH3

CH3 CH3

Si O Si CH3 CH3

H0915

Si

CH3 CH2I

M0759

CH3

M1882

CH3

Si CH2OCH3 CH3

D1825

Si

N

H

CH3

Si

O Si CH3

CH3

CH3

(CH3)3Si

P1172

P1250

OSO2CF3

OSO2CF3 Si

CH3

OCH3

M1883

CH2

CH3 CH3

CH3

CH3

OCH3

Si

Si

CH3 CH3

Si(CH3)3

CH CH OCH3

CH3

N

M1077

Si(CH3)3

CH3

CH3

Si

OSO2CF3

OSO2CF3

M1460

CH3

CH3 Li

M1885

OSi(CH3)3

N

CH3

CH3

M1884

CH2 C

CH3

CH3

CH2 C O Si

CH3

CH3

M1264

CH3

Si(CH3)3

CH3

SCH2

N

Si

O CH3

CH3

CH3

CH3

S CH2

Si

O

CH3

CH3

CH3

P1280

H0893

CH2

S0421

CH3

C O Si CH3

CH3 CH3

Si

CH3

T2043

CH3 K

CH3

S CF3

T1078

CH2CH3 CH

H Si

CH2CH3

CH3

T1588 i Pr i Pr

Si

iPr

iPr

i Pr

T0801

CH3 CH3

Si N3 CH3

CH3

Si

CH3

C OH

CH3

CH3

Si CH3 CH3

C CH

T0492

CH3

CH3 CH3

Si CH3

T1146

Si CN

H

Pr

CH3

O CH2

CH3

CH3 CH3

i

T1239

CH3 CH3

Pr

Si

(CH2)5CH3

CH3

T2284

i i Pr

CH3(CH2)5 Si H

CH3

CH3 C NH Si

O

T0990

CH2CH3

T1684

O

CH3CH2 Si H

T1533

CH3

O

Si O S CF3

Cl

(CH2)5CH3

Si CH3

Cl

CH2CH3

Si Cl

T0590

iPr

Cl

Si Cl

T1334

CF3

Cl

Cl CH2 CH

Cl

CH3

CH3

Cl CH3

T0662

Cl

S O Si O

CH2CH3 O

CH3 N Si

CH3 Na CH3

T1570

O CF3

Si

Cl

Si Cl

T1468

O

CH3

T0407

Cl

CH2CH3 O

NCS

NCS

Cl CH3

(CH2)3CH3

CH3CH2 Si

SCN Si

T0636

CH3

NCS CH3

T0398

(CH2)3CH3 CH3(CH2)3 Si H

164

CH3 N Si

M0450

T1689

H0894

Si

CHN2

CH3

Availability, price or specification of the listed products are subject to change without prior notice.

CH3

Si N CH3

CH2CH3 CH2CH3

Silicon Compounds for Organic Synthesis

T0591

T1514 S

CH3 CH3 Si N CH3 CH3

CH3

T1510

T1441

Si

T2544

CH3

CH3

Si

CH3

CH2CH2OH

P CH2OCH2CH2 Si CH3 CH3

CH3

CH3

NO2

N

CH3

CH3

S

T1458

Cl

N

N

C OCH2CH2Si(CH3)3 O

T0585

I0308

T1106

T1213

N CH3

CH3

CH3

N

P CH2CH2 Si CH3

CH3

CH3

CH3

Si

CH3

Si

CH3

I

Si

CH3 NCO

CH3

Si

CH3

CH3

CH2SH

CH3

CH3

I

T1250

T1184

T1451

T1579

T1277 CH3

CH3

Si

CH3

CH3

CH3 CH2OH

CH3

Si

CH2N3

CH3

Si

CF3

CH3

CH3

CH3

CH2MgCl

O

CH3

S OCH2

Si CH3

O

CH3

CH3

Si

CH3

N O

T2465

T2466

T1535

Si(CH3)3

N Si(CH3)3

T1536

O Si

CH3 CH3

O

O Si CH3

T1500

Si CH3

CH2 CH

CH3

CH3

T2746

(CH3)3SiO

T2089

C CH3

T1498

Si(CH3)3

CH3CH2CH2 C C Si CH3 CH3

T1299

T0871

N CH3

CH3 P CH2C C Si CH3

S

CH3

CH3

CH3

OSO2CF3

CH3

O

CH3 C CH

Si C C CH2OH

O Si CH3

C CH2

O

CH3

CH3 CH3 C C

CH3

OSi(CH3)3

CH3

CH3

CH3

T1123

O

Si CH3

T1573

CH3

T1556

CH3

OSO2CF3

OSO2CF3

T1648

T1469

Si

O CH3

CF3

CH3

CH3

S O Si CH3 O

CH3

Br

T0939

T0661

T2467

T1639

P1248

OSO2CF3 Si(CH3)3

O

(CH3)3SiO Si Cl

Si

C CH OSi(CH3)3

H (CH3)3Si CF3O2SO

P1217

OSi(CH3)3

OSi(CH3)3

OSO2CF3 Si(CH3)3

T1463

Si(CH3)3

OSi(CH3)3 (CH3)3SiO

(CH3)3SiO

(CH3)3SiO P

P

(CH3)3Si OSi(CH3)3

Si H Si(CH3)3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

165

Silicon Compounds for Organic Synthesis

Product No. Product Name A2298 A1326 A0927 A2299 A1858 A0729 B2334 B1856 B1728 B1906 B1688 B1813 B1699 B2004 B0511 B1090 B3047 B1298 B1302 B1857 B1768 B3563 B1245 B0830 B1103 B1695 B1892 B1087 B1654 B1769 B1436 B3577 B0995 B3565 T1525 B1223 B2898 B1663 D2262 C1492 D1147 T2116 C1339 C1358 C1370 C1419 C1402 C0862 C0306 C1982 D2469 D3135 D0358 D1608 D2144 D2403 D3761 D3386 D3883 D1789 D2196 D2934 D2935 D1390 D2406 D2820 E0478 T1584

166

Allyl(tert-butyl)dimethylsilane Allyl(chloromethyl)dimethylsilane Allyloxytrimethylsilane Allyltriethylsilane Allyltriisopropylsilane Allyltrimethylsilane Benzylchlorodimethylsilane Benzyltrimethylsilane N-Benzyltrimethylsilylamine N,O-Bis(tert-butyldimethylsilyl)acetamide [tert-Butyldimethylsilylating Agent] 1,2-Bis(chlorodimethylsilyl)ethane [Protecting Reagent for Primary Amines] Bis(chloromethyl)dimethylsilane 1,2-Bis(dimethylsilyl)benzene Bis(methylthio)(trimethylsilyl)methane N,O-Bis(trimethylsilyl)acetamide Bis(trimethylsilyl)acetylene 3,3'-Bis(trimethylsilyl)biphenyl-4,4'-diyl Bis(trifluoromethanesulfonate) 1,4-Bis(trimethylsilyl)-1,3-butadiyne Bis(trimethylsilyl) Malonate Bis(trimethylsilyl)methane 1,2-Bis(trimethylsilyloxy)cyclobutene 1,3-Bis(trimethylsilyloxy)propane Bis(trimethylsilyl) Sulfate N,O-Bis(trimethylsilyl)trifluoroacetamide N,N '-Bis(trimethylsilyl)urea (2-Bromoallyl)trimethylsilane (Bromomethyl)trimethylsilane Bromotrimethylsilane 3-Bromo-1-(trimethylsilyl)-1-propyne (1-Bromovinyl)trimethylsilane tert-Butoxydiphenylchlorosilane (stabilized with CaCO3) tert-Butyl[4-(dimethoxymethyl)phenoxy]dimethylsilane tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent] tert-Butyldimethylsilane tert-Butyldimethylsilyl Trifluoromethanesulfonate tert-Butyldiphenylchlorosilane tert-Butyldiphenylsilyl Trifluoromethanesulfonate tert-Butylmethoxyphenylsilyl Bromide Chlorodiethylisopropylsilane Chlorodiisopropylsilane Chlorodimethylphenylsilane Chloro(dimethyl)thexylsilane 2-(Chloromethoxy)ethyltrimethylsilane (stabilized with Diisopropylethylamine) Chloromethyl(dichloro)methylsilane (Chloromethyl)dimethylisopropoxysilane Chloromethyldimethylphenylsilane (Chloromethyl)triethoxysilane (Chloromethyl)trimethylsilane Chlorotrimethylsilane Cyclohexyl(dimethoxy)methylsilane Di-tert-butyldichlorosilane Di-tert-butylsilyl Bis(trifluoromethanesulfonate) Dichlorodimethylsilane 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane [Hydroxyl Protecting Agent] 1,2-Dichlorotetramethyldisilane Diethoxymethylsilane [Hydrosilylating Reagent] Diethylsilane Dimethoxymethylvinylsilane 4,5-Dimethoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate Dimethylketene Methyl Trimethylsilyl Acetal Dimethylphenylsilane 2-(Dimethylsilyl)pyridine 2-(Dimethylvinylsilyl)pyridine Diphenylmethylchlorosilane Diphenylsilane Diphenylsilane Ethylenedioxybis(trimethylsilane) [Protecting Reagent for Aldehydes and Ketones] Ethyl (Trimethylsilyl)acetate

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size

25ml 5ml

5g

10ml 5g 1g 1g

1g 5g 5g 5ml

5ml

1g 5g 25ml 1g 1g 5ml

5g

25g

5ml

5g 25ml 1g 1g 5ml 5g 5ml 5ml 5g 25ml 25ml 25ml 5g 1g 25ml 5g 5g 5ml 25g 1g 5ml

5g 5g 5g

5g 5g 25ml 5g 5g 250ml 5g 25ml 5g 5g 25g 10g 5ml 1g 100ml 25g 5g 5g 5ml 10ml 5g 25g 25g 25ml 25g 5g 25g 250ml 5g 5g 25ml 5g 100g 5g 25g 100ml 5g 1g 5g 25ml 25ml 25g 25ml 25g 25ml 25g 10g 250ml 500ml 500ml 25g 5g 500ml 25g 25g 25ml 25ml 250g 5g 25ml 25ml 1g 1g 25ml 25g 25g 25g 25g

Silicon Compounds for Organic Synthesis

Product No. Product Name F0518 H0638 H0089 H0091 I0449 I0324 H0915 M1264 M0759 M1884 M1885 M1077 D1825 M1460 M1883 M1882 P1172 P1250 P1280 H0893 S0421 H0894

(1-Fluorovinyl)methyldiphenylsilane Hexamethyldisilane 1,1,1,3,3,3-Hexamethyldisilazane Hexamethyldisiloxane (Iodomethyl)trimethylsilane Isopropenyloxytrimethylsilane [Trimethylsilylating Agent] Lithium Hexamethyldisilazide (29% in Tetrahydrofuran, ca. 1.6mol/L) Methoxymethyltrimethylsilane 1-Methoxy-3-(trimethylsilyloxy)-1,3-butadiene 3-Methoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate 4-Methoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate N-Methyl-N,O-bis(trimethylsilyl)hydroxylamine Methyldiphenylsilane Methylenebis[dimethyl(2-pyridyl)silane] 2-Methyl-6-(trimethylsilyl)phenyl Trifluoromethanesulfonate 4-Methyl-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate (Phenylthiomethyl)trimethylsilane Phenyl Trimethylsilylmethyl Sulfone 1-Phenyl-1-trimethylsilyloxyethylene Potassium Hexamethyldisilazide (11% in Toluene, ca. 0.5mol/L) Silicon Tetraisothiocyanate Sodium Hexamethyldisilazide (contains 2-Methyl-2-butene) (38% in Tetrahydrofuran,

T0636 T2043 M0450 T0398 T0407 T0662 T1689 T1468 T1570 T1334 T1533 T1078 T1588 T0590 T1684 T1239 T0801 T0990 T2284 T1146 T0492 T0591 T1514 T1441 T1458 T2544 T1510 T0585 I0308 T1106 T1213 T1250 T1184 T1451 T1579 T1277 T2465 T2466 T1535 T1469 T1556 T1648 T1536 T1573 T2746 T2089

Tetrachlorosilane Tributylsilane Trichloro(methyl)silane Trichlorosilane Trichlorovinylsilane Triethylsilane Triethylsilyl Trifluoromethanesulfonate Trifluoromethanesulfonic Acid Diethylisopropylsilyl Ester (Trifluoromethyl)trimethylsilane [Trifluoromethylating Reagent] Trihexylsilane Triisopropylsilane Triisopropylsilyl Chloride Triisopropylsilyl Trifluoromethanesulfonate N-Trimethylsilylacetamide Trimethylsilylacetic Acid Trimethylsilylacetylene Trimethylsilylazide Trimethylsilyl Cyanide 5-(Trimethylsilyl)-1,3-cyclopentadiene Trimethylsilyldiazomethane (ca. 10% in Hexane, ca. 0.6mol/L) N-(Trimethylsilyl)diethylamine N-(Trimethylsilyl)dimethylamine 2-Trimethylsilyl-1,3-dithiane 2-(Trimethylsilyl)ethanol 2-(Trimethylsilyl)ethoxymethyltriphenylphosphonium Chloride 2-(Trimethylsilyl)ethyl 3-Nitro-1H-1,2,4-triazole-1-carboxylate (2-Trimethylsilylethyl)triphenylphosphonium Iodide N-Trimethylsilylimidazole [Trimethylsilylating Reagent] Trimethylsilyl Iodide (stabilized with Aluminum) Trimethylsilyl Isocyanate Trimethylsilylmethanethiol Trimethylsilylmethanol Trimethylsilylmethyl Azide Trimethylsilylmethylmagnesium Chloride (20% in Ethyl Ether, ca. 1mol/L) (Trimethylsilyl)methyl Trifluoromethanesulfonate [Trimethylsilylmethylating Reagent] N-(Trimethylsilyl)morpholine 1-(Trimethylsilyl)-2-naphthyl Trifluoromethanesulfonate 3-(Trimethylsilyl)-2-naphthyl Trifluoromethanesulfonate 3-Trimethylsilyl-2-oxazolidinone [Trimethylsilylating Reagent] 2-Trimethylsilyloxy-1,3-butadiene 1-(Trimethylsilyloxy)cyclohexene 1-(Trimethylsilyloxy)cyclopentene 2-(Trimethylsilyloxy)furan 4-Trimethylsilyloxy-3-penten-2-one 1-(Trimethylsilyl)-1-pentyne 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate

Unit Size 10ml

1g 10ml 100ml 25ml 5ml 100ml

1g 1g 1ml

1g 1g 1g 100ml

ca. 1.9mol/L)

25g

5g

5ml 5ml

5ml 25ml 10ml

100ml 100g 5g 25g 25g 25g 25ml 5g 1g 5g 25ml 25ml 5g 1g 25ml 100ml 1g 25ml

5g 5ml 5g 1g 25g 5g 5g 1ml

5ml 1g

1g

5g 5ml 1g 1g 5ml 10ml 5g

1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 100ml 500ml 500ml 10g 25ml 500ml 5ml 5ml 5g 5g 5ml 25ml 100mg 5g 5g 5ml 5g 10ml 500ml 5g 500ml 500g 25g 500g 500g 500g 250ml 25g 5g 25g 10g 100ml 250ml 25g 25g 5g 250ml 25g 500ml 5g 100ml 25ml 25ml 25g 25ml 25g 5g 5g 100g 25g 25g 1ml 25ml 5g 100ml 25g 25ml 5g 5g 5g 25ml 25ml 10ml 25g 25ml 5g 5g

167

Silicon Compounds for Organic Synthesis

Product No. Product Name T1123 T1500 T1498 T1299 T0871 T0939 T0661 T2467 T1639 P1248 P1217 T1463

1-(Trimethylsilyl)-1-propyne 3-Trimethylsilyl-2-propyn-1-ol (3-Trimethylsilyl-2-propynyl)triphenylphosphonium Bromide 2-Trimethylsilylthiazole Trimethylsilyl Trifluoromethanesulfonate [Trimethylsilylating Agent] Triphenylchlorosilane Triphenylsilane 1,3,5-Tris[4-(trifluoromethanesulfonyloxy)-3-(trimethylsilyl)phenyl]benzene Tris(trimethylsilyloxy)ethylene Tris(trimethylsilyl) Phosphate Tris(trimethylsilyl) Phosphite Tris(trimethylsilyl)silane (stabilized with TBBP) [Reducing Reagent]

Other general silicon compounds are listed on our website. Please refer to it. [http://www.tokyokasei.co.jp/product/chemicals-class/C027.shtml]

168

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 5ml

5g

25ml 1g 1ml 25g 5g

5g 5g 5ml 5ml

100ml 5ml 5g 5ml 250g 25g 25g 1g 25g 25g 25ml 25ml

Sulfur Compounds for Organic Synthesis

Sulfur Compounds for Organic Synthesis Although a sulfur atom belongs to the same group 16 as an oxygen atom in the periodic table, it has specific properties which an oxygen atom does not. For example, the features of a sulfur atom include the following: the lone pair of a divalent sulfur atom has a soft and strong nucleophilicity but it has a weak affinity for hard acids such as a proton; the carbon-sulfur bond can be easily cleaved in various reactions; and it has a variety of atomic valences, etc. Organic sulfur compounds play important roles in organic synthetic chemistry because of the variety of their features. We introduce the following three examples of the role of sulfur compounds as reaction reagents in organic synthetic chemistry: (1) Oxidizing agents By the Swern oxidation and the Corey-Kim oxidization using DMSO, primary and secondary alcohols can be oxidized to aldehydes and ketones, respectively. In the Corey-Kim oxidation, dodecyl methyl sulfides can be used to prevent the offensive odor of dimethyl sulfide.1)

CH3

OH

1) C12H25SCH3 (D3767) (3 eq.) NCS (3 eq.) Toluene, -40ºC

H

CH3 H

CH3

H

H

CH3

2) Et3N (5 eq.)

H O

O

O

H Y. 97%

(2) C-C bond formation in the alpha position When 1,3-dithiane is treated with alkyllithium, an anion is generated in the C-2 position. The alkyl halide A reacts with this to give a monoalkylated 1,3-dithiane. Furthermore, by the same treatment, alkyl halide B reacts with this to give a dialkylated 1,3-dithiane. Therefore, two units, A and B, can be combined with a methylene unit.2) In addition, the dithioketal can be also obtained by protecting the ketone with 1,3-propanediol. It means that umpolung has occurred since the carbonyl carbon was originally positively-polarized. CH3

THF-HMPA (10:1) -78°C 5 min then rt 20 min

S D0119

THF-HMPA (10:1) -78°C 20 min then rt 20 min

CH3

S

C5H11

t-BuLi (1.5 eq.)

S

THF-HMPA (10:1) -78°C 20 min

C5H11 (1.6 eq.) THF-HMPA (10:1) -78°C 60 min then reflux 30 min

Y. 95%

CH3 C5H11

I

(1.1 eq.)

t-BuLi (1.5 eq.)

S

CH3 I

C5H11

S

S

H2, Raney-Ni

CH3 C5H11

i-PrOH reflux, 16 h

CH3 C5H11

CH3 C5H11

Y. 94%

Y. 88%

(3) Leaving groups Functional sulfur groups can be removed by treatment with reducing agents. Dithioketal shown in the examples above can be changed into methylene by reacting with hydrogen in the presence of the Raney-nickel catalyst. The modified Julia olefination is also known as the reductive elimination reaction of sulfones, and it is widely used for the total synthesis of natural products as a stereoselective olefin synthesis.3) selectivity varies with the type of aryl sulfone to be employed. Aryl sulfone is synthesized from the corresponding arylthiol. If ArSH is 2-mercaptobenzothiazole, the reaction is selective, but in the case of 2-mercaptopyridine, it becomes -selective.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

169

Sulfur Compounds for Organic Synthesis

Ar

NaH

R1

S

ArSH

+

R1 CH2Br

H2O2, cat. [W]

Ar

R1

S O O

S

Base

R1 CH CH R2

+ R2 CHO

N

N

ArSH =

N SH

SH

N N

SH

Ph

CF3

N

CF3

SH

In this section, we introduced the sulfur compounds used mainly in organic synthesis as reagents. We provide the building blocks, such as thiophenes and thiazoles, which can be found by a structure or keyword search on our website.

B3360

D0538 S

D1114

S N

Disulfides

O

CH3 CH3

S

O

N S S

S

N

S

S

N

D2477

N

S S

N

Product No. Product Name B3360 D0538 D1114 D2477

Unit Size

Bis(2-methyl-3-furyl) Disulfide 2,2'-Dibenzothiazolyl Disulfide 2,2'-Dipyridyl Disulfide [for Peptide Synthesis] 4,4'-Dipyridyl Disulfide

5g

A1341

B1650 S CH2N3

CH3S OCH3

CH2 CH3S

CH3S

B1378

B2004

B1444

B0907

CH3 SCH3

SCH3 NO2

CH3S

B1709

CH3S

Sulfides

C1601

H3C(H2C)3

CH3 Si

SCH2S

CH3 SCH3

D3992

H0871

CH3

(CH2)3CH3

CH3(CH2)3 Sn S Sn (CH2)3CH3 H3C(H2C)3

D0119

5g 500g 250g 25g

25g 25g 5g

CH3

(CH2)3CH3

D3767

Si

CH3 S Si

CH3

CH3

CH3

B1411

SCH2Cl S S CH3

170

CH3S

O P OCH3 OCH3

O

S CH3(CH2)11SCH3 S

Availability, price or specification of the listed products are subject to change without prior notice.

CH3S

O CN

CH3

Sulfur Compounds for Organic Synthesis

D1648

D2105

P1085

I0461

M1216

O S S

S O C OCH2CH3

P0753

S

O

O

C OCH2CH3

P1602

CH3 S

P1172

T2578 S

CH3 SCH2

OH

Si

CH3

S

CH3

OCH3

CH3

T1514

SCH2CN

S

S

CH3

S

O

CH3

CH3 Si

CH3

CH3

CH3

CH3

S

T2579 CH3 CH3

S

CH3

Product No. Product Name A1341 B1650 B1709 B1378 B2004 B1444 B0907 H0871 C1601 D3992 D0119 D3767 B1411 D1648 D2105 P1085 I0461 M1216 P0753 P1602 P1172 T1514 T2578 T2579

Unit Size

Azidomethyl Phenyl Sulfide 1,1-Bis(methylthio)ethylene 1,3-Bis(methylthio)-2-methoxypropane 1,1-Bis(methylthio)-2-nitroethylene Bis(methylthio)(trimethylsilyl)methane Bis(phenylthio)methane Bis(tributylstannyl) Sulfide Bis(trimethylsilyl) Sulfide Chloromethyl p-Tolyl Sulfide Dimethyl 1,3-Benzodithiol-2-ylphosphonate 1,3-Dithiane Dodecyl Methyl Sulfide Ethyl 3,3-Bis(methylthio)-2-cyanoacrylate Ethyl 1,3-Dithiane-2-carboxylate Ethyl 1,3-Dithiolane-2-carboxylate Ethyl (Phenylthio)acetate Isobutylene Sulfide Methoxymethyl Phenyl Sulfide (Phenylthio)acetic Acid (Phenylthio)acetonitrile (Phenylthiomethyl)trimethylsilane 2-Trimethylsilyl-1,3-dithiane (1R,4R,5R)-4,7,7-Trimethyl-6-thiabicyclo[3.2.1]octane (1S,4S,5S)-4,7,7-Trimethyl-6-thiabicyclo[3.2.1]octane

B1322

1g 1g 25g 5g 1g 5g

5g 5g 25g 1g 5g 5g 5ml 25g

5g 1g 1g

B1505

B2656 SH

SH

5g 5g 5g 250g 1g 25g 5g 25g 5g 1g 25g 25g 500g 5g 25g 25g 25ml 5g 250g 5g 5ml 25g 5g 5g

SH

SH

Thiols SH

HS

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

SH

171

Sulfur Compounds for Organic Synthesis

B2391

B2655 SH

E0032 Br

CF3

P0640

HS

HS

S

SH

P0763 N

N

SH

HS CF3

M0246

M0055 M0247

SH

N

T0266

N N

HS

N HS

SH

HS

CH3

Product No. Product Name B1322 B1505 B2656 B2391 B2655 E0032 M0055 M0247 M0246 P0640 P0763 T0266

SH

Unit Size

1,2-Benzenedithiol 1,4-Benzenedithiol 1,3,5-Benzenetrithiol 3,5-Bis(trifluoromethyl)benzenethiol 5-Bromo-1,3-benzenedithiol 1,2-Ethanedithiol 2-Mercaptobenzothiazole 2-Mercaptobenzothiazole 2-Mercaptopyridine 1-Phenyl-5-mercapto-1H-tetrazole 1,3-Propanedithiol Toluene-3,4-dithiol

1g 1g 1g 25g 25g 25g 25g 25g 1g

B2240

C1043

5g

5g 5g 1g 5g 1g 500g 500g 500g 100g 500g 25ml 25g

M0979

CH3 S

NH C CH3

O

O

CH3

Sulfenic Acid Derivatives

Cl

CH3O C SCl

SCl

T1237

C S Cl

Product No. Product Name B2240 C1043 M0979 T1237

Unit Size

N-tert-Butylbenzenesulfenamide Chlorocarbonylsulfenyl Chloride Methoxycarbonylsulfenyl Chloride Triphenylmethanesulfenyl Chloride

1g

D1944

D2113

Thiocarbonyl Compounds

172

N CH3

CH2

CH3

N

S

CH3

S S

25g 25g 25g 10g

M1473

S CH3

5g 5g 5g

Cl

CH3

Availability, price or specification of the listed products are subject to change without prior notice.

O CH2 O

O

S

Sulfur Compounds for Organic Synthesis

P1236

P1056

T0635

S O

B0479

CH3

Cl

S

N

CH3

C SCH2CH

N

CH2

S

S

B0486

S

CH3 N

S

CH3

N C S S C N

CH3

CH3

S

S

CH3

iPr

S i

Pr

N i

S

S

Pr

N

i

Pr

S

CH3

T1320

S

CH3

T1555

S

CH3

S

N C S S C N Cl

CH3

CH3

Cl

Product No. Product Name D1944 D2113 M1473 P1236 P1056 T0635 B0479 T1555 B0486 T1320

Unit Size

Dimethyldithiocarbamic Acid Allyl Ester Dimethylthiocarbamoyl Chloride 5-(Methacryloyloxy)methyl-1,3-oxathiolane-2-thione Phenyl Chlorothionoformate Pyrrolidinodithiocarbamic Acid Allyl Ester Tetrabutylthiuram Disulfide Tetraethylthiuram Disulfide Tetraisopropylthiuram Disulfide Tetramethylthiuram Disulfide Thiophosgene

5g 25g 25g 5g 25g 25g

D0798

M0805

M1148

O

Sulfoxides

CH3

P1135

T2545 O S

S

O

CH3

CH3

CH3

S

S CH3

CH3

O CH3

Fe

Product No. Product Name D0798 M0805 M1148 P1135 T2545 T2546

O

O S

T2546 O

O

S

5g 25g 25g 25g 25g 500g 500g 25g 500g 100g

5g

Dimethyl Sulfoxide Methyl (Methylsulfinyl)methyl Sulfide Methyl Phenyl Sulfoxide Phenylsulfinylacetic Acid Ethyl Ester (R)-(p-Toluenesulfinyl)ferrocene (S)-(p-Toluenesulfinyl)ferrocene

S

CH3

Fe

Unit Size 25g 5g 5g 1g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500g 25g 25g 5g 5g 5g

173

Sulfur Compounds for Organic Synthesis

B2907

B2908

M1044 CH3

O (CH3)3C S NH2

Sulfinic Acid Derivatives

O

O

O S

(CH3)3C S NH2 CH3

CH3 CH3

M1066 CH3 O O S CH3

CH3 CH3

Product No. Product Name B2907 B2908 M1044 M1066

Unit Size

(R)-(+)-tert-Butylsulfinamide (S)-(-)-tert-Butylsulfinamide (1R,2S,5R)-(-)-Menthyl (S)-p-Toluenesulfinate (1S,2R,5S)-(+)-Menthyl (R)-p-Toluenesulfinate

5g 1g

A1444

B2434

S CH2CH

N

CH2

O

C1304

C2428

ClCH2CH2 S CH2CH2CH2

D0959

Cl

Cl

E0466

O (CH2)7CH3

CH2

O

S CH2CH3

SO2CH2F

S C CH

CH3

O

O

M0875

F0341

O

CH S CH CH2

O

SO2CH3

SO2CH3

C OH

E0427

O

M0401

SO2CH2CN

O

D3161

CH3(CH2)7 S

C1237

O

O

SO2

SO2

O

C1236

SO2CH2CH2Cl O2 S

O2S

S O

B1574

B1573 CH2

O

Sulfones

1g 1g 25g 5g

O

P1250

P0982

D0557

SO2CH2SCH3 O

CH3

S CH2

Si

O

CH3

O CH3

S CH

CH2 O

O

S

O

CH3

Product No. Product Name A1444 B2434 B1573 B1574 C1304 C2428

174

Allyl Phenyl Sulfone 4-Benzylthiomorpholine 1,1-Dioxide cis-1,2-Bis(phenylsulfonyl)ethylene trans-1,2-Bis(phenylsulfonyl)ethylene 2-Chloroethyl Phenyl Sulfone 4-(2-Chloroethylsulfonyl)butyric Acid

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 1g

5g 5g 5g 1g 5g

25g 25g 25g 5g 25g 25g

Sulfur Compounds for Organic Synthesis

Product No. Product Name C1236 C1237 D3161 D0959 E0427 E0466 F0341 M0401 M0875 P1250 P0982 D0557

Unit Size

4-Chlorophenyl Cyanomethyl Sulfone 4-Chlorophenyl Methyl Sulfone Di-n-octyl Sulfone Divinyl Sulfone (stabilized with HQ) Ethyl Phenyl Sulfone Ethynyl p-Tolyl Sulfone Fluoromethyl Phenyl Sulfone Methyl Phenyl Sulfone Methylthiomethyl p-Tolyl Sulfone Phenyl Trimethylsilylmethyl Sulfone Phenyl Vinyl Sulfone 3-Sulfolene

5g 25g 5g 250g 25g 5g 5g 500g 25g 5g 25g 500g

5g 5g

I0758

B0030 B2678

T0267 SO3H

SO3H

SO3H

. H2O

I

. H2O

Sulfonic Acids

25g 10g 1g 1g 25g 5g 1g 5g 25g

. 2H2O CH3

Product No. Product Name B0030 B2678 I0758 T0267

Unit Size

Benzenesulfonic Acid Monohydrate Benzenesulfonic Acid Monohydrate 2-Iodobenzenesulfonic Acid Dihydrate p-Toluenesulfonic Acid Monohydrate

25g 25g 1g 25g

B1931

B1389

C1324

CH3 O

CH3

O

HN SCH3

O

O

SO2 N C SCH3

C1325

C1326

CH3

C1327

CH3

CH3

C1142 CH3

CH3

CH3

O

S O S

Sulfonic Acid Derivatives

500g 500g 5g 500g

S O

C0886

CH3 O

S O

S O O O

O

E0471

M1182

CH3

CH3

S O N C

CH3

O

I0777

CH3

CF3(CF2)7 S

M1186 SO2NH N C

O OCH2CH3

NO2

F

CH3

CH3

SO2Cl

CH3 CH3

O

CH3

S NCO O

H1176

O

Cl

SO2Cl

O S O O

CH3 O O S S CH2CH2 S S O O

Cl

N

N

NH

CH3 SO2Cl

M0071

M1382

N0576

SO2Cl CH3

N0604

T1471

O CH3

O CH3

S O

O

CH2CH2 S Cl SCH3

O

O2N

N

O

S N O

CH3

N

S O(CH2)17CH3 O

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

175

Sulfur Compounds for Organic Synthesis

T1461

T1562

T0272

T0998

SO2Cl CH3

O

SO2Cl CH3 CH3

CH3

O

CH3 CH3

S

CH3

S CH2NC O

O

D2390 SO2Cl

CH

CH

SK

CH3 CH3

O O S S(CH2)3S S O O

CH3

O CH

CH3

CH3 CH3

Product No. Product Name B1931 B1389 C1324 C1325 C1326 C1327 C1142 C0886 E0471 M1182 H1176 I0777 M1186 M0071 M1382 N0576 N0604 T1471 T1461 T1562 T0272 T0998 T1046 T1185 T0459 D2390

CH3

CH3

T0459

O

S NCO

SO2Cl CH3

T1185

O

O

S NSO

CH3

T1046

Unit Size

Benzenesulfonic Anhydride N-[Bis(methylthio)methylene]-p-toluenesulfonamide (+)-10,2-Camphorsultam (-)-10,2-Camphorsultam (2R,8aS)-(+)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent] (2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent] 2-Chloroethanesulfonyl Chloride Chlorosulfonyl Isocyanate Ethylene Di(thiotosylate) [Protecting Reagent for Active Methylene] Ethyl O-Mesitylsulfonylacetohydroxamate [Precursor of the Powerful Aminating Reagent] Heptadecafluoro-1-octanesulfonyl Fluoride N '-Isopropylidene-2-nitrobenzenesulfonohydrazide 2,4-Mesitylenedisulfonyl Dichloride 2-Mesitylenesulfonyl Chloride S-Methyl Methanethiosulfonate 2-(1-Naphthyl)ethanesulfonyl Chloride 1-(4-Nitrobenzenesulfonyl)-1H-1,2,4-triazole Octadecyl p-Toluenesulfonate N-Sulfinyl-p-toluenesulfonamide 2,4,5,6-Tetramethylbenzenedisulfonyl Dichloride p-Toluenesulfonyl Chloride p-Toluenesulfonyl Isocyanate p-Toluenesulfonylmethyl Isocyanide p-Toluenethiosulfonic Acid Potassium Salt 2,4,6-Triisopropylbenzenesulfonyl Chloride Trimethylene Di(thiotosylate) [Protecting Reagent for Active Methylene]

B1517

B3125

5g

25g 5g 5g 5g 5g 5g 500g 500g 25g 25g 250g 5g 25g 500g 25g 5g 5g 5g 5g 5g 500g 500g 25g 25g 500g 25g

1g 1g 1g 1g 25g 25g 5g 5g 25g

1g

5g 25g 1g

1g 25g 25g 5g 5g 25g 5g

B1151 O

SS P P SS

O

Others

S O

S O

B1376

B2188

C1380

S

C1159

BF4

S

O

C1122

CH3 CH3

176

S S S P P S S S

Cl CH3

S N C CH3 CH3

NCN S

(CH2)3Cl

BF4

CF3SCu

Availability, price or specification of the listed products are subject to change without prior notice.

CH3S

NHCH3

Sulfur Compounds for Organic Synthesis

C1390

D2078

D2114

D1945

O S

BF4

CH3

D0797

S

CH3

O S

D2159

CH3

CH3S

D2231

SCH3

D2685

CH3

S

O

SCH3

BF4

C CH2S

D2002

CH3 CH3

BF4

B1133 NH

O CH3O S OCH3

CH3

O

CH3

M1083

S P Cl

P1254

CH3

S

BF4

S

P0998

. H2O

T2136

P

CH3O

S S P

OCH3

S S

T1308

O CH2CH3

. SO3

N S

CH3NHSO3H

CH3CH2

N

N

CH2CH3

. SO3

CH3

S

S

P

P CH3

CH3 CH3

O

T1564

T1833

CH3(CH2)3

O

O

(CH2)3CH3 S

T1065

I

CH3

(CH2)3CH3

S CH3 Br CH3

CH3

S CH3

I

CH3

Product No. Product Name B1517 B3125 B1151 B1376 B2188 C1380 C1159 C1122 C1390 D2078 D2114 D1945 D2231 D0797 D2159 D2685 D2002 B1133 M1083 P1254 P0998 T2136 T1308 T1564 T1833 T1065

Unit Size

Belleau's Reagent [Sulfurating Reagent] 3H-1,2-Benzodithiol-3-one 1,1-Dioxide 1,3-Benzodithiolylium Tetrafluoroborate [Hydroxyl-Protecting Agent] 2,4-Bis(p-tolylthio)-1,3-dithia-2,4-diphosphetane-2,4-disulfide [Sulfurating Reagent] N-tert-Butylbenzenesulfinimidoyl Chloride [Oxidizing Reagent] (3-Chloropropyl)diphenylsulfonium Tetrafluoroborate Copper(I) Trifluoromethanethiolate N-Cyano-N ',S-dimethylisothiourea Cyclopropyldiphenylsulfonium Tetrafluoroborate S,S '-Diethyl Dithiocarbonate S,S '-Dimethyl Dithiocarbonate Dimethyl(methylthio)sulfonium Tetrafluoroborate Dimethylphenacylsulfonium Tetrafluoroborate Dimethyl Sulfate Dimethylthiophosphinoyl Chloride Diphenyl(methyl)sulfonium Tetrafluoroborate S,S-Diphenylsulfilimine Monohydrate Lawesson's Reagent [Sulfurating Reagent] Methylsulfamic Acid N-(Phenylthio)phthalimide Pyridine - Sulfur Trioxide Complex Sulfur Trioxide - Triethylamine Complex Tetramethyldiphosphine Disulfide Tributylsulfonium Iodide Trimethylsulfoxonium Bromide Trimethylsulfoxonium Iodide

1g 10g 1g 1g

1g 1g 25g 1g 1g 1g 25g 5g 5g 25g 5g

25g

5g 5g 5g 25g 5g 1g 5g 25g 1g 10g 5g 5g 5g 500g 5g 5g 5g 250g 25g 25g 500g 25g 5g 1g 25g 500g

References 1) K. Nishide, S. Ohsugi, M. Fudesaka, S. Kodama, M. Node, 2002, 2) D. Enders, T. Schüßeler, , 3746. 3) D. A. Alonso, C. Nájera, M. Varea, . 2004, 2002, 2563.

. 2002,

, 5177.

, 573; Review: P. R. Blakemore,

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

177

Phosphines for Organic Synthesis

Phosphines for Organic Synthesis Phosphorus belongs to group 15 in the periodic table, the same as nitrogen, and it binds with carbon to form various organophosphate compounds. However, since nitrogen belongs to the second-period and phosphorus to the third, they differ in atomic size, ionization energy and electronegativity etc. Therefore, organophosphate compounds show a characteristic reactivity which organic nitrogen compounds do not have, and it is utilized as a versatile reaction reagent in organic synthesis. For example, phosphorus has a high affinity for oxygen: phosphorus ylide and phosphonate are utilized for the Wittig reaction and the Horner-Emmons reaction, respectively, and it extracts oxygen from aldehydes to produce olefins. Phosphine extracts oxygen from alcohols to produce esters in the Mitsunobu reaction. Another feature of phosphine includes bearing a soft lone pair. Therefore, it forms comparatively stable complexes with transition metals such as palladium. This transition metal complex is used frequently as a catalyst in reactions such as the Suzuki-Miyaura cross-coupling reaction and the Heck reaction.1) Although phosphine also has a trigonal pyramidal structure like amines, its rotational barrier energy is considerably higher than the corresponding amine. Therefore, a phosphine which has three different substituents has optical isomers. This optically-active phosphine is utilized for asymmetric syntheses as a P-chiral ligand.2) In this section, we introduce tri-substituted alkyl and aryl phosphines, such as tricyclohexylphosphine and triphenylphosphine.

B3428

F

B2089

F

F

F

F

PCH2CH2P F

F

F F

2

B3449

F

2

B2711

BH3 (CH3)3C P CH3

Fe P

B1174

C(CH3)3 C(CH3)3 C(CH3)3

P Fe P

C(CH3)3

B2383

Fe

PPh2

PPh2

P (CH2)4

P

B1959

P

(CH2)6 P

Fe PPh2

B1960

2

B1112 H

CH3 O

CH2 P

CH3 O

CH2

P

CH3 O

CH2 P

CH3 O

CH2

P

B2867 H N

(CH2)5 P

PPh2

B1138

(C6H5)2P

P(C6H5)2 O

O

178

P

H

B2717

P

P CH2CH2 P

O

B1113

P

P

CH3

P

PPh2

P CH2

PPh2

2

B2027

H

PPh2

PPh2

B1137

CH3

2

P(C6H5)2

PPh2

P 2

B1982

CH3

CH3

B2709 CH3

P

C C

P

P

CH(CH3)2

PPh2 PPh2

B1246

CH3

P

CH3

B1405

P(C6H5)2

H

CH3

CH(CH3)2 CH(CH3)2

B1406

Fe

B2704

B2003

CH(CH3)2

Ph2P

PPh2

B2630

P

BH3 P CH3 C(CH3)3

B3196

B2710

PPh2

Availability, price or specification of the listed products are subject to change without prior notice.

P CH2CH2CH2

P

Phosphines for Organic Synthesis

B3035

B3036 OCH3

C1429

D3940

D3387

OCH3 (CH3)3C

C(CH3)3 PCH2CH2P

PCH2CH2P

CH3O

CH3O

D3834

D2411

C(CH3)3 P

P

P

C(CH3)3

D3388

D3389

D1019 P Et

2

N

N

P

P

P

C(CH3)3

P Et

C(CH3)3

(CH3)2N

D2478

D2537

D2538

D2535

CH3

(CH3)2N

N(CH3)2 PPh2

P

CH3

(CH3)2N Ph2P Fe

(CH3)2N Ph2P

Fe

Fe

Ph2P

PPh2

D3243

CH3

N(CH3)2 PPh2

Fe

D3242

D2536

CH3

D2774

D2775

D2766

O C OH

O C OH

OCH3 P

D2630

OCH3 P(C6H5)2

P(C6H5)2

P

D2404

D2471

E0519

P

I0583

P

CH3 P

P CH2CH2CH3

CH

P CH2CH3

P1176

P

CH3

N

M1318

CH2

P

D2043

T0361

T1912

F F

F

F

F

P CH3

P

T2248

T1643

T1005

O

P

T0519

t Bu

(CH2)7CH3

(CH2)5CH3

CH3(CH2)7 P

CH3(CH2)5 P

P

(CH2)7CH3

(CH2)5CH3

T1789

P

T0503

O

T1757

Bu

Bu

O P

t

P

SO3Na

P

T1165

t Bu

Bu Bu

T2725

T1656 O

OH

Br P 3

P

B 3

P

BH3

. HCl

P Br

HO

P O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

OH O

179

Phosphines for Organic Synthesis

T1614

T0861

T1024

T1025

T0862

OCH3

CH3

CH3

CH3O

P

P

CH3O

CH3

CH3

P

3

CH3O

T2484

OCH3

CH3

CH3

P P CH3

CH3

CH3

T1666 F

F

S

F

P F

F

S

P S

3

Product No. Product Name B3428 B2089 B2711 B2710 B1174 B3449 B3196 B2383 B1406 B1405 B2630 B2704 B1246 B2709 B1137 B2003 B2027 B1959 B1113 B1112 B1982 B1960 B2717 B2867 B1138 B3035 B3036 C1429 D3940 D3387 D3834 D2411 D3388 D3389 D1019 D2478 D2537 D2538 D2535 D2536 D3242 D3243 D2774 D2775 D2766

1,2-Bis[bis(pentafluorophenyl)phosphino]ethane (S,S)-1,2-Bis[(tert-butyl)methylphosphino]ethane Bis(borane) 1,1'-Bis(di-tert-butylphosphino)ferrocene 1,1'-Bis(diisopropylphosphino)ferrocene 1,2-Bis(dimethylphosphino)ethane (2R,3R)-(-)-2,3-Bis(diphenylphosphino)bicyclo[2.2.1]hept-5-ene (R,R '')-2,2''-Bis(diphenylphosphino)-1,1''-biferrocene (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 2,2'-Bis(diphenylphosphino)biphenyl (2S,3S)-(-)-Bis(diphenylphosphino)butane 1,4-Bis(diphenylphosphino)butane 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene 1,2-Bis(diphenylphosphino)ethane trans-1,2-Bis(diphenylphosphino)ethylene 1,1'-Bis(diphenylphosphino)ferrocene 1,6-Bis(diphenylphosphino)hexane (2R,3R)-(-)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol (2S,3S)-(+)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol Bis(diphenylphosphino)methane 1,5-Bis(diphenylphosphino)pentane 4,6-Bis(diphenylphosphino)phenoxazine Bis[2-(diphenylphosphino)phenyl] Ether 1,3-Bis(diphenylphosphino)propane (R,R)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane (S,S)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane Cyclohexyldiphenylphosphine Di-tert-butylphenylphosphine 2-(Di-tert-butylphosphino)biphenyl 1-[2-(Di-tert-butylphosphino)phenyl]-3,5-diphenyl-1H-pyrazole Dicyclohexylphenylphosphine 2-(Dicyclohexylphosphino)biphenyl 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl Diethylphenylphosphine 4-(Dimethylamino)phenyldiphenylphosphine (R)-N,N-Dimethyl-1-[(S)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine (S)-N,N-Dimethyl-1-[(R)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine (R)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine (S)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine 2-(Diphenylphosphino)benzoic Acid 4-(Diphenylphosphino)benzoic Acid (R)-(+)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl (S)-(-)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl 4-Diphenylphosphinomethyl Polystyrene Resin cross-linked with 2% DVB (200-400mesh)

D2630 D2404 D2471

Diphenylpropylphosphine Diphenyl-1-pyrenylphosphine Diphenyl-2-pyridylphosphine

Unit Size 100mg 100mg

100mg 5g 1g 1g 100mg 100mg 5g 1g 10g 1g

5g 1g

5g 100mg 5g 100mg 100mg 5g

1g 1g 1g 1g 1ml 1g

100mg 100mg

(0.5-1.0mmol/g)

180

Availability, price or specification of the listed products are subject to change without prior notice.

100mg

1g 100mg 1g 1g 100mg 100mg 500mg 25g 5g 5g 1g 1g 25g 5g 25g 1g 25g 5g 1g 1g 25g 1g 1g 5g 25g 1g 1g 25g 5g 1g 5g 5g 5g 5g 5ml 5g 100mg 100mg 100mg 100mg 1g 1g 1g 1g 5g 5g 1g 1g

Phosphines for Organic Synthesis

Product No. Product Name E0519 I0583 M1318 P1176 D2043 T0361 T1912 T1165

Ethyldiphenylphosphine Isopropyldiphenylphosphine Methyldiphenylphosphine (Pentafluorophenyl)diphenylphosphine Sodium Diphenylphosphinobenzene-3-sulfonate Tributylphosphine Tri-tert-butylphosphine Tricyclohexylphosphine (contains Tricyclohexylphosphine Oxide)

T2248 T1643 T1005 T0503 T1757 T0519 T1789 T2725 T1656 T1614 T0861 T1024 T1025 T0862 T2484 T1666

Tricyclopentylphosphine Tri(2-furyl)phosphine Trihexylphosphine Tri-n-octylphosphine Triphenylborane - Triphenylphosphine Complex Triphenylphosphine Triphenylphosphine Borane Triphenylphosphine Dibromide Tris(2-carboxyethyl)phosphine Hydrochloride Tris(2,6-dimethoxyphenyl)phosphine Tris(4-methoxyphenyl)phosphine Tris(2-methylphenyl)phosphine Tris(3-methylphenyl)phosphine Tris(4-methylphenyl)phosphine Tris(pentafluorophenyl)phosphine Tri(2-thienyl)phosphine

Unit Size 1g 1g 1g 1g 25ml 25ml 1g 1g

(ca. 18% in Toluene, ca. 0.60mol/L)

25ml 5g 25g

1g

5g 5g 5g 5g 5g 5g 1g 1g

5g 5g 5g 5g 5g 500ml 5g 500ml 5g 5g 25ml 500ml 25g 500g 25g 25g 25g 25g 25g 25g 25g 25g 5g 5g

References 1) Review: D. S. Surry, S. L. Buchwald, . 2008, , 6338. 2) T. Imamoto, J. Watanabe, Y. Wada, H. Masuda, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, 1998, , 1635.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

.

181

Hypervalent Iodine Compounds

Hypervalent Iodine Compounds Iodine is atomic number 53, in the 5th period, Group 17, halogens of the periodic table. Iodine is a large-sized halogen element, easily polarizable, and low in electronegativity. It forms hypervalent organoiodanes beyond the octet theory by readily extending its valence. For example, hypervalent organoiodane with three ligands is a 10-I-3 type compound as shown in the figure. The central iodine atom forms a plane with two lone pairs and one σ-bond, and furthermore, this iodine atom coordinates two ligands with larger electronegativity in an apical position orthogonal to the plane resulting in the formation of a linear three center-four electron bond. The I-L bond in the apical position is weaker and longer than the covalent bond. For example, the I-O bond length in PhI(OAc)2 is longer than the sum of their covalent bond radii (1.99 Å) and these bond lengths have a range of 2.15∼2.16 Å. Apical position

L Ar

I

: :

L

The stability and reactivity of hypervalent organoiodanes exhibit a greater dependence on the character of hypervalent bonds in the apical position. The hypervalent bonds in the apical position are easily cleaved, and the cleavage causes trivalent iodines with 10 electrons to be reduced to monovalent iodines of a more stable octet structure. For this reason, it exhibits good elimination and oxidation rate and finds application in organic syntheses.1∼3) (Diacetoxyiodo)benzene, the most typical trivalent iodine compounds, which is attempted to support the polymers. For example, Togo and coworkers have demonstrated several oxidative functional group conversion reactions using poly[4(diacetoxyiodo)styrene](1).4) After reaction, this polymer-supported reagent can be recovered by filtration and reused after re-oxidation with peracetic acid. Therefore, it is expected to be used as environmentallyfriendly chemical conversion reagent in the near future. OAc I OH R

B2539

R'

N

I

O

C O

I

O C CF3

CF3

time (h)

Y. (%)

4

83

Acetophenone

4

94

B2359

B2121

O

O C O

BF4

N

R'

B1616

O CF3

R

CH3CN, rt

B1175

Product Benzaldehyde

O

OAc 1 , TEMPO

I

CH3

O C CF3

F

F

F

F

CH3 CH3

N

CH3 I

CH3

N

CH3 C OO PF6

CH3

I

O

CH3

O

CH3

F

D2045

D2372

D2503

AcO OAc O AcO I

O C O O

182

D2356

I

Br

D2248

. H2O

I I

Cl

I

Availability, price or specification of the listed products are subject to change without prior notice.

AsF6

Hypervalent Iodine Compounds

D2238

D2373

D2357

D2243

I

I I

I

I

I NO3

PF6

E0467

D2253

P1298

ClO4

P1015

I0330

CF3SO3

I0479 O

HC C

I

O

BF4

HO

I

O

O

O S CH3

HO

I

CH3

O S

O

CH3 C O

O I

O C CH3

O

CH3 C O

I

O C CH3 CH3

CH3

O

CH3

I0072

I0073

I0591 CH3

I

O

HO

n

I

O

CH3

P1080

CH

O

I F

F

F 4

P1082

I

O

O S CF3

CF3CF2CF2

O

I

O S CF3 O

O S CF3

CF3 CF3

CF

I

OSO2CF3

B

P1620

O CF3(CF2)7

I

O

F

P1081

CH3

CF3(CF2)5

F

P1659 O

P1415

T2624

Si(CH3)3

O O C CH3

I

P

CF3

I

O

I

CH3 CH3

O C CH3

CF3SO3

O

P1239 CH3 CH3

Si C C

I

BF4

CH3

Product No. Product Name B2539 B1175 B1616 B2359 B2121 D2045 D2372 D2503 D2356 D2248 D2238 D2373 D2357 D2243 D2253 E0467 P1298 P1015 I0330 I0479 I0072 I0073 I0591 P1080

Bis(pyridine)iodonium Tetrafluoroborate [Bis(trifluoroacetoxy)iodo]benzene [Bis(trifluoroacetoxy)iodo]pentafluorobenzene Bis(2,4,6-trimethylpyridine)iodonium Hexafluorophosphate 1-(tert-Butylperoxy)-1,2-benziodoxol-3(1H)-one Dess-Martin Periodinane Diphenyliodonium Bromide Diphenyliodonium-2-carboxylate Monohydrate Diphenyliodonium Chloride Diphenyliodonium Hexafluoroarsenate Diphenyliodonium Hexafluorophosphate Diphenyliodonium Iodide Diphenyliodonium Nitrate Diphenyliodonium Perchlorate Diphenyliodonium Trifluoromethanesulfonate Ethynyl(phenyl)iodonium Tetrafluoroborate [Ethynylating Reagent] [Hydroxy(methanesulfonyloxy)iodo]benzene [Hydroxy(tosyloxy)iodo]benzene Iodobenzene Diacetate Iodomesitylene Diacetate Iodosobenzene 2-Iodosobenzoic Acid 4-Isopropyl-4'-methyldiphenyliodonium Tetrakis(pentafluorophenyl)borate (Perfluorohexyl)phenyliodonium Trifluoromethanesulfonate

Unit Size 5g 1g 1g

5g 5g 5g

1g

5g 5g 1g

10g

5g 5g 25g 5g

5g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

1g 25g 1g 5g 1g 25g 5g 25g 25g 1g 25g 5g 25g 1g 5g 1g 25g 25g 250g 25g 5g 10g 25g 5g

183

Hypervalent Iodine Compounds

Product No. Product Name P1659 P1081 P1082 P1620 P1415 T2624 P1239

(Perfluoroisopropyl)phenyliodonium Trifluoromethanesulfonate (Perfluoro-n-octyl)phenyliodonium Trifluoromethanesulfonate (Perfluoropropyl)phenyliodonium Trifluoromethanesulfonate Phenyl[2-(trimethylsilyl)phenyl]iodonium Trifluoromethanesulfonate Poly[4-(diacetoxyiodo)styrene] 1-Trifluoromethyl-3,3-dimethyl-1,2-benziodoxole Trimethylsilylethynyl(phenyl)iodonium Tetrafluoroborate

Unit Size 500mg 1g 1g 1g 1g 5g 1g 1g

Many hypervalent organoiodanes may decompose violently when exposed to heat, shock, and friction, etc. Sufficient safety measures, such as usage of safety shield, wearing of protective equipment, and extreme caution should be taken, when using this compound, from the opening up to the disposal of the reagents.

References 1) 2) 3) 4)

184

1984, 709. A. Varvoglis, P. J. Stang, V. V. Zhdankin, . 1996, , 1123. 1999, number M. Ochiai, , 2. 2002, H. Togo, K. Sakuratani, , 1018; H. Togo, K. Sakuratani, Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 2003 113131, 2003.

Availability, price or specification of the listed products are subject to change without prior notice.

2002, 1966; Tokyo

Phase-Transfer Catalysts

Phase-Transfer Catalysts A phase-transfer catalyst enables the reaction in a heterogeneous system between general organic compounds soluble in organic solvents and compounds soluble in water such as inorganic salts. The reaction can be accomplished in a biphasic system of an inexpensive nonpolar aprotic solvent and water without using DMSO or DMF which are high-polar solvents. A phase-transfer catalyst is soluble in both solvents, and it carries anions of inorganic salts into organic solvents and returns them into the water phase. Reactions usually progress under mild conditions with easy work-up procedures. For this reason, they are also used industrially. Typical phase-transfer catalysts are quaternary ammonium salts, crown ethers, and phosphonium compounds etc. Reaction examples are shown as follows.1-4) Alkylation CH3OCH2CHCH3 OH

TBAB

+ BuCl

50% NaOH aq.

OBu Y. 97%

TBAB : Tetrabutylammonium Bromide

Bu3P

C8H17Cl

+ Na2S

C16H33

1)

CH3OCH2CHCH3

2)

Br

(C8H17)2S

H2O

Y. 91%

Cyanation 3)

Cl(CH2)3Cl

18-Crown-6

+ KCN

NC(CH2)3CN

CH3CN

Y. 97%

Oxidation CH3(CH2)7CH CH2 + KMnO4

4)

(C8H17)3N CH3 Cl

CH3(CH2)7CO2H

Benzene – H2O

Y. 91%

Quaternary Ammonium Compounds (see p.337) Crown Ethers (see p.275) Phosphonium Compounds (see p.350) Pyridinium Compounds (see p.345) Viologens (see p.248) The asymmetric synthesis is realized using optically-active phase-transfer catalysts. The asymmetric synthesis using the cinchona alkaloid derivative as a phase-transfer catalyst was reported in the 1980s.5) Shibasaki . succeeded in the total synthesis of cylindricine C involving the asymmetric Michael addition catalyzed by tartaric acid derivatives.6) In this section, we introduce the cinchona alkaloid derivatives and the tartaric acid derivatives as the asymmetric phase-transfer catalysts. CH2 OH N

Ph2C N

Cl

N

O Ot-Bu

+

BnBr

O 10 mol% CH2Cl2 50% NaOH aq. 20 ºC, 9 h

Ph2C N

5)

Ot-Bu Bn

Y. 75% 66% e.e. (R)

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

185

Phase-Transfer Catalysts

5

O Ph

N

CO2Bn

O

(S,S)-TaDiAS-2nd* (cat.) 10 mol%

O

+ C6H13

5

Ph

O

Cs2CO3, PhCl -40 ºC, 66 h

Ph

O

N BnO2C

Ph

N

BnO2C

O tandem cyclization

C6H13

Y. 84% 82% e.e.

6)

N C6H13

C6H13

HO

(+)-cylindricine C total 6 steps

B1683

B1689

CH2

CH

H

H

CH2

CH

Cl

Cl HO

H

CH2

Cinchona Alkaloid Derivatives

Chiral Phase-Transfer Catalysts

N

B1684

HO

CH2

H

N

B1685 H

CH2

CH2

CH

CH

Cl N

HO

H Cl

CH2

HO

H

N CH2

H CH3O

CH3O

N

N

Product No. Product Name B1683 B1689 B1684 B1685

Unit Size

N-Benzylcinchonidinium Chloride N-Benzylcinchoninium Chloride N-Benzylquinidinium Chloride N-Benzylquininium Chloride

D3475 CH3 CH2Ph CH2 N CH2 O

Tartaric Acid Derivatives

O CH2 N CH2 CH2Ph CH3

10g 5g 5g 5g

D3476

CH3 CH3 2BF4

2

2

CH3 CH2Ph CH2 N CH2 O O CH2 N CH2 CH2Ph CH3

CH3 CH3

2

2

2BF4

Product No. Product Name D3475 D3476

186

N

N

6,10-Dibenzyl-N,N '-dimethyl-N,N,N ',N '-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane(2R,3R)-diylbis(methylammonium) Tetrafluoroborate [=(R,R)-TaDiAS-2nd] 6,10-Dibenzyl-N,N '-dimethyl-N,N,N ',N '-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane(2S,3S)-diylbis(methylammonium) Tetrafluoroborate [=(S,S)-TaDiAS-2nd]

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 200mg

1g

200mg

1g

Phase-Transfer Catalysts

References H. H. Freedman, R. A. Dubois, . 1975, , 3251. 1974, 565. D. Landini, F. Rolla, F. L. Cook, C. W. Bowers, C. L. Liotta, . 1974, , 3416. C. M. Starks, . 1971, , 195. M. J. O'Donnell, W. D. Bennett, S. Wu, . 1989, , 2353. T. Shibuguchi, H. Mihara, A. Kuramochi, S. Sakuraba, T. Ohshima, M. Shibasaki, . 2006, , 4635; H. 2007, Mihara, T. Shibuguchi, A. Kuramochi, T. Ohshima, M. Shibasaki, , 421. 7) Review: Phase-Transfer Catalysts M. Makosza, . 2000, , 1399; J. M. McIntosh, . 1978, , 235; 1976, 168; A. C. Knipe, P. Varughese, . 1977, , 666; G. W. Gokel, H. D. Durst, . 1976, 1973, 441. , 618; J. Dockx, 2003, Asymmertic Phase-Transfer Catalysts K. Nagasawa, , 670; K. Maruoka, T. Ooi, . 2003, , 3013.

1) 2) 3) 4) 5) 6)

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

187

Combinatorial Chemistry

Combinatorial Chemistry Combinatorial chemistry is a technique in which a number of compounds are simultaneously synthesized and has received much focus in the development of drugs. Of the array of products produced, which are called“libraries”, those with the desired functions and activity, are easily identified and isolated. Solid-phase syntheses are widely used. In the solid-phase syntheses, the desired compounds are held by covalent bond to the solid-phase. Therefore, the excess reaction reagents can easily be removed by washing. A variety of compounds can be synthesized quickly upon determination of their synthetic routes. Furthermore, they have the advantage of being capable of automatic synthesis. Currently, the reactions which can be utilized in the solid-phase syntheses are limited, however, other potentially utilizable reactions are vigorously being explored. In the other synthesis of libraries, the liquid-phase reactions are carried out utilizing conventional organic synthetic reactions. Some developments have been reported and future developments are being anticipated. We have put on the market various kinds of resins which have widely been utilized through the solidphase synthetic technique and useful diphenylphosphino polystyrene resin for liquid-phase Mitsunobu reaction. Any of these resins are easy to use in meshes, swelling volume and functional content. For the polymer-supported reagent used for liquid-phase synthesis, please refer to “Polymer-Supported Reagents” (p.24), and for a group of building blocks intended for the preparation of the combinatorial libraries, please refer to our website. We provide the structure search on the website. A2006

B2172

A2047 A1543 CH2NH2

CH2NHCH2CH2NH

Resins

B2372

P

P

P

B2370

P

CH2O

C NH(CH2)4NHO2S

P

CH2O

C1747 C1751 C1746 C1750 C1744 C1643 C1642 C1745

C NH(CH2)2NHO2S

O 2N

O 2N

C1679

B2371

Br

CH2Cl P

P1432 P1379

H0987 H0986 Cl

P

CH2O

P

C NH(CH2)3NHO2S

C Cl

P

CH2O

CH2OH

P

O 2N

S0545

T1889

SO2Cl P

P

C Cl

Product No. Product Name A2006

N-(2-Aminoethyl)aminomethyl Polystyrene Resin cross-linked with 1% DVB (50-100mesh)

A2047 A1543 B2172

Aminomethyl Polystyrene Resin cross-linked with 1% DVB (200-400mesh) (2.4-3.0mmol/g) Aminomethyl Polystyrene Resin cross-linked with 1% DVB (200-400mesh) (0.5-0.7mmol/g) 4-Bromo Polystyrene Resin cross-linked with 2% DVB (200-400mesh) (2.6-2.8mmol/g)

(3.1-3.5mmol/g)

188

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 5g 5g 5g 5g

25g 25g 25g 25g

Combinatorial Chemistry

Product No. Product Name

Unit Size

B2372

N-(4-Benzyloxytrityl)-N '-(2-nitrobenzenesulfonyl)-1,4-diaminobutane Resin

B2370

N-(4-Benzyloxytrityl)-N '-(2-nitrobenzenesulfonyl)-1,2-diaminoethane Resin

1g

cross-linked with 1% DVB (200-400mesh) (0.9-1.1mmol/g) cross-linked with 1% DVB (200-400mesh) (0.9-1.1mmol/g) Chloromethyl Polystyrene Resin cross-linked with 2% DVB Chloromethyl Polystyrene Resin cross-linked with 2% DVB Chloromethyl Polystyrene Resin cross-linked with 2% DVB Chloromethyl Polystyrene Resin cross-linked with 1% DVB Chloromethyl Polystyrene Resin cross-linked with 1% DVB Chloromethyl Polystyrene Resin cross-linked with 1% DVB Chloromethyl Polystyrene Resin cross-linked with 1% DVB Chloromethyl Polystyrene Resin cross-linked with 2% DVB

C1747 C1751 C1746 C1750 C1744 C1643 C1642 C1745 B2371

(100-200mesh) (100-200mesh) (200-400mesh) (100-200mesh) (100-200mesh) (200-400mesh) (200-400mesh) (200-400mesh)

5g 5g 5g 5g 5g 5g 5g

(2.0-2.5mmol/g) (0.8-1.2mmol/g) (0.8-1.2mmol/g) (2.0-2.5mmol/g) (0.8-1.2mmol/g) (1.6-1.8mmol/g) (0.8-1.3mmol/g) (2.0-2.7mmol/g)

1g 25g 25g 25g 25g 25g 25g 25g 5g

N-(4-Benzyloxytrityl)-N '-(2-nitrobenzenesulfonyl)-1,3-diaminopropane Resin

1g 5g

cross-linked with 1% DVB (200-400mesh) (0.9-1.1mmol/g)

C1679 H0987

2-Chlorotrityl Chloride Resin cross-linked with 1% DVB (200-400mesh) (1.0-1.8mmol/g) 4-(Hydroxymethyl)phenoxymethyl Polystyrene Resin cross-linked with 1% DVB (200-400mesh)

H0986

4-(Hydroxymethyl)phenoxymethyl Polystyrene Resin cross-linked with 1% DVB (200-400mesh)

P1432 P1379 S0545 T1889

Polystyrene Resin cross-linked with 1% DVB (100-200mesh) Polystyrene Resin cross-linked with 1% DVB (200-400mesh) Sulfonyl Chloride Polystyrene Resin cross-linked with 1% DVB (50-100mesh) (4.5-4.8mmol/g) Trityl Chloride Resin cross-linked with 1% DVB (200-400mesh) (1.0-1.8mmol/g)

(1.0-2.0mmol/g) (0.5-1.0mmol/g)

B2322

D2707

CH3O

CH3 CH3 Si

H0961

C

OH

OCH3

CH2OH

H1269 O

O C OCH3

OCH2

5g

C CH3

CH3 CH3

H1049

25g 100g 25g 25g 5g

C OH

O

NO2

CH2O

5g 25g

O

C OH

Linkers

25g

H0769

O OCH2

5g

OCH2 C OH

O

NO2 O CH2OH

OH

CH2OH

Product No. Product Name B2322 D2707 H0769 H1049 H0961 H1269

2-[4-(tert-Butyldimethylsilyloxymethyl)-2-nitrophenoxy]acetic Acid 2,4-Dimethoxy-4'-hydroxybenzophenone 4-Hydroxymethylbenzoic Acid 2-[4-(Hydroxymethyl)-2-nitrophenoxy]acetic Acid Methyl Ester 4-(Hydroxymethyl)phenoxyacetic Acid 3-Hydroxyxanthen-9-one

Unit Size 100mg 5g 10g 100mg 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

1g 25g 25g 1g 1g 5g

189

Combinatorial Chemistry

●TNBS & Chloranil Test Kit To conduct the solid phase synthesis, as simple methods TNBS and Chloranil Test are used to detect free amino group on the resin after reaction. Using TNBS Test, the primary amino group can be detected, while Chloranil Test can detect the presence of both primary and secondary amino groups. This method is much safe and simple detection method of free amino group compared to Kaiser Test which requires toxic substance, potassium cyanide fall under the Poisonous and Deleterious Substances Control Law in Japan. Product No. Product Name T2024

Picrylsulfonic Acid (ca. 1% in DMF) N,N-Diisopropylethylamine (ca. 10% in DMF) [for Detection of Primary Amines]

190

Unit Size

TNBS Test Kit 10ml×1 10ml×1

C1771

Chloranil Test Kit

P1447 D2937 C1770 A1640

Chloranil (ca. 2% in DMF) 10ml×1 Acetaldehyde (ca. 2% in DMF) 10ml×1 [for Detection of Primary and Secondary Amines] Picrylsulfonic Acid (ca. 1% in N,N-Dimethylformamide) N,N-Diisopropylethylamine (ca. 10% in N,N-Dimethylformamide) Chloranil (ca. 2% in N,N-Dimethylformamide) Acetaldehyde (ca. 2% in N,N-Dimethylformamide)

Availability, price or specification of the listed products are subject to change without prior notice.

1kit

1kit 10ml 10ml 10ml 10ml

Gas Cylinders

Gas Cylinders Our company is endeavoring to help you in your research by charging small-sized gas cylinders with gaseous reagents for easy dispensing. 【Characteristics】 • The flow of gas can be adjusted across a wide range. • Convenient for moving since gas cylinders are small sized (7 × 14 cm) and lightweight (under 500g). • Metallic pressure-tight container (14 kg/cm2). 【Storage Method】  Store in a cool place before opening and use the compressed reagent as soon as possible.* One-time, exhaustive use is recommended. If the reagents need to be stored, please keep the following in mind with the utmost caution.  *The valve packing may swell in storage and gas might not flow out. 1. The charge intake cover should be attached after insuring that the gas flow has ceased. 2. Select a low-temperature, well-ventilated place for storage. 3. Reagents that require refrigeration should be stored only in an explosion-proof refrigerator. Potential risks for explosion through ignition of a small gas leak from the spark of the thermostat may be present in ordinary refrigerators. B0748 1-Butyne can decompose explosively so these reagent cylinders should not be stored for re-use. 【Notes】 • These reagents are pressurized. Sufficient care should be taken in handling them, in addition to wearing appropriate protective equipment. • Take care to insure that the inner pressure of reaction apparatus does not exceed the inner pressure of the gas cylinders. As an extra precaution, we recommend that a check valve be attached within the gas introduction path. • Empty the contents thoroughly before disposing of the gas cylinder.

Hydrocarbons Product No. Product Name

bp(℃ )

B0675 B0677 B0689 B0690 B0691 B0692 B0748 I0090 I0091 M0177

-4.5 -0.5 -6.0 3.7 0.8 1.0 8.1 -11.6 -7.0 20.1

1,3-Butadiene (stabilized with TBC) Butane 1-Butene cis-2-Butene trans-2-Butene 2-Butene (cis- and trans- mixture) 1-Butyne Isobutane Isobutene 3-Methyl-1-butene

Unit Size 100g 100g 100g 100g 100g 100g 100g 100g 100g 100g

Ethers Product No. Product Name

bp(℃ )

M0110 M0224

10.8 -24.8

Ethyl Methyl Ether Methyl Ether

Unit Size 100g 100g

Amines Product No. Product Name E0245

Ethylamine Anhydrous

bp(℃ )

Unit Size

16.6

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

100g

191

Gas Cylinders

Halides Product No. Product Name

bp(℃ )

B1618 C0164 C1397 D0356 D0366 D0417 D2384 F0042 O0204 T1476 V0032

4.5 12.3 -9.5 -29.5 31.7 4.1 27.7 23.7 -6.0 -26.2 16.0

Bromomethane Chloroethane 1-Chloro-1,1-difluoroethane Dichlorodifluoromethane 1,1-Dichloroethylene (stabilized with MEHQ) 1,2-Dichloro-1,1,2,2-tetrafluoroethane 2,2-Dichloro-1,1,1-trifluoroethane Trichlorofluoromethane Octafluorocyclobutane 1,1,1,2-Tetrafluoroethane Vinyl Bromide (stabilized with MEHQ)

Unit Size 50g 200g 100g 400g 250g 100g 300g 400g 100g 100g 100g

To use these products charged in cylinder, 1) Charge valve & 2) Connectors which are sold separately are required. (Connectors are used for connection between the reaction apparatus and gas cylinders) 1) Charge valve 【Method of Use】(The actual form may differ slightly from the illustration.) 1. Before mounting the charge valve, turn the handle (A) to the left and pull the needle (B) upward as far as it can go. 2. Mount the charge valve on to the gas cylinder. 3. After the charge valve is mounted, tighten the disk (C) attached at the bottom of the charge valve. Be careful not to over tighten. 4. Turning the handle (A) to the right makes the needle (B) come down and perforate the sealing lid. 5. On turning the handle (A) to the left, the valve opens to allow the gas to flow. 6. To stop the gas flow, turn the handle (A) to the right. Do not remove the charge valve until the cylinder is empty and the inside pressure becomes equal to atmospheric pressure. 2) Connectors 【Method of Use】 1. Detach the charge intake cover from the charge valve. 2. Set the cap nut in the connector. Then, mount them in the charge intake. 3. Confirm that the connected side of the connector and the charge intake are normal. Afterwards, tighten the cap nut with the spanner etc. Be careful not to over tighten. 4. Use a commercially available tube fitting suitable for the outside diameter of the pipe connector when connecting to the gas introduction pipe of the reactor. We have two types of connectors, a tube connector for under ordinary pressure and a pipe connector for under increased pressure. The outside diameter of both connectors is 6.0 mm. Each connector is bundled with a cap nut. Please use both connectors according to the situation. Tube Connector (for under ordinary pressure)

Pipe Connector (for under increased pressure)

Tube Connector      Cap Nut

Pipe Connector      Cap Nut

Product No. Product Name V0030 V0070 V0071

192

Valve (for Gas cylinder) Tube Connector (for Gas cylinder) Pipe Connector (for Gas cylinder)

Availability, price or specification of the listed products are subject to change without prior notice.

Precursors

Precursors for Preparation of Highly Reactive Reagents The highly reactive reagents are generally unstable and frequently arrive to the customer in a decomposed state. Consequently, these compounds should be prepared immediately prior to use. The precursors required for such preparations are shown below. For details, please refer to references. Cyanamide Cyclopentadiene Diazomethane Dimethyl Ketene Ethyl Diazoacetate Hydrogen Bromide

●Preparation of Cyanamide1) Product No. Product Name

C0006

Unit Size

Calcium Cyanamide CaNCN

25g

500g

NH2CN + Ca(O2CCH3)2

+ 2CH3CO2H

Glacial acetic acid 57g (54mL, 0.75mol) and water 135mL are placed in a large sized agate mortar and while thoroughly stirring, calcium cyanamide 40g (0.5mol) is slowly added and the mixture is grounded. Acetylene gas is generated, yielding a dull grayish to dark colored paste. Subsequently, the paste is dried at 40∼50ºC for 12∼18 hours under reduced pressure 30mmHg to yield a gray powder which is placed in a Soxhlet extractor. The powder is extracted with 400mL of ether containing several drops of dilute acetic acid for 2∼3 hours (2×). The ether extraction is dried over anhydrous sodium sulfate (30g). Concentration under a reduced pressure gives 10.5∼15.8g (50∼70% from CaCN2) colorless viscous oil.

●Preparation of Cyclopentadiene2) Product No. Product Name

D0443

Unit Size

Dicyclopentadiene (stabilized with BHT)

25ml Δ

500ml

2

The reaction apparatus (Figure 1) is assembled by attaching a thermometer, Vigreaux distilling column and Liebig condenser to a 500mL two necked flask. The receiver is cooled by means of a refrigerants or freezing mixtures. Dicyclopentadiene (195g) is placed in the two necked flask and heated to about 160ºC with an electric heating mantle or oil bath. Thermal decomposition begins at about 150ºC and distillates at 43∼46ºC can be obtained (addition of iron powder expedites the thermal decomposition rate of cyclopentadiene). Heating is applied slowly, because rapid temperature increases cause dicyclopentadiene to distill prior to undergoing thermal decomposition. In such a case, re-distillation allows narrow boiling-point distillates. Cyclopentadiene dimerzes rapidly at room temperature and should be used immediately.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

193

Precursors

Figure 1. Reaction apparatus

●Preparation of Diazomethane3) Product No. Product Name

Unit Size

N-Methyl-N-nitroso-p-toluenesulfonamide

T0323

NO CH3

SO2N CH3

+

ROH

KOH

CH2N2

25g

+

CH3

SO2OR

+

500g

H2O

A reaction and distillation apparatus is assembled by connecting an addition funnel and condenser to a 100mL long-neck distillation flask. Two in series receiving flasks are connected to the apparatus with the second flask containing an induction tube. A solution containing 6g potassium hydroxide in 10mL water, and a solution containing 35mL carbitol (diethylene glycol monoethyl ether) and 10mL of ether are placed in the distillation flask. 20∼30mL ether is placed in the second receiving flask making sure the induction tube is immersed into the ether. Both receiving flasks are cooled to 0ºC. A solution containing -methyl-nitroso- -toluenesulfonamide (21.5g, 0.1mol) in 140mL ether is placed in the addition funnel. Heat the distillation flask to 70ºC in a warm water bath. As the ether begins to boil, start adding the -methyl- nitros- -toluenesulfonamide solution dropwise over a 20 minute period. Swirl distillation flask from time to time. About 3g of diazomethane (0.07mol) is dissolved in ether distillate. The reagent should be used at once without storing it. *Note: Diazomethane is explosive and highly toxic. Wear protective gloves, protective goggles, protective mask and work in a well ventilated fume hood. Also place a safety shield in front of distillation apparatus. Diazomethane may explode upon contact with ground glass joints or other scratched glass surfaces, so avoid handling or preparing this compound with such surfaces. Ordinarily, diazomethane is used as a solution in ether. *We have TMS diazomethane available. This reagent is analogous in reactivity to diazomethane, but less explosive and less toxic. Please consider using this reagent prior to preparing diazomethane. Product No. Product Name

T1146 194

Trimethylsilyldiazomethane (ca. 10% in Hexane, ca. 0.6mol/L)

Unit Size

10ml 25ml 100ml

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Precursors ●Preparation of Dimethyl Ketene44) Product No. Product Name

Unit Size

Tetramethyl-1,3-cyclobutanedione

D0258

25g

O Δ

(CH3)2C

(CH3)2C C O

C(CH3)2 O

Tetramethyl-1,3-cyclobutanedione is placed in the ketene generation apparatus, heated at 120ºC, and sublimed, then thermally decomposed by means of the red heated nichrome wire under the nitrogen atmosphere. Subsequently, the evolved gas is captured by means of a trap cooled in dry ice-acetone to obtain dimethylketene in about 60% yield. Dimethylketene is a yellowish liquid (bp 34ºC) with characteristic odor, remarkable reactivity, and transforms into a solid dimer when allowed to stand at room temperature. On exposure to air it generates white solid peroxides and explodes with even the slightest stimulus. For this reason, its monomer is stored under nitrogen at -78ºC and it is used immediately.

●Preparation of Ethyl Diazoacetate5) Product No. Product Name

Unit Size

Glycine Ethyl Ester Hydrochloride

G0102

H2NCH2CO2C2H5

. HCl

+

25g

NaNO2

N2CHCO2C2H5

+

NaCl

+

500g

2H2O

A solution containing 140g glycine ethyl ester hydrochloride (1mol) in 250mL water is placed in a 2L four neck flask. 600mL dichloromethane is added and the mixture is cooled to -5ºC under a nitrogen atmosphere. A solution containing 83g sodium nitrite in 250mL water is cooled to 0ºC and added with stirring to the reaction mixture. While keeping the reaction temperature below -9ºC, 95g 5% sulfuric acid is added dropwise to the reaction over a 3 minute period. After ten minutes addition stirring the reaction is transferred to a 2L separatory funnel while cold. The isolated yellow-greenish organic phase is poured into a cooled 1L 5% sodium carbonate solution, then placed into a separatory funnel and shaken. The isolated aqueous phase is extracted with 75mL dicholoromethane, dried over 15g anhydrous sodium sulfate, and concentrated under reduced pressure (350mmHg). Further concentration at 20mmHg and a bath temperature of 35ºC gives 90∼100g (79∼88%) yellow oily substance. The product is pure enough to be used for ordinary synthesizing purposes. It is explosive, and distillation under even reduced pressure is hazardous. *Ethyl diazoacetate is explosive and very toxic. Wear protective gloves, protective goggles, protective mask, and use a safety screen. Work in a well ventilated fume hood.

●Preparation of Anhydrous Hydrogen Bromide6) Product No. Product Name

Unit Size

1,2,3,4-Tetrahydronaphthalene

T0107

25ml

500ml

Br Br

+

4Br2

+

4HBr

Br Br

Bromine is slowly added dropwise to a round bottom flask containing a suspension of iron and 1,2,3,4tetrahydronaphthalene. In the early stage of the reaction, the flask is cooled with water. The reaction is warmed to 30 to 40ºC allowing gas evolution. The gas is passed through a wash bottle containing 1,2,3,4-tetrahydronaphthalene in order to eliminate any bromine in the hydrogen bromide. For optimum yields of hydrogen bromide, dry the 1,2,3,4tetrahydronaphthalene over anhydrous sodium sulfate and then distill it under a dry inert atmosphere (such as argon or nitrogen). If any moisture is introduced into the reaction, the yield of hydrogen bromide becomes remarkably poor. References 1) 2) a) b) 3) a) b)

. 1963, Coll. Vol. , . 1963, Coll. Vol. . 1962, , 50. . 1963, Coll. Vol. . 1973, Coll. Vol.

645. , 238;

4) 5) 6)

1963, , 467. . 1963, Coll. Vol. , 424. . 1939, , 149.

, 250; , 351.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

195

C60 & C70

C60 & C70 The Third Form of Carbon Fullerene C60 and C70 which are the third allotropes of carbon, subsequent to diamond and graphite, have a beautiful spherical structure as shown in the figure. The form of Fullerene C60 resembles the dome built by the architect, Buckminster Fuller, and therefore, it is called“Buckminsterfullerene”. The existence of Buckminsterfullerenes was hypothesized by Osawa1) more than 40 years ago and discovered by Smalley and co-workers2) relatively recently. Afterwards, Huffman, Kratschmer and coworkers3) have reported on the method to generate Fullerenes in a considerably large quantity. Fullerenes have been studied intensively, particularly in the fields of superconducting devices4), ferromagnets5), nonlinear optical materials6) , pharmaceuticals7) and the like. Moreover, solvent-soluble fullerene derivatives obtained by chemical modification8) , such as [60]PCBM9) or C60MC1210) , have been developed and applied in various fields including organic semiconducting or solar cell materials.

CH3 OCH3

(CH2)11CH3

N

O

C60

C70

Product No. Product Name B1641 B1660 B1642 B1694 M2088 C2415

Fullerene C60 (pure) Fullerene C60 Fullerene Extract, C60 (contains ca. 20% C70) Fullerene C70 Methyl [6.6]-Phenyl-C61-butyrate C60MC12

[60]PCBM

C60MC12

Unit Size 100mg 100mg 100mg

1g 1g 1g 100mg 100mg 100mg

Please note that B1642 is a mixture of C60 and C70 in an about 8 to 2 ratio containing a trace amount of other higher Fullerene.

References 1) 2) 3) 4)

5) 6)

7)

8)

9) 10) 11)

196

1970, E. Osawa, , 854. 1985, H. W. Kroto, J. R. Heath, S. C. O'Brein, R. F. Curl, R. E. Smalley, , 162. 1990, W. Kraetschmer, L. D. Lamb, K. Fostiropoulos, D. R. Huffman, , 354. A. F. Hebard, M. J. Rosseinsky, R. C. Haddon, D. W. Murphy, S. H. Glarum, T. T. M. Palstra, A. P. Ramirez, A. R. Kortan, 1991, 1991, , 600; K. Tanigaki, T. W. Ebbesen, S. Saito, J. Mizuki, J. S. Tsai, Y. Kubo, S. Kuroshima, , 222; S. Margadonna, K. Prassides, . 2002, , 639. 1991, P. M. Allemand, K. C. Khemani, A. Koch, F. Wudl, K. Holczer, S. Donovan, G. Gruner, J. D. Thompson, , 301; L. A. Zheng, E. V. Barrera, R. D. Shull, . 2002, , 523. Q. Gong, Y. Sun, Z. Xia, Y. H. Zou, Z. Gu, X, Zhou, D. Qiang, . 1992, , 3025; L. W. Tutt, A. Kost, 1992, , 225; R. A. Ganeev, A. I. Ryasnyansky, V. I. Redkorechev, K. Fostiropoulos, G. Priebe, T. Usmanov, . 2003, , 131. 1997, Y. Tabata, Y. Ikada, , 30; N. Miyata, Y. Yamakoshi, I. Nakanishi, 2000, , 1007; Y. Yamakoshi, N. Umezawa, A. Ryu, K. Arakane, N. Miyata, Y. Goda, T. Masumizu, T. Nagano, 2003, , 12803. 1992, H. Schwarz, , 293; A. Koch, H. Eckert, G. Srdanov, H. M. Webb, in Ser. 481, ed. by G. S. Hammond, V. J. Kuck, ACS, Washington D. C., 1992. S. Günes, H. Neugebauer, N. S. Sariciftci, . 2007, , 1324. 2010, , Y. Horii, K. Sakaguchi, M. Chikamatsu, R. Azumi, K. Yase, M. Kitagawa, H. Konishi, 101601. 1991, Review: H. W. Kroto, A. W. Allaf, S. P. Balm, . 1991, , 1213; ; R. E. Smalley, . 1992, , 98; M. S. Dresselhaus, . 1995, , 487; M. Iyoda, M. Yoshida, 1995, , 756; N. F. Goldshleger, . 2001, , 255. The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Carbon Nanotube

Carbon Nanotube

Carbon Nanotubes (CNT), which were discovered by Iijima in 1991, are composed entirely of carbon atoms, as is C60.1) As the name implies, this carbon structure is shaped like a tube on a nanometer scale. In 1991, Hufman and Kraetschmer reported a procedure for the preparation of C60 by an arc discharge. Many researchers had used this technique to obtain C60 from the soot which had collected on the anode. However, Iijima focused his attention on the soot which had accumulated on the cathode carbon rod. In this soot, Iijima found a needle like substance which he characterized as CNT. These early nanotubes were multi-walled carbon nanotubes (MWCNT), composed of many layers. Two years later, single-walled carbon nanotubes (SWCNT) were discovered. In 1996, Smalleys developed a mass production method of SWCNT2) and since then, research of CNT has progressed rapidly. Today, researchers are making advances in the applications of CNT as probes for Scanning Probe Microscopy, nano-tweezers,3) field-emitter of Field Emission Display (FED),4) nanoelectronics devices,5) hydrogen fuel cells,6) thin films,7) and organic solar cells.8) Moreover, CNT generally tend to form bundles due to their van der Waals interactions, which makes them insoluble in organic solvents. In response to that, solvent-soluble CNT obtained by chemical modification have been developed and applied in many fields.9) Product No. Product Name

Unit Size

C2142 C2143 C2149 C2148 C2150 C2153 C2152 C2155 C2154 C2157 C2156 C2159 C2158 C2151 C2147

Carbon Nanotube Single-walled (>55%) below 2nm(diam.), 5-15μm(length) Carbon Nanotube Double-walled (>50%) below 5nm(diam.), 5-15μm(length) Carbon Nanotube Multi-walled below 10nm(diam.), 1-2μm(length) Carbon Nanotube Multi-walled below 10nm(diam.), 5-15μm(length) Carbon Nanotube Multi-walled 10-20nm(diam.), 5-15μm(length) Carbon Nanotube Multi-walled 10-30nm(diam.), 1-2μm(length) Carbon Nanotube Multi-walled 10-30nm(diam.), 5-15μm(length) Carbon Nanotube Multi-walled 20-40nm(diam.), 1-2μm(length) Carbon Nanotube Multi-walled 20-40nm(diam.), 5-15μm(length) Carbon Nanotube Multi-walled 40-60nm(diam.), 1-2μm(length) Carbon Nanotube Multi-walled 40-60nm(diam.), 5-15μm(length) Carbon Nanotube Multi-walled 60-100nm(diam.), 1-2μm(length) Carbon Nanotube Multi-walled 60-100nm(diam.), 5-15μm(length) Carbon Nanotube Aligned Multi-walled 10-20nm(diam.), 5-15μm(length) Carbon Nanotube Bundled Multi-walled below 10nm(diam.), 5-15μm(length)

200mg 200mg

(allowable temperature limit : 620℃ )

200mg

C2146

Carbon Nanotube Herringbone 10-20nm(diam.), 5-15μm(length)

1g 1g 1g 1g 1g 1g

1g 1g 1g 5g 5g 1g 5g 1g 5g 1g 5g 1g 5g 1g 1g 200mg

C60 & C70 (see p.196)

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

197

Carbon Nanotube

References 1) 2) 3) 4) 5) 6) 7) 8) 9)

198

1991, S. Iijima, , 56. 1996, R. E. Smalley, , 483. H. Nishijima, . 1999, , 4061; S. Akita . 2001, , 1691. Q. H. Wang, . 1997, , 3308; Y. Nakayama, . 2001, , 207. 1998, 1997, S. J. Tans, , 49; S. J. Tans, , 474 ; M. Suzuki, 2002, 2001, , 2273; A. Bachtold, , 1317. 1997, A.C. Dillon, , 377. Review: L. Hu, D. S. Hecht, G. Grüner, . 2010, , 5790. T. Umeyama, M. Fujita, N. Tezuka, N. Kadota, Y. Matano, K. Yoshida, S. Isoda, H. Imahori, 11484. Review: D. Tasis, N. Tagmatarchis, A. Bianco, M. Prato, . 2006, , 1105.

.

2007,

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

,

Building Blocks for Dendrimers

Building Blocks for Dendrimers Dendrimers are a single dendritic polymer consisting of three layers, its core, dendron regularly branched from the core, and the exterior surface layer. The typical species become globular and their size is in a clear-cut nm scale, having physical properties different from conventional straight polymer. Since their report in 1984 by Tomalia and co-workers, dendrimers have received much attention in many areas.1) Nowadays, applications of dendrimers are examined in chemical sensors, catalysts, electronics, photonics and medicines.2, 3) Functional elements and functional groups can be introduced into the core, dendron and surface layer. The synthetic technique is divided mainly into the divergent method, where synthesis proceeds from the center core toward the outside, and the convergent method, where synthesis proceeds from the exterior shell to the core. For the synthesis of the regularly branched portions, multifunctional compounds have been utilized. The 1,3,5-trisubstituted benzenes, shown below are useful building blocks for dendrimers. Please refer to our website for other building blocks. We provide the structure search on the website and you can search by the substructure.

B2081

B2118

B2248 CH2Br

BnO

COOH

O

BnO

O

O

NH2

OCH3 CH3O

CH3O

B2246

B2247

B2866

CH2OH

CH2OH

CH2O

CH2O

R OCH2

H 3C tBu

CH2O

R R=

O C OCH3

R

Ph

tBu

Si O

CH3O

CH2OH

CH3O

O Si Ph

Ph

B2120 COOH

D2085

O

NO2

OBn

D2832

BnO

CHO

Br

Br

AcO

OBn

D2824

Br

OAc

D2651

BnO

Br OH

AcO

BnO

CH2Br

OBn

OBn

BnO

I0302 TMS

Br

OAc

B2093

D2724

Br

COOH

CH2OH

COCH3

COOH

Br

OCH3

COOH

D2353

D2844 COCH3

D2267

OBn

Si O CH2OH

D1978

CH3O

CHO

COCH3

H3C C H3C

CH2O

Cl

D3184

BnO

CH2Br

CH3O

CH3O

C1258

O

CH3O

CH2O

Ph CH3O

O2N

OCH3

CH3O

CH3O

OH

OCH3

O

CH2O

B2052

R

O O

BnO

B2865

O

O

CH3O

CH2Br

BnO

H2N

OCH3

OCH3

CH2O

NCO

Br

Cl

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

Cl

199

Building Blocks for Dendrimers

D1981

D2875 CONH2

COCH3

HO

OH

HO

D1164

OH

D1558

OCH3

CH3O

HO

D2657

CH3O

OCH3

D2950

NH2

OCH3

CH3O

H0794

CH3O

OH

D2609 COOH

CH2COOH

CH2Br

HO

OH

D1534

D1484 CH2OH

COOH

CONH2

CHO

D2656

D0570 D2554

D2594 CH2OH

COCl

CH3O

CH3O

OCH3

M1413

OCH3

B2051 COOCH3

OH

COOH

OCH3

tBu

OCH3

CH3O

B2092

CH3O

OCH3

M1929

OBn

Br

COOH

D2215

Br

CH3O

HO

OH

D1737

OH

CH3O

tBu

Si O

O Si Ph

Ph

Ph

D2655 COOCH3

COOCH3

COOCH3

COOCH3

BnO

HO

Ph

OCH3

COOCH2CCl3

HO

OH

T2647 COOH

HOOC

COOH

Product No. Product Name B2081 B2118 B2248 B2865 B2052 B2246 B2247 B2866 B2120 C1258 D1978 D2844 D2085 D3184 D2267 D2651 B2093 D2832 D2353 D2824 D2724 I0302 D1981 D2875

200

3,5-Bis(4-aminophenoxy)benzoic Acid 3,5-Bis[3,5-bis(benzyloxy)benzyloxy]benzyl Bromide 3,5-Bis[3,5-bis(3,5-dimethoxybenzyloxy)benzyloxy]benzyl Bromide 3,5-Bis[3,5-bis(methoxycarbonyl)phenoxymethyl]phenol 3,5-Bis(tert-butyldiphenylsilyloxy)benzyl Alcohol 3,5-Bis(3,5-dimethoxybenzyloxy)benzyl Alcohol 3,5-Bis(3,5-dimethoxybenzyloxy)benzyl Bromide 5-(tert-Butyldiphenylsilyloxy)-1,3-benzenedimethanol 3,5-Bis(4-nitrophenoxy)benzoic Acid 1-Chloro-3,5-dimethoxybenzene 3',5'-Diacetoxyacetophenone 3,5-Diacetoxybenzoic Acid 3',5'-Dibenzyloxyacetophenone 3,5-Dibenzyloxybenzaldehyde 3,5-Dibenzyloxybenzoic Acid 3,5-Dibenzyloxybenzyl Alcohol 3,5-Dibenzyloxybenzyl Bromide 3,5-Dibromobenzaldehyde 3,5-Dibromobenzoic Acid 3',5'-Dibromo-4'-hydroxyacetophenone 3,5-Dibromo-1-trimethylsilylbenzene 3,5-Dichlorophenyl Isocyanate 3',5'-Dihydroxyacetophenone 3,5-Dihydroxybenzamide

Unit Size 1g 1g

1g 1g 1g 10g 10g 1g 1g 5g 5g 5g 5g 5g 5g 10g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

5g 5g 1g 200mg 1g 5g 5g 5g 5g 25g 25g 5g 10g 5g 25g 25g 25g 25g 10g 25g 25g 10g 25g 5g

Building Blocks for Dendrimers

Product No. Product Name D0570 D2554 D2656 D1484 D1164 D1558 D1534 D2609 D2594 D2657 D2950 H0794 M1413 B2051 B2092 M1929 D2215 D1737 D2655 T2647

3,5-Dihydroxybenzoic Acid 3,5-Dihydroxybenzoic Acid 3,5-Dihydroxybenzyl Alcohol 3,5-Dimethoxyaniline 3,5-Dimethoxybenzaldehyde 3,5-Dimethoxybenzamide 3,5-Dimethoxybenzoic Acid 3,5-Dimethoxybenzoyl Chloride 3,5-Dimethoxybenzyl Alcohol 3,5-Dimethoxybenzyl Bromide 3,5-Dimethoxyphenylacetic Acid 5-Hydroxyisophthalic Acid 5-Methoxyresorcinol Methyl 3,5-Bis(tert-butyldiphenylsilyloxy)benzoate (ca. 20% in Toluene, ca. 0.28mol/L) Methyl 3,5-Dibenzyloxybenzoate Methyl 3,5-Dibromobenzoate Methyl 3,5-Dihydroxybenzoate Methyl 3,5-Dimethoxybenzoate 2,2,2-Trichloroethyl 3,5-Dihydroxybenzoate (ca. 20% in Dichloromethane, ca. 1mol/L) 1,3,5-Tris(4-carboxyphenyl)benzene

Unit Size 25g 25g 5g 5g 5g 25g 5g 5g 5g 1g 25g

5g 5g 25g 5g 1g

500g 500g 25g 25g 25g 5g 500g 25g 25g 25g 5g 500g 1g 25g 25g 25g 250g 25g 25g 5g

References 1) D. A. Tomalia, J. R. Dewald, M. R. Hall, S. J. Martin, P. B. Smith, Preprints of the 1st SPSJ International Polymer Conference, Society of Polymer Science Japan, Kyoto, 1984, p 65; D. A. Tomalia, J. M. J. Fréchet, 2002, , 2719. 2) F. Vögtle, G. Richardt, N. Werner, in , Wiley-VCH, Weinheim, 2009. 2010, 3) D. Astruc, E. Boisselier, C. Ornelas, , 1857.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

201

Organic Semiconducting Materials

Organic Semiconducting Materials S S

1 P0030

2 P1893

3 D3526

Pentacene (1) is a polyaromatic hydrocarbon consisting of five linearly condensed benzene rings. 1 has attracted much attention as an electronic devices materials in recent years, especially, in the field of p-type semiconductor research.1) Correspondingly, C60 is known as an n-type semiconductor, and both of it and 1 have been actively studied as a transistor consisting only of organic and molecular substance. 1 for use in such applications must be of extremely high purity. TCI offers 1 purified to a suitable standard by recrystallization and sublimation. On the other hand, picene (2), whose benzene rings are condensed in a w-shape, is a stable aromatic hydrocarbon compound. In this form, all five benzene rings can be described by the Kekulé structure.2) Kubozono have reported an efficiency modification of Field-effect transistors (FETs) with 2. Applying 2 into the active layer of FETs resulted in the field-effect mobility value (μ value) being measured 1.1 cm2/Vs. Furthermore, the μ value is improved up to 1.75 cm2/Vs after exposure to O2 atmosphere for 70 hours. This result showed that the modified FET is an O2-assisted devise, as well as having stability against O2.3) In addition, Kubozono have also reported the superconductivity of picene which was intercalated with alkaline metals, such as potassium and rubidium.4) Additionally, Takimiya have developed 2,7-diphenyl[1]benzothieno[3,2- ][1]benzothiophene (3) which includes chalcogen atoms in a molecule. They prepared thin film devices using 3 on silicon substrates by vacuum deposition, and measured their semiconducting properties (Fig.1). According to their results, the field-effect mobility of the device is very high (0.19-2.0 cm2/Vs), and indicates a high value comparable as pentacene (0.5-3.0 cm2/Vs). Moreover, the on-off current ratios were as high as 107, and the semiconducting properties were maintained for over 100 days.5)

Tsub / oC bare SiO2

HMDS

OTS

a

µFET a / cm2 V-1 s-1

Ion / Ioff

rt 60 100 rt 60 100

0.19-0.22 0.21-0.26 0.12-0.15

5 × 106 5 × 106 5 × 106

0.42-0.45 0.51-0.53 0.93-1.2

106 5 × 106 107

rt 60 100

0.36-0.46 0.43-0.58 1.0-2.0

5 × 106 107 >107

data from more than 20 devices.

Fig.1 It is expected that these types of organic semiconducting materials will significantly advance the field of electronic devices applied research.

202

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Organic Semiconducting Materials

B3441

B1200

B3562 C C Si[CH(CH3)2]3

S

p-Type Organic Semiconducting Materials D3526

N0001

S

S

S

S

S

S

S

S C C Si[CH(CH3)2]3

P0030

P1795

P1893 N NH

S

N

N

N N

S

HN N

P1628

S0220

S0504

T1196

T2269 CH3

N N N

N N

N

Cu N

N

4

S

S

4

S

S

S

N

D3526 N0001 P0030 P1795 P1893 P1628 S0220 S0504 T1196 T2269 T1812 T2233

CH3

T2233

N

Product No. Product Name B3441 B1200 B3562

N

S CH3

T1812

N

CH3

Unit Size

2,5-Bis(4-biphenylyl)thiophene Bis(ethylenedithio)tetrathiafulvalene 6,13-Bis(triisopropylsilylethynyl)pentacene (This product is unavailable for selling domestically in U.S.) 2,7-Diphenyl[1]benzothieno[3,2-b][1]benzothiophene Naphthacene Pentacene (purified by sublimation) Phthalocyanine (purified by sublimation) Picene (purified by sublimation) Pigment Blue 15 (purified by sublimation) p-Sexiphenyl α-Sexithiophene 2,2':5',2''-Terthiophene (=α-Terthienyl) N,N,N ',N '-Tetrakis(p-tolyl)benzidine N,N,N ',N '-Tetraphenylbenzidine 5,6,11,12-Tetraphenylnaphthacene (refined product of T0561)

B1641

B1694

1g 1g

100mg

100mg

5g 5g 100mg 100mg 5g 1g 1g 1g 1g 1g 1g 5g 5g 25g 1g

1g 100mg 100mg 100mg 100mg 1g 5g 250mg

H1194 F

F

F

F

F

F N F

n-Type Organic Semiconducting Materials

N N

Cu N

F

F

N N N

F

N F

F F

F

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

F

F

203

Organic Semiconducting Materials

M2088

N0755

P0972 O

O

T0078

O

OCH3

T2206 NC

O

O

O

O

O

O

C

CN F

O

F

O

T1131

O

O

NC

C

F F

S

F

S

F

4

F

S

F

CN

C2415 NC

C

CN

CH3

(CH2)11CH3

N

F

F

F

F NC

C

CN

Product No. Product Name

Unit Size

B1641 B1694 H1194

Fullerene C60 (pure) Fullerene C70 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyanine Copper(II)

100mg

1g 100mg

(purified by sublimation)

100mg

M2088 N0755 P0972 T0078 T2206 T1131 C2415

Methyl [6.6]-Phenyl-C61-butyrate Naphthalene-1,4,5,8-tetracarboxylic Dianhydride (purified by sublimation) 3,4,9,10-Perylenetetracarboxylic Dianhydride 7,7,8,8-Tetracyanoquinodimethane Tetradecafluoro-α-sexithiophene (purified by sublimation) Tetrafluorotetracyanoquinodimethane (purified by sublimation) C60MC12

1g 100mg 5g 500g 25g 50mg 1g 100mg

1g 25g 5g 100mg

C60 & C70 (see p.196) Carbon Nanotube (see p.197) Reagents for Conducting Polymer Research (see p.210) Electroluminescence (see p.218) Phthalocyanines (see p.273) References 2006, 2007, 1) J. E. Anthony, , 5028; Y. Shirota, H. Kageyama, , 953. 2005, 70, 2509; H. Klauk, U. Zchieschang, Z. T. 2) G. Portella, J. Poater, J. M. Bofill, P. Alemany, M. Solà, 2007, Weitz, H. Meng, F. Sun, G. Nunes, D. E. Keys, C. R. Fincher, Z. Xian, , 3882. 2008, 3) H. Okamoto, N. Kawasaki, Y. Kaji, Y. Kubozono, A. Fujiwara, M. Yamaji, , 10470. 4) R. Mitsuhashi, Y. Suzuki, Y. Yamanari, H. Mitamura, T. Kambe, N. Ikeda, H. Okamoto, A. Fujiwara, M. Yamaji, N. Kawasaki, Y. 2010, Maniwa, Y. Kubozono, , 76. 2006, 5) K. Takimiya, H. Ebata, K. Sakamoto, T. Izawa, T. Otsubo, Y. Kunugi, , 12604.

204

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Charge Transfer Complexes for Organic Metals

Charge Transfer Complexes for Organic Metals The discovery in 1973 of the metal-like electronic behavior of charge transfer complexes, consisting of an electron donor, Tetrathiafulvalene (TTF) and an electron acceptor, 7,7,8,8-Tetracyanoquinodimethane (TCNQ)1)‚ has led to intensive studies of the organic metals. In 1980 Jérome2), Bechgaad3) and their co-workers have found that each complex of (TMTSF)2PF6 or (TMTSF)2ClO4 using TMTSF analogue of TTF, becomes a superconductor at very low temperatures. Afterwards, organic superconductors utilizing BEDT-TTF4), M(dmit)25) (M=Ni, Pd), etc. have successively been designed one after another. Moreover, the complexes κ-(BEDT-TTF)2Cu[N(CN)2]Br (Tc=11.6K)6), and κ-(BEDT-TTF)2Cu[N(CN)2]Cl (0.3kbar; Tc=12.8K)7) having higher Tc have been found and vigorous studies have been conducted toward the development of still higher Tc organic superconductor. B1200

S

TTF Derivatives

Donors

B1218

S

B1244

S

S

S

S

D2067

S

S

S

S

S

S

T1143

S

S

S

S

S

T1205

S

S

S

S

S

D D D D

S

T0980

S

S

S

S

S

S

S

S

S

S

SCH2CH3

S

S

CH3(CH2)17S

S

S

S(CH2)17CH3

CH3CH2S

S

S

SCH2CH3

T1377

S(CH2)17CH3

CH3(CH2)4S

S

S

S(CH2)4CH3

S

S

CH3(CH2)4S

S

S

S(CH2)4CH3

S

S

D D D

CH3S

S

S

SCH3

CH3S

S

S

SCH3

T2468 NC

CH3(CH2)17S

D

T1119

CH3CH2S

CH3 S

S

S

T1571

CH3 S

S

B1299

D

S

S

D

D

S

S

D

S

S

S

S

C

CN

. NC

C

CN

T1282

S

S

S

S

.

(BF4)2

3

Product No. Product Name B1200 B1299 B1218 B1244 D2067 T1571 T1119 T1143 T1205 T0980 T1377 T2468 T1282

Bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) Bis(ethylenedithio)tetrathiafulvalene-d8 (BEDT-TTF-d8) Bis(methylenedithio)tetrathiafulvalene (BMDT-TTF) Bis(trimethylenedithio)tetrathiafulvalene (BPDT-TTF) Dimethyltetrathiafulvalene (SDM-TTF) Tetrakis(ethylthio)tetrathiafulvalene Tetrakis(methylthio)tetrathiafulvalene (TMT-TTF) Tetrakis(octadecylthio)tetrathiafulvalene (TODT-TTF) Tetrakis(pentylthio)tetrathiafulvalene (TPT-TTF) Tetrathiafulvalene (TTF) Tetrathiafulvalene-d4 (TTF-d4) Tetrathiafulvalene - 7,7,8,8-Tetracyanoquinodimethane Complex Tris(tetrathiafulvalene) Bis(tetrafluoroborate) Complex

Unit Size 100mg

1g

5g 100mg 100mg 100mg 100mg 1g 100mg 100mg 100mg 100mg 1g 5g 25g 100mg 1g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

205

Charge Transfer Complexes for Organic Metals

B2309

B1466 NC

C

CN O(CH2)2OH

TCNQ Derivatives

Acceptors

D3200

D2021 NC

C

CN

C

NC

C

NC

CN

T0078

C

CN

NC

C

C

T1246

NC

CN

NC

CN

NC

C C

CN

NC

NC

CN

C

F

F

S

S

F

F

S

S

NC

C

C

CN

.

CN

NC

C

CN

Product No. Product Name B2309 B1466 D3200 D2021 F0509 T0077 T1246 T0078 T1131 T2468

Unit Size

2,5-Bis(2-hydroxyethoxy)-7,7,8,8-tetracyanoquinodimethane Bis(tetrabutylammonium) Tetracyanodiphenoquinodimethanide 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane 2,5-Dimethyl-7,7,8,8-tetracyanoquinodimethane 2-Fluoro-7,7,8,8-tetracyanoquinodimethane Tetracyanoethylene 11,11,12,12-Tetracyanonaphtho-2,6-quinodimethane 7,7,8,8-Tetracyanoquinodimethane (TCNQ) Tetrafluorotetracyanoquinodimethane (purified by sublimation) Tetrathiafulvalene - 7,7,8,8-Tetracyanoquinodimethane Complex

B1350

B1437

S S

B1371 NC

CN

S Ni

S

S

S

S

CN

S

S

S S

S

(C18H37)2(CH3)2N

2 (C4H9)4N

S

S

Au S

S

S

2

S S

S

S

S

S

S

S

2

S

Pt

S S

S

S

NC

S

Ni S

S

NC [CH3(CH2)3]4N

S

S

S

S

S

S

CN

S

S

S

S

S

S

S

(C4H9)4N

CN

S

S

S

S

Ni

S

(C4H9)4P

S Zn S

206

S

2 (C4H9)4N

T0279

CH3

2

S

Zn S

Ni

S

S

T1416

S S

S S

2 (C4H9)4N

T1415

S S

B1221

S

S

T1272

S

5g 100mg 100mg 100mg 100mg 5g 25g 100mg 5g 25g 100mg 1g 1g

2 (C4H9)4N

2

S

S Pd

S

1g

B1438

S

D2134 S

NC

S

S Ni

Metal Dithiolenes

CN

T2468

CN

CN

CN

CN

C

NC

T1131 NC

C

CN

F

CH3

F

2

CN

C

CH3

F

CN 2 (C4H9)4N

NC

T0077 NC

CN

NC

HO(CH2)2O

F0509 NC

CN

NC

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Charge Transfer Complexes for Organic Metals

Product No. Product Name B1350 B1437 B1438 B1221 B1371 D2134 T1272 T1415 T1416 T0279

Unit Size

Bis(dithiobenzil)nickel(II) Bis(tetrabutylammonium) Bis(1,3-dithiole-2-thione-4,5-dithiolato)palladium(II) Bis(tetrabutylammonium) Bis(1,3-dithiole-2-thione-4,5-dithiolato)platinum(II) Bis(tetrabutylammonium) Bis(1,3-dithiole-2-thione-4,5-dithiolato)zinc Complex Bis(tetrabutylammonium) Bis(maleonitriledithiolato)nickel(II) Complex Dioctadecyldimethylammonium Bis(1,3-dithiole-2-thione-4,5-dithiolato)aurate(III) Tetrabutylammonium Bis(1,3-dithiole-2-thione-4,5-dithiolato)nickel(III) Complex Tetrabutylammonium Bis(maleonitriledithiolato)nickel(III) Complex Tetrabutylphosphonium Bis(1,3-dithiole-2-thione-4,5-dithiolato)nickel(III) Complex (Toluene-3,4-dithiolato)zinc(II)

B0089

1g 100mg

25g 1g 100mg 5g 25g 1g 100mg 100mg 1g 1g 1g 5g

B1416

T0617 NC

O

O

C CN Br

Other Donors & Acceptors

Br O

B1601

B1595

Br

Cl

Br

O

D2152

O

D3392

O

CH3

O Cl

NC

Cl

N

Cl

N

CH3

CH3CH2 C H3C

NH2

O

D1070

Br

C CH2CH3 H3C

CH3

Cl

D0343

CH3

NH2 Cl

O

D2249 O

D0101 O

Cl

Cl

CH3 O

Br O

C1336 O

O

C CN

NC

T0061

O

Br

Cl

Br O

D2250

D1956

M1045

CH3

CH3

OCH3

P0106 O

O

O CH3

CH3

O

D2234

O OCH3

NC O

O

H N

OCH3

OCH3

CH3O

S O

O

O

T1503

T0790

(CH3)3C

C(CH3)3

O

O

(CH3)3C

C(CH3)3

T0499

O

T1221

T1023

O

CH3

F

F

(CH3)2N (CH3)2N

F

NH2

N(CH3)2 CH3

O

CH3

N(CH3)2 H2N

F

T0151 CH3

CH3 N

CH3

CH3

N CH3

. 2HCl

T0875 NO2

NO2

O2N

NO2 O

O2N

NO2 NC

C

CN

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

207

Charge Transfer Complexes for Organic Metals

Product No. Product Name B0089 B1416 T0617 B1601 B1595 T0061 C1336 D0101 D2152 D2249 D0343 D1070 D3392 D2250 D1956 D2234 M1045 P0106 T1503 T0790 T1221 T1023 T0151 T0499 T0875

Unit Size

1,4-Benzoquinone 1,3-Bis(dicyanomethylidene)indan Bromanil 2-Bromo-1,4-benzoquinone 2-Bromo-5-methyl-1,4-benzoquinone Chloranil 2-Chloro-5-methyl-1,4-benzoquinone 1,5-Diaminonaphthalene 2,5-Di-tert-amylbenzoquinone 2,5-Dibromo-1,4-benzoquinone 2,5-Dichloro-1,4-benzoquinone 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 5,10-Dihydro-5,10-dimethylphenazine 2,5-Dimethoxy-1,4-benzoquinone 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 2,6-Dimethyl-1,4-benzoquinone Methoxybenzoquinone Phenothiazine 3,3',5,5'-Tetra-tert-butyl-4,4'-diphenoquinone Tetrafluoro-1,4-benzoquinone Tetrakis(dimethylamino)ethylene 3,3',5,5'-Tetramethylbenzidine N,N,N ',N '-Tetramethyl-1,4-phenylenediamine Dihydrochloride 2,4,7-Trinitro-9-fluorenone (wetted with ca. 20% Water, containing 5g on a dry weight basis) 2,4,7-Trinitro-9-fluorenylidenemalononitrile

B1322

B1199

25g

500g 5g 25g 1g 5g 500g 5g 500g 5g 5g 5g 250g 1g 25g 5g 25g 5g 500g 1g 5g 25g 25g 25g 5g 5g

5g

25g 25g 1g 1g 25g 5g 1g 5g 1g 25g

1g

1g 5g 5g 1g

1g

1g

B1272 O

SH

S

S

SH

C

S

Synthetic Intermediates

S

S

S

S

S

S

S

S

O

S

S

C

O

O

B2228

B2233

NC(CH2)2S

B1778

NC(CH2)2S

S

CH3S

S

S S

NC(CH2)2S

D3252

CH3S

S

S

S

O S

NC(CH2)2S

D3992

B1777

CH3S

D2127

S

S

CH3S

D1930

NC

S

NC

S

O

D2133

O

E0429

O S S

CH3O C

O OCH3

NaS

S

SNa

S

S

CH3O C

S

S

S

S

S

S

P OCH3

NC

S

S

CN

O

E0460

H1163

S

M1112

S

S

S

M1154

S

S

O S

208

S

P1635

S

S

S CH3(CH2)5

S

S

S

S

S

O S

S

S

S

S

S

CH3CH2CH2

S

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Charge Transfer Complexes for Organic Metals

T1132

T0266

S

HS

S

O

O S

S

HS

CH3

Product No. Product Name B1322 B1199 B1272 B2228 B2233 B1778 B1777 D3252 D3992 D2127 D1930 D2133 E0429 E0460 H1163 M1112 M1154 P1635 T1132 T0266

1,2-Benzenedithiol 4,5-Bis(benzoylthio)-1,3-dithiole-2-thione Bis(carbonyldithio)tetrathiafulvalene 4,5-Bis(2-cyanoethylthio)-1,3-dithiole-2-thione 4,5-Bis(2-cyanoethylthio)-1,3-dithiol-2-one 4,5-Bis(methylthio)-1,3-dithiole-2-thione 4,5-Bis(methylthio)-1,3-dithiol-2-one 4,5-Dicyano-1,3-dithiol-2-one Dimethyl 1,3-Benzodithiol-2-ylphosphonate Dimethyl 1,3-Dithiole-2-thione-4,5-dicarboxylate Disodium Dimercaptomaleonitrile 1,3-Dithiole-2-thione 4,5-Ethylenedithio-1,3-dithiole-2-thione 4,5-Ethylenedithio-1,3-dithiol-2-one 5-Hexyl-1,3-dithiolo[4,5-d][1,3]dithiole-2-thione 4,5-Methylenedithio-1,3-dithiole-2-thione 4,5-Methylenedithio-1,3-dithiol-2-one 5-Propyl-1,3-dithiolo[4,5-d][1,3]dithiole-2-thione 1,3,4,6-Tetrathiapentalene-2,5-dione Toluene-3,4-dithiol

Unit Size 1g 1g

1g 5g 1g

100mg 250mg 1g 5g 1g 5g

5g 5g 1g 1g 1g 1g 1g 1g 1g 10g 5g 5g 25g 5g 1g 1g 1g 1g 25g 25g

References 1) J. Ferraris, D. O. Cowan, V. Walatka, Jr., J. H. Perlstein, . 1973, , 948; L. B. Coleman, M. J. Cohen, D. J. Sandman, F. G. Yamagishi, A. F. Garito, A. J. Heeger, . 1973, , 1125. 2) D. Jérome, A. Mazaud, M. Ribault, K. Bechgaard, . 1980, , L-95. 3) K. Bechgaard, K. Carneiro, M. Olsen, F. B. Rasmussen, C. S. Jacobsen, . 1981, , 852. 4) S. S. P. Parkin, E. M. Engler, R. R. Schumaker, R. Lagier, V. Y. Lee, J. C. Scott, R. L. Greene, . 1983, , 270. 5) M. Bousseau, L. Valade, J.-P. Legros, P. Cassoux, M. Garbauskas, L. V. Interrante, . 1986, , 1908. 6) A. M. Kini, U. Geiser, H. H. Wang, K. D. Carlson, J. M. Williams, W. K. Kwok, K. G. Vandervoort, J. E. Thompson, D. L. Stupka, D. Jung, M.-H. Whangbo, . 1990, , 2555. 7) J. M. Williams, A. M. Kini, H. H. Wang, K. D. Carlson, U. Geiser, L. K. Montgomery, G. J. Pyrka, D. M. Watkins, J. M. Kommers, S. J. Boryschuk, A. V. S. Crouch, W. K. Kwok, J. E. Schirber, D. L. Overmyer, D. Jung, M.-H. Whangbo, . 1990, , 3272. 8) H. Kobayashi, T. Udagawa, H. Tomita, K. Bun, T. Naito, A. Kobayashi, . 1993, 1559; H. Kobayashi, H. Tomita, T. Naito, H. Tanaka, A. Kobayashi, T. Saito, . 1995, 1225; K. Takimiya, Y. Kataoka, Y. Aso, T. Otsubo, H. Fukuoka, S. Yamanaka, . 2001, , 1122; J. Yamada, M. Watanabe, H. Akutsu, S. Nakatsuji, H. Nishikawa, I. Ikemoto, K. Kikuchi, . 2001, , 4174.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

209

Reagents for Conducting Polymer Research

Reagents for Conducting Polymer Research In 1977, Shirakawa and co-workers reported that thin films of the semi-conducting polymer polyacetylene show a dramatic increase in electrical conductivity when doped with controlled amounts of iodine.1) Their reports triggered intensive R&D into the electrical conductivity of plastic materials. Studies of conducting polymers began and, as a result, many π-conjugated polymers such as polypyrrole2), polythiophene3), polyaniline4) and polyphenylenevinylene5) have been developed. Among these polymers, many of them have been utilized practically. One example is an electrolytic condenser using polypyrrole. This condenser has characteristic features such as being compact and lightweight, as well as having high-capacity and high-frequency compliance. These features have achieved a downsizing and weightsaving in electronic devices, and are utilized currently in some mobile phones. Thereby, conducting polymers are widely used for electronic devices vital to our everyday life. These and many other achievements were the reasons Shirakawa received to the Nobel Prize Award in 2000. Moreover, conducting polymers have been applied to solar cell materials. For instance, Kim have reported the synthesis of the co-polymers 3 and 4, using 4,7-dibromo-2,1,3-benzothiadiazole (1) and 4,7-dibromo-2,1,3-benzoselenadiazole (2) as starting materials, respectively. According to their results, the bulk heterojunction solar cells composed of 3 or 4 with PC71BM give power conversion efficiencies of 1.12%6) and 1.34%7), respectively. Thus, further applications using conducting polymers can be fully expected in many areas. R1O

OR1

Br N

S

N

N S S

N

S n

Br

3 1 R2

Br

R2 N

Se

N

N Se S

N

S

S

S n

4

Br 2

The page below shows the monomers and oligomers for conducting polymer research. M0440

E0378

P1128

CH3

3-Alkylthiophenes

B1458

S

P1127

S

(CH2)9CH3

210

S

(CH2)6CH3 S

U0056

(CH2)8CH3

O0213

(CH2)5CH3 S

D2098

(CH2)7CH3 S

D2016

(CH2)10CH3 S

CH2CH2CH3 S

H0722

(CH2)4CH3 S

N0533

S

H0756

(CH2)3CH3 S

CH2CH3

O0245

(CH2)11CH3 S

(CH2)17CH3 S

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Reagents for Conducting Polymer Research

Product No. Product Name M0440 E0378 P1128 B1458 P1127 H0756 H0722 O0213 N0533 D2098 U0056 D2016 O0245

Unit Size

3-Methylthiophene 3-Ethylthiophene 3-Propylthiophene 3-Butylthiophene 3-Pentylthiophene 3-Hexylthiophene 3-Heptylthiophene 3-n-Octylthiophene 3-Nonylthiophene 3-Decylthiophene 3-Undecylthiophene 3-Dodecylthiophene 3-Octadecylthiophene

1g 1g

1g

B3464

CH3

CH3 O

O

CH3

B

Thiophene Derivatives

CH3

S

B1838

500g 25ml 5g 5g 5g 25g 5g 25g 5g 5g 5g 25g 5g

B3363

S

B1276

25g 5ml 1g 1g 1g 5g 1g 5g 1g 1g 1g 5g 1g

S

O

O

CH3

B1874

CH3

B

S

CH3 CH3

B3507

B1540

(CH2)5CH3 O S

S

S

B1541

S

C H

B3385

CH3

Br

O Br

S

S

C H

B2058

S

CH3

Br

B1067

S

Br

B2862

Br

Br O

S

S

B2934

CH3

B3386

Br

Br

S

C1801

S

B(OH)2

C1192

Cl

CH3 S

O Br

C OH

C OH

S

S

D2755

H2N

. 2HCl

S

Br

D3701

Br

S

Cl

D3799

NH2

S

D3896

C H

S

O

D2378

CN

S

Br

C H

C1344

S

B2302

O S

Br

S

S

D3800

S

S

Br

D3928

Br

S

S Br

D3823

S S

Br

D2077

CH3(CH2)5 (CH2)5CH3

F

F

S S

Br

S

Br

(CH3)3Si

S

Si(CH3)3

S S

S

B(OH)2

S

CH

CHCH

CH

S

CH3(CH2)5

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

211

Reagents for Conducting Polymer Research

D3712

D2073

D2074

E0741

O

F0548

O S

S

S S

O

CH

CH

CH

CH

O

O

S

H C

S

S

S

B(OH)2

S

H1298

H1294

I0380

M1093

O0313

CH3(CH2)5 CH3 CH3

CH3

O

B

CH3

S

B CH3

O

CH3

(CH2)5CH3

O

I

OCH3

S

O

S

S

S

CH3

S

6

S

S

4

S

CH3

P1126

Q0078

Q0079

S

S

2

S

S0505

S

S

S

3

S0504

S

S

5

S

S

S

T1196

T1805

T2639

T2699

T2206 Br

O

S

S

S

S

S

S

C H

O

O

H C

S

S

S

C H

Br

S

S

Br

F

F

F F

S

F

S

F

4

F

S

Br

T1084

T2729

T2621

O

T0725

T0864 O

S

C OH S

S

S

S

T1152

T2388

S

B(OH)2

T2347

C H S

T1475

T1354 O

O

O

O S

S

C H

C OH

CH2CH2OH

C H

CH2 C OH

HO C

O S

C OH

CH

C OH O

S S

O

T1660

T0956

CH2OH S

Br Br

S

Br

Product No. Product Name B3464 B3363 B1276 B1838 B1874 B3507

212

C H

O

Benzo[1,2-b:4,5-b']dithiophene 5,5'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene 2,2'-Bithiophene 2,2'-Bithiophene-5-carboxaldehyde 5-Bromo-2,2'-bithiophene-5'-carboxaldehyde 2-Bromo-3-hexylthiophene

Unit Size 1g 1g 1g

10g 5g 1g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

5g 5g 25g 25g 5g 5g

F

Reagents for Conducting Polymer Research

Product No. Product Name B1540 B1541 B3385 B2058 B1067 B2862 B2934 B3386 B2302 C1801 C1192 C1344 D2378 D2755 D3799 D3800 D3896 D3701 D3928 D3823 D2077 D3712 D2073 D2074 E0741 F0548 H1298 H1294 I0380 M1093 O0313 P1126 Q0078 Q0079 S0505 S0504 T1196 T1805 T2639 T2699 T2206 T1084 T2729 T2621 T0725 T0864 T1152 T2388 T2347 T1475 T1354 T1660 T0956

Unit Size

2-Bromo-5-methylthiophene (stabilized with Copper chip + NaHCO3) 3-Bromo-4-methylthiophene 4-Bromo-2-methylthiophene 5''-Bromo-2,2':5',2''-terthiophene-5-carboxaldehyde 3-Bromothiophene 5-Bromo-2-thiopheneboronic Acid (contains varying amounts of Anhydride) 3-Bromothiophene-2-carboxaldehyde 4-Bromo-2-thiophenecarboxylic Acid 5-Bromo-2-thiophenecarboxylic Acid 2-Chloro-3-methylthiophene 3-Chlorothiophene 3-Cyanothiophene 3,4-Diaminothiophene Dihydrochloride 5,5'-Dibromo-2,2'-bithiophene 2,6-Dibromodithieno[3,2-b:2',3'-d]thiophene 3,5-Dibromodithieno[3,2-b:2',3'-d]thiophene 2,5-Dibromo-3-hexylthiophene 3,4-Difluoro-2,5-bis(trimethylsilyl)thiophene 3,4'-Dihexyl-2,2'-bithiophene Dithieno[3,2-b:2',3'-d]thiophene-2-boronic Acid (contains varying amounts of Anhydride) 1,4-Di(2-thienyl)-1,3-butadiene 1,4-Di(2-thienyl)-1,4-butanedione cis-1,2-Di(2-thienyl)ethylene trans-1,2-Di(2-thienyl)ethylene 3,4-Ethylenedioxythiophene 5'-Formyl-2,2'-bithiophene-5-boronic Acid (contains varying amounts of Anhydride) 3-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene 4-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene 3-Iodothiophene 3-Methoxythiophene α-Octithiophene 3-Phenylthiophene α-Quarterthiophene α-Quinquethiophene α-Septithiophene α-Sexithiophene 2,2':5',2''-Terthiophene (=α-Terthienyl) 2,2':5',2''-Terthiophene-5-carboxaldehyde 2,2':5',2''-Terthiophene-5,5''-dicarboxaldehyde 3,3',5,5'-Tetrabromo-2,2'-bithiophene Tetradecafluoro-α-sexithiophene (purified by sublimation) 3-Thenoic Acid Thieno[2,3-b]thiophene Thieno[3,2-b]thiophene-2-boronic Acid (contains varying amounts of Anhydride) 2-Thiophenaldehyde (stabilized with HQ) 3-Thiophenaldehyde Thiophene-3-acetic Acid 2,3-Thiophenedicarboxaldehyde 2,5-Thiophenedicarboxylic Acid 3-Thiopheneethanol 3-Thiophenemalonic Acid 3-Thiophenemethanol 2,3,5-Tribromothiophene

A1015

A1022

5g 5g 5g 100mg 1g 25g 1g 1g 5g 5g 1g 5g 5g 5g 100mg 1g 200mg 200mg

1g 200mg 1g 1g 1g 5g 1g 1g 1g 1g

100mg 1g

1g 5g 1g 25ml 5g 5g 1g 5g 5g 5g 5g 25g

25g 25g 25g 5g 250g 5g 25g 25g 5g 25g 25g 25g 1g 5g 1g 1g 5g 1g 5g 1g 5g 5g 1g 5g 25g 1g 5g 5g 5g 5g 100mg 5g 100mg 100mg 100mg 1g 5g 1g 1g 5g 50mg 25g 5g 1g 500ml 25g 25g 5g 25g 25g 25g 25g 250g

B2335

O C CH3

Pyrroles

N

N

N

NH2

CH2

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

213

Reagents for Conducting Polymer Research

B1622

B1623

C1347

D3876

N

N

N

CH2CH2Br

CH2CH2CH2Br

CH2CH2Cl

H0809

H0826

E0444

S

H0827

N H

N

S

CH2CH3

M0414

N0584 N

(CH2)6CH3 N H

N

N

N

CH2CH2OH

CH2CH2CH2OH

CH3 NO2

N0502

O0219

O0242

O0241

NO2

(CH2)7CH3 N

N H

N H

(CH2)7CH3

T1386

T1677

O N H

N

N

(CH2)17CH3

P0574

P1122

N S O

CH3

N CH3 CH3 CH3 HC Si CH CH 3 CH CH3 CH3

Product No. Product Name A1015 A1022 B2335 B1622 B1623 C1347 D3876 E0444 H0809 H0826 H0827 M0414 N0584 N0502 O0219 O0242 O0241 P1122 P0574 T1386 T1677

Unit Size

3-Acetyl-1-methylpyrrole 1-Aminopyrrole 1-Benzylpyrrole 1-(2-Bromoethyl)pyrrole 1-(3-Bromopropyl)pyrrole 1-(2-Chloroethyl)pyrrole 2,5-Di(2-thienyl)-1H-pyrrole 1-Ethylpyrrole 3-Heptylpyrrole 1-(2-Hydroxyethyl)pyrrole 1-(3-Hydroxypropyl)pyrrole 1-Methylpyrrole 1-(4-Nitrophenyl)pyrrole 3-Nitropyrrole 1-Octadecylpyrrole 1-n-Octylpyrrole 3-n-Octylpyrrole 1-Phenylpyrrole Pyrrole 1-(p-Toluenesulfonyl)pyrrole 1-(Triisopropylsilyl)pyrrole

5ml 1g 1g 1g

1g 1g 1g 25ml 1g 1g 5g 1g 10g 25ml 5ml

A1508

B1967 NH2

Carbazoles

214

N CH2CH3

B2864

N N

N

N

N C O

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

25ml 5g 5g 5g 5g 5g 1g 5g 5g 5g 1g 500ml 1g 5g 5g 25g 5g 25g 500ml 5g 25ml

Reagents for Conducting Polymer Research

B3558

B2804

B2805 O

B2713

O

C H

C0032

O

H C

C H N

N CH2

C1031

N

N

CH2

CH2

C0714

N

C Cl

D3932

D2982

D2981

Br

E0359

C H

CH3

N

N H

CH2CH3

M0960

N H

C CH3

H3C

H1014

Br

CH3

H3C C

N

Br

O H3C

N

N H

E0071 E0247

Br

Br

Br Br

D3952

Br

D2983

NH2 N H

K

O

N H

D2116 H2N

N

N

P1492

N

CH2CH3

CH2CH3

P0656

T0159

OH

O2N

NO2

N N H

T1934

N

N

CH3

CHCH2

NO2

n

N H

NO2

V0021 N

N

N

N

CH

CH2

Product No. Product Name A1508 B1967 B2864 B3558 B2804 B2805 B2713 C0032 C1031 C0714 D2116 D3932 D2983 D2982 D2981 D3952 E0071 E0247 E0359 H1014 M0960 P1492

3-Amino-9-ethylcarbazole 9-(1H-Benzotriazol-1-ylmethyl)-9H-carbazole 9-Benzoylcarbazole 9-Benzylcarbazole 9-Benzylcarbazole-3-carboxaldehyde 9-Benzylcarbazole-3,6-dicarboxaldehyde 4,4'-Bis(9H-carbazol-9-yl)biphenyl Carbazole Carbazole-9-carbonyl Chloride Carbazole Potassium Salt 3,6-Diaminocarbazole 2,7-Dibromocarbazole 3,6-Dibromocarbazole 3,6-Dibromo-9-ethylcarbazole 3,6-Dibromo-9-phenylcarbazole 3,6-Di-tert-butylcarbazole 9-Ethylcarbazole 9-Ethylcarbazole N-Ethylcarbazole-3-carboxaldehyde 4-Hydroxycarbazole 9-Methylcarbazole 9-Phenylcarbazole

Unit Size 1g 1g 1g

1g

1g

1g 25g 5g 1g 1g 5g 1g 1g 25g

1g 1g

5g 5g 5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 5g 5g 5g 5g 100mg 5g 500g 25g 25g 5g 5g 25g 5g 5g 1g 500g 25g 25g 25g 25g 25g

215

Reagents for Conducting Polymer Research

Product No. Product Name P0656 T0159 T1934 V0021

Unit Size

Poly(N-vinylcarbazole) 1,3,6,8-Tetranitrocarbazole (wetted with ca. 40% Water, containing 25g on a dry weight basis) 1,3,5-Tri(9H-carbazol-9-yl)benzene (purified by sublimation) 9-Vinylcarbazole

B0921

5g 1g

B1336

25g 25g 5g 25g

B2843

Cl

N

Others (see also p.282 Reagents for High-Performance Polymer Research) B3573

B3089 CH3

O CH3

B

N

S

N

N O

O

H C

C H

Cl

B2844

B3560

B2633

Br

CH3 CH3 CH3 O O B

N

N

Br

N S

Br

N

N

N

O

CH3 CH3 CH3

CH3

D3944

Br

CH3

D3842

D3302

D3303

Br

Br

D3872

Br

Br

N

N

N

Se

S

N

Br

Br N

N

Br

Br Br

D1910

A1122

Br

Br

N0536

Br

O

H N

P0972

N0369 N0755

O

O

NH2

O

O

N C CH O

N H

S0829

O

O

O

O

O

O

O

P0984

O

S0831

O

O

T2597

T1361 Br

O

O

B(OH)2 HN

Br

Br

Br

Br

NH

Se O

O

N Br

Br

T2310 O C H

N O H C

O C H

Product No. Product Name B0921 B1336 B2843 B3573 B3089 B2844

216

2,1,3-Benzothiadiazole N,N '-Bis(4-chlorophenyl)-N,N '-diphenyl-1,4-phenylenediamine Bis(4-formylphenyl)phenylamine 4,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole 4-Bromo-4',4''-dimethyltriphenylamine 4-Bromo-4'-(diphenylamino)biphenyl

Unit Size 10g

250mg

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

25g 1g 1g 1g 1g 1g

Reagents for Conducting Polymer Research

Product No. Product Name B3560 B2633 D3944 D3842 D3302 D3303 D3872 D1910 A1122 N0536 N0369 N0755 P0972 P0984 S0829 S0831 T2597 T1361 T2310

2-Bromo-9,9'-spirobi[9H-fluorene] 4-Bromotriphenylamine 4,7-Dibromo-2,1,3-benzoselenadiazole 4,7-Dibromo-2,1,3-benzothiadiazole 4,4'-Dibromo-4''-cyclohexyltriphenylamine 4,4'-Dibromo-4''-phenyltriphenylamine 2,2'-Dibromo-9,9'-spirobi[9H-fluorene] 4,4'-Dibromotriphenylamine 3-Ethynylaniline 1,4,5,8-Naphthalenetetracarboxdiimide Naphthalene-1,4,5,8-tetracarboxylic Dianhydride Naphthalene-1,4,5,8-tetracarboxylic Dianhydride (purified by sublimation) 3,4,9,10-Perylenetetracarboxylic Dianhydride 3,4,9,10-Perylenetetracarboxylic Diimide Selenophene 9,9'-Spirobi[9H-fluorene]-2-boronic Acid 2,2',7,7'-Tetrabromo-9,9'-spirobi[9H-fluorene] Tris(4-bromophenyl)amine Tris(4-formylphenyl)amine

Unit Size 5g 1g

10g

5g

1g 25g 1g 25g 1g 1g 1g

5g 25g 1g 25g 1g 1g 1g 100mg 10g 5g 250g 5g 500g 25g 5g 5g 5g 25g 500mg

References 1977, 578. 1) H. Shirakawa, E. J. Luois, A. G. MacDiarmid, C. K. Chiang, A. J. Heeger, 2) K. K. Kanazawa, A. F. Diaz, R. H. Geiss, W. D. Gill, J. F. Kwak, J. A. Logan, J. F. Rabolt, G. B. Street, 1979, 854; M. Salmon, A. F. Diaz, J. A. Logan, K. Krounbi, J. Bargon, 1982, , 1986, 265; M. Ogasawara, K. Funahashi, T. Demura, T. Hagiwara, K. Iwata, , 62. 1985, 713; S. Hotta, 1987, 3) M. Sato, S. Tanaka, K. Kaeriyama, , 103. 1984, 4) T. Kobayashi, H. Yoneyama, H. Tamura, , 281; J.-C. Chiang, A. G. MacDiarmid, 1986, , 193. 1979, 5) G. E. Wnek, J. C. W. Chien, F. E. Karasz, C. P. Lillya, , 1441; D. R. Ganon, J. D. Capistran, F. E. Karasz, 1987, R. W. Lenz, S. Antoun, , 567. 2010, 6) J. Kim, S. H. Park, S. Cho, Y. Jin, J. Kim, I. Kim, J. S. Lee, J. H. Kim, H. Y. Woo, K. Lee, H. Suh, , 390. 7) I. H. Jung, H. Kim, M.-J. Park, B. Kim, J.-H. Park, E. Jeong, H. Y. Woo, S. Yoo, H.-K. Shim, 2010, , 1423.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

217

Electroluminescence

Electroluminescence Electroluminescence (EL) is a phenomenon where electrical energy is directly converted into light. With the growing interest in EL, considerable attention has been directed toward organic electroluminescent materials and devices since Tang and Van Slyke reported the first high efficiency organic light emitting diode (OLED) in 1987.1) In recent years, OLED products have become commercially available in a limited range. OLEDs are self-emitting devices requiring low operating voltage and offer several advantages including wide viewing angle, fast response time, high brightness, etc.2-5) The OLED technology will play a leading role in display and lighting applications. An OLED device comprises a single or multi organic layers sandwiched between electrodes, typically emissive layer, hole-transport layer, electron-transport layer, etc. Emission colors are tunable by adding a small amount of dopant into an emissive layer.6) Polymeric and dendritic materials as well as small molecules have become a major focus of interest in terms of the ease of processing. 7-10)

B2077

B2078 S

O

N

Metal Complexes

Metal Complexes & Ligands

B1678

P1766

P1005 P1006 N

O

N N

N N

N

S

O

T1735

S

O Eu

Cu

N

N

CH O

N

N

N

CF3

N

N

N

N

O

N

3

. 6H2O

N

3

T1946

N

O

N Ir

Ir

T1527 T2238 O

N

N

N

Ir

N

O

N Al O

O

N

N

3

Product No. Product Name

218

O Eu

2Cl

Ru

CH3

B2077 B2078 B1678 P1005 P1006 P1766 T1655 T1735 T2557 T2685 T1946 T1527 T2238

O

N

N

N

T2685

CH3

O Zn

T1655

N

N

. xH2O T2557

O

2

Zn O

N

O Zn

Bis[2-(2-benzothiazolyl)phenolato]zinc(II) Bis[2-(2-benzoxazolyl)phenolato]zinc(II) Bis(8-quinolinolato)zinc(II) Hydrate Copper(II) Phthalocyanine (α-form) Copper(II) Phthalocyanine (β-form) (1,10-Phenanthroline)tris[4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedionato]europium(III) Tris(2,2'-bipyridyl)ruthenium(II) Chloride Hexahydrate Tris(1,3-diphenyl-1,3-propanedionato)(1,10-phenanthroline)europium(III) Tris(2,4-pentanedionato)iridium(III) Tris[1-phenylisoquinoline-C 2,N]iridium(III) (purified by sublimation) Tris(2-phenylpyridinato)iridium(III) (purified by sublimation) Tris(8-quinolinolato)aluminum Tris(8-quinolinolato)aluminum (purified by sublimation)

Unit Size 1g 5g 25g 25g 1g 1g

25g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

5g 5g 25g 250g 500g 1g 5g 5g 1g 100mg 200mg 250g 5g

Electroluminescence

P0052

B1733

O

O

C

C CH2 C O

T2037

N

CH3

M1132 O

O

CH3 CF3

O

C CH2 C

O

CH3

O

O

CH3

O N

O

CH3

H0476 O

CH3

OCH3

E0405

O

CH3

O

C CH2

CH3

CH3 CH3

O

CH3

D2512

CH3 CH3

CH3

D0910 O

O CH3O

Propanediones

D1678

D2413

CF3

O

CH3

CH3 CH3

CH3

T0434 O

CH2

C

(CF2)6CF3

C

(CF2)6CF3

O CF3

O CH3

O

Product No. Product Name

Unit Size

P0052 B1733 D2413 D0910 D1678 D2512 E0405 H0476 M1132 T2037 T0434

25ml 5g 5g 25g 5g

Acetylacetone 1,3-Bis(4-methoxyphenyl)-1,3-propanedione 2,6-Dimethyl-3,5-heptanedione 1,3-Diphenyl-1,3-propanedione Dipivaloylmethane 1,3-Di(2-pyridyl)-1,3-propanedione 3-Ethyl-2,4-pentanedione Hexafluoroacetylacetone 3-Methyl-2,4-pentanedione 9H,9H-Triacontafluoro-8,10-heptadecanedione Trifluoroacetylacetone

B2387

B0838 Br

D1235

M0523 CH3

Br

CH3

CH3

Phenanthrenes

P0079 P1310 P0331

500ml 25g 25g 500g 25g 5g 5ml 5g 25g 5ml 25ml 100mg 25g 100g

P1093

B(OH)2

Product No. Product Name B2387 B0838 D1235 M0523 P0079 P1310

3-Bromophenanthrene 9-Bromophenanthrene 3,6-Dimethylphenanthrene 3-Methylphenanthrene Phenanthrene Phenanthrene

Unit Size 100mg 250g 100mg 100mg 25g 500g 25g 500g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

219

Electroluminescence

Product No. Product Name P0331 P1093

Unit Size

Phenanthrene Zone Refined (number of passes:30) 9-Phenanthreneboronic Acid (contains varying amounts of Anhydride)

D0905 B2695

D0711 B2694

100mg

B2632

C1560 Cl

Br

N

N

N

N

Phenanthrolines N

N

CH3

C0786

N

CH3

D2565

D1559

(CH2)3CH3

N

N

N

N CH3(CH2)3

N0423

N N

P0221 CH3

N CH3

. HCl . H2O

N

N

N

N

N

CH3 CH3

. H2O CH3

. 1/2H2O

CH3

Product No. Product Name D0711 B2694 D0905 B2695 B2632 C1560 C0786 D2565 D0772 D1559 D3849 D0771 N0423 P0221 T0847

Unit Size

Bathocuproine Bathocuproine (purified by sublimation) Bathophenanthroline Bathophenanthroline (refined product of D0905) 3-Bromo-1,10-phenanthroline 2-Chloro-1,10-phenanthroline 5-Chloro-1,10-phenanthroline 2,9-Dibutyl-1,10-phenanthroline 4,7-Dimethyl-1,10-phenanthroline 5,6-Dimethyl-1,10-phenanthroline 2,9-Diphenyl-1,10-phenanthroline Neocuproine Hemihydrate Neocuproine Hydrochloride 1,10-Phenanthroline Monohydrate 3,4,7,8-Tetramethyl-1,10-phenanthroline

D3413

1g 1g

100mg 100mg 100mg

1g 1g 1g 1g

M2101

M2001

CH3 N

N F

220

5g 1g 5g 1g 200mg 1g 1g 1g 100mg 100mg 1g 25g 25g 25g 5g

M0932

F

Phenylpyridines

N

T0847 N

N

N

CH3

CH3 CH3

CH3

CH3

CH3

D3849

N

Cl

D0771

N

D0772

N

1sample 1g

N

CH3

N

OCH3

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Electroluminescence

P1731

P1039

P1889

P1671

T1228

O C H

N

O C H N

N

N

N CH3

T2688

N CF3

Product No. Product Name D3413 M2101 M2001 M0932 P1731 P1039 P1889 P1671 T1228 T2688

Unit Size

2-(2,4-Difluorophenyl)pyridine 2-(4-Methoxyphenyl)pyridine 2-Methyl-6-phenylpyridine 3-Methyl-2-phenylpyridine 1-Phenylisoquinoline 2-Phenylpyridine 3-(2-Pyridyl)benzaldehyde 4-(2-Pyridyl)benzaldehyde 2-(p-Tolyl)pyridine 2-[4-(Trifluoromethyl)phenyl]pyridine

B1190

1g

5g 1g 5g 1g 5g 1g

B3324

Br

Br

N OH

N

M0420

N OH

P0531 F

N

N

CH3CH2CH2

N OH

OH

H0305

N

CH3

OH

N OH

Product No. Product Name B1190 B3324 C0187 C0645 D0208 D0412

I OH

OH

N

F0038 I

Cl

Cl

OH

D1736 Cl

Br

I

OH

D0412

C0645 Cl

N

N OH

D0208

C0187 Br

Cl

Quinolines

5g 1g 1g 25g 5g 25g 1g 5g 25g 5g

7-Bromo-5-chloro-8-hydroxyquinoline 5-Bromo-8-hydroxyquinoline 5-Chloro-8-hydroxy-7-iodoquinoline 5-Chloro-8-hydroxyquinoline 5,7-Dibromo-8-hydroxyquinoline 5,7-Dichloro-8-hydroxyquinoline

Unit Size 5g 25g 25g 5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 25g 250g 250g 25g 25g

221

Electroluminescence

Product No. Product Name D1736 F0038 P0531 M0420 H0305

Unit Size

5,7-Diiodo-8-hydroxyquinoline 5-Fluoro-8-quinolinol 8-Hydroxy-7-propylquinoline 8-Hydroxyquinaldine 8-Quinolinol

25g 25g

B3464

B0093

B2893

B3441

S

S

Thiophenes

B3363

B1276

N

tBu

N

O

S

CH3

O

O B

CH3

O

O

S

S

S

S

S

S

S

B1067

S

CH3

B2862

CH3

O

S

B2827

Br

Br Br

B2302

S

B(OH)2

B1458

S

Br S

C H

O

C H

C2324

(CH2)3CH3

Br

O

C1801

Br

B3386

O S

S

S

Br

S

Br

Br

CH3

B2934

Br

B0941

S

O S

S

CH3

Br

B3226

B

Cl

B1540

Br

CH3 CH3

C H

CH3

B3200

Br

S

(CH2)5CH3

S

B3385

S

B1025

Br

Br

Br

B3507

Cl

CH3

O

CH3 CH3

Br

B1541

B1996

CH3

O

B3525

S

B1874

B

CH3

B2013

B(OH)2

CH3

CH3 tBu

S

S

S

B1554

25g 5g 5g 500g 500g

1g

S

C OH

S

Cl

C0807

CH3

O Br

S

C OH

C1192

S

S

C2066

Cl

C1722

CH3

S

Cl

C1230

D2098

(CH2)9CH3

Cl O

O S

222

Cl

S

B(OH)2

Cl

S

C H

Cl

S

C OH

S

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Electroluminescence

D2378

D3798

D2474 D0148

D2755

D2245

Br H2N

Br

NH2

. 2HCl

S

Br

S

S

Br

S

S

S

Br

S

Br

D3799

Br

D3800

S

S

Br

S

D3896

S

S

Br

D1548

D3678

(CH2)5CH3

S

Br

D1549

Br

S

D3679

Br

S

S S

Br

D1676

Br

D3928

Br

Br

S

D2611

CH3(CH2)5 Br S

Br Br

Br

S

Br S

S

Br

I

S

S

I

CH3(CH2)5

D2223

D1591

CH3

D3526

D3177

CH3

D3641

S

S

S CH3

S

D3823

S

CH3

D2016

(CH2)11CH3 S

B(OH)2

E0537

S

E0741

S S

S

E0380

O

E0378

CH2CH3

O S

S

CH2CH3

S

S

F0548

S

F0549

H0722

H1298 CH3(CH2)5

O CH3CH2

C H

S

(CH2)6CH3

O

O H C

S

S

B(OH)2

H C

S

CH3

O

CH3

B(OH)2

CH3

H1294

H0756

CH3 CH3

(CH2)5CH3

O B

CH3

I0374

O

S

M0899

I

M0911

S

S

M1850

S

CH3 O

CH3

O

H S

C H

CH3

M1459

CH3

CH3 S

CH3

I

S

M0440

S

M0635

(CH2)5CH3

S

CH3

I0380

B O

S

O CH3

S

B(OH)2

S

C OH

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

223

Electroluminescence

M1118

N0533

O0245

O0213

(CH2)8CH3 CH3

P1835

(CH2)17CH3

(CH2)7CH3

OH

S

S

O

P1127

S

P1397

S

S

P1126

P1128

(CH2)4CH3

B3561

(CH2)4CH3

CH2CH2CH3 S

S

S

S

N

S

T2699

T1149

T2518

Br S

S

T1084

CH3

Br Br

T0218

Br

Br

CH3

O

O

Br

S

Br

CH3

C OH

O

B

S

O

S

S

C OH S

CH3

Br

T2729

T2513

T2621

T0725

T0864 O

S

S

C H

O S

S

S

S

T0223

T1772

S

B(OH)2

T1975

C H S

T2388

T2347 O C H

B(OH)2

O S

S

B(OH)2

S

S

C H

HO C

O S

C OH

O

T0956

U0056

(CH2)10CH3

Br Br

S

Br

S

Product No. Product Name B3464 B0093 B2893 B3441 B1554 B3363 B1276 B1874 B1996 B2013 B3525 B3507 B1025 B1540

224

Benzo[1,2-b:4,5-b ']dithiophene Benzo[b]thiophene Benzo[b]thiophene-2-ylboronic Acid (contains varying amounts of Anhydride) 2,5-Bis(4-biphenylyl)thiophene 2,5-Bis(5-tert-butyl-2-benzoxazolyl)thiophene 5,5'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene 2,2'-Bithiophene 5-Bromo-2,2'-bithiophene-5'-carboxaldehyde 2-Bromo-5-chlorothiophene 3-Bromo-2-chlorothiophene 2-Bromodibenzothiophene 2-Bromo-3-hexylthiophene 2-Bromo-3-methylthiophene 2-Bromo-5-methylthiophene (stabilized with Copper chip + NaHCO3)

Unit Size 1g

1g

1g 5g 5g 1g 5g 10g 1g 5g 5g

5g 5g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

5g 25g 25g 5g 25g 5g 25g 5g 25g 25g 5g 5g 25g 25g

Electroluminescence

Product No. Product Name B1541 B3385 B3200 B3226 B0941 B1067 B2862 B2934 B2827 B3386 B2302 B1458 C1801 C2324 C0807 C1192 C2066 C1722 C1230 D2098 D2378 D2474 D0148 D3798 D2755 D2245 D3799 D3800 D3896 D3678 D3679 D1548 D1549 D1676 D3928 D2611 D2223 D1591 D3526 D3177 D3641 D3823 D2016 E0741 E0380 E0378 E0537 F0548 F0549 H0722 H1298 H1294 H0756 I0374 I0380 M0635 M0440 M0899 M0911 M1850 M1459 M1118 N0533 O0245 O0213 P1835 P1127 P1397

3-Bromo-4-methylthiophene 4-Bromo-2-methylthiophene 5-Bromo-5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene 3-Bromothieno[3,2-b]thiophene 2-Bromothiophene 3-Bromothiophene 5-Bromo-2-thiopheneboronic Acid (contains varying amounts of Anhydride) 3-Bromothiophene-2-carboxaldehyde 4-Bromothiophene-2-carboxaldehyde 4-Bromo-2-thiophenecarboxylic Acid 5-Bromo-2-thiophenecarboxylic Acid 3-Butylthiophene 2-Chloro-3-methylthiophene 2-Chloro-5-methylthiophene 2-Chlorothiophene 3-Chlorothiophene 5-Chloro-2-thiopheneboronic Acid (contains varying amounts of Anhydride) 5-Chlorothiophene-2-carboxaldehyde 5-Chlorothiophene-2-carboxylic Acid 3-Decylthiophene 3,4-Diaminothiophene Dihydrochloride Dibenzothiophene Dibenzothiophene 3,3'-Dibromo-2,2'-bithiophene 5,5'-Dibromo-2,2'-bithiophene 2,8-Dibromodibenzothiophene 2,6-Dibromodithieno[3,2-b:2',3'-d]thiophene 3,5-Dibromodithieno[3,2-b:2',3'-d]thiophene 2,5-Dibromo-3-hexylthiophene 2,5-Dibromothieno[3,2-b]thiophene 3,6-Dibromothieno[3,2-b]thiophene 2,3-Dibromothiophene 2,5-Dibromothiophene 3,4-Dibromothiophene 3,4'-Dihexyl-2,2'-bithiophene 2,5-Diiodothiophene 2,8-Dimethyldibenzothiophene 2,5-Dimethylthiophene 2,7-Diphenyl[1]benzothieno[3,2-b][1]benzothiophene 2,5-Diphenylthiophene Dithieno[3,2-b:2',3'-d]thiophene Dithieno[3,2-b:2',3'-d]thiophene-2-boronic Acid (contains varying amounts of Anhydride) 3-Dodecylthiophene 3,4-Ethylenedioxythiophene 2-Ethylthiophene 3-Ethylthiophene 5-Ethylthiophene-2-carboxaldehyde 5'-Formyl-2,2'-bithiophene-5-boronic Acid (contains varying amounts of Anhydride) 5-Formyl-2-thiopheneboronic Acid (contains varying amounts of Anhydride) 3-Heptylthiophene 3-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene 4-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene 3-Hexylthiophene 2-Iodothiophene 3-Iodothiophene 2-Methylthiophene 3-Methylthiophene 3-Methylthiophene-2-aldehyde 5-Methylthiophene-2-aldehyde 5-Methyl-2-thiopheneboronic Acid (contains varying amounts of Anhydride) 3-Methyl-2-thiophenecarboxylic Acid 5-Methyl-2-thiophenecarboxylic Acid 3-Nonylthiophene 3-Octadecylthiophene 3-n-Octylthiophene 2-Pentylthiophene 3-Pentylthiophene 2-Phenylthiophene

Unit Size 5g 5g 200mg 25g 25g 1g 1g 5g 5g 5g 1g 1g 5g 5g 5g 1g 1g 5g 1g 100mg 25g 5g 1g 1g 1g 200mg 200mg 200mg

1g 200mg 5g 5g 1g 5g 5ml

200mg 200mg 1g 5g 5g 5ml 1g 1g 1g 1g 1g

5g 25g 1g 25ml 25g 25g 1g 5g

1g

1g 1g 5g 1g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 25g 1g 1g 250g 250g 5g 25g 25g 25g 5g 5g 25g 25g 25g 25g 5g 5g 25g 5g 1g 250g 25g 5g 5g 5g 1g 1g 5g 5g 1g 25g 25g 25g 5g 25g 100mg 25ml 100mg 100mg 1g 1g 25g 25g 25ml 25ml 5g 1g 5g 5g 5g 5g 25g 250g 5g 500ml 500g 500g 10g 5g 25g 5g 5g 5g 25g 5g 5g 5g

225

Electroluminescence

Product No. Product Name P1126 P1128 B3561 T2699 T1149 T2518 T0218 T1084 T2729 T2513 T2621 T0725 T0864 T0223 T1772 T1975 T2388 T2347 T0956 U0056

Unit Size

3-Phenylthiophene 3-Propylthiophene 2-(2-Pyridyl)benzo[b]thiophene 3,3',5,5'-Tetrabromo-2,2'-bithiophene Tetrabromothiophene 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene 2-Thenoic Acid 3-Thenoic Acid Thieno[2,3-b]thiophene Thieno[3,2-b]thiophene Thieno[3,2-b]thiophene-2-boronic Acid (contains varying amounts of Anhydride) 2-Thiophenaldehyde (stabilized with HQ) 3-Thiophenaldehyde Thiophene 2-Thiopheneboronic Acid (contains varying amounts of Anhydride) 3-Thiopheneboronic Acid (contains varying amounts of Anhydride) 2,3-Thiophenedicarboxaldehyde 2,5-Thiophenedicarboxylic Acid 2,3,5-Tribromothiophene 3-Undecylthiophene

B1336

CH3

CH3

Triphenylamines

N

N

N

5g 5g 5g 5g 25g 5g 250g 25g 5g 5g 1g 500ml 25g 500ml 25g 5g 5g 25g 250g 5g

B2843 CH3

N

N N

CH3

CH3

25ml 5g 25ml 5g 1g 1g 5g 25g 1g

1g

CH3 CH3

CH3 CH3

N

1g 5g 1g 25g 5g 1g 1g

B2269

B2079 B3146

Cl

1g 1g

CH3 CH3

CH3

N O

O

H C

C H

Cl

B2305

B3089

B2844

B2633

D3302

Br N

Br

N N

Br

N

CH3

D3303

Br

CH3

D1910

Br

N

N

N

D2347

Br

Br N

N

D2172

D3739 O

CH3

CH3

Br

C H

N

N N

Br

D3537 B(OH)2

D2737

D2448 D3236

I0490

I0776

O

I

C H CH3 N

I

N

N

CH3

N CH3

N0831 CH3

T2269 NO2

T1812

CH3

OCH3

CH3O

CH3

CH3

M1898

N

N

T2616

CH3 N

N

N

N

N

N N

CH3

226

N

N

N

CH3

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Electroluminescence

T0507

T2332

T1361

T2310

T1724

Br

NH2

I

O C H

N

N

N

H2N

T2333

O2N

NH2

Br

N

N O

Br

O

H C

C H

I

T2558 NO2

CH3

N

N NO2

CH3

CH3

Product No. Product Name B1336 B2079 B3146 B2269 B2843 B2305 B3089 B2844 B2633 D3302 D3303 D1910 D2347 D2172 D3739 D3537 D2448 D3236 D2737 I0490 I0776 M1898 N0831 T2269 T1812 T2616 T0507 T2332 T1361 T2310 T1724 T2333 T2558

I

Unit Size

N,N '-Bis(4-chlorophenyl)-N,N '-diphenyl-1,4-phenylenediamine 1,1-Bis[4-[N,N-di(p-tolyl)amino]phenyl]cyclohexane 1,1-Bis[4-[N,N-di(p-tolyl)amino]phenyl]cyclohexane (purified by sublimation) 4,4'-Bis[di(3,5-xylyl)amino]-4''-phenyltriphenylamine Bis(4-formylphenyl)phenylamine 4,4'-Bis[N-(1-naphthyl)-N-phenylamino]-4''-phenyltriphenylamine 4-Bromo-4',4''-dimethyltriphenylamine 4-Bromo-4'-(diphenylamino)biphenyl 4-Bromotriphenylamine 4,4'-Dibromo-4''-cyclohexyltriphenylamine 4,4'-Dibromo-4''-phenyltriphenylamine 4,4'-Dibromotriphenylamine 4,4'-Dimethyltriphenylamine 4-(N,N-Diphenylamino)benzaldehyde 3-(Diphenylamino)dibenzo[g,p]chrysene 4-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride) N,N '-Diphenyl-N,N '-di(m-tolyl)benzidine N,N '-Diphenyl-N,N '-di(m-tolyl)benzidine (purified by sublimation) 4-(Di-p-tolylamino)benzaldehyde N-(4'-Iodobiphenyl-4-yl)-N-(m-tolyl)aniline 4-Iodo-4',4''-dimethoxytriphenylamine 4-Methyltriphenylamine 4-Nitrotriphenylamine N,N,N ',N '-Tetrakis(p-tolyl)benzidine N,N,N ',N '-Tetraphenylbenzidine 4,4',4''-Tri-9-carbazolyltriphenylamine Triphenylamine Tris(4-aminophenyl)amine Tris(4-bromophenyl)amine Tris(4-formylphenyl)amine Tris(4-iodophenyl)amine Tris(4-nitrophenyl)amine Tri-p-tolylamine

B0482

CH3

Diphenylamines

CH3

N

B2429

NH

N

CH3 CH3

1g 100mg

250mg 5g

1g

5g 5g

1g 1g 1g

1g

5g 1g 25g 1g

5g 1g 5g

B2684

B2803

CH3

CH3 NH

Br

1g 5g 1g 1g 1g 100mg 1g 1g 25g 1g 1g 100mg 25g 25g 200mg 1g 5g 5g 5g 1g 1g 5g 1g 5g 25g 5g 250g 5g 25g 500mg 25g 25g 25g

NH

Br

CH3 C

NH

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

C CH3 CH3

227

Electroluminescence

B2685

B2960

C0711

D2952

D0632

Cl I

NH

CH3CH2

I O2N

D3398

NH

NO2

D3845

N

NH

D2986

NH

NH

CH3

D0812

NH

NH

NH

M1135

NH

NH

D1512

D0609 D0906

NH

D3567

OCH3

NH

D2987

D0950

CH3 NH

CH3O

CH3

D0878

NH

N N

D2988

CH3

CH3

CH

CH3CH2

NH

H N

CH3

NH

M2069

NH

CH3

NH

M1258

CH3

M1173 CH3

OCH3 NH

NH

OCH3

NH

NH

CH3

NH

CH3

CH3

CH3

P1497

P1498

P0197

P0198

NH

T2201

NH NH

T2065

NH

T1831 NH

NH

CH3 HN

NH

Product No. Product Name B0482 B2429 B2684 B2803 B2685 B2960 C0711 D2952 D0632 D3398 D3845 D2986 D2988 D2987

228

Bindschedler's Green Leuco Base Bis(4-biphenylyl)amine Bis(4-bromophenyl)amine Bis(4-tert-butylphenyl)amine Bis(4-iodophenyl)amine Bis(4-nitrophenyl)amine 3-Chlorodiphenylamine 4-(Diethylamino)benzaldehyde Diphenylhydrazone 4,4'-Dimethoxydiphenylamine 2,4-Dimethyldiphenylamine 3,4-Dimethyldiphenylamine 1,1'-Dinaphthylamine 1,2'-Dinaphthylamine 2,2'-Dinaphthylamine

Unit Size 1g 1g 1g 25g 1g

1g 25g

1g

5g 5g 5g 500g 5g 1g 5ml 1g 5g 500g 25g 1g 5g 1g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Electroluminescence

Product No. Product Name

Unit Size

N,N '-Di-2-naphthyl-1,4-phenylenediamine N,N '-Diphenylbenzidine N,N '-Diphenyl-1,4-phenylenediamine N,N '-Diphenyl-1,4-phenylenediamine m,m '-Ditolylamine p,p '-Ditolylamine N,N '-Di-p-tolylbenzidine 3-Methoxydiphenylamine 4-Methoxydiphenylamine 3-Methyldiphenylamine 4-Methyldiphenylamine N-Phenyl-3-biphenylamine N-Phenyl-4-biphenylamine N-Phenyl-1-naphthylamine N-Phenyl-2-naphthylamine N-(p-Tolyl)-1-naphthylamine N-(p-Tolyl)-2-naphthylamine N,N ',N ''-Triphenyl-1,3,5-benzenetriamine

D0812 D0878 D0609 D0906 D1512 D0950 D3567 M1135 M2069 M1258 M1173 P1497 P1498 P0197 P0198 T2201 T2065 T1831

B2169

25g 5g 25g 25g 5g 5g 1g 25g 5g 1g

25g 25g

5g

B1066 N

N

D2757

B1767 B2696 N

N

N

N

N O

Oxazoles & Oxadiazoles D1429

O

t

NH2

Bu

NEt2

Et2N

H0291 N

N

N

O

OH

O

Product No. Product Name B2169 B1066 B1767 B2696 D2757 D1429 H0291

N O

O

H2N

500g 25g 500g 500g 25g 25g 5g 500g 25g 25g 5g 500mg 500mg 500g 500g 500mg 500mg 25g

Unit Size

2,5-Bis(4-aminophenyl)-1,3,4-oxadiazole 2,5-Bis(4-diethylaminophenyl)-1,3,4-oxadiazole 2-(4-tert-Butylphenyl)-5-(4-biphenylyl)-1,3,4-oxadiazole 2-(4-tert-Butylphenyl)-5-(4-biphenylyl)-1,3,4-oxadiazole (purified by sublimation) 2,5-Di(1-naphthyl)-1,3,4-oxadiazole 2,5-Diphenyl-1,3,4-oxadiazole 2-(2-Hydroxyphenyl)benzoxazole

B3573

D3842 CH3

Thiazoles & Thiadiazoles

CH3 CH3 CH3 O O B

N O CH3

B

5g 1g

1g

5g 25g 25g 5g 5g 10g 25g

H0973 Br N

OH

N

N S

N

O

CH3 CH3 CH3

1g

S

S

Br

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

229

Electroluminescence

Product No. Product Name B3573 D3842 H0973

Unit Size

4,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole 4,7-Dibromo-2,1,3-benzothiadiazole 2-(2-Hydroxyphenyl)benzothiazole

B0987

A1340

1g

B2489

5g 5g

B2294

NH2

B(OH)2 B(OH)2

NH2

-Phenyls

B2490

B3019

B3151

B1711

(HO)2B

O

CH3

B

B(OH)2

CH3

CH3

O

O B O

O

CH3

O

CH3

B

H2N

Br NH2

CF3

CH3

B2001

B0559 F3C

CH3 CH3

1g 25g 25g

B1330

B3648

B2155

D3390

Br Br

D1344

I

D3372

CH3O

Br

D2315

Br

D2759 CH3

OCH3

H2N

NH2

D3394

Br

Br

I0785

I

I

N0193

I

H2N

NH2

D3534 CH3 I

N0610

I

I

Q0001

NO2 O2N

I

NO2

Q0018

S0220

NO2

T0020

T2412

T1023 CH3

B(OH)2 H2N 3

CH3 NH2

4

CH3

CH3

T0253 CH3 H2N

230

CH3 NH2

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Electroluminescence

Product No. Product Name B0987 A1340 B2489 B2294 B2490 B3019 B3151 B1711 B0559 B2001 B1330 B3648 B2155 D3390 D1344 D3372 D2315 D2759 D3534 D3394 I0785 N0193 N0610 Q0001 Q0018 S0220 T0020 T2412 T1023 T0253

Unit Size

3-Aminobiphenyl 4-Amino-p-terphenyl 3-Biphenylboronic Acid (contains varying amounts of Anhydride) 4-Biphenylboronic Acid (contains varying amounts of Anhydride) 4,4'-Biphenyldiboronic Acid 2-(4-Biphenylyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4,4'-Bis(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)biphenyl 2,2'-Bis(trifluoromethyl)benzidine 2-Bromobiphenyl 3-Bromobiphenyl 4-Bromobiphenyl 4-Bromo-4'-iodobiphenyl 4-Bromo-p-terphenyl 4,4''-Diamino-p-terphenyl o-Dianisidine 4,4''-Dibromo-p-terphenyl 4,4'-Diiodobiphenyl 4,4'-Diiodo-3,3'-dimethylbiphenyl 4,4''-Diiodo-p-terphenyl 4,4''-Dinitro-p-terphenyl 4-Iodobiphenyl 3-Nitrodiphenyl 4-Nitro-p-terphenyl p-Quaterphenyl p-Quinquephenyl p-Sexiphenyl p-Terphenyl 2-p-Terphenylboronic Acid (contains varying amounts of Anhydride) 3,3',5,5'-Tetramethylbenzidine o-Tolidine

B2111

Coumarins

N

O

5g 1g 1g 1g 5g 100mg 100mg 25g 1g

5g 25g

S

O

Et2N

O

O

Product No. Product Name

Unit Size

3-(2-Benzimidazolyl)-7-(diethylamino)coumarin 3-(2-Benzothiazolyl)-7-(diethylamino)coumarin

1g 1g

Q0057 Q0083

D2687 D3227 CH3

O

N

Quinacridones

H N

N O

CH3

O

Product No. Product Name D2687 D3227 Q0057 Q0083

5g 5ml 5g 25g 5g 1g 1g 25g 1g 25g 5g 1g

25g 25g 25g 25g 1g 5g 1g 25g 25ml 25g 250g 25g 5g 5g 500g 5g 250g 25g 5g 1g 25g 25g 5g 25g 1g 1g 500g 1g 25g 500g

N N H

CH2CH3

B2111 B2088

1g

5g 5g 5g 5g

B2088 N

CH3CH2

1g 1g

N,N '-Dimethylquinacridone N,N '-Dimethylquinacridone (refined product of D2687) Quinacridone Quinacridone (purified by sublimation)

O

N H

Unit Size 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 1g 25g 1g

231

Electroluminescence

P0972

P0078 P1629

Perylenes

P0984

O

O

O

O HN

O

O

O

O

O NH O

Product No. Product Name P0078 P1629 P0972 P0984

Unit Size

Perylene Perylene (refined product of P0078) 3,4,9,10-Perylenetetracarboxylic Dianhydride 3,4,9,10-Perylenetetracarboxylic Diimide

A0632

5g 25g

A2180

B1495

25g 1g 500g 25g

B2807 Br

NH2

Pyrenes NH2

D2167

D2160

D2168

N0419

NH2

NH2

Br

N0838

NH2

NO2

H2N

NH2

NO2 NH2

P1104

P1625 B(OH)2

Product No. Product Name A0632 A2180 B1495 B2807 D2167 D2160 D2168 N0419 N0838 P1104 P1625

Unit Size

1-Aminopyrene 4-Aminopyrene 1-Bromopyrene 4-Bromopyrene 1,3-Diaminopyrene 1,6-Diaminopyrene 1,8-Diaminopyrene 1-Nitropyrene 4-Nitropyrene Pyrene 1-Pyreneboronic Acid (contains varying amounts of Anhydride)

A2051

B2804

I

I

O

232

5g

1g

25g 5g

25g 1g 25g 5g 100mg 100mg 100mg 25g 1g 500g 25g

B2713

O

O

H C

C H

N C CH3

5g 5g 1g

B2805 O C H

Carbazoles

1g

N

N

N

CH2

CH2

N

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Electroluminescence

B3458

B3459

C0032

D2116

Br

Br

H2N

N

N H

N H

CH2CH3

D2983

D2982 Br

D2981

Br

D3952 H3C

C CH3 CH3

N

N H

CH2CH3

E0571

M0960

Br

CH3

H3C

N

N H

E0071 E0247

H3C C

N

E0359

Br

Br

Br

N H

NH2 N H

Br Br

D3932

CH2CH3

P1492

T1934

O N

C H CH

N

N N

N

N

N

CH2CH3

CH2CH3

T2700

N

N

CH3

T2616

V0021 N

N N N

N N

N

N N

N N

CH

CH2

Product No. Product Name A2051 B2804 B2805 B2713 B3458 B3459 C0032 D2116 D3932 D2983 D2982 D2981 D3952 E0071 E0247 E0359 E0571 M0960 P1492 T1934 T2700 T2616 V0021

Unit Size

9-Acetyl-3,6-diiodocarbazole 9-Benzylcarbazole-3-carboxaldehyde 9-Benzylcarbazole-3,6-dicarboxaldehyde 4,4'-Bis(9H-carbazol-9-yl)biphenyl 3-Bromocarbazole 3-Bromo-9-ethylcarbazole Carbazole 3,6-Diaminocarbazole 2,7-Dibromocarbazole 3,6-Dibromocarbazole 3,6-Dibromo-9-ethylcarbazole 3,6-Dibromo-9-phenylcarbazole 3,6-Di-tert-butylcarbazole 9-Ethylcarbazole 9-Ethylcarbazole N-Ethylcarbazole-3-carboxaldehyde 9-Ethylcarbazole-3-carboxaldehyde Diphenylhydrazone 9-Methylcarbazole 9-Phenylcarbazole 1,3,5-Tri(9H-carbazol-9-yl)benzene (purified by sublimation) 2,4,6-Tri(9H-carbazol-9-yl)-1,3,5-triazine 4,4',4''-Tri-9-carbazolyltriphenylamine 9-Vinylcarbazole A0621

Fluorenes & Fluorenones

A1040

NH2

1g 1g 1g

1g

1g 25g 1g 1g 5g 1g 1g 25g

1g

5g 5g 1g 1g 1g

5g 5g 100mg 5g 5g 5g 500g 5g 5g 25g 5g 5g 1g 500g 25g 25g 1g 25g 25g 5g 5g 5g 25g

B1715

B1549 B2654

NH2 O HO H2N

OH

NH2

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

233

Electroluminescence

B3069

B1046

B3109

B3560

D0092

Br Br

Br

D3933

D3859

Br CH3(CH2)5

Br (CH2)5CH3

D3872

Br

D3934

CH3

H2N

O

Br

Br

CH3

D0834

D3556

Br CH3(CH2)7

Br (CH2)7CH3

F0061

NH2

D3557

Br

Br

F0333

Br

Br O

F0229

Br O Br

F0021

O2N

NO2

F0590

C H

F0263

H0329

OH

N0201

O O

O

S0800

T2597

B(OH)2

Br

Br

Br

Br

Product No. Product Name A0621 A1040 B1549 B2654 B1715 B3069 B1046 B3109 B3560 D0092 D3933 D3859 D3934 D3556 D3557 D3872 D0834 F0061 F0333 F0229 F0021 F0590 F0263 H0329

234

NO2

O

O

O

S0831

OH

C OH

C OH

2-Aminofluorene 2-Amino-9-fluorenone 9,9-Bis(4-aminophenyl)fluorene 9,9-Bis(4-aminophenyl)fluorene (purified by sublimation) 9,9-Bis(4-hydroxyphenyl)fluorene 2-Bromofluorene 9-Bromofluorene 2-Bromo-9-fluorenone 2-Bromo-9,9'-spirobi[9H-fluorene] 2,7-Diaminofluorene 2,7-Dibromo-9,9-dihexylfluorene 2,7-Dibromo-9,9-dimethylfluorene 2,7-Dibromo-9,9-di-n-octylfluorene 2,7-Dibromofluorene 2,7-Dibromo-9-fluorenone 2,2'-Dibromo-9,9'-spirobi[9H-fluorene] 2,7-Dinitrofluorene Fluorene Zone Refined (number of passes:70) 2-Fluorenecarboxaldehyde 9-Fluorenol 9-Fluorenone 9-Fluorenone-1-carboxylic Acid 9-Fluorenone-2-carboxylic Acid 2-Hydroxy-9-fluorenone

Unit Size 5g 1g

5g

5g

25g 5g 25g 1g 25g 500g 25g 100g 25g 5g 25g 5g 5g 25g 5g 25g 5g 25g 5g 25g 25g 100g 5g 25g 1g 5g 25g 1sample 5g 25g 250g 25g 500g 1g 5g 10g 1g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Electroluminescence

Product No. Product Name N0201 S0800 S0831 T2597

Unit Size

2-Nitrofluorene 9,9'-Spirobi[9H-fluorene] 9,9'-Spirobi[9H-fluorene]-2-boronic Acid 2,2',7,7'-Tetrabromo-9,9'-spirobi[9H-fluorene]

A1709

25g 5g 5g 5g

1g 1g 1g

A1687

A0495 A0992 A0405

NH2

A1843

NH2

B(OH)2

Anthracenes

B2801

P1137 O CH2 P

CH2 P O

OCH2CH3

B2615

B2616

C C

B2871 B0872

Br

OCH2CH3

Br

Br

OCH2CH3

C C

OCH2CH3

B3442

C1962

D3183

D3171

D0166

Br

Br Br

Cl

Br

Br Br

D0327

D1689

P0138

Br

P1494

P1495

Ph

Cl

NH NH

Cl

Ph

P1496 NH

Product No. Product Name A1709 A1687 A0495 A0992 A0405 A1843 B2801 P1137 B2615 B2616 B2871 B0872 B3442 C1962

1-Aminoanthracene 2-Aminoanthracene Anthracene Anthracene Anthracene Zone Refined (number of passes:30) 2-Anthraceneboronic Acid (contains varying amounts of Anhydride) 9,10-Bis(diethylphosphonomethyl)anthracene 9,10-Bis(phenylethynyl)anthracene 1-Bromoanthracene 2-Bromoanthracene 9-Bromoanthracene 9-Bromoanthracene 2-Bromo-9,10-diphenylanthracene 2-Chloroanthracene

Unit Size 1g 1g 25g 500g 25g 500g 1sample 250mg 1g 1g 1g 10g 500mg 1g 1g 5g 5g 25g 100g 5g 25g 1g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

235

Electroluminescence

Product No. Product Name D3183 D3171 D0166 D0327 D1689 P0138 P1494 P1495 P1496

Unit Size

1,5-Dibromoanthracene 2,6-Dibromoanthracene 9,10-Dibromoanthracene 9,10-Dichloroanthracene 9,10-Diphenylanthracene 9-Phenylanthracene N-Phenyl-1-anthramine N-Phenyl-2-anthramine N-Phenyl-9-anthramine

B0618

1g 1g 500g 10g 25g 5g 500mg 1g 5g

25g 1g 1g 1g

1g

B0619

D2359

D3624 Br

Br

Br

Br

Br

Naphthalenes Br

I0266

N0630 I

N0649

N0052

B(OH)2

NH2

B(OH)2

Product No. Product Name B0618 B0619 D2359 D3624 I0266 N0630 N0649 N0052 N0212

N0212 NO2

Unit Size

1-Bromonaphthalene 2-Bromonaphthalene 1,4-Dibromonaphthalene 2,7-Dibromonaphthalene 1-Iodonaphthalene 1-Naphthaleneboronic Acid (contains varying amounts of Anhydride) 2-Naphthaleneboronic Acid (contains varying amounts of Anhydride) 1-Naphthylamine 1-Nitronaphthalene

25g 5g 5g 5g 1g 1g

5g 5g 25g

B0017

B2982

B2983

C0339

B3562

B1603

C1961 C0386

C1689

500g 25g 25g 25g 25g 25g 25g 25g 500g

Polycyclic Aromatic Hydrocarbons (PAHs) B0085

C C Si[CH(CH3)2]3

C C Si[CH(CH3)2]3

Br

236

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Electroluminescence

D0145

B0403

D0677

I0222

D1005

D3736

D1311

M0248

M1411

N0001

O

CH3

CH3

N0599

CH3

O

P0030

P1893

Product No. Product Name B0017 B2982 B2983 C0339 B0085 B3562 B1603 C1961 C0386 C1689 D0145 B0403 D1005 D3736 D1311 D0677 I0222 M0248 M1411 N0001 N0599 P0030 P1893 T0561 T2233 T0513

Benz[a]anthracene Benzo[b]fluoranthene Benzo[ghi]perylene Benzo[a]phenanthrene 3,4-Benzopyrene 6,13-Bis(triisopropylsilylethynyl)pentacene 7-Bromobenz[a]anthracene Coronene (refined product of C0386) Coronene 1H-Cyclopenta[l]phenanthrene Dibenz[a,h]anthracene Dibenzo[a,c]anthracene Dibenzo[b,def]chrysene Dibenzo[g,p]chrysene 1,2:8,9-Dibenzopentacene 7,12-Dimethylbenz[a]anthracene Isoviolanthrone 7-Methylbenz[a]anthracene 2-Methylcyclopenta[l]phenanthrene Naphthacene Naphtho[2,3-a]pyrene Pentacene (purified by sublimation) Picene (purified by sublimation) 5,6,11,12-Tetraphenylnaphthacene 5,6,11,12-Tetraphenylnaphthacene (refined product of T0561) Triphenylene

CH3

T0513

T0561 T2233 Ph

Ph

Ph

Ph

Unit Size 1g

5g

100mg 1g 1g 100mg

200mg 1g

100mg

100mg 1g 100mg 100mg 100mg 250mg 100mg

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 100mg 100mg 1g 1g 100mg 5g 100mg 5g 1g 100mg 100mg 100mg 1g 100mg 5g 10g 100mg 1g 5g 100mg 1g 1g 1g 1g 1g

237

Electroluminescence

B0054

B3088

B2076

C1719

H2N

N

Others

NH2

N

NHCH2

N H

C0130

N H

C0248

C0460

F0011

Cl

I0429 O

O

Cl

Cl

H N

N

Cl N

N H

S

Cl

N

N N

O

NH

T0337

O

Cl O

J0007

HN

N

N0659

O

P1047

P1136 P0080

NH2 N

N

N

CH3CH2

H2N

P0082

N N

NH2

P0106

O

NH

N

N HN

S

Product No. Product Name B0054 B3088 B2076 C1719 C0130 C0248 C0460 F0011 I0429 J0007 T0337 N0659 P1136 P0080 P1047 P0082 P0106 T1358

O O

T1358

N

N

O

CH2CH3

H N

N

N

Unit Size

Benzimidazole N-Benzyl-2-naphthylamine 1,1-Bis(4-aminophenyl)cyclohexane 2-Chlorobenzimidazole 5-Chlorobenzimidazole 2-Chlorophenothiazine Cyanuric Chloride Flavanthrone Indanthrone Julolidine Melamine Monomer Nile Red 9,10-Phenanthrenequinone 9,10-Phenanthrenequinone Phenanthridine Phenazine Phenothiazine meso-Tetraphenylchlorin

25g 5g 5g 5g 25g 25g 1g 5g 25g 500mg 25g 5g 1g

5g 25g

500g 25g 25g 5g 25g 500g 500g 5g 25g 25g 500g 1g 250g 25g 10g 25g 500g 100mg

Purification just before use is recommended.

Phthalocyanines (see p.273) Reagents for Conducting Polymer Research (see p.210) Dichlorosilanes (for Polysilanes) (see p.292)

238

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Electroluminescence

References 1987, C. W. Tang, S. A. Van Slyke, , 913. 1990, C. Adachi, T. Tsutsui, S. Saito, , 799. 2001, S. Seki, S. Miyashita, , 70. 2001, J. Kido, , 333. 2001, K. Hachise, N. Takada., N. Tanigaki, , 455. 1998, M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, , 151. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friend, P. L. Burn, A. B. Holmes, 1990, , 539. 8) R. H. Friend, R. W. Gymer, A. B. Holmes, J. H. Burroughes, R. N. Marks, C. Taliani, D. D. C. Bradley, D. A. Dos Santos, J. 1999, L. Bredas, M. Logdlund, W. R. Salaneck, , 121. 2001, 9) R. H. Friend, , 425. 2007, 10) S.-C. Lo, P. L. Burn, , 1097. 1) 2) 3) 4) 5) 6) 7)

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

239

Reagents for Solar Cell Research

Reagents for Solar Cell Research Photovoltaic power generation has attracted much attention for the mitigation options of climate change and as an alternative energy source. Dye-sensitized solar cells and organic thin-film solar cells are lightweight and have high process ability while maintaining low production costs and have been studied for the next generation of solar cells.

●Dye-Sensitized Solar Cells Grätzel and co-worker reported solar energy-to-electricity conversion efficiencies as high as 7-8% on dye-sensitized fractal-type TiO2 electrodes1). These solar cells, also known as the Grätzel cell, are composed of I) transparent electrode, II) TiO2, III) dyes, IV) electrolytes, V) counter electrode.

Transparent Electrode

Electrolyte

Counter Electrode

Dye

1)Dyes A large numbers of dyes (photosensitizer) have been synthesized to improve the efficiency of solar cells. Ruthenium complex dyes are most widely used for sensitizer. N719 dye (red dye) is a typical Rucomplex dye and a modification of the classical N-3 dye, to increase cell voltage. O

O

HO C

C O N

N 2 (C4H9)4N

SCN Ru NCS N

N

HO C

C O

O

O

N719 Dye

Many ruthenium complex dyes are composed of bipyridine derivatives as ligands. TCI offers a variety of bipyridine derivatives such as 2,2'-bipyridine-4,4'-dicarboxylic acid for ligands, 4,4'-dibromo-2,2'-bipyridyl and 4,4'-bis(chloromethyl)-2,2'-bipyridyl for building blocks in ligand synthesis. TCI also offers custom synthesis to provide chemicals not available in this catalog. Please contact us for a quote. 2)Electrolytes The iodide/triiodide electrolyte is used as a redox mediator between the dyes and the electrode in most dye-sensitized solar cells. Electrolyte solutions such as an acetonitrile solution are effective for achieving high conversion efficiencies. Ionic liquids and gelated electrolytes are also applied for dye-sensitized solar cells because of their advantages of stability and safety.

240

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Reagents for Solar Cell Research

B3514 O

O

HO C

C O N

N 2 (C4H9)4N

SCN Ru NCS

Dye

N

N

HO C

C O

O

O

Product No. Product Name B3514

Unit Size

Bis(tetrabutylammonium) Dihydrogen Bis(isothiocyanato)bis(2,2'-bipyridyl4,4'-dicarboxylato)ruthenium(II) (=N719 Dye)

100mg

D0905

D0711 B2694

B0989 NaO3S

SO3Na

. xH2O

Bipyridyls N

N

N

CH3

B3509

B1077 O

O

HO C

KO

C OH

O

C

C OK

N

B0863

B1876 CH3

B0468

O

CH3

O

HO C

N

N

N

. xH2O

N

N

B0470

N

CH3

B0841 O

N

C OH N

N

N

B3510

N

N

B3511

B3218 Br

N

N N

N

CH2OH

N

N

N

N H

N

CH2OH N

N H

N

B3219

D2913

D3919

D2565 Br

Br

N

N

D3886 (CH2)3CH3

Br

OCH3

OCH3

N

N

N CH3(CH2)3

N

N

N

B0852

H2N

N

N

NH2

B2138 CH3

CH3

N

N

CH3

N0423

CH3

N

CH3

N CH3

. xH2O

N

N

CH3

N

. HCl . H2O

N

SO3Na

NaO3S

N

N

P0081 N

N

B0985

(CH2)8CH3 (CH2)8CH3

P0221

N CH3

D3917

CH3 N

N

N

B0842

N

M0300

N

N CH3

CH3

T0024 N

. H2O

N

. HCl . H2O

N

N

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

N

241

Reagents for Solar Cell Research

T0847 CH3

N N

CH3

CH3 CH3

Product No. Product Name D0711 B2694 D0905 B0989 B3509 B1077 B0841 B1876 B0468 B0863 B0470 B3510 B3511 B3218 B3219 D2913 D3919 D2565 D3886 B0852 B2138 B0842 D3917 B0985 M0300 N0423 P0221 P0081 T0024 T0847

Unit Size

Bathocuproine Bathocuproine (purified by sublimation) Bathophenanthroline Bathophenanthrolinedisulfonic Acid Disodium Salt Hydrate 2,2'-Bicinchoninic Acid 2,2'-Bicinchoninic Acid Dipotassium Salt Hydrate 2,2'-Bi-4-lepidine 2,2'-Bipyridine-4,4'-dicarboxylic Acid 2,2'-Bipyridyl 2,4'-Bipyridyl 2,2'-Biquinoline 2,6-Bis(2-benzimidazolyl)pyridine 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine 4'-(4-Bromophenyl)-2,2':6',2''-terpyridine 4'-Bromo-2,2':6',2''-terpyridine 6,6'-Diamino-2,2'-bipyridyl 4,4'-Dibromo-2,2'-bipyridyl 2,9-Dibutyl-1,10-phenanthroline 4,4'-Dimethoxy-2,2'-bipyridyl 4,4'-Dimethyl-2,2'-bipyridyl 5,5'-Dimethyl-2,2'-bipyridyl 6,6'-Dimethyl-2,2'-bipyridyl 4,4'-Dinonyl-2,2'-bipyridyl Disodium Bathocuproinedisulfonate 5-Methyl-1,10-phenanthroline Neocuproine Hydrochloride 1,10-Phenanthroline Monohydrate 1,10-Phenanthroline Hydrochloride Monohydrate 2,2':6',2''-Terpyridine 3,4,7,8-Tetramethyl-1,10-phenanthroline

1g 1g 1g 1g 1g 100mg 25g 1g 1g 1g 1g 1g 1g 1g 100mg 1g 1g 5g 1g 5g 100mg 1g 1g 100mg 100mg 1g 1g 100mg 1g

B2708

D3903

N

E0556

CH3

N

CH3

N

E0190

E0549

H1286 CH3

I0552

CH2CH2CH3

N

Fe

CH3

I

CH3 CH3

N

I

(CH2)5CH3

M1440

M0253

N P CH(CH3)2 I

I

I

CH2CH3

CH2 N CH3

CH3CH2 N CH2CH2CH3

CH3

N

F0167

CH2CH2CH3

P+ CH2CH3 I -

I

CH3

N

P0242

CH3

T1011

CH2CH3 I

CH2CH2CH3

242

CH3

CH2CH2CH3

E0191

CH3 CH3CH2 N CH3

N

(CH2)3CH3

N

I

I

Electrolytes

5g 1g 5g 5g 5g 5g 100mg 1g 500g 5g 5g 5g 5g 5g 5g 250mg 5g 1g 5g 25g 25g 5g 5g 1g 1g 25g 25g 25g 1g 5g

P CH3

I

N CH2CH3 CH2CH3

(CH2)4CH3

I

CH3(CH2)4 N

(CH2)4CH3 I

(CH2)4CH3

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Reagents for Solar Cell Research

T0057

T0097

(CH2)3CH3

I

CH3CH2 N CH2CH3

(CH2)3CH3

I

CH3(CH2)6 N

T0172

I

I

CH3CH2CH2 N CH2CH2CH3

CH3(CH2)5 N

CH3(CH2)3 P

CH2CH2CH3

CH3

(CH2)3CH3

CH3 N CH3

P0246

CH3

(CH2)3CH3

I CH3(CH2)3

I

CH3

T1564 (CH2)3CH3

I

CH3

(CH2)5CH3 I

(CH2)5CH3

M1455

CH2CH2CH3

P

T0139

(CH2)5CH3

(CH2)6CH3

(CH2)6CH3

CH2CH3

T1450

T1010

(CH2)6CH3

CH2CH3

(CH2)3CH3 CH3(CH2)3 N

T1396

S

N CH3

I (CH2)3CH3

I

CH3

T1056

CH3 CH3

S

I CH3

Product No. Product Name B2708 D3903 E0556 E0190 E0549 E0191 F0167 H1286 I0552 M1440 M0253 P0242 T1011 T0057 T0097 T1396 T1010 T0139 T1450 T0172 M1455 T1564 P0246 T1056

1-Butyl-3-methylimidazolium Iodide 1,2-Dimethyl-3-propylimidazolium Iodide 1-Ethyl-3-methylimidazolium Iodide Ethyltrimethylammonium Iodide Ethyltriphenylphosphonium Iodide Ethyltripropylammonium Iodide (Ferrocenylmethyl)trimethylammonium Iodide 1-Hexyl-2,3-dimethylimidazolium Iodide Isopropyltriphenylphosphonium Iodide 1-Methyl-3-propylimidazolium Iodide Methyltriphenylphosphonium Iodide Phenyltriethylammonium Iodide Tetraamylammonium Iodide Tetrabutylammonium Iodide Tetraethylammonium Iodide Tetraheptylammonium Iodide Tetrahexylammonium Iodide Tetramethylammonium Iodide Tetraphenylphosphonium Iodide Tetrapropylammonium Iodide Tributylmethylphosphonium Iodide Tributylsulfonium Iodide Trimethylphenylammonium Iodide Trimethylsulfonium Iodide

Unit Size 5g 5g 5g 25g

5g 5g 25g 25g 5g 25g 25g

25g

5g 100g 10g 25g

25g 25g

25g 25g 25g 25g 250g 25g 5g 5g 25g 25g 500g 25g 500g 500g 25g 25g 500g 25g 500g 25g 1g 500g 500g

●Organic Thin-film Solar Cells The developments of organic thin film solar cells (organic semiconductor solar cells) have received a tremendous boost over the last decade. There are two typical manufacturing processes, spin-coating and vacuum sublimation. A spin-coating technique involves first the dissolution of the semiconductor materials in an appropriate organic solvent followed by its deposition on the supporting substrate. A vacuum sublimation technique involves depositing insoluble materials under high vacuum to produce a thin-film. These organic thin-film solar cells are lightweight and have high process ability while maintaining low production costs and can be expected to emerge as the next generation of solar cells replacing silicon solar cells which are currently in common use. Currently, TCI is exercising considerable efforts in the development of high purity organic semiconductor materials by employing the sublimation refining technique.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

243

Reagents for Solar Cell Research

C2415

B1641 (CH2)11CH3

CH3 N

n-Type Organic Semiconductors

Organic Semiconducting Materials H1194

M2088

F

F

P0972

F

OCH3

N F

N N

Cu

N N

O

O

O

O

F

F

N F F

O F

O

F F

O

F

N

N

F

T2206

F

F

F

F

F F

S

F

S

F

F

S

4

F

F

Product No. Product Name

Unit Size

C2415 B1641 H1194

C60MC12 Fullerene C60 (pure) 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyanine Copper(II)

100mg

(purified by sublimation)

100mg

M2088 P0972 T2206

Methyl [6.6]-Phenyl-C61-butyrate 3,4,9,10-Perylenetetracarboxylic Dianhydride Tetradecafluoro-α-sexithiophene (purified by sublimation)

B3441

100mg 1g

1g 100mg 25g 500g 50mg

B1200

B3562

D3526 C C Si[CH(CH3)2]3

S

p-Type Organic Semiconductors N0001

S

S

S

S

S

S

S

S S

S C C Si[CH(CH3)2]3

P0030

P1795

P1893

P1628 N

N NH

N

N

N

N

N N

S0504

T1196

T2269

T1812

CH3

CH3

N

4

S

S

4

S

S

S

N N

N

N

S0220

N Cu

N

HN

N

N

N

S CH3

CH3

T2233

244

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Reagents for Solar Cell Research

Product No. Product Name B3441 B1200 B3562

Unit Size

2,5-Bis(4-biphenylyl)thiophene Bis(ethylenedithio)tetrathiafulvalene 6,13-Bis(triisopropylsilylethynyl)pentacene (This product is unavailable for selling domestically in U.S.) 2,7-Diphenyl[1]benzothieno[3,2-b][1]benzothiophene Naphthacene Pentacene (purified by sublimation) Phthalocyanine (purified by sublimation) Picene (purified by sublimation) Pigment Blue 15 (purified by sublimation) p-Sexiphenyl α-Sexithiophene 2,2':5',2''-Terthiophene (=α-Terthienyl) N,N,N ',N '-Tetrakis(p-tolyl)benzidine N,N,N ',N '-Tetraphenylbenzidine 5,6,11,12-Tetraphenylnaphthacene (refined product of T0561)

D3526 N0001 P0030 P1795 P1893 P1628 S0220 S0504 T1196 T2269 T1812 T2233

B2694

1g 1g

100mg

100mg

5g 5g 100mg 100mg 5g 1g 1g 1g 1g 1g 1g 5g 5g 25g 1g

1g 100mg 100mg 100mg 100mg 1g 5g 250mg

B2695

Others N

N

N

CH3

CH3

N

Product No. Product Name B2694 B2695

Unit Size

Bathocuproine (purified by sublimation) Bathophenanthroline (refined product of D0905)

1g 1g

B1996

B3507

(CH2)5CH3

Thiophenes

Polymer Materials

B3200

B2862

Cl

D2755

Br

O B

CH3

S

O

S

Br

Br

S

B(OH)2

Br

S

S

CH3

D3678

Br

D1549

O S

Br

S

Br

Br

D3896

S

S S

(CH2)5CH3

Br Br

S

Br

E0741

S Br

Br

D3799

CH3 CH3

S

S

O

Br S

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

245

Reagents for Solar Cell Research

Product No. Product Name B1996 B3507 B3200 B2862 D2755 D3799 D3896 D3678 D1549 E0741

Unit Size

2-Bromo-5-chlorothiophene 2-Bromo-3-hexylthiophene 5-Bromo-5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene 5-Bromo-2-thiopheneboronic Acid (contains varying amounts of Anhydride) 5,5'-Dibromo-2,2'-bithiophene 2,6-Dibromodithieno[3,2-b:2',3'-d]thiophene 2,5-Dibromo-3-hexylthiophene 2,5-Dibromothieno[3,2-b]thiophene 2,5-Dibromothiophene 3,4-Ethylenedioxythiophene

D3842

D2983

5g

1g 1g 200mg 200mg

1g 5g

D3302

25g 5g 1g 5g 5g 1g 5g 5g 25g 25g

D2982

Br

Br Br

Br

Br

N

Others

N

Br

N

S

N

N H

CH2CH3

Br Br

D2981

D3303

Br

Br

D1910

Br

N

T1361 Br

Br N

N

Br

Br

Br

Br

N Br

Br

Product No. Product Name D3842 D2983 D3302 D2982 D2981 D3303 D1910 T2597 T1361

T2597

Br

Br

Unit Size

4,7-Dibromo-2,1,3-benzothiadiazole 3,6-Dibromocarbazole 4,4'-Dibromo-4''-cyclohexyltriphenylamine 3,6-Dibromo-9-ethylcarbazole 3,6-Dibromo-9-phenylcarbazole 4,4'-Dibromo-4''-phenyltriphenylamine 4,4'-Dibromotriphenylamine 2,2',7,7'-Tetrabromo-9,9'-spirobi[9H-fluorene] Tris(4-bromophenyl)amine

1g 1g

5g 5g

25g 25g 1g 1g 5g 1g 5g 1g 100mg 1g 5g 25g

Reference 1) B. O' Reagan, M. Grätzel,

246

1991,

, 737.

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Photochromic Compounds

Photochromic Compounds Photochromism is the phenomena that of reversible transformation between two forms that have different absorption spectra by photo-irradiation. The history of photochromism dates back to the era of the Alexander the Great. Inspired by Fischer and co-workers who first reported photochromism in spiropyran analogues in 1952, intense studies on photochromic compounds have continued up to the present. The mechanism for photochromism of spiropyran analogues is shown below. CH3 CH3 R N

R

CH3 CH3 hν hν' or Δ

O

N

CH3

O

CH3

Today, research for the application of photochromism is being achieved in a variety of fields including light modulation materials, optical recording materials, optical switches, and photochromic ink. Some of them are being put into practical use. Furthermore, an energetic attempt to introduce photochromic compounds into functional materials for photochemical control is being studied. Especially, diarylethenes 1 and 2 developed by Irie and co-workers are stable at high temperature and have been shown high repeated durability. In addition, various functional molecules can easily be introduced to the aromatic ring of 1 and 2. The solution of 1 changes to red upon irradiation of UV light, but rapidly converts back to colorless by visible light. In this reversible reaction, 1 has been shown a repeated durability over 10,000 times. The crystal of 2 changes to blue upon irradiation of UV light, and returns to colorless by visible light. These changes are rapidly finished within ten pico second. Moreover, the photocyclization quantum yields is limitlessly near to one. Therefore 2 shows extremely effective photochromic reaction. 1 and 2 are ideal optical device material and are expected as one of the material supporting the photonics age in the 21th century. F

F

F

F

F

F

S

F

CH3

F

F

F

CH3 CH3

S

S

CH3 CH3

F

F

CH3 S

2

1

B2629

B2287 F

CH3

Diarylethenes

S

F

F

F

F

F

CH3 CH3

F CH3

B1535 O

O

O

CH3

S

CH3 CH3

S

CH3

CH3

CH3

CH3

F

CH3 CH3

S

B1536

O

CH3

F

F

S

S

B1534

F

F

H N

NC

O CH3

S

CH3 CH3

S

CH3

CN CH3

CH3 CH3

S

CH3 CH3

S

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

247

Photochromic Compounds

Product No. Product Name B2629 B2287 B1534 B1535 B1536

Unit Size

1,2-Bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene 1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-3,3,4,4,5,5-hexafluoro-1-cyclopentene 2,3-Bis(2,4,5-trimethyl-3-thienyl)maleic Anhydride 2,3-Bis(2,4,5-trimethyl-3-thienyl)maleimide cis-1,2-Dicyano-1,2-bis(2,4,5-trimethyl-3-thienyl)ethene

H1042

T0344

T0416

N HOH2CH2C

T0423 CH3

CH3

CH3

CH3

CH3

N

O

Br

O

CH3

CH3

T1259

CH3

CH3

N

NO2

O

1g 1g 1g 1g 5g

T0370 CH3

CH3 CH3

Spiropyrans

100mg 100mg 100mg 100mg 1g

T0366

CH3 CH3

CH3 CH3

N

N

O CH3 CH3O

N

O

N

CH3

O

N

CH3

O

NO2

CH3

Product No. Product Name H1042 T0344 T0370 T0416 T0423 T1259 T0366

Unit Size

1-(2-Hydroxyethyl)-3,3-dimethylindolino-6'-nitrobenzopyrylospiran 1,3,3-Trimethylindolinobenzopyrylospiran 1,3,3-Trimethylindolino-6'-bromobenzopyrylospiran 1,3,3-Trimethylindolino-8'-methoxybenzopyrylospiran 1,3,3-Trimethylindolino-β-naphthopyrylospiran 1,3,3-Trimethylindolinonaphthospirooxazine 1,3,3-Trimethylindolino-6'-nitrobenzopyrylospiran

D3618

1g 1g

5g 5g 1g 25g 5g 1g 25g

1g 1g 1g

D3619 NH2

O NH2

Spiroperimidines

HN

NH

NH NH

HN

Product No. Product Name D3618 D3619

Unit Size

2,3-Dihydro-2-spiro-4'-[8'-aminonaphthalen-1'(4'H)-one]perimidine (contains o-form) 2,3-Dihydro-2-spiro-7'-[8'-imino-7',8'-dihydronaphthalen-1'-amine]perimidine

B0469

100mg 100mg

B1518 NO2

Viologens (Related Compounds)

248

N

N

O2N

O2N

N

N

NO2

2Cl

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Photochromic Compounds

D2137

D1593

CH2 N

N CH2

2Cl

CH3(CH2)6 N

. xH2O

D1854

D0713 D3685 N (CH2)6CH3

CH3 N

N CH3

2Cl

CH3(CH2)7 N

N

. xH2O

2Br

(CH2)7CH3

2Br

D2165

N

N 2Cl

Product No. Product Name B0469 B1518 D2137 D1593 D0713 D3685 D1854 D2165

Unit Size

4,4'-Bipyridyl 1,1'-Bis(2,4-dinitrophenyl)-4,4'-bipyridinium Dichloride 1,1'-Dibenzyl-4,4'-bipyridinium Dichloride Hydrate 1,1'-Diheptyl-4,4'-bipyridinium Dibromide 1,1'-Dimethyl-4,4'-bipyridinium Dichloride Hydrate 1,1'-Dimethyl-4,4'-bipyridinium Dichloride 1,1'-Di-n-octyl-4,4'-bipyridinium Dibromide 1,1'-Diphenyl-4,4'-bipyridinium Dichloride

1g

25g 5g 5g 1g 1g

500g 25g 25g 5g 10g 5g 5g 1g

Others Product No. Product Name A0565 D3197 N0346 T1489

Unit Size

Azobenzene 3,3-Diphenyl-3H-naphtho[2,1-b]pyran 2,5-Norbornadiene (stabilized with BHT) Thioindigo

25g 25ml

500g 5g 500ml 25g

References 1) 2) 3) 4) 5) 6)

E. Fischer, Y. Hirshberg, . 1952, 4522. G. H. Brown, in S. Irie, T. Yamaguchi, H. Nakazumi, S. Kobatake, M. Irie, 2001, S. Kohata, M. Irie, , 19. M. Irie, . 2000, , 1685. 2003, number K. Matsuda, M. Irie, , 2.

, Wiley-Interscience, 1971. . 1999, , 1139.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

249

Liquid Crystals & Related Compounds

Liquid Crystals & Related Compounds Liquid crystals possess properties of both the liquid and solid phases, which results in the characteristic fluidity and optical birefringence (anisotropy) properties. Generally, the liquid crystal molecules consist of long chain moiety, rigid core and readily polarized functional groups. In some instances, they may form into plate shapes. In the liquid crystal state, the molecules are constrained to rotate, and line up into a regular array. Depending on how these molecules are arranged, the liquid crystal phases are classified as nematic, smectic or cholesteric phases. The regularity of these molecular arrangement is reflected in the anisotropic properties of permittivity and refractive index. Therefore, it is possible to control the optical property of the liquid crystal by changing the molecular arrangement electrically. The response speed of liquid crystals is fast due to the fluidity properties, and phase changes can easily occur both electrically and by heating.1) The application of liquid crystals for display purposes originated in HeiMeir when he and his co-workers (1968) reported using light scattering in the display material.2) Since then, Schiff base3) and azoxybenzene types4) were also developed; both have shown liquid crystalline state at room temperature. These developments have fundamentally contributed to today's prosperity within the liquid crystal industry. Some related compounds are shown as follows.

C0319

C0320 CH3 H3C

C0694 H3C H3C

CH3

CH3

H3C

C0617

C0618 H3C H3C

CH3 H3C

H3C

H3C H3C

CH3

HCOO

C0692 H3C H3C

CH3 H3C

CH3 CH3

H3C

COOH

C0321

H3C H3C

CH3(CH2)10COO

C0559

CH3

H3C CH3 H3C

CH3

H3C

H3C

CH3 CH3

H3C

C0334

CH3

H3C H3C

CH3 CH3

HOCO(CH2)2COO

H3C H3C

CH3

H3C

C0620

H3 C

C0675 CH3

C0674

H3C

CH3

H3C

CH3(CH2)4COO

CH3

CH3

H3C H3C

CH3(CH2)5COO

CH3

COO

Ph(CH2)2COO

CH3 CH3

H3C

H3C

COO

C0619

C0673

CH3

H3C

CH3

CH3(CH2)8COO

C0672

CH3

H3C

H3C H3C

PhCH=CHCOO

CH3

CH3

H3C

CH3 CH3

H3C

C0671

Cl

BzO

CH3

ClCOO

C1260

Cl

CH3COO

H3C

CH3 CH3

H3C

CH3

H3C

CH3

CH3(CH2)2COO

CH3

H3C

Cholesteryl Compounds

C0668

CH3 H3C

CH3

H3C

CH3 CH3

CH3 CH3

H3C

H3C

O O

250

O (CH2)7

(CH2)4CH3

O

O

CH3(CH2)6COO

(CH2)12CH3

O

(CH2)7

(CH2)7CH3

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Liquid Crystals & Related Compounds

C0322

N0347 CH3 H3C

C0693

CH3

CH3 H3C

CH3

H 3C

C0676

H3C

CH3(CH2)7COO

C0323 CH3 H3C

CH3

CH3 H3C

H3C

C0610 CH3 H3C

CH3

CH3 H

CH3

H3C

H3C

CH3(CH2)16COO

CH3CH2COO

C0695

CH3

H3C H

Unit Size 25g 25g

25g 10g 5g 25g 25g 10g 25g

C0720

CH3

CH3 H3C

CH3

H3C O

CH3(CH2)3O C O

C0725

C0719 CH3

CH3

H3C

CH3

CH3

CH3 H3C

CH3

H3C O CH3(CH2)5O C O

CH3 CH3

O

CH3(CH2)4O C O

H3C O CH3(CH2)6O C O

CH3 H3C H 3C

O

B0264 CH3 H3C

CH3 CH3

H 3C

Cholesteryl Alkyl Carbonates

500g 25g 500g 25g 25g 25g 25g 10g 25g 25g 10g 10g 10g 25g 500g 25g 25g 500g 25g 500g 10g 25g 500g 10g 10g 25g

C0718 CH3 H3C

CH3CH2O C O

H

Cholesterol Acetate Cholesterol Benzoate Cholesterol Butyrate Cholesterol Chloroformate Cholesterol trans-Cinnamate Cholesterol Decanoate Cholesterol 2,4-Dichlorobenzoate Cholesterol Formate Cholesterol Heptanoate Cholesterol Hexanoate Cholesterol Hydrocinnamate Cholesterol Hydrogen Phthalate Cholesterol Hydrogen Succinate Cholesterol Laurate Cholesterol Linoleate Cholesterol Myristate Cholesterol n-Octanoate Cholesterol Oleate Cholesterol Palmitate Cholesterol Pelargonate Cholesterol Phenylacetate Cholesterol Propionate Cholesterol Stearate Cholesterol Valerate Cholesteryl Bromide from Beef Fat Cholesteryl Chloride from Beef Fat

C0716

CH3

Cl

Product No. Product Name C0319 C0320 C0668 C0694 C0617 C0618 C1260 C0671 C0672 C0673 C0619 C0692 C0674 C0620 C0321 C0675 C0334 C0559 C0322 N0347 C0693 C0676 C0323 C0677 C0695 C0610

H

H H

Br

CH3

CH3 H3C

CH3

H H

CH3(CH2)3COO

CH3

H3C

PhCH2COO

C0677

CH3

H3C

CH3

H3C

H3C

CH3(CH2)14COO

CH3

CH3

CH3

CH3 CH3

CH3 CH3

H3C O (CH3)2CHCH2O C O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

251

Liquid Crystals & Related Compounds

C0717

C0715 CH3 H3C

B0256 CH3

CH3

C0721

CH3

H3C H3 C

H3C O

CH3 H3C

CH3

CH3O C O

CH3 CH3

H 3C

H3C O

O CH3(CH2)8O C O

O

(CH3)2CHO C O

CH3

CH3 H3C

CH3

CH3

CH3(CH2)7O C O

C0691 CH3

CH3

H3C

CH3

H3C

O O

O(CH2)8

(CH2)7CH3

Product No. Product Name C0720 C0718 C0716 B0264 C0725 C0719 C0717 C0715 B0256 C0721 C0691

Unit Size

Cholesterol Amyl Carbonate Cholesterol Butyl Carbonate Cholesterol Ethyl Carbonate Cholesterol Heptyl Carbonate Cholesterol Hexyl Carbonate Cholesterol Isobutyl Carbonate Cholesterol Isopropyl Carbonate Cholesterol Methyl Carbonate Cholesterol Nonyl Carbonate Cholesterol n-Octyl Carbonate Cholesterol Oleyl Carbonate

1g

1g 10g

C0772

10g 10g 10g 10g 10g 10g 10g 10g 10g 10g 25g

A0608 O O C O(CH2)4CH3

O HOOC

Carbonates

O C O(CH2)4CH3 C O

OCH2CH3

O

C0773

E0257

O HOOC

O C O(CH2)3CH3 CH3CH2O

M0261 O O C O O C

O O C OCH3

O O C OCH2CH3

OCH2CH3

Product No. Product Name C0772 A0608 C0773 E0257 M0261

Unit Size

Amyl 4-Carboxyphenyl Carbonate Amyl 4-(4-Ethoxyphenoxycarbonyl)phenyl Carbonate Butyl 4-Carboxyphenyl Carbonate 4-(4-Ethoxyphenoxycarbonyl)phenyl Ethyl Carbonate Methyl 4-(4'-Ethoxyphenoxycarbonyl)phenyl Carbonate

1g

B0063

B0077

Phenyl Esters

252

P0896 OH

O C O

1g 1g 5g 1g 1g

O Cl

C O

O CH3(CH2)4

C O

O(CH2)3CH3

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Liquid Crystals & Related Compounds

S0274

S0129

B1586 OH

OH

H0810

HOOC O

O t

C O

Bu

P0305

I0416

O

O C O

CH2 CHCH2CH2O

C O

CN

CH3(CH2)6

C O

CN

PhOOC

B0375

B1091

P0897

COOPh

H0766

COOPh O CH3(CH2)3

C O

OCH2CH3

O C O

CH3(CH2)3

O

O

O(CH2)5CH3

CH3(CH2)4

C O

O(CH2)5CH3

HO(CH2)6O

C O

OCH3

COOPh

M2106

B1108

A0842

S0146

B1092

O C O

OCH3

O

NH2 O

C O

OH O

C O

NO2

C O

NO2

O C O

CH3(CH2)3

O(CH2)7CH3

OCH2CH2CH CH2

P0898

S0016

B0075

O

OH O CH3(CH2)4

C O

S0017

O O(CH2)7CH3

C O

HO

OH

O C O

C O

T1370

OH

O

O

C O

C O

O CH3

CH3OOC

O C

Product No. Product Name B0063 B0077 P0896 S0274 S0129 B1586 H0810 I0416 P0305 B0375 B1091 P0897 H0766 M2106 B1108 A0842 S0146 B1092 P0898 S0016 B0075 H0218 H0797 S0017

H0797

O

C O

(CH2)7CH3

S0018 OH

H0218

Benzoic Acid 4-Chlorophenyl Ester Benzoic Acid 3-Hydroxyphenyl Ester 4-Butoxyphenyl 4-Pentylbenzoate 4-tert-Butylphenyl Salicylate 2-Carboxyphenyl Salicylate 4-Cyanophenyl 4-(3-Butenyloxy)benzoate 4-Cyanophenyl 4-Heptylbenzoate Diphenyl Isophthalate Diphenyl Phthalate 4-Ethoxyphenyl 4-Butylbenzoate 4-(Hexyloxy)phenyl 4-Butylbenzoate 4-Hexyloxyphenyl 4-Pentylbenzoate 4-(6-Hydroxyhexyloxy)benzoic Acid 4-Methoxyphenyl Ester 4-Methoxyphenyl 4-(3-Butenyloxy)benzoate 2-Naphthyl Benzoate 4-Nitrophenyl Anthranilate 4-Nitrophenyl Salicylate 4-n-Octyloxyphenyl 4-Butylbenzoate 4-n-Octyloxyphenyl 4-Pentylbenzoate 4-Octylphenyl Salicylate Phenyl Benzoate Phenyl 4-Hydroxybenzoate Phenyl 1-Hydroxy-2-naphthoate Phenyl Salicylate

O C O

COOCH3

Unit Size

25g 25g 1g 10g 25g

25g 5g

25g 25g 25g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 25g 1g 500g 500g 1g 5g 25g 500g 1g 1g 1g 100mg 1g 500g 25g 25g 1g 5g 25g 500g 500g 500g 500g

253

Liquid Crystals & Related Compounds

Product No. Product Name S0018 T1370

Unit Size

Salicylic Acid p-Tolyl Ester Terephthalic Acid Bis[4-(methoxycarbonyl)phenyl] Ester

25g 25g

B0253

B0261

N CH CH3(CH2)4O

Schiff Bases

B0372

B0252

CH N

B1713

B0374

CH N CH3(CH2)3O

O C CH3

CH N

CN

(CH2)4CH3 O

CH3(CH2)3O

CH

N

CN

CH3(CH2)3O C O

CH

N

OCH3

O(CH2)3CH3

B0255

C0743

C0744

C0742

O CH3O

CH N

CH

CH

C O(CH2)3CH3

E0254

CH3(CH2)3O

CN

E0262 O

CH

N CH

N

CH3CH2O

N CH

CN

E0240

CH3(CH2)5O

N CH

CN

M0602

(CH2)3CH3

C CH3 CH3CH2O

CH

N

CN

CH3O

CH N

CH CHCOOCH2CH3

OCH2CH3

N CH OCH2CH3

H0419

M0581

M0583

M0604

O CH CH3(CH2)5O

CH N

N

N N

O C CH3

CH3O

CN

N CH

OCH3

M0588

M0603

CH N

CH CHCOOH

CH3O

M0582

CH

N

CH CH

N

CN

OCH3

M0275 CH

CH3O

CH

CH3O

CH

N

(CH2)3CH3

N

OCH3

M0605

B0250

B0875

B0871 CH

N

F

OH CH3O

CH

N

OH

CH3O

CH N

CH3CH2O

(CH2)3CH3 CH

254

N

N CH

CH N

OCH2CH3

F

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Liquid Crystals & Related Compounds

Product No. Product Name B0253 B0261 B0372 B0252 B1713 B0374 B0255 C0743 C0744 C0742 E0254 E0262 E0240 M0602 H0419 M0581 M0583 M0604 M0588 M0603 M0582 M0275 M0605 B0250 B0875 B0871

Unit Size

4'-(Amyloxy)benzylidene-4-cyanoaniline Benzylidene-2-naphthylamine N-(4-Butoxybenzylidene)-4-acetylaniline 4'-Butoxybenzylidene-4-cyanoaniline 4-Butoxybenzylidene-4'-pentylaniline 4'-Butoxycarbonyloxybenzylidene-4-methoxyaniline Butyl 4-[(4-Methoxybenzylidene)amino]cinnamate 4'-Cyanobenzylidene-4-butoxyaniline 4'-Cyanobenzylidene-4-ethoxyaniline 4'-Cyanobenzylidene-4-hexyloxyaniline N-(4-Ethoxybenzylidene)-4-acetylaniline 4'-Ethoxybenzylidene-4-butylaniline 4'-Ethoxybenzylidene-4-cyanoaniline Ethyl 4-[(4-Methoxybenzylidene)amino]cinnamate 4'-Hexyloxybenzylidene-4-cyanoaniline N-(4-Methoxybenzylidene)-4-acetoxyaniline 4-[(4-Methoxybenzylidene)amino]azobenzene 4-[(4-Methoxybenzylidene)amino]benzonitrile 4-[(4-Methoxybenzylidene)amino]cinnamic Acid 4-[(Methoxybenzylidene)amino]stilbene N-(4-Methoxybenzylidene)aniline N-(4-Methoxybenzylidene)-4-butylaniline 4-(4-Methoxybenzylidene)-4-hydroxyaniline N-(4-Methoxy-2-hydroxybenzylidene)-4-butylaniline Terephthalbis(4-fluoroaniline) Terephthalbis(p-phenetidine)

25g

5g

5g

1g 25g 1g 1g 5g 1g 1g 1g 1g 1g 1g 500g 1g 1g 1g 25g 10g 1g 1g 1g 25g 25g 5g 1g 10g 25g

B0878

Cl

Benzidines

CH3O

Cl

CH N

N CH

OCH3

Product No. Product Name

Unit Size

3,3'-Dichloro-N,N '-bis(4-methoxybenzylidene)benzidine

B0878

25g

A0554

CH3O

A0683

N N

Azoxybenzenes

D1093

CH3(CH2)4O

D1096

N

N O

O(CH2)4CH3

OCH3 CH3CH2O

CH3(CH2)3O

D0553

N

N O

O(CH2)3CH3

CH3(CH2)11O

N N

OCH2CH3

O

O

A1065

N

N O

O O(CH2)11CH3 CH CH O C 3 2

N N

O C OCH2CH3

O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

255

Liquid Crystals & Related Compounds

D1092

CH3(CH2)5O

D1518

N

N

O(CH2)5CH3

CH3(CH2)8O

O

D1123

N

N

O(CH2)8CH3

CH3(CH2)7O

O

D1094

N

N

O(CH2)7CH3

CH3CH2CH2O

N N

Product No. Product Name A0554 A0683 D1093 D1096 D0553 A1065 D1092 D1518 D1123 D1094

Unit Size

4,4'-Azoxydianisole 4,4'-Azoxydiphenetole 4,4'-Diamyloxyazoxybenzene 4,4'-Dibutoxyazoxybenzene 4,4'-Didodecyloxyazoxybenzene Diethyl Azoxybenzene-4,4'-dicarboxylate 4,4'-Dihexyloxyazoxybenzene 4,4'-Dinonyloxyazoxybenzene 4,4'-Di-n-octyloxyazoxybenzene 4,4'-Dipropoxyazoxybenzene

5g 1g 1g

25g 5g 5g 1g 5g 1g 1g 100mg 1g 5g 5g

A1828

Cyanobiphenyls & Analogs

C1606

C1550

CN CH3(CH2)4

CH3(CH2)6O

H0812

CH3(CH2)4

CN CH3(CH2)6

CN

C1551

CN CH3(CH2)4O

CN

Product No. Product Name A1828 H0812 C1606 C1550 C1551

OCH2CH2CH3

O

O

Unit Size

4-(trans-4-Amylcyclohexyl)benzonitrile 4-Cyano-4'-heptylbiphenyl 4-Cyano-4'-heptyloxybiphenyl 4-Cyano-4'-pentylbiphenyl 4-Cyano-4'-pentyloxybiphenyl

5g 1g 1g

5g 1g

25g 5g 1g 25g 5g

Nematic Crystals Product No. Product Name T0697 T0698 T0699

Unit Size

Liquid Crystal, TK-LQ 2040 Electric effect type, Mesomorphic range:20-40℃ Liquid Crystal, TK-LQ 3680 Electric effect type, Mesomorphic range:36-80℃ Liquid Crystal, TK-LQ 3858 Electric effect type, Mesomorphic range:38-58℃

1g 1g 1g

References 1) 2) 3) 4)

256

H. Hattori, Y. Kakuno, G. H. HeilMeier, L. A. Zanoni, L. A. Barton, . 1968, H. Kelker, B. Scheurle, . 1969, , 884. R. Steinstrasser, L. Pohl . 1971, , 1921.

1984,

, 13.

, 1162.

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Building Blocks for Liquid Crystals

Building Blocks for Liquid Crystals The first nematic liquid crystal materials, the Schiff base types, were sensitive to moisture, while the azoxybenzene types were sensitive to light. Therefore, research to improve the stability of liquid crystals to moisture and lights had been undertaken. The chemically stable biphenylcarboxylates and cyanobiphenyls were developed one after another. The cyanobiphenyls were found to be exceptional in possessing the necessary properties of display material. They exhibited low viscosity and low voltage operation, leading to many reports on the cyanobiphenyls. The phenylcyclohexane-based liquid crystals also have low viscosity and high response speeds, thus drawing to attention their use as display material. Furthermore, these bicylic liquid crystals were modified by the addition of benzene and cyclohexane rings to produce tricyclic and tetracyclic liquid crystals. As a result, the upper range of temperature was increased. In recent years, further improvements in the various physical properties were made by introduction of fluorine and another functional groups to the liquid crystals, and there are now widely used. The optically active compounds are important components of chiral nematic liquid crystals and chiral smectic liquid crystals. More recently, antiferroelectric liquid crystals of the chiral smectic liquid crystal type, are now undergoing vigorous synthetic studies to develop novel liquid crystal compounds. Larger high-resolution displays are the target for the next generation of liquid crystal materials.

A1410

A1322

B1866

O

Br

Biphenyls

B1304

CH3(CH2)6

H0690

Br

C1239

HO

Cl

OH

CH3(CH2)6

CN

CH3(CH2)4O

CN

CH3(CH2)5O

Br

CH3(CH2)6O

CN

CH3(CH2)9O

CN

Br

HO

COOH

CH3(CH2)4O

CN

HO

COOH

CH3

CN

D1082

O(CH2)4CH3

F0704

CH2CH3

t Bu

C1741

D1090

E0463

O(CH2)5CH3

CH3(CH2)2

C O

B1986

H0523

D2041

D1089

OCH2CH3

CH3(CH2)4

COCH3

B1306

C1606

C1551

D1127

CH3CH2O

B1305

H0812

C1550

CH3(CH2)4

Br

COCH3 CH3

CH3(CH2)3O

O(CH2)3CH3

H0708

F

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

CO(CH2)5CH3

257

Building Blocks for Liquid Crystals

H0709

CH3(CH2)6

H0710

HO

CO(CH2)4CH3

COOH

H0695

H0711

B1924

COOH

CH3(CH2)5

H0767

COOH

O0214

O(CH2)17CH3

HOCH2(CH2)5O

H0819

OCH3

P1133

CO(CH2)6CH3

CH3O

OH

P1212

COCH2CH3

(CH2)4CH3

P1037

CH3CH2CH2

COOH

Product No. Product Name A1410 A1322 B1866 B1304 H0690 B1305 B1306 B1986 C1239 H0812 C1606 H0523 C1741 C1550 C1551 D2041 D1090 D1082 D1127 D1089 E0463 F0704 H0708 H0709 H0710 H0711 H0767 H0819 H0695 B1924 O0214 P1133 P1212 P1037

258

4-Acetyl-4'-bromobiphenyl 4-Acetyl-4'-methylbiphenyl 4-Biphenyl Benzoate 4-Bromo-4'-heptylbiphenyl 4-Bromo-4'-hydroxybiphenyl 4-Bromo-4'-pentylbiphenyl 4-Bromo-4'-propylbiphenyl 4-(4-tert-Butylphenyl)benzoic Acid 4-Chloro-4'-hydroxybiphenyl 4-Cyano-4'-heptylbiphenyl 4-Cyano-4'-heptyloxybiphenyl 4-Cyano-4'-hydroxybiphenyl 4-Cyano-4'-methylbiphenyl 4-Cyano-4'-pentylbiphenyl 4-Cyano-4'-pentyloxybiphenyl 4'-Decyloxybiphenyl-4-carboxylic Acid 4,4'-Diamyloxybiphenyl 4,4'-Dibutoxybiphenyl 4,4'-Diethoxybiphenyl 4,4'-Dihexyloxybiphenyl 4-Ethylbiphenyl 4-Fluoro-4'-hydroxybiphenyl 4-Heptanoylbiphenyl 4-(4-Heptylphenyl)benzoic Acid 4-Hexanoylbiphenyl 4-(4-Hexylphenyl)benzoic Acid 4-(6-Hydroxyhexyloxy)-4'-methoxybiphenyl 4-Hydroxy-4'-methoxybiphenyl 4-(4-Hydroxyphenyl)benzoic Acid 4-Octadecyloxybiphenyl 4-n-Octanoylbiphenyl 4-Pentylbiphenyl 4-Propionylbiphenyl 4-(4-Propylphenyl)benzoic Acid

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 5g 5g 5g 1g 1g 1g

1g

5g 5g 5g 1g 1g

5g

1g 5g

5ml 5g

25g 5g 25g 5g 25g 5g 25g 5g 5g 5g 1g 25g 25g 25g 5g 5g 5g 25g 5g 5g 25g 25g 25g 5g 10g 5g 1g 5g 25g 25g 10g 25ml 25g 10g

Building Blocks for Liquid Crystals

A0885

A1024

A0269

COOH

COOH

COOH

OCOCH3

COCH3

NH2

Benzoic Acids

A0741

A0708

A0482

COOH

(CH2)4CH3

B1950

B0553

COOH

COOH

COOH

O(CH2)4CH3

OCH3

OBn

Br

B1585

B0896

COOH

COOH

B1665

COOH

B0241 COOH

D2859 COOH

COOH

F

OCH2CH2CH

Br

E0045

CH2

E0379

O(CH2)3CH3

F0337

(CH2)3CH3

H0774

COOH

COOH

COOH

OCH2CH3

CH2CH3

O(CH2)7CH3

O(CH2)11CH3

H0792 COOH

COCl

F

H0248

H0829

H0247

COOH

COOH

O(CH2)6CH3

(CH2)5CH3

H0695

O0137

HO

H0207

(CH2)6CH3

H0642

COOH

COOH

O(CH2)5CH3

OH

O0117 COOH

(CH2)6CH3

P0206

COOH

O

OH

P0945

COOH

COOH

COOH

O(CH2)7CH3

OCH2CH2CH3

CH2CH2CH3

COOH

(CH2)7CH3

T0293

U0072 COOH

COOH

CH3

O(CH2)10CH3

Product No. Product Name A0885 A1024 A0269 A0741 A0708 A0482

4-Acetoxybenzoic Acid 4-Acetylbenzoic Acid 4-Aminobenzoic Acid 4-Amylbenzoic Acid 4-Amyloxybenzoic Acid p-Anisic Acid

Unit Size

5g

25g 1g 25g 25g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500g 5g 500g 250g 25g 500g

259

Building Blocks for Liquid Crystals

Product No. Product Name B1665 B0553 B1950 B1585 B0896 B0241 D2859 E0045 E0379 F0337 H0774 H0792 H0248 H0829 H0247 H0207 H0642 H0695 O0137 O0117 P0206 P0945 T0293 U0072

Unit Size

4-Benzyloxybenzoic Acid 4-Bromobenzoic Acid 4-Bromo-2-fluorobenzoic Acid 4-(3-Butenyloxy)benzoic Acid 4-Butoxybenzoic Acid 4-Butylbenzoic Acid 4-(Dodecyloxy)benzoic Acid 4-Ethoxybenzoic Acid 4-Ethylbenzoic Acid 3-Fluoro-4-n-octyloxybenzoic Acid 4-Heptylbenzoic Acid 4-Heptylbenzoyl Chloride 4-(Heptyloxy)benzoic Acid 4-Hexylbenzoic Acid 4-(Hexyloxy)benzoic Acid 4-Hydroxybenzoic Acid 4-(4-Hydroxyphenoxy)benzoic Acid 4-(4-Hydroxyphenyl)benzoic Acid 4-n-Octylbenzoic Acid 4-n-Octyloxybenzoic Acid 4-Propoxybenzoic Acid 4-Propylbenzoic Acid p-Toluic Acid 4-Undecyloxybenzoic Acid

5g 25g 5g

5g 5g

1g 5g 25g

1g

25g 25g 1g 5g 5g

25g 25g

A1467

A0707

25g 500g 25g 5g 25g 25g 25g 25g 25g 5g 10g 25g 500g 5g 500g 500g 5g 25g 25g 25g 25g 500g 500g 5g

A0480

CHO

CHO

CHO

OCOCH3

O(CH2)4CH3

OCH3

Benzaldehydes

B1325

B0549

B2002

CHO

B0126 CHO

CHO

B1014 CHO

CHO

F

OBn

Br

D1124

E0042

E0325

H0238

(CH2)3CH3

H0166

CHO

CHO

CHO

CHO

CHO

O(CH2)9CH3

OCH2CH3

CH2CH3

O(CH2)6CH3

O(CH2)5CH3

H0198

260

O(CH2)3CH3

Br

O0223

O0116

P0182

T0259

CHO

CHO

CHO

CHO

CHO

OH

O(CH2)17CH3

O(CH2)7CH3

OCH2CH2CH3

CH3

Product No. Product Name

Unit Size

A1467 A0707 A0480 B1325 B0549 B2002

5g 25ml 25ml 25g 25g 5g

4-Acetoxybenzaldehyde 4-Amyloxybenzaldehyde p-Anisaldehyde 4-Benzyloxybenzaldehyde 4-Bromobenzaldehyde 4-Bromo-2-fluorobenzaldehyde

Availability, price or specification of the listed products are subject to change without prior notice.

25g 500ml 500ml 500g 250g 25g

Building Blocks for Liquid Crystals

Product No. Product Name B0126 B1014 D1124 E0042 E0325 H0238 H0166 H0198 O0223 O0116 P0182 T0259

Unit Size

4-Butoxybenzaldehyde 4-Butylbenzaldehyde 4-Decyloxybenzaldehyde 4-Ethoxybenzaldehyde 4-Ethylbenzaldehyde 4-Heptyloxybenzaldehyde 4-(Hexyloxy)benzaldehyde 4-Hydroxybenzaldehyde 4-Octadecyloxybenzaldehyde 4-n-Octyloxybenzaldehyde 4-Propoxybenzaldehyde p-Tolualdehyde

5ml 5g 25g 25ml

25g

25ml

A0384

A0728

25ml 25ml 25g 500g 500ml 25ml 25g 500g 5g 25g 25ml 500ml

P0843

OH

OH

OH

NH2

O(CH2)4CH3

(CH2)4CH3

Phenols

H0239

B0945

B1835

OH

H0690

B0787

OH HO

C

OH F

CF3 OH

Br

OH

CF3

CH2Ph

B0923

Br

Br

B1026

C0400

D2304

OH

OH

OH

E0216 OH

OH CH3

O(CH2)3CH3

E0159

(CH2)3CH3

F0160 OH

CH2CH3

H0611

H0441

H0615

H0439

OH

OH

OH

OH

F

O(CH2)6CH3

(CH2)6CH3

O(CH2)5CH3

H0198 OH

OCH2CH3

(CH2)11CH3

CH3

H0207 OH

H0642 OH

H0695

COOH

HO

(CH2)5CH3

M0123

CHO

COOH

H0825 OH

OCH3

O0140

O C O

OH

OCH3

O

COOH

OH

P0955

P0698

OH

OH

OH

O(CH2)7CH3

OCH2CH2CH3

CH2CH2CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

261

Building Blocks for Liquid Crystals

Product No. Product Name A0384 A0728 P0843 H0239 B0945 B1835 H0690 B0787 B0923 B1026 C0400 D2304 E0216 E0159 F0160 H0441 H0615 H0439 H0611 H0198 H0207 H0642 H0695 M0123 H0825 O0140 P0955 P0698

Unit Size

4-Aminophenol 4-(Amyloxy)phenol 4-Amylphenol 4-Benzylphenol 2,2-Bis(4-hydroxyphenyl)hexafluoropropane 4-Bromo-2-fluorophenol 4-Bromo-4'-hydroxybiphenyl 4-Bromophenol 4-Butoxyphenol 4-Butylphenol p-Cresol 4-Dodecyl-o-cresol 4-Ethoxyphenol 4-Ethylphenol 4-Fluorophenol 4-Heptyloxyphenol 4-Heptylphenol 4-Hexyloxyphenol 4-Hexylphenol 4-Hydroxybenzaldehyde 4-Hydroxybenzoic Acid 4-(4-Hydroxyphenoxy)benzoic Acid 4-(4-Hydroxyphenyl)benzoic Acid 4-Methoxyphenol 4-Methoxyphenyl 4-Hydroxybenzoate 4-n-Octyloxyphenol 4-Propoxyphenol 4-Propylphenol

25g 25ml 25g 5g 5g 5g 25g 25g 5g 25g 25g 25g 25g 5g 5g 5g 25g 25g 1g 5g 25g 5g 5g 5g

A0269

A0384

500g 5g 500ml 500g 25g 25g 25g 500g 500g 25g 500g 10g 500g 500g 500g 5g 25g 25g 25g 500g 500g 5g 25g 500g 25g 25g 25g 25g

A0938

NH2

NH2

COOH

OH

NH2

Anilines

A0487

B1393

B1003

B0272

NH2

NH2

NH2

OCH3

Br

O(CH2)3CH3

H0588

H0890 NH2

(CH2)6CH3

O0186 NH2

(CH2)5CH3

E0061

(CH2)7CH3

(CH2)3CH3

CH2CH3

B0271 NH2

NH2

OCH2CH3

CH2CH2CH3

T0300 NH2

CH3

262

NH2

NH2

P0090 NH2

(CH2)4CH3

Availability, price or specification of the listed products are subject to change without prior notice.

Building Blocks for Liquid Crystals

Product No. Product Name A0269 A0384 A0938 A0487 B1393 B1003 B0272 E0061 H0588 H0890 O0186 P0090 B0271 T0300

Unit Size

4-Aminobenzoic Acid 4-Aminophenol 4-Amylaniline p-Anisidine 4-Bromoaniline 4-Butoxyaniline 4-Butylaniline 4-Ethylaniline 4-Heptylaniline 4-Hexylaniline 4-n-Octylaniline p-Phenetidine 4-Propylaniline p-Toluidine

25g 25g 25g 25g 5g 25ml 25ml 5ml 5g 25g 25g

B0537

B1501

500g 500g 25ml 500g 500g 25g 500ml 500ml 25ml 25g 25g 500g 25ml 500g

B1000

COCH3

COCH3

Br

O(CH2)3CH3

COCH3

Acetophenones

E0318

H0678 COCH3

H0669 COCH3

CH2CH3

(CH2)6CH3

O0207

P1035 COCH3

(CH2)5CH3

M0135 COCH3

COCH3

OCH3

CH3

P1036 COCH3

(CH2)7CH3

M0105 COCH3

(CH2)3CH3

COCH3

(CH2)4CH3

CH2CH2CH3

Product No. Product Name B0537 B1501 B1000 E0318 H0678 H0669 M0105 M0135 O0207 P1035 P1036

Unit Size

4'-Bromoacetophenone 4'-Butoxyacetophenone 4'-Butylacetophenone 4'-Ethylacetophenone 4'-Heptylacetophenone 4'-Hexylacetophenone 4'-Methoxyacetophenone 4'-Methylacetophenone 4'-n-Octylacetophenone 4'-Pentylacetophenone 4'-Propylacetophenone

25g 25g 25ml

25g 25ml 5g 25g

A0695

A1213 CN

500g 5g 500g 500ml 25ml 25g 500g 500ml 25g 25g 500g

A1249 CN CF3 NC

Benzonitriles NH2

NH2

NH2

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

263

Building Blocks for Liquid Crystals

B1365

B1426

C0135

C1141

C0443

CN

CN

CN

CN

CN

OBn

Br

Cl

COCH3

CHO

C0445

C1182 CN

C1985

C1299

H0523

CN

CN

CN COOH

F0221

H0778

C0842

P1617

CN

CN CH3CH2

CN

CH2Cl

COCl

E0703

HO

CN

CN

CH3CH2CH2

(CH2)6CH3

F

CN

OH

T0307 CN

CH3

Product No. Product Name A0695 A1213 A1249 B1365 B1426 C0135 C1141 C0443 C0445 C1182 C1985 C1299 H0523 E0703 F0221 H0778 C0842 P1617 T0307

Unit Size

4-Aminobenzonitrile 5-Amino-2-cyanobenzotrifluoride 4-Amino-4'-cyanobiphenyl 4-Benzyloxybenzonitrile 4-Bromobenzonitrile 4-Chlorobenzonitrile 4'-Cyanoacetophenone 4-Cyanobenzaldehyde 4-Cyanobenzoic Acid 4-Cyanobenzoyl Chloride 4-Cyanobenzyl Chloride 4-Cyanobiphenyl 4-Cyano-4'-hydroxybiphenyl 4-(trans-4-Ethylcyclohexyl)benzonitrile 4-Fluorobenzonitrile 4-Heptylbenzonitrile 4-Hydroxybenzonitrile 4-(trans-4-Propylcyclohexyl)benzonitrile p-Tolunitrile

10g 1g 1g

5g

25g 25g 10g 5g 25g 5g 5g 5g 25g 1ml 25g 25g

B2986

B1136

M1621

O

O

O

C OH

C OH

C OH

4-Alkylcyclohexanecarboxylic Acids (CH2)3CH3

264

(CH2)3CH3

Availability, price or specification of the listed products are subject to change without prior notice.

CH3

250g 5g 5g 25g 250g 500g 25g 25g 250g 25g 25g 25g 25g 5g 500g 5ml 500g 5g 500g

Building Blocks for Liquid Crystals

M1783

P0944

P1656

P0943

O

O

O

O

C OH

C OH

C OH

C OH

CH2CH2CH3

CH2CH2CH3

(CH2)4CH3

CH3

Product No. Product Name B2986 B1136 M1621 M1783 P0944 P1656 P0943

Unit Size

4-Butylcyclohexanecarboxylic Acid (cis- and trans- mixture) trans-4-Butylcyclohexanecarboxylic Acid 4-Methylcyclohexanecarboxylic Acid (cis- and trans- mixture) trans-4-Methylcyclohexanecarboxylic Acid trans-4-Pentylcyclohexanecarboxylic Acid 4-Propylcyclohexanecarboxylic Acid (cis- and trans- mixture) trans-4-Propylcyclohexanecarboxylic Acid

B1907

5g 5g 5g 5g 5g 5g 5g

B1611

B1612 B1802 Br

Br

25g 25g 25g 25g 25g 25g 25g

Br

4-Alkylbromobenzenes

B1879

B1608

B1606 Br

Br

B1889

B1605 Br

(CH2)4CH3

Br

(CH2)7CH3

(CH2)8CH3

B0661 Br

Br

CH2CH2CH3

CH3

Product No. Product Name B1907 B1611 B1612 B1802 B1879 B1608 B1606 B1596 B1610 B2117 B1605 B1889 B0661

B1610 B2117 Br

(CH2)5CH3

(CH2)6CH3

CH2CH3

B1596 Br

(CH2)11CH3

(CH2)9CH3

(CH2)3CH3

1-Bromo-4-butylbenzene 1-Bromo-4-decylbenzene 1-Bromo-4-dodecylbenzene 1-Bromo-4-dodecylbenzene 1-Bromo-4-ethylbenzene 1-Bromo-4-heptylbenzene (stabilized with Copper chip) 1-Bromo-4-hexylbenzene 1-Bromo-4-nonylbenzene 1-Bromo-4-n-octylbenzene 1-Bromo-4-n-octylbenzene 1-Bromo-4-pentylbenzene 1-Bromo-4-propylbenzene 4-Bromotoluene

Unit Size 1g

5g 5g 5g 5g 1g 5g 5g 5g 5g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 25g 25g 25g 25g 5g 25g 25g 25g 5g 25g 5g 500g

265

Building Blocks for Liquid Crystals

A1024

A0269

A1278

COOH

COOH

COOH

COCH3

NH2

NH2

Bifunctional Compounds

A0384

B1665

B1104

B0537

B1393

OH

COOH

OH

COCH3

NH2

NH2

OBn

OBn

Br

Br

B0549

B0553 CHO

H0690

H0198

COOH Br

Br

H0642

COOH

OH

OH

OH

Br

H0612

H0207 CHO

H0695

COOH COOH HO

COOH

HO O

OH

Product No. Product Name A1024 A0269 A1278 A0384 B1665 B1104 B0537 B1393 B0549 B0553 H0690 H0198 H0207 H0612 H0642 H0695

Unit Size

4-Acetylbenzoic Acid 4-Aminobenzoic Acid 4-Aminocyclohexanecarboxylic Acid (cis- and trans- mixture) 4-Aminophenol 4-Benzyloxybenzoic Acid 4-(Benzyloxy)phenol 4'-Bromoacetophenone 4-Bromoaniline 4-Bromobenzaldehyde 4-Bromobenzoic Acid 4-Bromo-4'-hydroxybiphenyl 4-Hydroxybenzaldehyde 4-Hydroxybenzoic Acid 6-Hydroxy-2-naphthoic Acid 4-(4-Hydroxyphenoxy)benzoic Acid 4-(4-Hydroxyphenyl)benzoic Acid

H0923

5g

H1201 OAc

266

OH Br

OH

AcO

Br

HO

AcO

Br

HO

. xH2O

Br

OAc OAc

5g 500g 25g 500g 25g 500g 500g 500g 250g 500g 25g 500g 500g 500g 5g 25g

H0907 Br

OAc

Building Blocks for Discotic Liquid Crystals

1g 25g 5g 25g 5g 25g 25g 25g 25g 25g 5g 25g 25g 25g 1g 5g

Br

Availability, price or specification of the listed products are subject to change without prior notice.

OH OH

Building Blocks for Liquid Crystals

H0898 OCH3 OCH3 CH3O CH3O OCH3 OCH3

Product No. Product Name H0923 H1201 H0907 H0898

Unit Size

2,3,6,7,10,11-Hexaacetoxytriphenylene 2,3,6,7,10,11-Hexabromotriphenylene 2,3,6,7,10,11-Hexahydroxytriphenylene Hydrate 2,3,6,7,10,11-Hexamethoxytriphenylene

100mg 100mg 1g 5g 1g 5g

Chiral Compounds Product No. Product Name B0926 B0925 C2109 C1377 C1365 C1372 C1371 C1373 L0144 M0170 M0965 M0964 H0705 H0704 H0703 H0702 L0136 M0966 M0963 O0145 O0144 P0744 P0743 P0795 P0796

(R)-(-)-2-Butanol (S)-(+)-2-Butanol (R)-2-Chlorobutyric Acid (S)-2-Chlorobutyric Acid (S)-2-Chloro-3-methylbutyric Acid (2S,3S)-2-Chloro-3-methylvaleric Acid (S)-2-Chloro-4-methylvaleric Acid (S)-(-)-2-Chloropropionic Acid Lithium L-Lactate (S)-(-)-2-Methyl-1-butanol (S)-(+)-5-Methyl-1-heptanol (S)-(+)-4-Methyl-1-hexanol Methyl (R)-(-)-3-Hydroxybutyrate Methyl (S)-(+)-3-Hydroxybutyrate Methyl (R)-(-)-3-Hydroxyisobutyrate Methyl (S)-(+)-3-Hydroxyisobutyrate Methyl D-(+)-Lactate (S)-(+)-6-Methyl-1-octanol (S)-(+)-3-Methyl-1-pentanol (R)-(-)-2-Octanol (S)-(+)-2-Octanol (R)-(-)-2-Pentanol (S)-(+)-2-Pentanol (R)-(+)-1-Phenylethyl Alcohol (S)-(-)-1-Phenylethyl Alcohol

Unit Size

1g

1ml 1ml 1g 1g 1g 1g 1g 5g

1g 1g

1ml 10ml 5ml 5g 5g 5g 1ml 1ml 5ml 5ml 1ml 1ml 5g 5g

5ml 5ml 5g 5g 5g 5g 5g 25g 25g 25ml 1ml 5ml 25ml 25ml 25g 25g 25g 5ml 5ml 25ml 25ml 5ml 5ml 25g 25g

Others Product No. Product Name B2127 B0884 B1772 B2297 B2741 D2151 E0505 E0564 F0423 H0234 H0385 H1175 H0612 H0995 M0586 M0576 T1773

1-Benzyloxy-4-bromobenzene 4-Bromofluorobenzene 1-Bromo-4-(trifluoromethoxy)benzene 4-Butylbenzoyl Chloride 4-Butyl-4'-hydroxychalcone 1,4-Diethynylbenzene 4-Ethynylaniline 1-Ethynyl-4-hexylbenzene 4-(4-Fluorophenylethynyl)phenol 2-Hydroxychalcone 2'-Hydroxychalcone trans-4-Hydroxycyclohexanecarboxylic Acid 6-Hydroxy-2-naphthoic Acid 6-Hydroxy-2-naphthonitrile 2-[(4-Methoxybenzylidene)amino]fluorene 4-Methoxycinnamic Acid 4-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)

Unit Size 5g 25g 5g 5g 1g 5g

5g

5g 25g 5g 25g

5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 500g 25g 25g 1g 5g 10g 25g 1g 25g 500g 25g 500g 5g 5g 25g 25g

267

Building Blocks for Liquid Crystals

References 1) 2) 3) 4) 5) 6)

268

1992, T. Kitamura, , 72. 1998, H. Numata, , 40. 1995, Y. Suzuki, , 8. 1997, , 9. T. Inukai, K. Miyazawa, G. W. Gray, G. R. Luckhurst, in P. G. Gennes, J. Prost, in

, Academic Press, 1979, pp.1-29, pp.263-284. , Oxford University Press, 1993.

Availability, price or specification of the listed products are subject to change without prior notice.

Organic Nonlinear Optical Materials

Organic Nonlinear Optical Materials The nonlinear optical material is a general term for the materials efficiently make appearance of nonlinear phenomenons optically as the responses to optical wavelength conversion, optical amplification as well as the refractive index changes due to its intensity. Nonlinear optical materials are largely divided into inorganic and organic materials. In 1930, the nonlinear optical effect related to optical wavelength conversion was predicted, which was said to be the first finding knowledge about the nonlinear optical phenomenon. In 1960, laser oscillation using inorganic material was reported. Since then researches of inorganic nonlinear optical materials were actively taken place, but now-a-days, probably there is no more that undiscovered. On the other hand, the 1982 ACS symposium report added momentum to the organic nonlinear optical material studies. Since then the studies have started to become active. It revealed organic compounds with the delocalized conjugated electrons which have excellent nonlinear optical property and high-speed responsiveness due to high mobility of electrons. The 21st Century is said to be an age of photonics. As one of the basic technology of photonics, improvements of the wavefront control technology using organic nonlinear optical effects are considered very important. Now R&D on the organic materials with excellent nonlinear optical properties, and vigorous applied studies have been carried out.

A0621

A1251

A0838

A0794

NO2 O2N

O2N

O2N

NO2

NH2

NH2

C0214

C0943

N

C1209 NH2

NH2

N

C1349

D2020 CH3

NHCH3 Cl

NH2

Cl

D2263

N(CH3)2

N CH2CN

Cl

N

O

NH C CH3

CH3 O2 N

N CH3

NO2

NO2

D2505

NO2

NO2

D0289

D2135

H0747

M0997

O CH3

O O2N

CH CH

N

CH3 CH3

H3C

CH3

N H

N H

OCH3 O2N

HN

M0909

M0985 NO2

CH3 O2N

CH CH

OCH3

N H

M1011

N H

N0529 NHCH3

NO2

CH3

N

NH2 CH3

N NO2

M1677

N0527

M0953 NO2

NH2

CH3

NO2

N0118 NHCH3

CH3

NO2

OCH3

NO2

O2N

M0999

OH O2N

CH3

N0117 NH2

NH2 NO2

N O

NO2

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

NO2

269

Organic Nonlinear Optical Materials

N0119

N0400

N0547

N0546

N0540

NH2 O2N N H

HOCH2

N H

NO2

O2N

NO2

CH3

NO2 N

N HOCH2

N H

N

N

HOCH2

N0281 O O2N

NH N H

O

Product No. Product Name A0621 A1251 A0838 A0794 C0943 C0214 C1209 C1349 D2020 D2263 D2505 D0289 D2135 H0747 M0997 M0999 M0909 M0985 M1011 N0529 M1677 N0527 M0953 N0118 N0117 N0119 N0400 N0547 N0546 N0540 N0281

2-Aminofluorene 4-Amino-4'-nitrobiphenyl 2-Amino-3-nitropyridine 2-Amino-5-nitropyridine 2-Chloro-3,5-dinitropyridine 2-Chloro-4-nitroaniline 2-Chloro-4-nitro-N-methylaniline N-Cyanomethyl-N-methyl-4-nitroaniline 2'-(N,N-Dimethylamino)-5'-nitroacetanilide 4-Dimethylamino-4'-nitrobiphenyl 4-Dimethylamino-4'-nitrostilbene 1,3-Dimethylurea N-(2,4-Dinitrophenyl)-L-alanine Methyl Ester 4-Hydroxy-4'-nitrobiphenyl 4-Methoxy-4'-nitrobiphenyl 4-Methoxy-4'-nitrostilbene (R)-(+)-2-(α-Methylbenzylamino)-5-nitropyridine (S)-(-)-2-(α-Methylbenzylamino)-5-nitropyridine N-Methyl-4-nitroaniline 2-Methyl-4-nitroaniline 3-Methyl-4-nitroaniline 3-Methyl-4-nitropyridine N-Oxide N-Methyl-4-nitro-o-toluidine 2-Nitroaniline 3-Nitroaniline 4-Nitroaniline 5-Nitroindole (S)-(-)-N-(5-Nitro-2-pyridyl)alaninol (S)-N-(5-Nitro-2-pyridyl)phenylalaninol (S)-(-)-N-(5-Nitro-2-pyridyl)prolinol 5-Nitrouracil

Unit Size 5g 1g 25g 1g 25g

1g 25g 1g 100mg

1g 25g 5g 5g 25g 25g 25g 5g

1g 5g

25g 5g 5g 250g 5g 500g 5g 5g 1g 5g 5g 500g 1g 5g 1g 5g 5g 5g 500g 25g 25g 25g 5g 500g 500g 500g 25g 100mg 1g 5g 25g

References 1) 2) 3) 4) 5) 6)

270

S. Miyata, ., Preprints of IUPAC 32nd International Symposium on Macromolecules, Kyoto, 1988, p.582. D. S. Chemla, ., in , Academic Press, New York, 1987. L. M. Hyden, . 1987, , 351. C. Flytzanis, ., in , Springer, Berlin, 1986. P. N. Prasad, ., in , Plenum, New York, 1988. A. J. Heeger, ., in , Material Research Society, Pittsbourgh, 1988.

Availability, price or specification of the listed products are subject to change without prior notice.

Phthalonitriles & Naphthalonitriles

Phthalonitriles & Naphthalonitriles Phthalocyanines (Pc) are the general term for compounds that contain the tetrabenzotetraazap-orphine (H2-Pc) ring, which is the porphyrin analog and metal phthalocyanines (M-Pc). M-Pc has attractive physical properties associated with their structures, and this has led to a broad spectrum of studies being done on synthetic methods and properties. Amongst the many synthetic methods, ones using 1,2-dicyanobenzene or 1,3-diiminoisoindoline, are the most common, since these methods produce the products in high purity.1) M-Pc possesses a large delocalized π electron system due to the tetraazaporphine ring, which leads to interesting and useful photochemical properties. The photochemical and photophysical properties of these systems have been studied extensively, and some of these compounds have been put to practical use. The weather-resistant blue and green pigments are one example, and in other examples, the photoelectric properties have been applied to optical memory disks, luminescent devices and solar batteries. M-Pc is also utilized as carrier-generation-layer of electrophotographic photoconductor.2) Furthermore, M-Pc has redox properties which find use as an electrochromic material3), which results in a reversible discoloration phenomenon caused by changing the applied electric potential. M-Pc is also used as a deodorant and antibacterial agent by selection of the appropriate central metals and the making of pendant-type polymers.1) In other examples, M-Pc has uses in M-Pc derivative sensor4), liquid crystal5), photochemical therapy for cancer and many others. M-Pc is the functional material of the 21st-Century, and more is anticipated upon further research and development. A1166

B1353

H2N

CH3(CH2)3O

CN

Phthalonitriles

B1334

CN

D2189

D1610

D3963

Cl

CN

CN

D2079

Cl

CN

CN

NH CN

CH3 O

C

NH

CN

CH3

F

D2237 CH3

NH

F

OH

D1983

CN CN

CN

OH CN

Bu

CN

CN

C1163

t

H0691

H0813

M1379

CN CH3(CH2)11O

O

CN

CH3(CH2)5O

CN

HO

CN

CH3

CN

CN CN

CN

CN

CN

CH3

N0566

N0524 NO2 CN

P1071

O2N

CN CN

CN

T0988

CH3(CH2)4O

P0404

P1070

CN

CN

CN

CN

CH3CH2CH2O

CN CN

T1402 F

NC

CN

F

NC

CN

F

CN CN F

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

271

Phthalonitriles & Naphthalonitriles

Product No. Product Name A1166 B1353 B1334 C1163 D2189 D1610 D3963 D2079 D1983 D2237 H0691 H0813 M1379 N0566 N0524 P1071 P0404 P1070 T0988 T1402

Unit Size

4-Aminophthalonitrile 4-Butoxyphthalonitrile 4-tert-Butylphthalonitrile 4-(4-α-Cumylphenoxy)phthalonitrile 4,5-Dichlorophthalonitrile 2,3-Dicyanohydroquinone 4,5-Difluorophthalonitrile 1,3-Diiminoisoindoline 4-(2',6'-Dimethylphenoxy)phthalonitrile 4-Dodecyloxyphthalonitrile 4-Hexyloxyphthalonitrile 4-Hydroxyphthalonitrile 4-Methylphthalonitrile 3-Nitrophthalonitrile 4-Nitrophthalonitrile 4-Pentyloxyphthalonitrile Phthalonitrile 4-Propoxyphthalonitrile 1,2,4,5-Tetracyanobenzene Tetrafluorophthalonitrile

5g 1g 5g 1g 5g

25g 5g 25g 5g 25g 25g 5g 25g 5g 5g 5g 5g 5g 25g 25g 5g 500g 5g 5g 25g

1g 5g 1g 1g 1g 1g 5g 1g 25g 1g 1g 5g

B1390

D2282

D2434 OH

Br

Naphthalonitriles

CN

Br

CN

CN

Br

CN

CN CN NO2 OH

D1977

D2027

D2009

N0578 NH

CN

CN

CN

CN

NH CN

O2N

CN NH

Product No. Product Name B1390 D2282 D2434 D1977 D2027 D2009 N0578

Unit Size

6-Bromo-2,3-dicyanonaphthalene 2,3-Dibromo-6,7-dicyanonaphthalene 2,3-Dicyano-1,4-dihydroxy-5-nitronaphthalene 2,3-Dicyanonaphthalene 2,3-Dicyano-6-nitronaphthalene 1,3-Diiminobenz[f]isoindoline 1,2-Naphthalenedicarbonitrile

1g 1g

1g

D2269

A1292

D2148 O

Others

H2N

N

CN

Cl

N

CN

H2N

NH2

CN

N N H

CN

CN

CN O

272

1g 1g 5g 10g 1g 1g 5g

Availability, price or specification of the listed products are subject to change without prior notice.

NH2

Phthalonitriles & Naphthalonitriles

D2270

D2271

D2026

D2281

H2N

N

CN

Cl

N

CN

NC

H2N

N

CN

Cl

N

CN

NC

P1218

N

D1751

CH3

N H

N

CN

N

CN

N

CN

N

CN

T1472

N

CN

O

H N

CN

CN

O

N H

CN

Product No. Product Name D2269 A1292 D2148 D2270 D2271 D2026 D2281 D1751 P1218 T1472

Unit Size

5-Amino-6-chloro-2,3-dicyanopyrazine 2-Amino-4,5-dicyano-1H-imidazole 1,4-Diamino-2,3-dicyano-9,10-anthraquinone 5,6-Diamino-2,3-dicyanopyrazine 5,6-Dichloro-2,3-dicyanopyrazine 4,5-Dicyanoimidazole 2,3-Dicyano-5-methylpyrazine 2,3-Dicyanopyrazine Pyridine-2,3-dicarbonitrile 1,4,5,6-Tetrahydro-5,6-dioxo-2,3-pyrazinedicarbonitrile

P0887

10g 25g 5g 5g 1g

T1256

P1005 P1006

tBu

N N N

Phthalocyanines

tBu

N

N

N N

Co N

10g 25g 25g 10g 25g 250g 25g 25g 5g 10g

N

N

N N

N

N

N

N Cu

N

N

N

Cu

N

N

N

N tBu

N tBu

H1194

P0774

F

F

P1018

F

F

N

N F

N N

Cu N

F

F

N

N N

N N

Fe

N F F

F

N

N

N

N

N

N

N

N

Pb

N

N

Cl

Cl

N

N N

N

Cl

N Cl

Cl Cl

N

Cl

Cl

N

N N

N Cl N Sn N Cl N

N

N

N

P0767

N N

N N

N Na2

N

N

Cu

N

Cl

Ag2

N

N

N N

P1024

Cl

N

N

N

N

N

Cl

Cl

N Cl

N

N

P0997

N

Cl

Cu

HN

N

P0973

Cl

N

N Al N Cl N

N

N Cl N Si N Cl N

N

P0660

N

N

N N

N

N

N

N

S0363

N N

P0655 P1628

N

N

N

P0996

N Li2

NH

N

N

N

N

N N

N

P0766

N

Mg

F

P1049

N

N

N

N

N

F F

N

N

N

N

F

C1167

P0355 P1795

F

F

N

N N

N

N

N N

N Sn

N

N N

N

N

N N

Zn N

N N

Cl

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

273

Phthalonitriles & Naphthalonitriles

Product No. Product Name P0887 P1005 P1006 T1256 H1194

Cobalt(II) Phthalocyanine Copper(II) Phthalocyanine (α-form) Copper(II) Phthalocyanine (β-form) Copper(II) 2,9,16,23-Tetra-tert-butylphthalocyanine 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyanine Copper(II)

P0774 P1018 P0355 P1795 C1167 P1049 P0766 P0996 S0363 P0997 P0655 P1628 P0660 P0973 P1024 P0767

Iron(II) Phthalocyanine Magnesium(II) Phthalocyanine Phthalocyanine Phthalocyanine (purified by sublimation) Phthalocyanine Chloroaluminum Phthalocyanine Dilithium Phthalocyanine Lead Phthalocyanine Silicon Dichloride Phthalocyanine Silver Phthalocyanine Tin(IV) Dichloride Pigment Blue 15 Pigment Blue 15 (purified by sublimation) Pigment Green 7 Sodium Phthalocyanine Tin(II) Phthalocyanine Zinc Phthalocyanine

Unit Size 25g 25g 100mg

(purified by sublimation)

1g

1g

1g 1g 10g

25g 250g 500g 100mg 1g 25g 1g 25g 1g 1g 1g 25g 1g 1g 1g 25g 1g 25g 5g 5g 25g

References 1999, 1996, 1) N. Kobayashi, , 968; N. Kobayashi, , 312. 1987, 2) D. Wohrle, M. Kaneko, , 837; H. Shirai, K. Hanabusa, 1987, , 422. 3) B. Schumann, D. Wohrle, N. I. Jaeger, . 1985, , 2144; M. Chigane, 1995, , 26. 1985, 4) W. R. Barger, A. W. Snow, H. Wohltjen, L. Jarvis, , 382; A. W. Snow, W. R. Barger, M. Klusty, 1986, , 513. 2002, 5) K. Sakamoto, , 286.

274

Availability, price or specification of the listed products are subject to change without prior notice.

Macrocycles for Host-Guest Chemistry

Macrocycles for Host-Guest Chemistry Host-compounds recognize and incorporate specific molecules, atoms or ions (guests) into the molecules to form complexes. In the formation of these complexes, a variety of forces such as electrostatic interaction, hydrophobic interaction, hydrogen bonding, etc. are utilized to create high selectivity. Molecular sensors, synthetic enzymes, separation systems, etc. utilize the high guest selectivity of these host compounds. Synthesis of new host compounds with even higher selectivity are currently being developed. For example, Shinkai and co-workers have developed exciting purification techniques for fullerene C60 employing calixarene. According to these techniques, the stirring of crude fullerene and butylcalix[8]arene in toluene causes only C60 to be incorporated in the calixarene to form and precipitate a complex. Filtration and subsequent stirring of the complex in chloroform cause it to decompose to yield C60 of high purity as a precipitate. This method has been reported to be an efficient purification technique in obtaining C60 compared with conventional column purification techniques.

A1603

A1604 O

O

A1404

O

O

O

C CH3

O

O

O O

O

B1154

O

O

NH2

O

O

O

O

O

O

O

O

O

B2189 O

O O O

B2245 O

O

O

NH

O

O

B1249

O

B1539

O

O

HN

CH2

O

A1324

O

NH

C CH3

O

A1323

O

CH2OCH2CH

O

O

O

O

O

O O

A1552

O

O

O

O

Crown Ethers

A1568

B2181 O

O

O

O

O

O

O

O

O O

O

O

O O

O

C1713

C1714

O

O

O

C1942

O

O

O

Br

O

O

Br

O

C1943

C0858

O

O

O

O

O

O

O

O O

O

C OH

O O

O

C OH

O2N

O HO

O

O

N N

NO2

O

O

O

O2N

HO O

N N

O

O

O

O

O

O

NO2

O

O

C0859

C0860

C1736 O

O

O

O

O O

O

O O

D2743 O

O

O

O

O O

D2744

O

O

O

NH

O

O

O HN

HN

NH O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

275

Macrocycles for Host-Guest Chemistry

D2323

D2877 O

D1533

O

HN

NH

O

O

O

O

O O

O

O

Bn O

N O

O

O

H0932 H N

NH

HN

NH

HN

NH

HN

NH

N H

. 6HCl

N

M1489

O

C H

O

O

O C H

O

H0983 CH2OH

O

O

O

O

N H

O

H0982 O

HN

O

O O

O

H1215 H N

H0990

O

O

O

O

O O

O O

F0451

O

O

N Bn

O

H1070

O O

O

O

O

F0448

O

O

O

O O

D1668

O

O

O

O

D2321 O

O

O

O

O

O

O

O

O

O

D2684 O

D1830

O

O

O

D2878

O

O

O

O

O

CH2OH

N

O

O O

O

N0561

N0562

O

O

P1143 O

O

O

O

O

CH2OH

O

O

O

O

O O

O

O

O

C OCH3

T1875

O

O O

O

NO2

O

O

N

NO2

O

O

O

T1874

O

O

O

T1426

T1691

T1597

O CH2 C OH

NH NH

HN

O HO C CH2

N N

N

HN

O CH2 C OH

N CH2 C OH O

T2540

T1959

O CH3CH2O C CH2

O CH2 C OCH2CH3 N

NH

HN

NH

HN

T1876

N

S

O CH2 C OCH2CH3

S

S S

T2541

NH

HN

NH HN

NH

HN

T1600

HN

NH

NH H N

H N

N O CH2 C OCH2CH3

T2642

NH HN

T1878

HN

N

. 4HCl

T1879

HN

NH

. 3HCl

N H

T1972

O O

CH2 C OC(CH3)3

CH2 C OC(CH3)3 N

O HO C CH2

N

N

O

O N

CH2 C OC(CH3)3

N CH2 C OC(CH3)3 O

HN

N

CH2 C OC(CH3)3

CH3

N

N

S

S

N

N CH2 C OC(CH3)3

CH3

CH3

S

O

Product No. Product Name A1603 A1604 A1568 A1404 A1552 A1323

276

4'-Acetylbenzo-15-crown 5-Ether 4'-Acetylbenzo-18-crown 6-Ether 2-(Allyloxymethyl)-18-crown 6-Ether 4'-Aminobenzo-15-crown 5-Ether 1-Aza-12-crown 4-Ether 1-Aza-15-crown 5-Ether

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 100mg 250mg 1g

1g 1g 1g 1g 1g 5g

Macrocycles for Host-Guest Chemistry

Product No. Product Name A1324 B1249 B1154 B1539 B2245 B2189 B2181 C1713 C1714 C1942 C1943 C0858 C0859 C0860 C1736 D2743 D2744 D2323 D2877 D1533 D2878 D1830 D2684 D2321 D1668 F0448 F0451 H1070 H1215 H0932 H0982 H0983 H0990 M1489 N0561 N0562 P1143 T1874 T1875 T1426 T1691 T1597 T2540 T1959 T1876 T1878 T1600 T2642 T2541 T1879 T1972

Unit Size

1-Aza-18-crown 6-Ether Benzo-12-crown 4-Ether Benzo-15-crown 5-Ether Benzo-18-crown 6-Ether Bis(1,4-phenylene)-34-crown 10-Ether 4'-Bromobenzo-15-crown 5-Ether 4'-Bromobenzo-18-crown 6-Ether 4'-Carboxybenzo-15-crown 5-Ether 4'-Carboxybenzo-18-crown 6-Ether 15-Crown-4 [4-(2,4-Dinitrophenylazo)phenol] 18-Crown-5 [4-(2,4-Dinitrophenylazo)phenol] 12-Crown 4-Ether 15-Crown 5-Ether 18-Crown 6-Ether 24-Crown 8-Ether 4,10-Diaza-12-crown 4-Ether 4,10-Diaza-15-crown 5-Ether 4,13-Diaza-18-crown 6-Ether Dibenzo-15-crown 5-Ether Dibenzo-18-crown 6-Ether Dibenzo-21-crown 7-Ether Dibenzo-24-crown 8-Ether Dibenzo-30-crown 10-Ether N,N '-Dibenzyl-4,13-diaza-18-crown 6-Ether Dicyclohexano-18-crown 6-Ether 4'-Formylbenzo-15-crown 5-Ether 4'-Formylbenzo-18-crown 6-Ether 1,4,7,10,13,16-Hexaazacyclooctadecane 1,4,7,10,13,16-Hexaazacyclooctadecane Hexahydrochloride 4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane 2-(Hydroxymethyl)-12-crown 4-Ether 2-(Hydroxymethyl)-15-crown 5-Ether 2-(Hydroxymethyl)-18-crown 6-Ether 4'-Methoxycarbonylbenzo-15-crown 5-Ether 4'-Nitrobenzo-15-crown 5-Ether 4'-Nitrobenzo-18-crown 6-Ether N-Phenylaza-15-crown 5-Ether 1,4,7,10-Tetraazacyclododecane 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic Acid 1,4,7,10-Tetraazacyclododecane Tetrahydrochloride 1,4,8,12-Tetraazacyclopentadecane 1,4,8,11-Tetraazacyclotetradecane Tetraethyl 1,4,8,11-Tetraazacyclotetradecane-1,4,8,11-tetraacetate 1,4,8,11-Tetrathiacyclotetradecane 1,5,9-Triazacyclododecane 1,4,7-Triazacyclononane 1,4,7-Triazacyclononane Trihydrochloride Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetate Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate 1,4,7-Trimethyl-1,4,7-triazacyclononane (stabilized with NaHCO3) 1,4,7-Trithiacyclononane

B1809

1g 1g 1g 1g 1g 1g 100mg

5g

100mg 1g 5g 1g 1g 1g 1g 100mg

1g 1g 1g 5g 200mg 1g 1g 1g 1g 200mg 1g 1g 200mg 200mg

Calixarenes

H0714 t

Bu

tBu

Bu

CH2 OH

1g 1g 100mg 1g

B2221 t

1ml 5ml 25g

CH2 4

5g 5g 5g 5g 100mg 5g 5g 1g 1g 100mg 100mg 5ml 25ml 100g 1g 1g 1g 5g 1g 25g 5g 5g 1g 5g 5g 1g 500mg 100mg 100mg 5g 5g 25g 1g 1g 5g 5g 5g 5g 1g 5g 1g 5g 200mg 1g 100mg 5g 5g 1g 200mg 5g 500mg

OH

CH2 5

OH

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

6

277

Macrocycles for Host-Guest Chemistry

B1750

T2563 t

C1455

H0713

C1435

tBu

Bu

CH2

OH

CH2

CH2

CH2

4

CH2

O

4

OH

6

OH

8

OH

CH2 C OCH2CH3

8

O

H0889

S0469

S0470

CH3

SO3H

S0471

U0069 SO3H

SO3H

HO

. xH2O CH2

CH2

O C CH3

OH

n

B2296

B2310

OH

6

OH

SO3Na

4

CH2 C OCH2CH3

4

S

SO2

4

O

8

4

S0477 t Bu

S

S

. H2O

CH CH3(CH2)10

. xH2O

B2312 t Bu

tBu

OH

. xH2O

n = 6,8

CH2

CH2 4

O

OH

OH

OH

4

O

Product No. Product Name B1809 B2221 H0714 B1750 T2563 C1455 H0713 C1435 H0889 S0469 S0470 S0471 U0069 B2296 B2310 B2312 S0477

Unit Size

4-tert-Butylcalix[4]arene 4-tert-Butylcalix[5]arene 4-tert-Butylcalix[6]arene (contains 5-10% Benzene) 4-tert-Butylcalix[8]arene Tetraethyl 4-tert-Butylcalix[4]arene-O,O ',O '',O '''-tetraacetate Calix[4]arene (contains ca. 8% Chloroform) Calix[6]arene (contains ca. 5% Benzene) Calix[8]arene 4-Methyl-1-acetoxycalixarene [mixture of [6] and [8]] (contains 5-10% Acetone) 4-Sulfocalix[4]arene Hydrate 4-Sulfocalix[6]arene Hydrate 4-Sulfocalix[8]arene Hydrate C-Undecylcalix[4]resorcinarene Monohydrate 4-tert-Butylthiacalix[4]arene 4-tert-Butyl-1-(ethoxycarbonylmethoxy)thiacalix[4]arene 4-tert-Butylsulfonylcalix[4]arene 4-Sulfothiacalix[4]arene Sodium Salt

C1749

Cyclophanes

1g

5g 5g 200mg 100mg 1g 1g 100mg 1g 1g 1g 1g 1g 1g 1g

D2210

N +

N +

+ N

+ N

4PF6

S

P1165

S

T1378 HN(CH2)4NH

H2C

CH2

HN(CH2)4NH

278

5g

Availability, price or specification of the listed products are subject to change without prior notice.

25g 100mg 25g 25g 1g 1g 5g 5g 1g 5g 5g 5g 1g 5g 5g 5g 5g

Macrocycles for Host-Guest Chemistry

Product No. Product Name C1749 D2210 P1165 T1378

Unit Size

Cyclobis(paraquat-1,4-phenylene) Tetrakis(hexafluorophosphate) 2,11-Dithia[3.3]paracyclophane [2.2]-Paracyclophane 1,6,20,25-Tetraaza[6.1.6.1]paracyclophane

A2122

100mg 100mg 500mg 1g 100mg

A1916

A2123

α-CD

Cyclodextrins

. xH2O

NH2

C0776

. xH2O

NH2

(2AS, 3AS)-α-CD

B3026

γ-CD

β-CD

C0869

C0900 C0777

G0263 OH O

HO HO

CH3 RO

C

. xH2O

NH2

(2AS, 3AS)-γ-CD

(2AS, 3AS)-β-CD

HO

OR

CH3

α-CD

R = permethyl-α-CD

O

γ-CD

β-CD

β-CD

H0979

M1219 OR O

HO

RO RO CH3 R=

M1356

O

7

n

M1212 O SO2Mes

O

OCH3 O

OR O

O

HO HO

HO

CH2CHO

D1732

OH O

HO HO

RO

O

O

RO

7

HO

R = H, CH3

CH3O

H

O

γ-CD

7

β-CD

n = 0,1,2...

M1876

M1956

M1741

M1957

M1644 OTs

α-CD

RO

β-CD

γ−CD α-CD

R = permethyl-α-CD

OTs

M1381

OTs

M1645

OTs

P0977

OTs

T2452

OTs

OH O

OR NH N

O 7 HO cross-linked by Epichlorohydrin

γ-CD

T1844

T1094

OR

OR

RO

HO

β-CD

T2451

RO

RO

N HN RO

NH N

OR

N HN

OR RO

OR

R = permethyl-α-CD

R = permethyl-α-CD OR

T2450 CH3

OCH3 O

OAc O AcO AcO

RO

O

CH3O 7

CH3O

C

OR

O 7

OR R = permethyl-α-CD

Product No. Product Name A2122 A1916 A2123 B3026 C0776 C0900 C0777

3A-Amino-3A-deoxy-(2AS,3AS)-α-cyclodextrin Hydrate 3A-Amino-3A-deoxy-(2AS,3AS)-β-cyclodextrin Hydrate 3A-Amino-3A-deoxy-(2AS,3AS)-γ-cyclodextrin Hydrate 2,2-Bis[4-(per-O-methyl-α-cyclodextrin-6-yloxy)phenyl]propane α-Cyclodextrin β-Cyclodextrin β-Cyclodextrin

Unit Size

10g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

1g 1g 1g 10mg 25g 500g 25g

279

Macrocycles for Host-Guest Chemistry

Product No. Product Name C0869 G0263 H0979 M1219 M1356 D1732 M1212 M1876 M1956 M1741 M1957 M1644 M1381 M1645 P0977 T2452 T2451 T1844 T1094 T2450

Unit Size

γ-Cyclodextrin 6-O-α-D-Glucosyl-β-cyclodextrin Hydroxypropyl-β-cyclodextrin 6-O-α-D-Maltosyl-β-cyclodextrin Methyl-β-cyclodextrin (mixture of several Methylated) Methyl-β-cyclodextrin (2,6-Di-O-methyl- and partially 2,3,6-Tri-O-methyl- mixture) Mono-6-O-mesitylenesulfonyl-γ-cyclodextrin Mono-6-O-(2-naphthyl)-per-O-methyl-α-cyclodextrin Mono-2-O-(p-toluenesulfonyl)-α-cyclodextrin Mono-2-O-(p-toluenesulfonyl)-β-cyclodextrin Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin Mono-6-O-(p-toluenesulfonyl)-α-cyclodextrin Mono-6-O-(p-toluenesulfonyl)-β-cyclodextrin Mono-6-O-(p-toluenesulfonyl)-γ-cyclodextrin Poly-β-cyclodextrin [Cross-linked by Epichlorohydrin] 5,10,15,20-Tetrakis[3,5-bis(per-O-methyl-α-cyclodextrin-6-yloxy)phenyl]-21H,23H-porphine 5,10,15,20-Tetrakis[4-(per-O-methyl-α-cyclodextrin-6-yloxy)phenyl]-21H,23H-porphine Triacetyl-β-cyclodextrin Trimethyl-β-cyclodextrin 1,1,1-Tris[4-(per-O-methyl-α-cyclodextrin-6-yloxy)phenyl]ethane

References 1) Calixarene A. Ikeda, S. Shinkai, . 1997, , 1713; M. Ayabe, S. Shinkai, 2) Cyclodextrin K. Takahashi, . 1998, , 2013. 3) Thiacalixarene 2004, number N. Morohashi, S. Miyano, , 2.

280

2003, number

Availability, price or specification of the listed products are subject to change without prior notice.

, 2.

5g 1g 1g 25g

200mg

1g

25g 5g 25g 5g 250g 1g 1g 10mg 1g 1g 1g 1g 200mg 200mg 5g 10mg 10mg 25g 1g 10mg

Diacetylene Monocarboxylic Acids for LB Films

Diacetylene Monocarboxylic Acids for LB Films Recently, the Langmuir-Blodgett Method1) is receiving much attention as a means to obtaining functional organic super thin films in the electric field. This method can control rearrangement in molecular dimensions while retaining highly orderly structure. New diversified applications utilizing the method are being developed in a variety of fields such as molecular electronics, bioelectronics, etc.2) Amphiphilic diacetylene monocarboxylic acids are readily polymerised by heat, light3) and radiation while polymerized films3,4) are thermally and mechanically stable. As a result, application to photoresist material5) having a high degree of resolving power and nonlinear optical material6) are expected.

Diacetylene Monocarboxylic Acids CH3(CH2)m-1

C C C C

m=4,10,12,14,16

(CH2)n

COOH

n=0,8

Product No. Product Name H0668 H0666 H0667 H0775 N0514 N0515 P1030 P1032 T1200

Unit Size

2,4-Heneicosadiynoic Acid 10,12-Heptacosadiynoic Acid 2,4-Heptadecadiynoic Acid 10,12-Heptadecadiynoic Acid 10,12-Nonacosadiynoic Acid 2,4-Nonadecadiynoic Acid 10,12-Pentacosadiynoic Acid 2,4-Pentadecadiynoic Acid 10,12-Tricosadiynoic Acid

100mg 100mg 500mg 100mg 100mg 100mg 100mg 100mg 1g 100mg 100mg 1g

(m=16, n=0) (m=14, n=8) (m=12, n=0) (m=4, n=8) (m=16, n=8) (m=14, n=0) (m=12, n=8) (m=10, n=0) (m=10, n=8)

Related Compounds Product No. Product Name B1298 B1342 B1340 B1348 C1195 H0619 H0663 P1065 N0718 O0193 O0192 P1053 P1054 P1055 P0497 T1211 T1239 T1123 U0054 U0055

Unit Size

1,4-Bis(trimethylsilyl)-1,3-butadiyne 1-Bromo-4,6-nonadecadiyne 1-Bromo-10,12-pentacosadiyne 1-Butynyl Iodide (stabilized with Copper chip) 3-Chloro-1-butyne 2,4-Hexadiyne-1,6-diol 2,4-Hexadiyne-1,6-diol Bis(azobenzene-4-sulfonate) 1-Iodo-1-propyne 4,6-Nonadecadiyn-1-ol 1-Octadecyl-4-(4-phenyl-1,3-butadienyl)pyridinium Bromide N-Octadecyl-4-stilbazole Bromide 10,12-Pentacosadiyn-1-ol 1-(10,12-Pentacosadiynyl)pyridinium Bromide 1-Pentynyl Iodide Propiolic Acid 22-Tricosenoic Acid Trimethylsilylacetylene 1-(Trimethylsilyl)-1-propyne 10-Undecynoic Acid 10-Undecyn-1-ol

1g

1g 1g 1g

100mg

5g 100mg 5ml 25ml 5ml 25ml 1g

5g 100mg 100mg 5g 5g 5g 100mg 1g 500mg 1g 1g 1g 100mg 1g 25g 1g 250ml 100ml 5g 5g

References 1) K. Blodgett, 2) a) M. Sugi, c) K. Hukuda,

., in

3) a) B. Tieke, Barraud, 4) a) D. Day, 5) a) A. Barraud, , 317. 6) a) F. Kajzar,

. 1935, , 1007. 1983, , 567; b) M. Sugi, , CMC, 1986; d) Review: 1986, . . 1976, , 764; b) B. Tieke, . 1977, , 509; d) G. Lieser, 1980, , 1478; b) I. R. Perterson, 1979, , 120; b) A. Barraud, . 1983,

1985,

, 133; b) P. A. Chollet,

1986,

1980, 1983,

1985,

1985, , 102; ; e) Review: . 1977, , 521; c) A. , 77. , 252. 1980, , 91, 99; 1983, , 1; c) F. Kajzar,

, 11.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

281

Reagents for High-Performance Polymer Research

Reagents for High-Performance Polymer Research Polyvinyl chloride and polyethylene polymers, which have long been the mainstay of industrial polymers, are now making way for new high performance polymers. Engineering plastics are polymers that have various properties designed into the polymer. For example, some polymers are designed for thermal resistance, such as polyamide, and polycarbonate, which are widely used these days. The thermal resistance of a polymer is determined by the softening point, as the softening point rises with the increase in the material strength. To make improvements in the softening points and material strength, the super engineering plastics such as polysulfone, polyether sulfone, polyarylate and polyimide have been developed. The softening points of these polymers are all above 150 ºC, and these utilized in materials of fireman uniform and bulletproof vest, and so on. Active R&D is continuing to take place to further improve the performance.1) On the other hand, there have been active experiments in adding new functions to the polymers, such as the electrical, optical, medical and biological properties. For example, copolymers which are obtained by the polymerization of fluorine containing monomers and variety of monomers have been utilized as photoresists, optical fiber dressings, oxygen enrichment membranes, and membrane oxygenators. Polysilane has the maximum absorption in the ultraviolet region, and also has photosensitivity; therefore, it can be used as a positive type resist with excellent oxygen plasma resistance.2) Polylactic acid (PLA) has been commercialized as an environmentally-friendly polymer, being compatible with the natural environment. Furthermore, it can save fossil resources as it is made of biomass raw materials.3) Further broad applications are expected to be made with functional polymers, thus R&D in this field is highly promising. The page below shows a wide variety of monomers and intermediates as building blocks for functional polymers. These are surely useful for the development of novel polymers. A1322

A1251

COCH3 O2N

CH3

Biphenyls

B0813

B0464

A1340

B1181

NH2

B1308

NH2

B2854

OH HO

OH

NC

CN

Cl

O

O

C

C Cl

O

O

H C

C H

HO

D0864

B1191

B2623

B1664

B1165

O C OH

O

O O HO C

O C OH

HOCH2

CH2OH

S OH

HO S O

. xH2O

O

ClO2S

SO2Cl

HO C O

B2285

B1326 O

O

O

B1711

B1921

B2099

O

SH O

HS

B1671

H2N

O

O

NH2

BrCH2

CH2Br

ClCH2

CH2Cl

O

B3648

D2266

D1550

D1902

F3C O

H2N

NH2

I

Br

CH3 C O

O O C CH3

O

O

CH3 C HN

NH C CH3

CF3

282

Availability, price or specification of the listed products are subject to change without prior notice.

O CH3 C

O C CH3

Reagents for High-Performance Polymer Research

D0077 H2N

D0078 H2N

NH2

H2N

D1632

NH2

NH2

H2N

NH2

F

F

F

F

OCH2CH3

D2315

F

OCN

NCO

D1777

F

CH3O C

F

OH NH2

F

H3C CH3

CH3 N CH3 F

F

F

D0826

D0878

D1519 F

F

F

F

O C OCH3

O2N

NO2

NH

NH

HO

OH F

Product No. Product Name A1322 A1251 A1340 B0813 B0464 B1181 B1308 B2854 D0864 B1191 B2623 B1664 B1165 B2285 B1326 B1671 B1921 B2099 B1711 B3648 D2266 D1550 D1902 D0077 D0078 D1632 D1695 D1696 D1127 B0831 D2180 D2181

F

H2N

O2N NO2 O

F

D1717

OCH3 O2N F

B1309

F

Br

HO

F

D2263

CH3O

F

D2312

F

CH3

F

F

Br

F

D2330

CH3

I

Br

D2181

O C OCH2CH3

O CH3CH2O C

Br

F

D2180

D2051

I

F

F

F CH3CH2O

D1696

F NH2

F

B0831

F

H2N

. 4HCl . 2H2O

D1127

D1695

4-Acetyl-4'-methylbiphenyl 4-Amino-4'-nitrobiphenyl 4-Amino-p-terphenyl 2,2'-Biphenol 4,4'-Biphenol 4,4'-Biphenyldicarbonitrile 4,4'-Biphenyldicarbonyl Chloride 4,4'-Biphenyldicarboxaldehyde 2,2'-Biphenyldicarboxylic Acid 4,4'-Biphenyldicarboxylic Acid 4,4'-Biphenyldimethanol 4,4'-Biphenyldisulfonic Acid 4,4'-Biphenyldisulfonyl Chloride 4,4'-Biphenyldithiol 4,4'-Biphthalic Anhydride 4,4'-Bis(4-aminophenoxy)biphenyl 4,4'-Bis(bromomethyl)biphenyl 4,4'-Bis(chloromethyl)biphenyl 2,2'-Bis(trifluoromethyl)benzidine 4-Bromo-4'-iodobiphenyl 4,4'-Diacetoxybiphenyl N,N '-Diacetylbenzidine 4,4'-Diacetylbiphenyl 3,3'-Diaminobenzidine 3,3'-Diaminobenzidine Tetrahydrochloride Hydrate 4,4'-Diaminooctafluorobiphenyl 4,4'-Dibromobiphenyl 4,4'-Dibromooctafluorobiphenyl 4,4'-Diethoxybiphenyl Diethyl 4,4'-Biphenyldicarboxylate 3,3'-Difluorobiphenyl 4,4'-Difluorobiphenyl

F

F

F

Unit Size 1g

1g 5g 25g 25g 1g 1g 25g 5g 5g 5g

10g 1g 25g 5g 5g 25g 10g 5g 5g 25g 1g 1g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 5g 25g 500g 500g 5g 10g 5g 250g 25g 5g 25g 25g 1g 25g 25g 5g 500g 25g 25g 500g 1g 25g 25g 25g 5g 250g 5g 5g 5g 1g 5g

283

Reagents for High-Performance Polymer Research

Product No. Product Name D2312 D2315 D2051 D2330 D2263 D1717 B1309 D1777 D0826 D0878 D1519

Unit Size

3,3'-Dihydroxybenzidine 4,4'-Diiodobiphenyl 4,4'-Diisocyanato-3,3'-dimethylbiphenyl 4,4'-Dimethoxyoctafluorobiphenyl 4-Dimethylamino-4'-nitrobiphenyl 2,2'-Dimethylbiphenyl Dimethyl 4,4'-Biphenyldicarboxylate 2,2'-Dinitrobiphenyl 4,4'-Dinitrobiphenyl N,N '-Diphenylbenzidine Octafluoro-4,4'-biphenol

5g 25g 25g 1g 1g 1g 5g 5g

B1823

B0483

Cl

B1109 O

O

N

CH2

O

NH2

CH3

H2N

CH2

CH3

N

CH3

CH2

CH3

N

CH3

NH2 H2N

CH2

N H3CH2C O

M0220

NH2

NH2

CH2

O CH2CH3

D1684

H2N

H3C O

N

Cl

D1683

CH3

N

O CH3

CH2 Cl

D2046

B1971

Cl

H2N

Diphenylmethanes

25g 250g 250g 5g 5g 5g 25g 25g 5g 25g 5g

H2N

CH2

CH2

NH2

O

D1925

D1939

D1940

B0819

OH F

CH2

HO

CH2

F

D2711

HO

HO

CH2

OH HO

CH2

OH

C

HO

D2097

D0833

CH3

M0217 (CH3)3C

CH3

OCN

CH2

M0215

NCO

O2N

CH2

OH

HO

C(CH3)3

M0214 OH

HO CH2

HO

Cl

Cl

M1684

CH2

(CH3)3C

OH C(CH3)3

D0897

CH3

HO

CH2

CH3

HO

OH

OCN

CH2

NCO

CH2

OH CH2

284

NH2

Availability, price or specification of the listed products are subject to change without prior notice.

HO CH2

NH2 CH2CH3

C OH

HO

OH

CH3

O

HO C

CH2

M1134

M0221

CH3 CH2

CH3CH2

Cl

Cl H2N

CH2CH3

CH3

OH H2N

CH3

O CH3

C(CH3)3

M1238

CH3

C(CH3)3

HO

CH3CH2

CH3

M1099

(CH3)3C

OH CH2

CH3

M0213

(CH3)3C

CH2

NO2

M0609

CH3

CH3

Reagents for High-Performance Polymer Research

Product No. Product Name B1823 B0483 B1971 B1109 D2046 D1683 D1684 M0220 D1925 D1939 D1940 B0819 D2711 D2097 D0833 M0217 M0215 M0609 M0213 M0214 M1099 M1238 M1134 M1684 D0897 M0221

Unit Size

Bis(4-amino-2,3-dichlorophenyl)methane Bis[4-(dimethylamino)phenyl]methane Bis(3-ethyl-5-methyl-4-maleimidophenyl)methane 4,4'-Bismaleimidodiphenylmethane 4,4'-Diamino-3,3'-dimethyldiphenylmethane 3,3'-Diaminodiphenylmethane 3,4'-Diaminodiphenylmethane 4,4'-Diaminodiphenylmethane 4,4'-Difluorodiphenylmethane 2,2'-Dihydroxydiphenylmethane 2,4'-Dihydroxydiphenylmethane 4,4'-Dihydroxydiphenylmethane 4,4'-Dihydroxytetraphenylmethane 4,4'-Diisocyanato-3,3'-dimethyldiphenylmethane 4,4'-Dinitrodiphenylmethane 2,2'-Methylenebis(6-tert-butyl-p-cresol) 2,2'-Methylenebis(6-tert-butyl-4-ethylphenol) 4,4'-Methylenebis(2-chloroaniline) 2,2'-Methylenebis(4-chlorophenol) 4,4'-Methylenebis(2,6-di-tert-butylphenol) 4,4'-Methylenebis(2,6-dimethylphenol) 4,4'-Methylenebis(2-ethyl-6-methylaniline) 2,2'-Methylenebis(4-methylphenol) 4,4'-Methylenebis(2-methylphenol) Methylenediphenyl 4,4'-Diisocyanate Methylenedisalicylic Acid (mixture of isomers)

1g

25g 25g

B0084

B1741

O

H2N O

C OH O

C

Benzophenones

O C OH

C

O

B1267 O

B1433

D1682

O O

O

O

CH3

S

CH3NH

O

C

C OH

NH2

O

O

C

NHCH3

H2N

C

C

NH2

O

O

D0230

D1621

D1796

Cl Cl

C

D0577

F

Cl

C

Cl

C

C

F

C

OCH3

C

D1688

C

NO2

O2N

O CH3O

HO O

HO O

OCH3

OH

D0765

OH

OH O

OH CH O 3

F

C

D0586

OH

O

F

D1099

O

O

D0575

C

D1797

O

O

HO

Bz

O

D1561

H2N

C

O HO C

. H2O

Cl

B0948

5g 25g

1g 5g 5g 1g 1g 25g 25g 25g 25g 25g 25g

A1128 Cl

25g 500g 500g 500g 25g 5g 25g 500g 25g 5g 5g 25g 25g 5g 5g 500g 500g 500g 500g 500g 500g 25g 25g 25g 500g 500g

25g 25g 25g

O OCH3

C

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

285

Reagents for High-Performance Polymer Research

T0118

T1371

OH

T0584

HO

HO C

C

OCH3 O

O

O OH HO

CH3O

HO

HO

O HO

T2028

OH HO

OH

C

C

OCH3

Product No. Product Name A1128 B0084 B1741 B0948 B1267 B1433 D1682 D1561 D0230 D1621 D1796 D1797 D1099 D0577 D0575 D0586 D0765 D1688 T0118 T1371 T0584 T2028

Unit Size

2-Amino-2',5-dichlorobenzophenone Benzophenone-2,4'-dicarboxylic Acid Monohydrate Benzophenone-4,4'-dicarboxylic Acid 3,3',4,4'-Benzophenonetetracarboxylic Dianhydride 4-Benzoyl 4'-Methyldiphenyl Sulfide 4,4'-Bis(methylamino)benzophenone 3,3'-Diaminobenzophenone 4,4'-Diaminobenzophenone 2,4'-Dichlorobenzophenone 4,4'-Dichlorobenzophenone 2,4'-Difluorobenzophenone 4,4'-Difluorobenzophenone 2,2'-Dihydroxybenzophenone 4,4'-Dihydroxybenzophenone 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone 2,2'-Dihydroxy-4-methoxybenzophenone 4,4'-Dimethoxybenzophenone 3,3'-Dinitrobenzophenone 2,2',4,4'-Tetrahydroxybenzophenone 2,3',4,4'-Tetrahydroxybenzophenone 2,4,4'-Trihydroxybenzophenone 2,2',4-Trimethoxybenzophenone

25g

1g 25g 25g 5g 25g 10g 25g

25g 5g

5g

D0041

D2285

H2N

Diphenylamines

D1556

NH

D0812

N2

HSO4

286

N2 HSO4

D1512

D0609 D0906

NH

OCH3

NH

NH

NH

CH3

NH

NH

M1173

H N

NH

CH3

CH3

Product No. Product Name D0041 D2285 D2290 D1556 D0632 D0812

NH

CH3 CH3O

D0950

CH3O

OCH3

OH NH

CH3

NH2

D2290

. H2SO4 . xH2O

D0632

HO

NH

10g 25g 25g 500g 10g 1g 5g 1g 500g 500g 25g 500g 25g 500g 25g 25g 500g 25g 25g 5g 10g 25g

4,4'-Diaminodiphenylamine Sulfate Hydrate 4-Diazo-3-methoxydiphenylamine Sulfate 4-Diazo-4'-methoxydiphenylamine Sulfate 3,3'-Dihydroxydiphenylamine 4,4'-Dimethoxydiphenylamine N,N '-Di-2-naphthyl-1,4-phenylenediamine

Availability, price or specification of the listed products are subject to change without prior notice.

Unit Size 25g

1g 25g

500g 25g 25g 1g 5g 500g

Reagents for High-Performance Polymer Research

Product No. Product Name

Unit Size

N,N '-Diphenyl-1,4-phenylenediamine N,N '-Diphenyl-1,4-phenylenediamine m,m '-Ditolylamine p,p '-Ditolylamine 4-Methyldiphenylamine

D0609 D0906 D1512 D0950 M1173

25g 25g 5g 5g 1g

C1069

B1370

B1680

H2N

Cl

Diphenyl Ethers

B1243

B0834

O

NH2

B1646

O

O

NH2

Br

O

NH2 O

Br

B1454

O

O

O

HO

C2335

CH3O

CH3O

O

O

O

O

HO

O

D2115

O

H2N

O

H2N

O

D0832

O

NH2

D2017

Br

Br

Cl Br

D2150

Br

HO C

Br

O Br

Br

Br

D2121 OH

NH2

OH

OCH3

OCH3

O0088

O

D1388

Br

D1924

O

NH2

CH2OH

B1486

OH

O

CH2OH

Br HO

O

B1484

CHO

B1485

H2N

O

B1643 CHO

H2N

500g 500g 25g 25g 5g

HO

O O

C OH

O0298

HO

O

O

OH

O0237 O

O O

O2N

O

NO2

O

O

ClO2S

O

SO2Cl

O O

Product No. Product Name C1069 B1370 B1680 B1243 B0834 B1646 B1643 B1484 B1485 B1454 B1486 C2335 D1388 D1924

4-Amino-4'-chlorodiphenyl Ether 1,3-Bis(3-aminophenoxy)benzene 1,3-Bis(4-aminophenoxy)benzene 1,4-Bis(4-aminophenoxy)benzene Bis(4-bromophenyl) Ether Bis(2-formylphenyl) Ether 2,2'-Bis(hydroxymethyl)diphenyl Ether 1,3-Bis(4-hydroxyphenoxy)benzene 1,4-Bis(3-hydroxyphenoxy)benzene 1,3-Bis(4-methoxyphenoxy)benzene 1,4-Bis(3-methoxyphenoxy)benzene 4-Chloro-4'-hydroxydiphenyl Ether Decabromodiphenyl Ether 3,4'-Diaminodiphenyl Ether

O O

Unit Size 5g

1g 1g 1g

5g 25g 5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 25g 25g 25g 25g 10g 5g 5g 1g 5g 5g 25g 500g 25g

287

Reagents for High-Performance Polymer Research

Product No. Product Name O0088 D2115 D2150 D2121 D0832 D2017 O0298 O0237

Unit Size

4,4'-Diaminodiphenyl Ether 4,4'-Dicarboxydiphenyl Ether 2,2'-Dihydroxydiphenyl Ether 4,4'-Dihydroxydiphenyl Ether 4,4'-Dinitrodiphenyl Ether 1,4-Diphenoxybenzene 4,4'-Oxybis(benzenesulfonyl Chloride) 4,4'-Oxydiphthalic Anhydride

25g

500g 25g 1g 500g 10g 25g 25g 25g

25g 1g 5g

B1267

T0632

B0850 OH

CH3

Diphenyl Sulfides

S

Bz

H2N

S

Cl S

NH2

Cl

B1527

HO

D1356

S CH3

OH

HO

B1662

S

OH

CH3

P0230

T1427

D0847

O CH2 C C S CH3

O S C C CH2 CH3

S

T0865 Cl

B3484

CH3 O 2N

S

HS

S

S

NO2

T0208 OH

HO

Cl

O

O C OH

S

SH

HO

Cl

S

OH

Cl

Product No. Product Name B1267 T0632 B0850 B1527 D1356 B1662 D0847 B3484 P0230 T1427 T0865 T0208

Unit Size

4-Benzoyl 4'-Methyldiphenyl Sulfide Bis(4-aminophenyl) Sulfide Bis(2-hydroxy-5-chlorophenyl) Sulfide Bis(4-hydroxy-3-methylphenyl) Sulfide Bis(4-hydroxyphenyl) Sulfide Bis(4-methacryloylthiophenyl) Sulfide Bis(4-nitrophenyl) Sulfide 4-tert-Butyldiphenyl Sulfide Phenyl Sulfide 4,4'-Thiobisbenzenethiol 2,2'-Thiobis(4,6-dichlorophenol) 5,5'-Thiodisalicylic Acid

25g 25g 5g 25g 25g 25g 5g

B2859 NH2

H2N O

O

288

HO

10g 25g 25g 500g 500g 25g 25g 100g 500g 5g 500g 25g

B1681

H2N

Diphenyl Sulfones

C CH3 CH3

HO C

S

HO

S

OH

O

O

Availability, price or specification of the listed products are subject to change without prior notice.

S

O

O NH2

Reagents for High-Performance Polymer Research

B1682

B0394

D0089

D0536

H2N H2N

O

O2N

O

O S

O

S

NH2

O

O

O H2N

NH2 F

S

F

S

O

O

O NO2

NH2

B1572

D0537 Br HO(CH2)2O Br

O(CH2)2OH

F

O

F HO

S

O

Cl

S

Cl

O

S O

CH3

CH3 H2N

S O

D0916

O

O

O

HO C

S

C OH

NH2

O

O

D2309

NaO3S

SO3Na

O

O SO2

O

O

O

S O

O

O

Product No. Product Name B2859 B1681 B1682 B0394 D0089 D0536 B1572 D0537 B1577 B0495 B1590 D1927 T1419 D2367 B0810 P0231 D0916 D2309

Unit Size

Bis(3-amino-4-hydroxyphenyl) Sulfone Bis[4-(3-aminophenoxy)phenyl] Sulfone Bis[4-(4-aminophenoxy)phenyl] Sulfone Bis(3-aminophenyl) Sulfone Bis(4-aminophenyl) Sulfone Bis(4-fluoro-3-nitrophenyl) Sulfone Bis[3,5-dibromo-4-(2-hydroxyethoxy)phenyl] Sulfone Bis(4-fluorophenyl) Sulfone Bis(4-hydroxy-3,5-dimethylphenyl) Sulfone Bis(4-hydroxyphenyl) Sulfone Bis[4-(2-hydroxyethoxy)phenyl] Sulfone Bis(4-nitrophenyl) Sulfone 3,7-Diamino-2,8-dimethyldibenzothiophene Sulfone (contains 2,6-Dimethyl isomer) 4,4'-Dicarboxydiphenyl Sulfone 4,4'-Dichlorodiphenyl Sulfone Diphenyl Sulfone Diphenylsulfone-3,3'-disulfonic Acid Disodium Salt 3,3',4,4'-Diphenylsulfonetetracarboxylic Dianhydride

B1286

O

Bisphenol A type Compounds

OH

D2367

NO2

S O

P0231

O

O2N

S O

CH3

T1419

O

O(CH2)2OH

OH HO

CH3

D1927

O S O

O

S O

O

B1590

B0810

CH3

O

Br

HO(CH2)2O

B0495

CH3

Br O S O

B1577

CH3 C O

5g 25g 25g 500g 500g 10g 500g 250g 500g 500g 500g 25g 25g 25g 500g 500g 25g 25g

25g 25g

10g

25g 25g 25g 25g 25g

25g 25g 5g

B1551

CH3 C CH3

O O C CH3 H2N

CH3 O

C

O

NH2

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

289

Reagents for High-Performance Polymer Research

B1562

B2748

CH3 H2N

C

CH3 C

CH3

CH3

CH3

NH2

CH3CH2

B1335

HC

CH CH3

HO

C

B1251

CH3 CH2CH3

Cl

O

CH3

C O

C

OH

CH3

O O C Cl

NCO

C

CH3

B2749

B1796

OCN

CH3

CH3

B2750

B1850 CH3

CH3 CH2O

CH3 HO

C

OH

C

OCH2

CH3

O

O

HO

C

B1464

B2751

CH3

CH3

CH3

CH3 C

OH

CH3

B1567

HC

CH CH3

HO

CH3 CH3

C

CH3

CH3

C

C

CH3

CH3

OH

CH3

CH3

OH

CH3

C

C

CH3

CH3

HO

C

HO

CH3 HO

OH

CH2 C C O CH3

T0851

C

OH

CH2CH3

I0356

O

C CH3

T0032

OH

I0389

CH3 OH

CH3 CH3 CH3

B0494

CH3

B1050

CH3

CH3

CH3

CH3

B1563

HO

OH

CH3 CH3

CH3

CH3

HO

HO

CH3

CH3 C

O

O O C C CH2 CH3

CH3

HO C CH2O

CH3 C

O OCH2 C OH

CH3

T1428 OH

Br

Br Br

CH3 HO

OH

C

HO(CH2)2O

CH3 Br

Br

CH3 C CH3

Br O(CH2)2OH

HO

Br

CH3 C

C CH3

CH3

Br OH

Product No. Product Name B1286 B1551 B1562 B2748 B1335 B1251 B2749 B1796 B2750 B1850 B1464 B2751 B1567 B1050 B1563 B0494 I0389 I0356 T0032 T0851 T1428

290

2,2-Bis(4-acetoxyphenyl)propane 2,2-Bis[4-(4-aminophenoxy)phenyl]propane α,α'-Bis(4-aminophenyl)-1,4-diisopropylbenzene 2,2-Bis(3-sec-butyl-4-hydroxyphenyl)propane 2,2-Bis(4-chloroformyloxyphenyl)propane 2,2-Bis(4-cyanatophenyl)propane 2,2-Bis(3-cyclohexyl-4-hydroxyphenyl)propane 2,2-Bis(4-glycidyloxyphenyl)propane 2,2-Bis(2-hydroxy-5-biphenylyl)propane α,α'-Bis(4-hydroxy-3,5-dimethylphenyl)-1,4-diisopropylbenzene 2,2-Bis(4-hydroxy-3,5-dimethylphenyl)propane 2,2-Bis(4-hydroxy-3-isopropylphenyl)propane 2,2-Bis(4-hydroxy-3-methylphenyl)propane 2,2-Bis(4-hydroxyphenyl)butane α,α'-Bis(4-hydroxyphenyl)-1,4-diisopropylbenzene 2,2-Bis(4-hydroxyphenyl)propane 4,4'-Isopropylidenediphenol Dimethacrylate 4,4'-Isopropylidenediphenoxyacetic Acid Tetrabromobisphenol A Tetrabromobisphenol A Bis(2-hydroxyethyl) Ether α,α,α'-Tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene

Unit Size 25g 25g 25g 1g

25g 25g

25g 5g 25g 25g 5g 25g 25g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

500g 250g 500g 25g 5g 10g 25g 500g 5g 500g 25g 25g 500g 25g 500g 500g 25g 25g 500g 500g 25g

Reagents for High-Performance Polymer Research

B1415

B1397

H2N

NH2

H2N

CF3 HO

Bisphenol AF type Compounds

B1704 H2N

NH2

CF3 H2N

C

OH

O

C

NH2

HO C

C

CH3

B0945

H2N

O

O C OH

HO

CF3 C CF3

O

NH2

B1509

CF3

CF3 C

CF3

C

CF3

CF3

CF3

CH3

CF3

B1401

CF3

NH2 CF3

C CF3

B1400

B1398

OH OCN

C

NCO

CF3

CF3

H0771 O

O

CF3 C

O

O

CF3

O

O

Product No. Product Name B1415 B1397 B1398 B1704 B1400 B1401 B0945 B1509 H0771

Unit Size

2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane 2,2-Bis(3-amino-4-methylphenyl)hexafluoropropane 2,2-Bis[4-(4-aminophenoxy)phenyl]hexafluoropropane 2,2-Bis(3-aminophenyl)hexafluoropropane 2,2-Bis(4-aminophenyl)hexafluoropropane 2,2-Bis(4-carboxyphenyl)hexafluoropropane 2,2-Bis(4-hydroxyphenyl)hexafluoropropane 2,2-Bis(4-isocyanatophenyl)hexafluoropropane 4,4'-(Hexafluoroisopropylidene)diphthalic Anhydride

5g 5g 5g 5g 5g 5g 5g 5g

B1317

B0948 B1726 O

O

B1326

O

O

25g 25g 25g 25g 25g 25g 25g 1g 25g

O

O

O

C

C2262

O

O

C0857

O

O

O

Aromatic Tetracarboxylic Dianhydrides

D2192

O

O

O O

O

O

O

O

O

O

H0771 O

CF3 C

O O

O

CF3

O

O

O

O

O

SO2 O

O

O

O

O

O

CH3

O

P0972

O

O

O

O

O

O0237

N0369 N0755

O

D2309

O

O

O

O

O

O

O

O

O

D1901

O

O

O

O

O

B0040

O

O

O

O

O

O

O

O

O O

O

O

O

O

O

O O

O O

O O

O

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

291

Reagents for High-Performance Polymer Research

Product No. Product Name B0948 B1726 B1317 B1326 C2262 C0857 D2192

Unit Size

3,3',4,4'-Benzophenonetetracarboxylic Dianhydride 3,3',4,4'-Benzophenonetetracarboxylic Dianhydride Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Dianhydride 4,4'-Biphthalic Anhydride 1,2,3,4-Cyclobutanetetracarboxylic Dianhydride 1,2,3,4-Cyclopentanetetracarboxylic Dianhydride 4-(2,5-Dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic Anhydride 5-(2,5-Dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic Anhydride 3,3',4,4'-Diphenylsulfonetetracarboxylic Dianhydride 4,4'-(Hexafluoroisopropylidene)diphthalic Anhydride Naphthalene-1,4,5,8-tetracarboxylic Dianhydride Naphthalene-1,4,5,8-tetracarboxylic Dianhydride (purified by sublimation) 4,4'-Oxydiphthalic Anhydride 3,4,9,10-Perylenetetracarboxylic Dianhydride Pyromellitic Dianhydride

D1901 D2309 H0771 N0369 N0755 O0237 P0972 B0040

D2704

D2469

Dichlorosilanes (for Polysilanes)

D2348

D1976

D2710

D0362

Cl

Cl Si

Cl

Cl

D2144

Cl

Cl

Product No. Product Name

292

Dibutyldichlorosilane Di-tert-butyldichlorosilane Dichlorocyclohexylmethylsilane Dichlorodecylmethylsilane Dichlorodiethylsilane Dichlorodihexylsilane

CH3 CH3

Cl

Si

CH3

Cl

O0264

Cl CH3(CH2)17 Si CH3 Cl

Cl

T1590

CH3 CH3 Cl

Cl

CH3

CH3(CH2)5 Si CH3

Cl

Si CH3

Si CH3 Cl

Cl

Cl

Cl

Cl CH3(CH2)7 Si CH3

Cl

H0855

CH3(CH2)11 Si CH3

P0790

Cl

D0358

Si CH3

D2349

CH3(CH2)4 Si (CH2)4CH3

O0265

CH3

Si (CH2)5CH3 Cl

Cl

Cl

D2704 D2469 C1399 D2348 D1976 D2712

CH3(CH2)5

25g 25g

CH3

D2603

Cl

CH3CH2 Si CH2CH3

5g 25g 1g

10g

H3C Cl CH3

D2712

25g 500g 25g 25g 250g 5g 25g 500g 500g

25g

C1399

H3C C Si C

Cl

Cl

Cl CH3(CH2)9 Si CH3

Si (CH2)3CH3

500g 500g 500g 25g 5g 25g

1g 5g

H3C Cl CH3

Cl CH3(CH2)3

25g 25g 25g

Si

Si Cl

CH3 CH3

Cl Cl CH3

Si Si CH3 Cl Cl

Unit Size 5g 5g

5g 5g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

25g 25g 25g 25ml 25g 25g

Reagents for High-Performance Polymer Research

Product No. Product Name

Unit Size

D2603 D0358 D2710 D0362 D2349 H0855 O0264 O0265 P0790 D2144 T1590

5g 25ml 5g 25g

Dichlorodiisopropylsilane Dichlorodimethylsilane Dichlorodipentylsilane Dichlorodiphenylsilane Dichlorododecylmethylsilane Dichlorohexylmethylsilane Dichloro(methyl)octadecylsilane Dichloro(methyl)-n-octylsilane Dichloro(methyl)phenylsilane 1,2-Dichlorotetramethyldisilane 1,1,2,2-Tetrachloro-1,2-dimethyldisilane

25g 5g 5g

B0767

C0702

Lactones & Lactides

L0115

H0168

O

O

CH3

CH3

O

O

O

O

O

O

L0091

O

O

O

O

CH3

CH3

O

O

V0039

O O

Product No. Product Name

Unit Size

γ-Butyrolactone ε-Caprolactone DL-Lactide L-(-)-Lactide β-Propiolactone δ-Valerolactone

B0767 C0702 L0091 L0115 H0168 V0039

25ml 25ml

500ml 500ml 25g 250g 25g 500g

25g 5g 25g

G0196

H0228

HO

L0226

OH

O

Hydroxycarboxylic Acids

25g 500ml 25g 500g 25ml 25ml 25ml 25ml 250g 25g 25g

OH

CH3

O

O

CH3

OH

OH OH

L0165 O CH3

OH OH

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

293

Reagents for High-Performance Polymer Research

Product No. Product Name G0196 H0228 L0226 L0165

Unit Size

Glycolic Acid DL-3-Hydroxybutyric Acid (contains Polymolecular esterification product) DL-Lactic Acid L-Lactic Acid

25g 5g 25g 25g

A1988

B2935 O

CH3

Diacrylates & Dimethacrylates

B2937

O

O O

O

O

B2340

O

O

O

CH2 CH C O(CH2)4O C CH CH2

B2863

O

O

CH2

OH

CH2

B2936

500g 25g 500g 500g

O

O

O

CH2 CH C O(CH2)10O C CH CH2 CH2 CH C O(CH2)6O C CH CH2 CH2 CH C OC9H18O C CH CH2

CH2 CH C OCH2(CF2)4CH2O C CH CH2

B1065

E0102

D1530 O

CH2

CH3 O O

B2938

O

O

O

O O

CH2

O OH

CH3

O

CH3

O 4

CH2 CH C O(C3H6O)2 C CH CH2

O O

CH3

H3C O

C CH CH2 CH 2

CH3

O

CH2

O

N0780

T1352

CH3

CH3

T0948

CH2 CH C O CH2CH2O

O

O O CH3 O CH3 O O CH3 CH CH C OCH CCH O C CH CH CH C C OCH CCH O C C CH CH C C O 2 2 2 2 2 2 2 2 2

CH2

T1569

O

CH2

N0790

CH3

294

O CH3

CH3

CH3

CH2

O

O

CH2 CH2

O

D3470

CH3

CH3

O CH2CH2O n C C CH2 CH3

T2389

O CH3

O

O

C C (OCH2CH2)3O C C CH2 CH2 CH C O(C3H6O)3 C CH CH2

Product No. Product Name

Unit Size

A1988 B2935 B2937 B2936 B2863 B2340 B1065 D1530 D3470 E0102 B2938 N0790 N0780 T1352

25g 25g 25g 25g 25g 1g 25ml 25ml 25g 25ml 25g 25g 25g 25g

1-(Acryloyloxy)-3-(methacryloyloxy)-2-propanol (stabilized with MEHQ) 1,4-Bis(acryloyloxy)butane (stabilized with MEHQ) 1,10-Bis(acryloyloxy)decane (stabilized with MEHQ) 1,6-Bis(acryloyloxy)hexane (stabilized with MEHQ) 1,9-Bis(acryloyloxy)nonane (stabilized with MEHQ) 1,6-Bis(acryloyloxy)-2,2,3,3,4,4,5,5-octafluorohexane 1,3-Butanediol Dimethacrylate (stabilized with MEHQ) Diethylene Glycol Dimethacrylate (stabilized with MEHQ) Dipropylene Glycol Diacrylate (stabilized with MEHQ) Ethylene Glycol Dimethacrylate (stabilized with HQ) Glycerol Dimethacrylate (mixture of 1,2- and 1,3-form) (stabilized with MEHQ) Neopentyl Glycol Diacrylate (stabilized with MEHQ) Neopentyl Glycol Dimethacrylate (stabilized with MEHQ) Polyethylene Glycol Dimethacrylate n≒4 (stabilized with MEHQ)

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

500g 500g 500g 500g 500g 5g 500ml 500ml 500g 500ml 500g 500g 500g 500g

Reagents for High-Performance Polymer Research

Product No. Product Name

Unit Size

T1569 T0948 T2389

25g 25ml 25g

Tetraethylene Glycol Diacrylate (stabilized with MEHQ) Triethylene Glycol Dimethacrylate (stabilized with MEHQ) Tripropylene Glycol Diacrylate (stabilized with MEHQ)

A1019

D0605

500g 500ml 500g

B1505 SH

H2N

Related Compounds

CH

CH2

HOCH2

CH2OH SH

B2076

B1549

B1499

B1336

B2752

Cl

H2N

NH2

HO O HO C

H2N

OH

O O(CH2)10O

N

C OH

N

NH2 Cl

B1500

B1403

B1419

F0447

OH CF3 O

C CF3 F3C

O

CH3CH2O C

O(CH2)10O

C OCH2CH3

CF3

HO C

CF3

C OH

F3C

C OH

CF3

.

xH2O

HOCH2CH2O

OCH2CH2OH

CF3

B2038

B1525

B2753

O

HOCH2

C OH

B2396

CH2OH

HO

CH3

B1715

HO

OH

CH3CH2 C CH2OH CH2OH

B1568

CH3

CH3

OH

B2664

CH3

CH3

HO

OH

B1180

OH

B1585 COOH

HO

HO

CH3

CH3

C

C

CH3

CH3

OH

O

N C N

O

CH2 OCH2CH2CH

OH

D2179

D2022

D2236

NH2

CH3

NH2

. 2HCl

H2N NH2

N CH3

N

NH2

N N

N NH2

D2227

CH3 CH3

CH3

SH

D1888

D2232

NH2

SH Cl

CHO

D2143

OH

NH2

N N

N NH2

CH3O

N N

NH2

D3872

NH2

H2N

. 2HCl OH NH2

D2225

CH2

Br N

N N

NHCH2

CH2NH

NH2

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

Br

295

Reagents for High-Performance Polymer Research

D1910

D3223

Br

D2151

D1957

Br

CH3

C CH Cl

N HO

C CH2

Cl

C

D1973

C

CH3

CH3

CH2 C

OH

C CH2

CH3 C CH2

C CH

D2202

D3267

D2183

D2208

D2247 O

NH2 CH3 CH3O

CH

OCH3

HO

C

NH2

OH

C OH

CH3

O2N

CH3

OH CH3

CH3

CH2CH(CH3)2

OH C OH

NH2

NO2

O

D0958 CH

E0391 CH

CH2

E0392

E0448

O

CH2

O

HO

C OH

O

O

O CH

E0415

O

OCH2CH2O

CH2

CH

CH2

E0414

OCH2CH2O

C OH

OH

O

O

O

HO C

C OH

E0664

E0432

A1122 NH2

O

O

CH3CH2O C

O(CH2)2O

HO

CH

CH3

OH HO

C OCH2CH3

CH

OH

CH3(CH2)3 CH CH2CH3

C CH

H1166

M1098

CH3

CH3

HO

CH3

M1683

CH3

P0984 CH2OH

CH3

OH HO

CH

N0519

C

OH

OH

OH CH2

OH CH2

OH

O

NO2

CH2

O

HN OH

CH3

CH3

CH3

CH3

CH3

CH3

O

CH2OH

P0170

P0169 P1892

T0010

NH

T0017

O

T1457 NH2

NH2 O H2N

NH2

O

H C

C H

Cl

O

O

C

C Cl

CH3

CH3

NH2

CH3 NH2

C0046

T1079

T1361

V0059 Br

O

CH3

O

O

HO C

Cl

V0054 O

O

C OH

C

O

CH

O N

O

O

Br

V0057

N

296

CH

CH2

X0022 NH2

H2N

Br

CH2NCO

N N

CH

CH2

CH2NCO

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

CH2

Reagents for High-Performance Polymer Research

Product No. Product Name A1019 D0605 B1505 B2076 B1549 B1499 B1336 B2752 B1500 B1403 B1419 F0447 B2038 B1525 B2753 B2396 B1568 B1715 B2664 B1180 B1585 D2179 D2022 D2236 D2225 D2232 D1888 D2227 D2143 D3872 D1910 D3223 D2151 D1957 D1973 D2202 D3267 D2183 D2208 D2247 D0958

4-Aminostyrene (stabilized with HQ) 1,4-Benzenedimethanol 1,4-Benzenedithiol 1,1-Bis(4-aminophenyl)cyclohexane 9,9-Bis(4-aminophenyl)fluorene 1,10-Bis(4-carboxyphenoxy)decane N,N '-Bis(4-chlorophenyl)-N,N '-diphenyl-1,4-phenylenediamine 1,1-Bis(3-cyclohexyl-4-hydroxyphenyl)cyclohexane 1,10-Bis[4-(ethoxycarbonyl)phenoxy]decane 1,3-Bis(hexafluoro-α-hydroxyisopropyl)benzene 1,4-Bis(hexafluoro-α-hydroxyisopropyl)benzene Hydrate 9,9-Bis[4-(2-hydroxyethoxy)phenyl]fluorene 2,2-Bis(hydroxymethyl)butyric Acid 2,6-Bis(hydroxymethyl)-p-cresol 1,1-Bis(4-hydroxy-3-methylphenyl)cyclohexane 9,9-Bis(4-hydroxy-3-methylphenyl)fluorene 1,1-Bis(4-hydroxyphenyl)cyclohexane 9,9-Bis(4-hydroxyphenyl)fluorene 1,3-Bis[2-(4-hydroxyphenyl)-2-propyl]benzene 1,1-Bis(morpholino)ethylene 4-(3-Butenyloxy)benzoic Acid 2-Chloro-5-methyl-1,4-phenylenediamine 2,5-Diamino-1,4-benzenedithiol Dihydrochloride 2,4-Diamino-6-dimethylamino-1,3,5-triazine 2,4-Diamino-6-isopropoxy-1,3,5-triazine 2,4-Diamino-6-methoxy-1,3,5-triazine 4,6-Diaminoresorcinol Dihydrochloride 2,4-Diamino-1,3,5-triazine α,α'-Dianilino-p-xylene 2,2'-Dibromo-9,9'-spirobi[9H-fluorene] 4,4'-Dibromotriphenylamine 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene 1,4-Diethynylbenzene 1,3-Diisopropenylbenzene (stabilized with TBC) 1,4-Diisopropenylbenzene 4,4'-Dimethoxybenzhydrylamine 4,4'-(1,3-Dimethylbutylidene)diphenol 2,5-Dimethyl-1,4-phenylenediamine 2,5-Dimethylterephthalic Acid 4,6-Dinitroresorcinol (wetted with ca. 20% Water, containing 5g on a dry weight basis) Divinylbenzene (m- and p- mixture) (contains Ethylvinylbenzene, Diethylbenzene)

E0391 E0392 E0448 E0415 E0414 E0664 E0432 A1122 H1166 M1098 M1683 N0519 P0984 P0169 P1892 P0170 T0010 T0017 T1457 C0046 T1079 T1361 V0059 V0054 V0057 X0022

exo-3,6-Epoxy-1,2,3,6-tetrahydrophthalic Acid exo-3,6-Epoxy-1,2,3,6-tetrahydrophthalic Anhydride 3,3'-Ethylenedioxydiphenol Ethylene Glycol Bis(4-carboxyphenyl) Ether Ethylene Glycol Bis[4-(ethoxycarbonyl)phenyl] Ether 4,4'-(2-Ethylhexylidene)diphenol 4,4'-Ethylidenebisphenol 3-Ethynylaniline 4,4'-(2-Hydroxybenzylidene)bis(2,3,6-trimethylphenol) 4,4'-(α-Methylbenzylidene)bisphenol 2,2'-Methylenebis[6-(2-hydroxy-5-methylbenzyl)-p-cresol] 2-Nitro-p-xylylene Glycol 3,4,9,10-Perylenetetracarboxylic Diimide 1,3-Phenylenediamine 1,3-Phenylenediamine 1,4-Phenylenediamine Terephthalaldehyde Terephthaloyl Chloride 2,3,5,6-Tetramethyl-1,4-phenylenediamine Trimellitic Anhydride Trimellitic Anhydride Chloride Tris(4-bromophenyl)amine 4-Vinylbenzoic Acid (stabilized with BHT) 4-Vinylbiphenyl 2-Vinyl-4,6-diamino-1,3,5-triazine m-Xylylene Diisocyanate

Unit Size 5g 25g 1g 5g

5g 5g 5g 25g 25g 25g 25g 25g 25g

5g

5g 1g 1g

1g 25ml 1g

5g 25g 5g 25ml

(stabilized with TBC)

25g 1g

25g

25g

25g 25g 25g 25g 25g 5g 25g 25g 1g

5g 1g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 500g 5g 25g 25g 5g 1g 25g 5g 25g 25g 25g 500g 500g 25g 250g 500g 500g 250g 10g 5g 25g 25g 5g 1g 5g 25g 5g 5g 1g 100mg 5g 5g 500ml 10g 25g 500g 25g 25g 5g 500ml 25g 500g 25g 5g 5g 25g 500g 10g 25g 500g 25g 5g 25g 500g 500g 250g 500g 500g 25g 500g 500g 25g 25g 5g 25g 500g

297

Reagents for High-Performance Polymer Research

References 1) M. Ishikawa, 2) J. Furukawa, 3) N. Kawashima,

298

1990,

, 203; M. Ishikawa, 1992, , 57; J. Furukawa,

1993,

, 564. 1992, 2003,

, 62. , 496.

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Metal-Organic Frameworks (MOFs / PCPs)

Metal-Organic Frameworks (MOFs / PCPs) Porous metal-organic frameworks (MOFs) (other name: porous coordination polymers (PCPs)) have attracted wide scientific attention for the potential application to gas storage, gas separation, catalysis and nanospace engineering.1) MOFs (PCPs) are constructed mainly by coordination bonds between metal cations and multidentate ligands. Their specificities depend on the pore shape, size, and chemical environments of the voids or channels. Kitagawa . have reported the first utilization of a MOF as an electrocatalyst for oxidation of ethanol to aldehyde, for which the potential was comparable with Pt-based catalysts.2) Recently, Kaneko, Kanoh, Kondo, Kajiro . have developed a quite unique Cu complex MOF [Cu(bpy)(BF4)2(H2O)2]bpy (bpy = 4,4’ -bipyridine),3) named as pre-ELM-11 (ELM stands for Elastic LayerStructured MOF). Upon heating and dehydration, pre-ELM-11 converts to an innovative and stable gas absorbent ELM-11 [Cu(bpy)2(BF4)2] (Figure 1). ELM-11 has structural flexibility, and its structural transformation occurs easier than traditional rigid MOFs. And the gate type adsorption isotherm on ELM-11, which has a predominantly rectangular shaped hysteresis, is quite unique (Figure 2).

Figure 1. Structure Transformation between pre-ELM-11 and ELM-11 Pre-ELM-11 is easily converted to ELM-11 by an activation process (dehydration). Recommended conditions are 120℃ for 3 h in vacuo. ELM-11 is stable on drying at rt. ELM-11 rapidly absorbs moisture in atmospheric conditions and changes its structure to pre-ELM-11, but can be re-transformed.

Figure 2. Schematic representation of the gate adsorption of CO23a) Pre-ELM-11 is also utilized as a catalyst in organic synthesis for molecular oxygen-derived oxidation and epoxide alcoholysis (Scheme).4)

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

299

Metal-Organic Frameworks (MOFs / PCPs)

OSi(CH3)3 CH3

4a) O2, pre-ELM-11 (10 mol%)

O CH3

O

Y. 85 %

EtOH - H2O, 0 ºC, 4.5 h

OH CH3 4b)

O2, pre-ELM-11 (10 mol%) (0.5 eq.) LiOH - H2O (0.8 eq.) P(OEt)3

Y. 84 %

EtOH, 80 ºC, 14.5 h

OCH3

O pre-ELM-11 (9 mol%)

CH3OH

4c)

OH

rt, 2 h Y. 94 %

Scheme. Molecular oxygen-derived oxidation and epoxide alcoholysis using pre-ELM-11

C2409

[Cu(bpy)(BF4)2(H2O)2]bpy

MOF / PCP

Product No. Product Name C2409

Unit Size

pre-ELM-11

5g

B0043

B1191

B3622 O O

COOH O HO C

Materials for MOF / PCP

B0469

HOOC

C2410

HO C C OH

O C OH

COOH

D3899

N

I0001

N

I0155

O

O

C OH

N

OH

N

N

Cu(BF4)2

C OH

N H

HO

O

C OH

C OH

O

M1835

M0345

N0377

O N N H

O

300

C OH

O

OH

C OH

OH CH3

N0272 O

O

C OH

CH3O

N0520

HO

NO2

O O

O2N

C OH

O

OH

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Metal-Organic Frameworks (MOFs / PCPs)

P0545

T0166

T2647 O

O N N

O C OH

C OH

C OH C OH C OH

O

O

O HO C

Product No. Product Name B0043 B1191 B3622 B0469 C2410 D3899 I0001 I0155 M1835 M0345 N0377 N0520 N0272 P0545 T0166 T2647

1,3,5-Benzenetricarboxylic Acid 4,4'-Biphenyldicarboxylic Acid 2,2'-Bipyridine-3,3'-dicarboxylic Acid 4,4'-Bipyridyl Copper(II) Tetrafluoroborate (ca. 45% in Water) 2,5-Dihydroxyterephthalic Acid Imidazole Isophthalic Acid 5-Methoxyisophthalic Acid 2-Methylimidazole 2,6-Naphthalenedicarboxylic Acid 5-Nitroisophthalic Acid Nitroterephthalic Acid 2,3-Pyrazinedicarboxylic Acid Terephthalic Acid 1,3,5-Tris(4-carboxyphenyl)benzene

O C OH

Unit Size 25g 5g 1g 25g 5g 25g 25g 25g 25g 25g

25g 1g

500g 25g 5g 500g 500g 25g 500g 500g 5g 500g 250g 500g 25g 25g 500g 5g

References 1) Reviews of metal-organic frameworks (MOFs / PCPs) a)“Chemistry of Coordination Space”, ed. by H. Nishihara, . 2007, , 2489-2766. b) M. P. Suh, Y. E. Cheon, E. Y. Lee, . 2008, , 1007. c) A. Corma, H. García, F. X. L. Xamena, . 2010, , 4606. 2) Electrocatalyst for ethanol oxidation L. Yang, S. Kinoshita, T. Yamada, S. Kanda, H. Kitagawa, M. Tokunaga, T. Ishimoto, T. Ogura, R. Nagumo, A. Miyamoto, M. Koyama, . 2010, , 5348. 3) For gas storage and gas separation research of pre-ELM-11 a) D. Li, K. Kaneko, . 2001, , 50. b) A. Kondo, H. Noguchi, S. Ohnishi, H. Kajiro, A. Tohdoh, Y. Hattori, W.-C. Xu, H. Tanaka, H. Kanoh, K. Kaneko, . 2006, , 2581. 2007, c) H. Noguchi, A. Kondo, Y. Hattori, H. Kajiro, H. Kanoh, K. Kaneko, , 248. d) H. Kanoh, A. Kondo, H. Noguchi, H. Kajiro, A. Tohdoh, Y. Hattori, W.-C. Xu, M. Inoue, T. Sugiura, K. Morita, H. Tanaka, T. Ohba, K. Kaneko, . 2009, , 1. e) H. Kajiro, A. Kondo, K. Kaneko, H. Kanoh, . 2010, , 3803. f) Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd., Institute of Research and Innovation, Jpn. Kokai Tokkyo Koho 2005 162624; Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd., Institute of Research and Innovation, Jpn. Kokai Tokkyo Koho 2005 162625; Nippon Steel Corporation, Institute of Research and Innovation, Jpn. Kokai Tokkyo Koho 2005 336129; Nippon Steel Corporation, Jpn. Kokai Tokkyo Koho 2005 232031. 4) For catalysis research of pre-ELM-11 a) T. Arai, H. Takasugi, T. Sato, H. Noguchi, H. Kanoh, K. Kaneko, A. Yanagisawa, . 2005, , 1590. b) T. Arai, T. Sato, H. Noguchi, H. Kanoh, K. Kaneko, A. Yanagisawa, . 2006, , 1094. c) D. Jiang, T. Mallat, F. Krumeich, A. Baiker, . 2008, , 390.

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

301

Photopolymerization Initiators

Photopolymerization Initiators Photopolymerization initiators are used in many fields to generate photocurable composites. These composites are polymerized by irradiation with UV light and electron beam which leads to altered physical properties of the composites such as solubility, viscosity and adhesiveness. In particular, the phenomenon in which a liquid changes into a solid is most useful and is applied to surface-treating techniques in fields including paints, printing inks, dental materials, lithography, photoresist, etc. A growing number of intensive studies have been made for the development of improved properties for novel photopolymerization initiators. Radicals



Photopolymerization Initiators

Cations

Anions

Photopolymerization initiators can be divided roughly into three groups with the generated active species, as shown in the upper figure. The conventional photopolymerization initiators generate free radicals upon light irradiation, and the resulting radical starts the polymerization process. Typical initiators are represented by benzoin derivatives. Photo-acid generators which produce cations (acid) by light irradiation, were put to practical use in the late 1990s. Photo-base generators, which produce anions (base) by light irradiation, are of current interest in research. Photopolymerization initiators are divided roughly into three groups as shown above. For a photopolymerization initiator to be an excellent initiator the following properties must be considered; (1) High quantum yields in the generation of radicals, cations and anions (2) Overlap in absorption wavelength of the photopolymerization initiators and emission wavelength of the light source (3) High thermal stability and high stability in darkness (4) Highly soluble in monomers and oligomers In addition to those just developed, we have a wide assortment of initiators, such as benzoin derivatives which are already in use. A0061

A1028

O CH3O

C C

B0079 B0222

CCl3 O O

O O

C CH3

B3633

B0050 B0221

N

OH O

N

C C

OCH3

CH C Cl3C

O

N O

B1019

B1015

B0942

B0869

B0083

O

O

O

O

O

CH C

CH C

CH C

CH C

C

OCH2CH3

OCH2CH(CH3)2

OCH(CH3)2

OCH3

B0103

B1164

B1267

B2380

B2381

O C COOH

302

O

O

C

C OH

t Bu

CH3

S

t Bu

I

t Bu

I

t Bu

Bz

PF6

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

CF3SO3

Photopolymerization Initiators

B1225

B0481

B0139 B1275

C0014

Cl

C1150 CH3

O

N

N N

Et2N

N

O

C

NEt2

Me2N

CH3 CH3

O

C

Cl O

NMe2

C O

Cl

relative

C0292

C1485 C0136

D1801

D1621

D1640

O O Cl

Cl

S

D2375

O OCH2CH3

O

Cl

C

C

Cl

C CH OCH2CH3

O

D1702

D2963

D2248

D2238

O CCl3

O OCH3

CH2CH3

N

C C S

Cl3C

OCH3

I

OCH3

N CH CH

N

I

OCH3

D2253

D3358

E0063

PF6

AsF6

CH2CH3

F0021

F0362

O

O

P

I

CCl3

CH2CH3

C O

N O

CH3

CH3

CH

CH

N N

CF3SO3

O

O

CCl3

CH3

H0617

H0991

P0211

I0591 CH3

O OH

O OH

C

CH3

O NOH

C C CH3

CH3

O CH

F

F

F 4

CH3 CH3

B

S

M2140

M0792

B1231

M1209

O

N

CCl3

O

N

C

N

Cl3C

I F

F

CCl3 N

CH

C C CH3

CH3

M1245

I0678

N

Cl3C

N

CH CH

OCH3

M2028

CH

CH

N

COOCH3

CH3

N0528

O

N

N

OCH3

CCl3 N CH3

P1410

CCl3

P1377

B0486

O CH3 O O

N C

NO2

C

SCH3

CH3O C

CH3

O CH3

T0157

O

O

SO2

S

CH3

C CH

C OCH3

T1188

S

S

N

CH3

T1608

CH3

O

CH3

O

S CBr3

N C S C N CH3

CH3 CH3

CH3

SO2CBr3

CH3

N H

T2041

T2042 CH3

CH3

CH3

S

N C S S C N

S

S

BF4

S

PF6 CH3

CH3

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

CH3 CF3SO3

303

Photopolymerization Initiators

Product No. Product Name A0061 A1028 B0050 B0221 B3633 B0079 B0222 B1019 B1015 B0942 B0869 B0083 B0103 B1164 B1267 B2380 B2381 B1225 B0139 B1275 B0481 C0014 C1150 C1485 C0136 C0292 D1801 D1621 D1640 D2375 D1702 D2963 D2248 D2238 D2253 D3358 E0063 F0021 F0362 H0617 H0991 P0211 I0591 I0678 M1245 M2140 M0792 B1231 M1209 M2028 N0528 P1410 P1377 B0486 T0157 T1188 T1608 T2041 T2042

Unit Size

Acetophenone p-Anisil Benzil Benzil Zone Refined (number of passes:22) 2-(1,3-Benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Benzoin Benzoin Zone Refined (number of passes:40) Benzoin Ethyl Ether Benzoin Isobutyl Ether Benzoin Isopropyl Ether Benzoin Methyl Ether Benzophenone 2-Benzoylbenzoic Acid 4-Benzoylbenzoic Acid 4-Benzoyl 4'-Methyldiphenyl Sulfide Bis(4-tert-butylphenyl)iodonium Hexafluorophosphate Bis(4-tert-butylphenyl)iodonium Trifluoromethanesulfonate 2,2'-Bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole 4,4'-Bis(diethylamino)benzophenone 4,4'-Bis(diethylamino)benzophenone 4,4'-Bis(dimethylamino)benzophenone (±)-Camphorquinone 2-Chlorobenzophenone 4-Chlorobenzophenone 4-Chlorobenzophenone 2-Chlorothioxanthone Dibenzosuberone 4,4'-Dichlorobenzophenone 2,2-Diethoxyacetophenone 2,4-Diethylthioxanthen-9-one 2,2-Dimethoxy-2-phenylacetophenone 2-(3,4-Dimethoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine Diphenyliodonium Hexafluoroarsenate Diphenyliodonium Hexafluorophosphate Diphenyliodonium Trifluoromethanesulfonate Diphenyl(2,4,6-trimethylbenzoyl)phosphine Oxide 2-Ethylanthraquinone 9-Fluorenone 2-[2-(Furan-2-yl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine 1-Hydroxycyclohexyl Phenyl Ketone 2-Hydroxy-2-methylpropiophenone 2-Isonitrosopropiophenone 4-Isopropyl-4'-methyldiphenyliodonium Tetrakis(pentafluorophenyl)borate 2-Isopropylthioxanthone 2-(4-Methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine 2-(4-Methoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine N-Methyl-9-acridone Methyl 2-Benzoylbenzoate 2-[2-(5-Methylfuran-2-yl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine 2-Methyl-4'-(methylthio)-2-morpholinopropiophenone Nifedipine 2-Phenyl-2-(p-toluenesulfonyloxy)acetophenone 2-Pyridyl Tribromomethyl Sulfone Tetramethylthiuram Disulfide Tetramethylthiuram Monosulfide Tribromomethyl Phenyl Sulfone Triphenylsulfonium Tetrafluoroborate Tri-p-tolylsulfonium Hexafluorophosphate Tri-p-tolylsulfonium Trifluoromethanesulfonate

25g

1g

500g 25g 25g 500g 1sample 5g 25g 500g 1sample 25g 500g 25g 500g 25g 500g 25g 500g 25g 500g 25g 500g 5g 25g 10g 1g 5g 1g 5g 25g 25g 500g 25g 500g 25g 500g 5g 25g 25g 500g 25g 500g 25g 5g 25g 25g 500g 25g 500g 25g 500g 25g 250g 25g 500g 5g 1g 5g 25g 1g 5g 25g 25g 500g 25g 500g 5g 25g 500g 25g 500g 25g 5g 25g 25g 5g 25g 5g 5g 25g 25g 500g 5g 25g 500g 10g 25g 1g 5g 25g 25g 500g 25g 500g 25g 1g 5g 1g 1g 5g

References 1) M. Kakuoka, 2) M. Kakuoka, 3) T. Yamaoka,

304

2001, 497. 1999, 592. 1989, , 144.

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Silane Coupling Agents

Silane Coupling Agents Silane coupling agents are organosilicone compounds having two functional groups with different reactivity. One of the two functional groups reacts with organic materials and the other reacts with inorganic materials. Their general structure is as follows: Y R Si

X

3

Where Y denotes a functional group that links with organic materials, e.g. vinyl, epoxy, amino group and so on. X is a functional group that undergoes hydrolysis by water or moisture to form silanol. This silanol links with inorganic materials. Representative examples of X include chlorine, alkoxy, and acetoxy group. Silane coupling agents are effective for the improved adhesion at the interface between the organic and inorganic materials and have been frequently utilized to enhance the strength and improve the performance of glass-fiber reinforced plastics. Recently, they have been used in the manufacture of inorganic-organic hybrid materials such as the laminating board for printed circuit boards, artificial marble, plastic magnets, and silica-immobilized bioactive compounds. In addition to the original purpose of improving the adhesiveness of an interface, different applications are being explored. Examples include synthesis of moisture crosslinkable polymers using the reactivity of hydrolytic functional group, to give antistatic and antibacterial properties from surface treatment using silane coupling agents. It is expected that silane coupling agents will be applied in many fields.

A1538

A0785

OCH2CH3

Cl CH2 CHCH2

Vinyl Group

D2318

D3386

CH

Si CH3

Cl

CH2 CHCH2

T0407

OCH3 CH2 CH

OCH2CH3

Si

CH3

OCH3

Si OCH2CH3

V0044

Si OCH3 OCH3

V0042

OCH2CH3 CH2 CH SiCl3

OCH3 CH2 CHCH2

OCH2CH3

Cl

OCH2CH3 CH2

Si

A1504

CH2 CH Si OCH2CH3 OCH2CH3

OCH3 CH2 CH Si

OCH3

OCH3

V0048

OCH2CH2OCH3 CH2 CH Si OCH2CH2OCH3 OCH2CH2OCH3

Product No. Product Name A1538 A0785 A1504 D2318 D3386 T0407

Allyltrichlorosilane Allyltriethoxysilane Allyltrimethoxysilane Diethoxymethylvinylsilane Dimethoxymethylvinylsilane Trichlorovinylsilane

Unit Size 5g 5ml 25g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 10ml 25ml 25ml 250g 500g

305

Silane Coupling Agents

Product No. Product Name

Unit Size

V0044 V0042 V0048

25ml 25ml 25ml

Triethoxyvinylsilane Vinyltrimethoxysilane Vinyltris(2-methoxyethoxy)silane

D2632

G0261

G0210

OCH2CH3 CH2O(CH2)3 Si

Epoxy Group

O

OCH3

CH3

OCH2CH3

CH2O(CH2)3

OCH3

O

OCH3

Si CH3

CH2O(CH2)3

A1923

A0774

OCH3 H2NCH2CH2NH(CH2)3 Si

Amino Group

OCH2CH3 CH3

T1255

OCH2CH3

OCH2CH3

OCH3

OCH3

OCH3

H2NCH2CH2CH2 Si OCH3

NH(CH2)3

Si OCH3 OCH3

OCH3

OCH2CH3

Product No. Product Name

Unit Size

A0876 A1923 A0774 D1980 A0439 T1255 P1458

25ml

3-(2-Aminoethylamino)propyldimethoxymethylsilane 3-(2-Aminoethylamino)propyltriethoxysilane 3-(2-Aminoethylamino)propyltrimethoxysilane 3-Aminopropyldiethoxymethylsilane 3-Aminopropyltriethoxysilane 3-Aminopropyltrimethoxysilane Trimethoxy[3-(phenylamino)propyl]silane

C1402

Others

ClCH2 Si

OCH2CH3

OCH2CH3

500ml 25g 500g 500ml 500g 500ml 250g

25g 25ml 25g 25ml 25g

C1168

OCH2CH3

306

H2NCH2CH2NH(CH2)3 Si OCH3

P1458

OCH2CH3 H2N(CH2)3 Si OCH2CH3

OCH3

OCH2CH3

CH3 H2NCH2CH2NH(CH2)3 Si OCH2CH3

OCH3

A0439

25ml 500g 500g

25g 25g

A0876

H2N(CH2)3 Si

OCH3

Unit Size

Diethoxy(3-glycidyloxypropyl)methylsilane 3-Glycidyloxypropyl(dimethoxy)methylsilane 3-Glycidyloxypropyltrimethoxysilane

D1980

Si

OCH3

O

Product No. Product Name D2632 G0261 G0210

500ml 500ml 500ml

C0844

OCH3 Cl(CH2)3 Si CH3

Cl Cl(CH2)3 Si Cl

OCH3

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

Cl

Silane Coupling Agents

T1253

E0327

OCH2CH3 Cl(CH2)3 Si

OCH2CH3

M1323

O

OCH3 CH2CH2

OCH2CH3

T2705

Si OCH3

O

Si OCH3 OCH3

U0048

O H2N C NH(CH2)3

OCH3

OCH2CH3

O

OCH3 OCH3

OCH2CH3

T2720

O

OCH3

OCH3

H2N C NH(CH2)3

Si

OCH3

CH3

CF3(CF2)5CH2CH2 Si OCH2CH3

OCH2CH3

T1915

CH2 C C O(CH2)3 Si

OCH2CH3

OCH2CH3

CH2 C C O(CH2)3 Si CH3

OCH2CH3

OCH3 ClCH2CH2CH2 Si OCH3

OCH3

T1770

O

OCH2CH3

M0725

OCH3

CH2 CH C O(CH2)3

OCH2CH3 OCN(CH2)3 Si

HS(CH2)3 Si OCH3

OCH2CH3

T2676

Cl

C0840

OCH3

HS(CH2)3 Si OCH2CH3

OCH3

Cl CF3(CF2)5CH2CH2 Si Cl

Cl

A1597

Si (CH2)3SH

I0556

Cl

M0928

OCH2CH3

OCH3 CH3

OCH3

T2577

CF3(CF2)7CH2CH2 Si Cl

M1505

OCH3

CF3CH2CH2 Si OCH3

OCH3

OCH3

V0050

OCH2CH3 Si

OCH2CH3

CH

CH2 H N

OCH2CH3

. HCl N H

Si(OCH3)3

Product No. Product Name C1402 C1168 C0844 T1253 E0327 M1323 M1505 M0928 T2705 T2577 I0556 T2676 T1770 A1597 C0840 M0725 T1915 T2720 U0048 V0050

Unit Size

(Chloromethyl)triethoxysilane 3-Chloropropyldimethoxymethylsilane 3-Chloropropyltrichlorosilane 3-Chloropropyltriethoxysilane 2-(3,4-Epoxycyclohexyl)ethyltrimethoxysilane 3-Mercaptopropyl(dimethoxy)methylsilane (3-Mercaptopropyl)triethoxysilane (3-Mercaptopropyl)trimethoxysilane Trichloro(1H,1H,2H,2H-heptadecafluorodecyl)silane Trichloro(1H,1H,2H,2H-tridecafluoro-n-octyl)silane 3-(Triethoxysilyl)propyl Isocyanate 3-(Triethoxysilyl)propyl Methacrylate Triethoxy-1H,1H,2H,2H-tridecafluoro-n-octylsilane 3-(Trimethoxysilyl)propyl Acrylate (stabilized with MEHQ) 3-Trimethoxysilylpropyl Chloride 3-(Trimethoxysilyl)propyl Methacrylate (stabilized with BHT) 1-[3-(Trimethoxysilyl)propyl]urea Trimethoxy(3,3,3-trifluoropropyl)silane 3-Ureidopropyltriethoxysilane (40-50% in Methanol) N-[2-(N-Vinylbenzylamino)ethyl]-3-aminopropyltrimethoxysilane Hydrochloride

5g 25ml 25ml 25g 25ml 5g 25g 5g 25ml 25ml 25g 5g 25ml

25ml

(30-40% in Methanol)

B0393

C1259

Cl

Intermediates

10g 25g 25g 500ml 500ml 25ml 500g 100ml 25g 5g 100g 25g 25g 25g 500ml 500ml 250g 25g 500ml

CH3(CH2)3 Si Cl Cl

C0892

OCH2CH3 NCCH2CH2 Si

SiCl3

OCH2CH3

OCH2CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

307

Silane Coupling Agents

D1486

D1553

D0454

CH3

O

Cl CH3(CH2)9 Si Cl

CH3

O

C O Si O C CH3

D2319

CH3(CH2)11 Si Cl

OCH3

CH3(CH2)11 Si OCH2CH3

O0165

O0256

O0168

OCH3

OCH2CH3 CH3(CH2)17 Si OCH2CH3

CH3(CH2)17 Si OCH3

P0240

T1786

OCH3

Cl Cl

CH3(CH2)5 Si

P0736

OCH2CH3

Cl

CH3(CH2)7 Si OCH2CH3

OCH2CH3 CH3(CH2)4 Si OCH2CH3

OCH2CH3

Cl

T1322

OCH3

OCH3

Cl

O0171

CH3(CH2)7 Si Cl

OCH3

OCH2CH3

H0879

CH3CH2 Si

OCH2CH3

Cl

OCH3

E0188

OCH2CH3

Cl

Si CH3

Si

CH3

D1510

OCH3

OCH3

CH3O Si OCH3

CH3

D1509

D1731

CH3

CH3 CH3CH2O Si OCH2CH3

CH3

Cl

D1052

H0547

OCH2CH3

M0450

O

SiCl3

O

O C CH3

CH3 C O Si

CH3

O C CH3

Si

Cl

Cl

Cl NCCH2CH2

Cl

CH3(CH2)5 Si Cl

CH3

Cl

Cl

Si Cl Cl

O

O0079

P0371

T0924

Cl

CH3(CH2)2 Si Cl

Cl

P0857

OCH3

Si

Si

OCH3

OCH3

OCH3

Product No. Product Name

308

CH3CH2

Si OCH2CH3 OCH2CH3

OCH2CH3 CH3

Si OCH2CH3 OCH2CH3

T1801

OCH3 OCH3

B0393 C1259 C0892 D1486 D1553 D0454 D1052 D1731 D2319 D1509 D1510 E0188 H0879 O0165

Cl

Cl

M0660

CH3

CH3(CH2)13 Si Cl

M0451

OCH2CH3

Cl

Cl

CH3(CH2)17 Si Cl

E0189

Butyltrichlorosilane 2-Cyanoethyltriethoxysilane Cyclohexyltrichlorosilane Decyltrichlorosilane Diacetoxydimethylsilane Diethoxydimethylsilane Dimethoxydimethylsilane Dimethoxydiphenylsilane Dimethoxymethylphenylsilane Dodecyltrichlorosilane Dodecyltriethoxysilane Ethyltrichlorosilane Hexyltrimethoxysilane Octadecyltriethoxysilane

OCH3 CH3(CH2)2 Si OCH3 OCH3

Unit Size 25ml 5g

25ml 25g 25ml 25ml 10ml 25g 25ml

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

25g 250ml 25g 25ml 10g 500ml 500g 500ml 100ml 25ml 10ml 500g 500ml 25g

Silane Coupling Agents

Product No. Product Name O0256 O0168 O0171 P0736 P0240 T1786 T1322 H0547 M0450 O0079 P0371 T0924 E0189 M0451 M0660 P0857 T1801

Octadecyltrimethoxysilane n-Octyltrichlorosilane n-Octyltriethoxysilane Pentyltriethoxysilane Phenyltrichlorosilane Triacetoxymethylsilane Trichloro-2-cyanoethylsilane Trichlorohexylsilane Trichloro(methyl)silane Trichlorooctadecylsilane Trichloro(propyl)silane Trichlorotetradecylsilane Triethoxyethylsilane Triethoxymethylsilane Trimethoxy(methyl)silane Trimethoxyphenylsilane Trimethoxy(propyl)silane

Unit Size 25g 25ml 5ml 25g

25g 25g

25ml 25ml 25ml 25ml

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25ml 250g 500ml 25ml 500g 25g 25g 25ml 500g 500g 25g 10ml 25ml 500ml 500ml 500ml 500ml

309

Pressure & Heat Sensitive Recording Materials

Pressure & Heat Sensitive Recording Materials Fluoran compounds, which are a type of colorless dye (color former), develop color via a ring-opening reaction when interacted with acids (developer), as shown in the following scheme. Because this reaction is reversible, decoloration occurs in a reversible manner under basic conditions. CH3 CH3

CH3

CH3

N

N

O

CH3

CH3

CH3

N

N

O

CH3

HX O

COOH

X

Base

O

CH3 N CH3

CH3

N

CH3

[Violet]

[Non Color]

Pressure and heat sensitive recording systems utilize this color developing mechanism in which color formers, developers and sensitizers are intimately incorporated. In pressure sensitive recording, the coloration occurs as follows: Capsules containing color former are destroyed by pressure and the color former makes contact with the developer coated support material. In heat sensitive recording, both color former and developer, which are dispersed on the support material, are thermally melted, thus contacting each other to initiate the coloring reaction. Furthermore, a low melting point sensitizer is also added to achieve a high sensitivity. Recently, the technique has been applied to re-writable recording paper, which can be used for repeated writing and erasing. This technique has been applied to print on commuter passes or prepaid cards. By combining acid-generating methods with the coloring mechanism, new applications can be expected for these materials. Capsule containing color former and oil

Pressure Thermal head Support

Binding resin

Heat

Heat sensing layer Base paper Developer coated layer Developed color

Color former (colorless dye) Developer (solid acid including bisphenol A) Colored dye

B0207

B2628 O

CH3CH2

C

CH3CH2

N

C1946 O

N

CH2CH3 CH2CH3

CH3(CH2)3 CH3(CH2)3

O

N

N

Color Formers

CH3

C0741

D3204

CH3 CH3

NH

N

S

N

D3203

CH3 O

CH3

NO2

D3202

Cl O

D3205

CH3

N

N

O C O

CH3

CH3CH2 CH3CH2 CH3CH2 N

CH3CH2

O

N

CH3CH2

O

CH3CH2

CH3

N

N

O

CH3

CH3O

O

OCH3

CH2 N

O

CH2

O

O

O

310

O

N

CH3

O

O CH3 O

CH3

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

O

Pressure & Heat Sensitive Recording Materials

D3201 CH3CH2 CH3CH2

CH3 CH3

N

C

N

O

CH3

O

Product No. Product Name B0207 B2628 C1946 C0741 D3204 D3203 D3202 D3205 D3201

Unit Size

Benzoyl Leuco Methylene Blue 3',6'-Bis(diethylamino)-2-(4-nitrophenyl)spiro[isoindole-1,9'-xanthene]-3-one 2'-(2-Chloroanilino)-6'-(dibutylamino)fluoran Crystal Violet Lactone 2'-(Dibenzylamino)-6'-(diethylamino)fluoran 6'-(Diethylamino)-1',2'-benzofluoran 6'-(Diethylamino)-1',3'-dimethylfluoran 3',6'-Dimethoxyfluoran 3-(1,2-Dimethyl-3-indolyl)-3-[4-(diethylamino)-2-methylphenyl]phthalide

H0209

1g

25g 25g 500g 25g 25g 25g 25g 25g 25g

25g

B0813

B0464

O OH

C OCH2

HO

Developers

OH

HO OH

B2748

B2752 CH3 CH3CH2

HC

CH CH3

HO

C

CH3

B2749

HO

B2750

OH

CH2CH3 HO

CH3

B2753

HC

CH CH3

HO

C

CH3

C

B1567

B1568

CH3

HO

B1715

HO

OH

CH3

OH

CH3

CH3

CH3 CH3

OH HO

C

CH3

B2751

CH3

CH3

OH

OH

CH3 CH3

CH3

HO

OH

C

OH

CH3

CH3

HO

B1563

B0494

HO

D1356

CH3

CH3

C

C

CH3

CH3

B2664

CH3 OH

HO

C

HO

OH

CH3

B0495

OH

B0735

D2121

CH3

CH3

C

C

CH3

CH3

OH

B0819

OH O HO

S

OH HO

S

HO

OH

O

OH HO

CH2

OH

O

CH3 C CH3 CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

311

Pressure & Heat Sensitive Recording Materials

D3267

E0664

E0432

H1166 CH3

CH3 HO

OH HO

C

OH HO

HO

CH

CH3

N0026

CH3

OH OH

CH3

H0216

CH3

CH3

CH

OH

CH3(CH2)3 CH CH2CH3

CH2CH(CH3)2

M1410

CH

CH3

M1684

CH3

N0027

HO

CH3 CH2

OH

P0201

O C OCH3

OH

OH

OH OH

CH2 OH

OH

R0008

T0032

T0144

T2259

T1254 CH3

Br

OH

Br CH3

CH3 HO

OH

C Br

CH3 C CH2 C CH3

CH3

OH

HO

CH3 CH3

HO

OH

C

OH

CH2

OH

Br OH

T1428 OH

HO

CH3 C

C CH3

CH3

OH

Product No. Product Name H0209 B0813 B0464 B2748 B2752 B2749 B2750 B2751 B2753 B1567 B1568 B1715 B1563 B0494 B2664 D1356 B0495 B0735 D2121 B0819 D3267 E0664 E0432 H1166 M1684 M1410 H0216 N0026 N0027 P0201 R0008 T0032

312

Benzyl 4-Hydroxybenzoate 2,2'-Biphenol 4,4'-Biphenol 2,2-Bis(3-sec-butyl-4-hydroxyphenyl)propane 1,1-Bis(3-cyclohexyl-4-hydroxyphenyl)cyclohexane 2,2-Bis(3-cyclohexyl-4-hydroxyphenyl)propane 2,2-Bis(2-hydroxy-5-biphenylyl)propane 2,2-Bis(4-hydroxy-3-isopropylphenyl)propane 1,1-Bis(4-hydroxy-3-methylphenyl)cyclohexane 2,2-Bis(4-hydroxy-3-methylphenyl)propane 1,1-Bis(4-hydroxyphenyl)cyclohexane 9,9-Bis(4-hydroxyphenyl)fluorene α,α'-Bis(4-hydroxyphenyl)-1,4-diisopropylbenzene 2,2-Bis(4-hydroxyphenyl)propane 1,3-Bis[2-(4-hydroxyphenyl)-2-propyl]benzene Bis(4-hydroxyphenyl) Sulfide Bis(4-hydroxyphenyl) Sulfone 4-tert-Butylphenol Zone Refined (number of passes:19) 4,4'-Dihydroxydiphenyl Ether 4,4'-Dihydroxydiphenylmethane 4,4'-(1,3-Dimethylbutylidene)diphenol 4,4'-(2-Ethylhexylidene)diphenol 4,4'-Ethylidenebisphenol 4,4'-(2-Hydroxybenzylidene)bis(2,3,6-trimethylphenol) 4,4'-Methylenebis(2-methylphenol) 1,1'-Methylenedi-2-naphthol Methyl 4-Hydroxybenzoate 1-Naphthol 2-Naphthol 4-Phenylphenol Resorcinol Tetrabromobisphenol A

Unit Size 25g 25g 25g

500g 500g 500g 25g 25g 25g 5g 25g 25g 25g 500g 25g 500g 25g 500g 25g 500g 25g 500g 25g 250g 25g 500g 25g 500g 1sample 25g 500g 5g 25g 25g 500g 25g 25g 500g 25g 25g 25g 25g 500g 25g 500g 25g 250g 25g 500g 25g 500g 25g 500g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

OH

Pressure & Heat Sensitive Recording Materials

Product No. Product Name T0144 T2259 T1254 T1428

Unit Size

4-(1,1,3,3-Tetramethylbutyl)phenol 2,3,4-Trihydroxydiphenylmethane 1,1,1-Tris(4-hydroxyphenyl)ethane α,α,α'-Tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene

25g 25g

B1248

B1519

B1619

O

D0159

D0001

D1598

T0015

D2017 O

OCH2 CH

O CH2 S CH2

CH3 CH3

CH3 O

O

P0231

O

OCH3

D0866

F0016

O

O

S

C CH2 C

O C O

O

CH

O

D0910

OCH3

CH3

OCH2

C0043

OCH2

CH2

CH3(CH2)20 C OH

Sensitizers

500g 5g 500g 25g

OCH2CH2O

O

F0017

H0067

C0024

L0011

H0283 O O

O

O CH3(CH2)14 C NH2

OCH3 CH3(CH2)4

NH2

CH3(CH2)10

OH OH

M0476

O0238

O0107

O CH3(CH2)12

S0075

CH3(CH2)6

NH2

S0314

(CH2)7 C NH2

OH

O

O C O

CH3(CH2)14 C OH

T0018

NH2

CH3(CH2)16 C NH

Product No. Product Name B1248 B1519 B1619 D0159 D0001 D1598

CH3(CH2)7

H0797

O

O CH3(CH2)16

O

O OH

P0002

Behenic Acid 4-Benzylbiphenyl Benzyl 2-Naphthyl Ether 1,4-Dibenzyloxybenzene Dibenzyl Sulfoxide 2,6-Diisopropylnaphthalene

Unit Size 5g 5g 25g 5g 25g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 25g 500g 25g 250g 500g

313

Pressure & Heat Sensitive Recording Materials

Product No. Product Name T0015 D2017 C0043 D0910 P0231 D0866 F0016 F0017 H0067 C0024 L0011 H0283 M0476 O0238 O0107 P0002 H0797 S0075 S0314 T0018

314

Dimethyl Terephthalate 1,4-Diphenoxybenzene Diphenyl Carbonate 1,3-Diphenyl-1,3-propanedione Diphenyl Sulfone Ethylene Glycol Diphenyl Ether Fluoranthene Fluorene Hexadecanamide Hexanamide Lauric Acid Methyl 3-Hydroxy-2-naphthoate Myristic Acid n-Octanamide Oleamide Palmitic Acid Phenyl 1-Hydroxy-2-naphthoate Stearamide Stearanilide m-Terphenyl

Unit Size 25g 5g 25g 25g 25g 25g 25g 10g 25g 25g 25g 10g 25g 25g 25g 25g 25g 25g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

500g 25g 500g 500g 500g 5g 500g 500g 25g 25g 500g 500g 500g 25g 500g 500g 500g 500g 500g 500g

Ethylene Glycols & Monofunctional Ethylene Glycols

Ethylene Glycols & Monofunctional Ethylene Glycols Ethylene Glycols Product No. Product Name

Unit Size

E0105 D0495 T0428 T0099 P1154 H0934 H1045 O0295 N0698 D2900 D2901

25g 100g 25g 25g 5g

Ethylene Glycol Diethylene Glycol Triethylene Glycol Tetraethylene Glycol Pentaethylene Glycol Hexaethylene Glycol Heptaethylene Glycol Octaethylene Glycol Nonaethylene Glycol Decaethylene Glycol Dodecaethylene Glycol

500g 500g 500g 500g 25g 5g 1g 1g 1g 1g 1g

Monofunctional Ethylene Glycols Product No. Product Name M0111 E0047 E0514 E0110 B0698 E0301 E0354 H0343 E0264 E0518 E0326 A0301 D1756 D0298 A1059 A0743 P0115 E0504 C0169 C0251 E0302 E0303 B0426 H1048

Ethylene Glycol Monomethyl Ether (=2-Methoxyethanol) Ethylene Glycol Monoethyl Ether (=2-Ethoxyethanol) Ethylene Glycol Monopropyl Ether Ethylene Glycol Monoisopropyl Ether Ethylene Glycol Monobutyl Ether Ethylene Glycol Monoisobutyl Ether Ethylene Glycol Mono-tert-butyl Ether Ethylene Glycol Monohexyl Ether Ethylene Glycol Monododecyl Ether Ethylene Glycol Monovinyl Ether (stabilized with KOH) Ethylene Glycol Monoallyl Ether Ethylene Glycol Mono(2-aminoethyl) Ether [=2-(2-Aminoethoxy)ethanol] Ethylene Glycol Mono[2-(dimethylamino)ethyl] Ether [=2-[2-(Dimethylamino)ethoxy]ethanol] Ethylene Glycol Mono[2-(diethylamino)ethyl] Ether [=2-[2-(Diethylamino)ethoxy]ethanol] Ethylene Glycol Monoacetate (=2-Hydroxyethyl Acetate) Ethylene Glycol Monoacrylate (=2-Hydroxyethyl Acrylate) (stabilized with MEHQ) Ethylene Glycol Monophenyl Ether (=2-Phenoxyethanol) Ethylene Glycol Mono(4-bromophenyl) Ether Ethylene Glycol Mono-2-chloroethyl Ether Ethylene Glycol Mono(4-chlorophenyl) Ether Ethylene Glycol Mono-m-tolyl Ether Ethylene Glycol Mono-p-tolyl Ether Ethylene Glycol Monobenzyl Ether [=2-(Benzyloxy)ethanol] Ethylene Glycol Mono-4-(hydroxymethyl)-2-nitrophenyl Ether

E0113 M0537 E0048 B0699 D0501 D1233 D2623 D3408 T0709 E0167 T1373 T0915 T0768 C1416 T1996 T1372 T0769 T1796

Ethylene Glycol Monosalicylate Diethylene Glycol Monomethyl Ether Diethylene Glycol Monoethyl Ether Diethylene Glycol Monobutyl Ether Diethylene Glycol Monohexyl Ether Diethylene Glycol Monododecyl Ether Diethylene Glycol Monovinyl Ether (stabilized with KOH) Diethylene Glycol Monobenzyl Ether Triethylene Glycol Monomethyl Ether Triethylene Glycol Monoethyl Ether Triethylene Glycol Monoisopropyl Ether Triethylene Glycol Monobutyl Ether Triethylene Glycol Monododecyl Ether Triethylene Glycol Monochlorohydrin [=2-[2-(2-Chloroethoxy)ethoxy]ethanol] Triethylene Glycol Monobenzyl Ether Tetraethylene Glycol Monomethyl Ether Tetraethylene Glycol Monododecyl Ether Tetramethylene Glycol Monovinyl Ether (stabilized with KOH)

[=2-[4-(Hydroxymethyl)-2-nitrophenoxy]ethanol]

Unit Size 25ml 25ml 25ml 25ml 25ml 25ml 25ml 25ml 25ml 25ml 25ml 25ml 25g 25ml 25ml 25g 25ml 5ml 5g 25ml 100mg 25g 25ml 25g 25ml 25ml 25ml 25g 25ml 25ml 5g 25ml 25g 5g 5g 25ml

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500ml 500ml 500ml 500ml 500ml 500ml 500ml 500ml 5ml 500ml 500ml 500ml 500ml 500g 500ml 500ml 500g 25g 500ml 25g 25ml 25g 250ml 1g 500g 500ml 500g 500ml 500ml 5ml 500ml 500g 500ml 500ml 25g 500ml 5ml 100g 25g 25g 5ml 500ml

315

Ethylene Glycols & Monofunctional Ethylene Glycols

Product No. Product Name T1997 P1159 P0372 P1435 H0808 H0444 H1043 H1046 H0445 O0296 O0139 N0699 D2903 D2904 P0671 P1777 P0841 P1776 P0711 P0713 P0714 P0715 P0716 P0872 P0717 P0718 P0719 P0720 P0721 P0722 P0723 P0873 P1775 P0704 P0705 P0706 P0707 P0708 P0709 P0710

316

Tetraethylene Glycol Monobenzyl Ether Pentaethylene Glycol Monomethyl Ether Pentaethylene Glycol Monododecyl Ether Pentaethylene Glycol Monobenzyl Ether Hexaethylene Glycol Monomethyl Ether Hexaethylene Glycol Monododecyl Ether Hexaethylene Glycol Monobenzyl Ether Heptaethylene Glycol Monomethyl Ether Heptaethylene Glycol Monododecyl Ether Octaethylene Glycol Monomethyl Ether Octaethylene Glycol Monododecyl Ether Nonaethylene Glycol Monomethyl Ether Decaethylene Glycol Monomethyl Ether Dodecaethylene Glycol Monomethyl Ether Polyethylene Glycol Monododecyl Ether n≒25 Polyethylene Glycol Monododecyl Ether n≒25 [for Biochemical Research] Polyethylene Glycol Monocetyl Ether n≒23 Polyethylene Glycol Monocetyl Ether n≒23 [for Biochemical Research] Polyethylene Glycol Monooleyl Ether n≒2 Polyethylene Glycol Monooleyl Ether n≒7 Polyethylene Glycol Monooleyl Ether n≒10 Polyethylene Glycol Monooleyl Ether n≒20 Polyethylene Glycol Monooleyl Ether n≒50 Polyethylene Glycol Monolaurate n≒10 Polyethylene Glycol Monostearate n≒2 (palmitate and stearate mixture) Polyethylene Glycol Monostearate n≒4 (palmitate and stearate mixture) Polyethylene Glycol Monostearate n≒10 (palmitate and stearate mixture) Polyethylene Glycol Monostearate n≒25 (palmitate and stearate mixture) Polyethylene Glycol Monostearate n≒40 (palmitate and stearate mixture) Polyethylene Glycol Monostearate n≒45 (palmitate and stearate mixture) Polyethylene Glycol Monostearate n≒55 (palmitate and stearate mixture) Polyethylene Glycol Mono-4-octylphenyl Ether n≒10 Polyethylene Glycol Mono-4-octylphenyl Ether n≒10 [for Biochemical Research] Polyethylene Glycol Mono-4-nonylphenyl Ether n≒2 Polyethylene Glycol Mono-4-nonylphenyl Ether n≒5 Polyethylene Glycol Mono-4-nonylphenyl Ether n≒7.5 Polyethylene Glycol Mono-4-nonylphenyl Ether n≒10 Polyethylene Glycol Mono-4-nonylphenyl Ether n≒15 Polyethylene Glycol Mono-4-nonylphenyl Ether n≒18 Polyethylene Glycol Mono-4-nonylphenyl Ether n≒20

Unit Size 1g

1g

1g 5g

1g 1g 500mg

25g 5g 25g 5g 25g 25g 25g 25g 25g 25g 25g 25g 25g 25g 25g 25g 25g 25g 5g 25g 25g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

5g 5g 5g 5g 25g 5ml 1g 5g 5g 5g 5g 1g 100mg 100mg 500g 25g 500g 25g 500g 500g 500g 500g 500g 500g 500g 500g 500g 500g 500g 500g 500g 500g 25g 25g 500g 25g 500g 25g 25g 25g

Monoprotected Diaminoalkanes

Monoprotected Diaminoalkanes -Boc-diaminoalkanes CH3 CH3

O

C O C NH(CH2)nNH2 CH3

Product No. Product Name N-(tert-Butoxycarbonyl)-1,2-diaminoethane N-(tert-Butoxycarbonyl)-1,3-diaminopropane N-(tert-Butoxycarbonyl)-1,4-diaminobutane N-(tert-Butoxycarbonyl)-1,5-diaminopentane N-(tert-Butoxycarbonyl)-1,6-diaminohexane N-(tert-Butoxycarbonyl)-2,2-dimethyl-1,3-propanediamine

A1371 A1372 A1373 A1374 A1375 B3052

Unit Size 1g 1g

5g 1g 5g 1g 1g

25g 5g 25g 5g 5g 5g

-Cbz-diaminoalkanes O CH2O C NH(CH2)nNH2

Product No. Product Name N-Carbobenzoxy-1,2-diaminoethane Hydrochloride N-Carbobenzoxy-1,3-diaminopropane Hydrochloride N-Carbobenzoxy-1,4-diaminobutane Hydrochloride N-Carbobenzoxy-1,5-diaminopentane Hydrochloride N-Carbobenzoxy-1,6-diaminohexane Hydrochloride

C1511 C1512 C1519 C1520 C1521

Unit Size 1g

5g 1g 1g 1g 1g

25g 5g 5g 5g 5g

-( -Ns)-diaminoalkanes NO2 O S NH(CH2)nNH2 O

Product No. Product Name A2329 A1628 A1630 A1661 A1662

N-(2-Aminoethyl)-2-nitrobenzenesulfonamide Hydrochloride N-(3-Aminopropyl)-2-nitrobenzenesulfonamide N-(4-Aminobutyl)-2-nitrobenzenesulfonamide N-(5-Aminopentyl)-2-nitrobenzenesulfonamide Hydrochloride N-(6-Aminohexyl)-2-nitrobenzenesulfonamide Hydrochloride

Unit Size 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 1g 1g 1g 1g

317

3-Aminopyrrolidines

3-Aminopyrrolidines

A1108

A1113

A1112

O NH C CH3 N H

A1104

A1055

B1355

. 2HCl N H

N H

B1559

B1357

B1560

N CH2

M1096

N

CH2

CH2

NHCH2

CH3

N H

D1965

CH2CH3

CH3

N CH2CH3

N CH3

NHCH3 N

M1106

N H

CH3

T1247 O

NHCH3 N H

NH N H

C CF3

. HCl

Product No. Product Name

318

CH3

C O C CH3 CH3

D1859

N H

NHCH2CH3

A1108 A1113 A1112 A1104 A1055 B1355 B1354 B1357 B1559 B1560 B1558 B1356 B1358 M1096

NH N H

CH2

N CH2

E0431

O

NH C CF3 N

D1857

CH3

B1358 O

NHCH3

N C O C CH3

CH2

B1356

N

D1964

N

CH2

NHCH2CH3

N CH3

CH3

NH C O C CH3 CH3

N

N

B1558

O

NH2

NH C CH3

CH2

CH3

O N H

B1354

NH2

NH2

N H

N C CH3

N H

O

O

CH3

N C CH3 O

Racemic

CH3

CH2CH3

3-Acetamidopyrrolidine 3-(N-Acetyl-N-ethylamino)pyrrolidine 3-(N-Acetyl-N-methylamino)pyrrolidine 3-Aminopyrrolidine 3-Aminopyrrolidine Dihydrochloride 1-Benzyl-3-acetamidopyrrolidine 1-Benzyl-3-aminopyrrolidine 1-Benzyl-3-(tert-butoxycarbonylamino)pyrrolidine 1-Benzyl-3-(dimethylamino)pyrrolidine 1-Benzyl-3-(ethylamino)pyrrolidine 1-Benzyl-3-(methylamino)pyrrolidine 1-Benzyl-3-(trifluoroacetamido)pyrrolidine 3-(tert-Butoxycarbonylamino)pyrrolidine 3-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine

Unit Size 5g 5g 5g 5g

5g 5g 5g

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

25g 5g 25g 25g 25g 25g 25g 10g 5g 5g 25g 25g 25g 25g

3-Aminopyrrolidines

Product No. Product Name

Unit Size

N,N '-Dibenzyl-3-aminopyrrolidine 3-(Diethylamino)pyrrolidine 3-(Dimethylamino)pyrrolidine N,N '-Dimethyl-3-aminopyrrolidine 3-(Ethylamino)pyrrolidine 3-(Methylamino)pyrrolidine 3-(Trifluoroacetamido)pyrrolidine Hydrochloride

D1964 D1857 D1859 D1965 E0431 M1106 T1247

25g 25g 25g 10g 5g 25g 10g

5g 10g

5g

A1169

A1170

A2323 NH2

O

O

NH C CH3

NH C CH3

. HCl

N

Chiral

N H

A2324

A1167 NH2

A1168

. HCl

C OCH2

N H

O

A1053

NH2

A1054

NH2

NH2

N N H

N H

C OCH2

NH2

. 2HCl

N H

N H

. 2HCl

O

A1173

A1174

B1932

NH2

NH2

N

N

CH2

CH2

B1582

B1580

N CH2

A1171

NHCH3

O NH

N

CH2

CH2

B2921 NH2 N

B2920 O

CH3

C O C CH3

NH

D2193

E0433

CH3

CH3 N CH3

N

CH3

C O C CH3

N H

N CH3

NH2

CH3

C O C CH3 CH3

N H

N H

CH3

M1107

O

CH3

E0434 NHCH2CH3

N H

N H

M1108

T1369

NHCH3 N H

CH2

NHCH2CH3

CH3

C O C CH3 O

N

CH2

CH3

D2149

NHCH2CH3

N

A1172

NHCH3

N

NHCH2CH3

NH C O C CH3 CH3

B1583

B1581

CH3

O

NHCH3 N H

N H

N H

T1366 O

O

NH C CF3

NH C CF3

. HCl

N H

. HCl

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

319

3-Aminopyrrolidines

Product No. Product Name A1169 A1170 A2323 A2324 A1167 A1168 A1053 A1054 A1173 A1174 B1932 B1580 B1581 B1582 B1583 A1171 A1172 B2920 B2921 D2149 D2193 E0433 E0434 M1107 M1108 T1369 T1366

Unit Size

(3R)-(+)-3-Acetamidopyrrolidine (3S)-(-)-3-Acetamidopyrrolidine (R)-3-Amino-1-carbobenzoxypyrrolidine Hydrochloride (S)-3-Amino-1-carbobenzoxypyrrolidine Hydrochloride (3R)-(+)-3-Aminopyrrolidine (3S)-(-)-3-Aminopyrrolidine (3R)-(-)-3-Aminopyrrolidine Dihydrochloride (3S)-(+)-3-Aminopyrrolidine Dihydrochloride (3R)-(-)-1-Benzyl-3-aminopyrrolidine (3S)-(+)-1-Benzyl-3-aminopyrrolidine (3R)-(+)-1-Benzyl-3-(tert-butoxycarbonylamino)pyrrolidine (3R)-(-)-1-Benzyl-3-(ethylamino)pyrrolidine (3S)-(+)-1-Benzyl-3-(ethylamino)pyrrolidine (3R)-(-)-1-Benzyl-3-(methylamino)pyrrolidine (3S)-(+)-1-Benzyl-3-(methylamino)pyrrolidine (3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine (3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine (3R)-(+)-1-(tert-Butoxycarbonyl)-3-aminopyrrolidine (3S)-(-)-1-(tert-Butoxycarbonyl)-3-aminopyrrolidine (3R)-(+)-3-(Dimethylamino)pyrrolidine (3S)-(-)-3-(Dimethylamino)pyrrolidine (3R)-(+)-3-(Ethylamino)pyrrolidine (3S)-(-)-3-(Ethylamino)pyrrolidine (3R)-(+)-3-(Methylamino)pyrrolidine (3S)-(-)-3-(Methylamino)pyrrolidine (3R)-(+)-3-(Trifluoroacetamido)pyrrolidine Hydrochloride (3S)-(-)-3-(Trifluoroacetamido)pyrrolidine Hydrochloride

1g 1g 5g 5g 5g 5g 10g 10g

5g 5g 5g 5g 1g 1g 1g 1g

1g 1g 1g 1g

References 1) 2) 3) 4)

320

Tokyo Tokyo Tokyo Tokyo

Kasei Kasei Kasei Kasei

Kogyo Kogyo Kogyo Kogyo

Co., Co., Co., Co.,

Ltd., Ltd., Ltd., Ltd.,

Jpn. Kokai Tokkyo Koho 2 218664, 1990. Eur. Patent Appl., EP 218249, 1987. Jpn. Kokai Tokkyo Koho 63 41453, 1988. Jpn. Kokai Tokkyo Koho 63 41452, 1988.

The chemical, physical and toxicological properties of some chemicals have not been thoroughly investigated. Please handle with care.

5g 5g 5g 5g 25g 25g 25g 25g 25g 25g 5g 5g 5g 25g 25g 25g 25g 5g 5g 5g 5g 1g 1g 5g 5g 25g 25g

-Substituted Maleimides, Succinimides & Phthalimides

-Substituted Maleimides, Succinimides & Phthalimides

A0825

B1149 O

N

B1805 O

O

N

-Substituted Maleimides

N

N H

O

N

O

CH2

O

NH2

B1971

B1109

E0482

B1787

O O CH3

H3C O

N

CH2

O CH2CH3

O

N

N

H3CH2C O

O

CH2

N

N

N

O

CH2CH2

N

N

(CH2)6 N

O

O

O

M1962

A5591

N

O

O

P0976 O

O

N

O

CH2Br

N

O

O

O

O

N

O

N

P0900

O

O

N

N

O

O

O N

N

NO2

P1214

S0399

O

O

S0428

O

S0427

O

O

O

O

N

N O C CH2CH2CH2

N

N O C

O

O

O

O N O C

N

O

S0398 O

O

CH3

O

P0778

O

O

N

O

N

O

M0807

O

O O

N

CH2CH2 C OH

N0638

O

Cl

O CH3

CH2CH3

N

Cl

M0881

O O

O

O

O

E0136

O

O

O

O

C1044

B1973

O

O

N

N O C CH2CH2

N

O

O

O

O

O

O

O O

(CH2)5

T1987 O

N

Cl

O Cl

Cl

Product No. Product Name A0825 B1149 B1805 B1971 B1109 E0482

N-(4-Aminophenyl)maleimide N-[4-(2-Benzimidazolyl)phenyl]maleimide N-Benzylmaleimide Bis(3-ethyl-5-methyl-4-maleimidophenyl)methane 4,4'-Bismaleimidodiphenylmethane 1,2-Bis(maleimido)ethane

Unit Size 100mg 50mg 100mg 5g 25g 25g 500g 25g 500g 100mg

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

321

-Substituted Maleimides, Succinimides & Phthalimides

Product No. Product Name B1787 B1973 C1044 E0136 M1962 M0881 M0807 A5591 N0638 P0976 P0778 P0900 P1214 S0398 S0399 S0428 S0427 T1987

Unit Size

1,6-Bismaleimidohexane N-Bromomethyl-2,3-dichloromaleimide N-Cyclohexylmaleimide N-Ethylmaleimide 3-Maleimidopropionic Acid 6,7-Methylenedioxy-4-methyl-3-maleimidocoumarin [for HPLC Labeling] N-Methylmaleimide NAM [=N-(9-Acridinyl)maleimide] [for HPLC Labeling] N-(4-Nitrophenyl)maleimide N,N '-1,3-Phenylenedimaleimide N,N '-1,4-Phenylenedimaleimide N-Phenylmaleimide N-(1-Pyrenyl)maleimide N-Succinimidyl 3-Maleimidobenzoate [Cross-linking Reagent] N-Succinimidyl 4-Maleimidobutyrate [Cross-linking Reagent] N-Succinimidyl 6-Maleimidohexanoate [Cross-linking Reagent] N-Succinimidyl 3-Maleimidopropionate [Cross-linking Reagent] N-(2,4,6-Trichlorophenyl)maleimide

A1819

100mg 5g 25g 25g 1g 100mg 500g 100mg 5g 500g 5g 500g 250mg 1g 1g 1g 1g 25g

1g 1g

5g 200mg 25g 50mg 25g 1g 25g 100mg 100mg 100mg 100mg

B0656

B2205

O

O

-Substituted Succinimides

B3433

CH3S

O

N Boc

O

Boc

C2334

O

CH3

O O

HN

N N H

O

Cbz

CH2O C O N

CH2O C O N

O

O

O

O

O O

O

N

N O C O N

O

Cl

O

F0239

O

H0623 B0249 O O

O

N

CH2O C O N

O

CH2CH3

O

P1359

O

O

O

N

S0431

S0814

O

OH

O

2

I0074

CH2O C O N

D1662

O

O

O

O

Cbz

O

O

N O C (CH2)6 C O N

N O C CH2CH2S

O CH3 HN

O

E0175

N

O

N

O

Cl

O Boc

O

C0291

O

D3895

CH3 O

Boc

O

D2473

O

HN

O

O

O HN

O N

C1131 O

O

O

C1124

O O

Br

N

N

C2353 O

C1298 CH3 O

O

Br

O N

. HCl

B3435

O O

HN

O

NH2

B3414 O

N

S0491 O

O

O

O O

N I

O

N

O

O

HN

O

O

CH3 C SCH2 C O N

CH2 CH

C O N

NH

H

H S

O

(CH2)4

O O C O N

O O

322

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

-Substituted Maleimides, Succinimides & Phthalimides

S0503

S0808

D2255 O

O

C

NH(CH2)5 C O N N N

O

O CH3

CH3

S0428 O N

N O C CH2CH2

N

O

O

O

T1513 CH3

O CH3

O CH3

O O C O N CH3 O

NO2

O

N O C

N

N O C CH2CH2CH2

N

O

O

O

O

O

O O2N

O

CH2

S0808 D2255 S0398 S0399 S0428 S0427 S0812 A5522 S0819 S0599 T1513 T2224 T2591

O

C O N

CH3

N

S

SCH2CH2 C O N

O

O

O

T2591

O N O C

O

O

CH2 C C O N

O

CCl3CHO C O N

S0819

O

N(CH3)2 N(CH3)2

O

BF4

(CH3)3SiCH2CH2O C O N

O

Product No. Product Name A1819 B0656 B2205 B3433 B3414 B3435 C2353 C1124 C2334 C1298 C1131 C0291 D1662 D2473 D3895 E0175 F0239 H0623 B0249 I0074 P1359 S0431 S0814 S0491 S0503

O O

A5522

T2224 O

Cl

(CH2)5 NH

O

O O

S0599

O

N O C

S0812

O

O

O

O O

NO2

S0427

(CH2)5

O

O2N

O

O

OCH2

SO2N(CH3)2

N O C

S0399

O CH2CH2 C O N

O

O

O

S0398

O

O

N-Aminosuccinimide Hydrochloride N-Bromosuccinimide N-(tert-Butoxycarbonyl)-O-benzyl-L-serine N-Succinimidyl Ester N-(tert-Butoxycarbonyl)-L-methionine N-Succinimidyl Ester N-(tert-Butoxycarbonyl)-D-proline Succinimidyl Ester Nα-(tert-Butoxycarbonyl)-L-tryptophan N-Succinimidyl Ester N-Carbobenzoxy-L-leucine N-Succinimidyl Ester N-Carbobenzoxyoxysuccinimide N-Carbobenzoxy-L-valine Succinimidyl Ester Carbonic Acid 2-Bromobenzyl Succinimidyl Ester N-(2-Chlorobenzyloxycarbonyloxy)succinimide N-Chlorosuccinimide Di(N-succinimidyl) Carbonate Di(N-succinimidyl) 3,3'-Dithiodipropionate [Cross-linking Reagent] Di(N-succinimidyl) Suberate N-Ethylsuccinimide N-[(9H-Fluoren-9-ylmethoxy)carbonyloxy]succinimide N-Hydroxysuccinimide N-Hydroxysuccinimide [Coupling Reagent for Peptide] N-Iodosuccinimide N-Phenylsuccinimide N-Succinimidyl S-Acetylthioglycolate [Cross-linking Reagent] N-Succinimidyl Acrylate N-Succinimidyl D-Biotinate Succinimidyl 6-[[7-(N,N-Dimethylaminosulfonyl)-2,1,3-benzoxadiazol4-yl]amino]hexanoate Succinimidyl 4-[3,5-Dimethyl-4-(4-nitrobenzyloxy)phenyl]-4-oxobutyrate N-Succinimidyl 6-(2,4-Dinitroanilino)hexanoate N-Succinimidyl 3-Maleimidobenzoate [Cross-linking Reagent] N-Succinimidyl 4-Maleimidobutyrate [Cross-linking Reagent] N-Succinimidyl 6-Maleimidohexanoate [Cross-linking Reagent] N-Succinimidyl 3-Maleimidopropionate [Cross-linking Reagent] N-Succinimidyl Methacrylate N-Succinimidyl 4-Nitrophenylacetate [for HPLC Labeling] N-Succinimidyl 3-(2-Pyridyldithio)propionate Succinimidyl (2R)-6-(Tetrahydro-2H-pyran-2-yloxy)-2,5,7,8-tetramethylchroman2-carboxylate N-(1,2,2,2-Tetrachloroethoxycarbonyloxy)succinimide N,N,N ',N '-Tetramethyl-O-(N-succinimidyl)uronium Tetrafluoroborate N-[2-(Trimethylsilyl)ethoxycarbonyloxy]succinimide

O

Unit Size 25g

1g 100g 1g 1g

25g

25g 5g 1g 1g 5g 25g 5g

25g 5g 1g

100mg 100mg 100mg 100mg 5g

1g 1g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 500g 5g 5g 5g 5g 5g 250g 5g 10g 10g 500g 25g 5g 5g 25g 25g 500g 25g 100g 25g 5g 5g 100mg 100mg 100mg 1g 1g 1g 1g 1g 25g 1g 100mg 50mg 10g 5g 5g

323

-Substituted Maleimides, Succinimides & Phthalimides

A0108

A1447 O

A1561 O

O

O

H2N

N C CH3

-Substituted Phthalimides

N OCH2CH O

O

A0843

B1997 O

B1394

N NH2

O

O

B1697

O

N CH2Br

N CH2CH2Br

O

B2707

O

O

N (CH2)3CH2Br

O

B3443

P1192

O

N CH2

O

O

B0597

O

N CH3

CH2

B1328

O

O

B1881 O

O

Br N CH3

N

Br

N Br

O

O

B0736

A5503

(CH2)3CH3

CH3 O

C0802

N CH2Cl

O

AcO AcO

N CH2

G0327

OAc BnO O O O N O

N CH2

O O O N O

N CH2OH O

O

H0933

O

I0738

O

O

O O

N

N OH O

Ph

O O

N

O

N OH

OCH3

Ph

O O

O N O

OCH3

OH

O

M1609

O O O

N CH

N

O

M1598 OBn O

AcO BnO

(CH2)8OH

O

M1834

OH

O O O

N

O

OCH3

M1479 OH O

HO BnO

Ph

O O

CH3 CH3

O

M1610

O O BnO

OCH3

O

N CH2CH2OH

O2N

324

O O

O O

H0395

O

O OAc

H0648

O

H0834

OAc Ph O

AcO

O

O

O

H1036

OCH2CH3

O

N CH2

OBn

N C OCH2CH3

H0245

O OCH3

AcO

O

G0328

OBn O O

P

OCH2CH3

O

O

G0311 O

O

N S

O

Cl

O

C0683

O

N Cl

N

N CH2Cl O

P1193

O

O

O2N O

C1452

G0299

O

CH3

N O C O C CH3

O

C1958

O O

N

O

A5504

O

N CH2CH2CH CH2

O

O

C1573 O

N CH2CH2CH2Br

N

O

OCH3

O O HO

O O O

N

OCH3

O

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

-Substituted Maleimides, Succinimides & Phthalimides

M1615

M1480 OBn O

HO BnO

O N

O

OCH3

M1310

O N

O

O

M1649

O

OAc O

AcO AcO

M0299

OCH3

O

N CH3

O

N0574

O0365

P1235

O

O

O

P1254

O

SCH3 N

O

N CH3

O

OAc O

AcO AcO

O2N

O

P0403 O

O

O2N

N

N

N

O

O

N S

O

P1229

P1180 O

N CH2CH

N CH2

OCH2CH3

O

C CH3

P0620

P0963

CH3 O N CH

C OCH2CH3

C OH

N

O

P1227

P0338

O

T2047

N CH2

O

O

OH

O N

C OH

N

O

O

T2054

T2055

F

O

N CH3

R

R

O O H

R

. 2 CH3

O

Rh Rh O O O H R

R

O

Cl

O Cl Cl

O

H

. 2 CH3

O

Cl

C OCH2CH3

O O O

R

H

O

. 2 CH3

R'

H R

R

O

R=

Cl

R

C OCH2CH3

Cl

. 2 CH3

O

O

Cl

C OCH2CH3

O O O

R

R

O

O

Rh

H R

R'=

N

R=

CH2

O H R'

O

. CH3

C OCH2CH3

T1526 R H

H OO

Rh Rh

N

O H

O Cl

H R' OO

O

H

R

O

R

T2661 H

H OO

Rh Rh

N

R=

O

R

O

R

C OCH2CH3

Rh O O O

N

R=

O

R H

H OO

O

O

T2660

R O

O

R

Rh

H

O

T2659 H

OO

Rh O O O

N

R=

H

O

O

O

Rh

H

O

T2658

R

OO

Rh O O O

R

F

H

H

O

R' H

R

H

O

T1551

R

O

F

OAc N

O

CH2CH2 C OH O

O

T2421 F

OAc O

AcO AcO

N CH C OH

O

O O

O

O

O

O

O

O O

O

O

O

O

C OCH2CH3

N CH

O

P1789

O

O OCH2CH3

O

P0695

O

O

N H

O

O

P1203

NK

N

O

R

O

O F

R=

F O

. 2 CH3

O

F

C OCH2CH3

H OO

Rh Rh

N

O H

F

O O O

R H

R

O

O R R=

O

F F F

. 2 CH3

O

O

F

CBr

N

N

O H

Cl Cl O

3

C OCH2CH3

V0065 O N CH

CH2

O

Product No. Product Name A0108 A1447 A1561 A0843 B1997 B1394

N-Acetylphthalimide N-Allyloxyphthalimide 4-Amino-N-methylphthalimide N-Aminophthalimide N-Benzylphthalimide N-(4-Bromobutyl)phthalimide

Unit Size 5g 5g 5g 5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

25g 25g 25g 25g 25g 25g

325

-Substituted Maleimides, Succinimides & Phthalimides

Product No. Product Name B0597 P1192 B3443 B2707 B1697 B1328 B1881 B0736 C1573 A5503 A5504 C1958 C0802 C1452 P1193 C0683 G0311 G0299 G0327 G0328 H0245 H0648 H1036 H0834 H0395 H0933 I0738 M1834 M1598 M1609 M1610 M1479 M1615 M1480 M1310 M0299 M1649 N0574 O0365 P1254 P1235 P0403 P1229 P1203 P1180 P0695 P1789 P0620 P0963 P1227 P0338 T2047 T2421 T2054 T2055 T1551 T2658 T2659 T2660 T2661 T1526 V0065

326

N-(2-Bromoethyl)phthalimide N-(Bromomethyl)phthalimide 4-Bromo-N-methylphthalimide N-(4-Bromophenyl)phthalimide N-Bromophthalimide N-(3-Bromopropyl)phthalimide N-(3-Buten-1-yl)phthalimide N-Butylphthalimide Carbonic Acid tert-Butyl Phthalimido Ester N-Chloromethyl-4-nitrophthalimide [for HPLC Labeling] N-Chloromethylphthalimide [for HPLC Labeling] N-(4-Chlorophenyl)phthalimide N-Chlorophthalimide N-(Cyclohexylthio)phthalimide Diethyl (Phthalimidomethyl)phosphonate N-Ethoxycarbonylphthalimide [for Peptide Synthesis] Gal[2346Ac]β(1-3)GlcNPhth[46Bzd]-β-MP GlcNPhth[346Ac]β(1-3)Gal[246Bn]-β-MP (R)-N-Glycidylphthalimide (S)-N-Glycidylphthalimide N-(2-Hydroxyethyl)phthalimide N-Hydroxymethylphthalimide N-Hydroxy-4-nitrophthalimide N-(8-Hydroxyoctyl)phthalimide N-Hydroxyphthalimide (S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid N-Isopropylphthalimide 4-Methoxyphenyl 4-O-Acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 4-Methoxyphenyl 3-O-Allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimidoβ-D-glucopyranoside 4-Methoxyphenyl 3-O-Benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 4-Methoxyphenyl 4,6-O-Benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 4-Methoxyphenyl 3,6-Di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 4-Methoxyphenyl 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside N-Methyl-4-nitrophthalimide N-Methylphthalimide Methyl 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 4-Nitro-N-phenylphthalimide N-(4-Oxocyclohexyl)phthalimide N-(Phenylthio)phthalimide Phthalimide DBU Salt Phthalimide Potassium Salt 2-Phthalimidoacetaldehyde Diethyl Acetal Phthalimidoacetone Phthalimidomalonic Acid Diethyl Ester Phthaloyl-DL-alanine N-Phthaloyl-DL-glutamic Anhydride N-Phthaloyl-L-glutamic Anhydride N-Phthaloylglycine N-Phthaloyl-L-phenylalanine Phthalyl-DL-glutamic Acid 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 3,4,5,6-Tetrafluoro-N-methylphthalimide Tetrakis[N-phthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-phthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-phthaloyl-(S)-phenylalaninato]dirhodium Ethyl Acetate Adduct Tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-tetrafluorophthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct Tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct 4,4',4''-Tris(4,5-dichlorophthalimido)trityl Bromide [Protecting Reagent for Primary Alcohol] N-Vinylphthalimide

Unit Size 25g 5g 5g 5g 5g 25g

500g 25g 25g 25g 25g 500g 5g 25g 5g 1g 5g 5g 5g 25g 500g 25g 500g 5g 25g 25g 500g 1g 5g Price on request 5g 25g 5g 25g 25g 500g 25g 250g 5g 1g 25g 500g 5g 25g 1g 5g 1g 5g 1g Price on request 5g 1g 5g 5g 25g 25g 1g 5g 25g 5g 25g 5g 25g 25g 25g 500g 25g 25g 5g 10g 25g 5g 25g 1g 5g 25g 500g 5g 5g 25g 5g 25g 5g 25g 100mg 100mg 100mg 50mg 100mg 50mg 100mg 1g 5g 25g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

1,4-Disubstituted Cyclohexanes

1,4-Disubstituted Cyclohexanes

A1278

4-Substituted Cyclohexanecarboxylic Acids A1656

B3248

A1448

4-Amino Substituted B3249

O

O

C OH

C OH

NH2

NH2

B3250

C2036

O

O

O

O

O

C OH

C OH

C OH

C OH

C OH

O HN C OC(CH3)3

NH2

HN C OC(CH3)3 O

O

M1985

HN C OC(CH3)3

NH C OCH2

O

M1986 O

O

C OCH3

C OCH3

. HCl

. HCl NH2

NH2

Product No. Product Name A1278 A1448 A1656 B3248 B3249 B3250 C2036 M1985 M1986

E0838

4-Hydroxy Substituted

Unit Size

4-Aminocyclohexanecarboxylic Acid (cis- and trans- mixture) cis-4-Aminocyclohexanecarboxylic Acid trans-4-Aminocyclohexanecarboxylic Acid 4-(tert-Butoxycarbonylamino)cyclohexanecarboxylic Acid (cis- and trans- mixture) cis-4-(tert-Butoxycarbonylamino)cyclohexanecarboxylic Acid trans-4-(tert-Butoxycarbonylamino)cyclohexanecarboxylic Acid trans-4-(Carbobenzoxyamino)cyclohexanecarboxylic Acid Methyl cis-4-Aminocyclohexanecarboxylate Hydrochloride Methyl trans-4-Aminocyclohexanecarboxylate Hydrochloride

H0960

H0980

5g 5g 5g 5g

1g

5g 1g

O

O

O

C OCH2CH3

C OH

C OH

C OH

OH

OH

OH

OH

Ethyl trans-4-Hydroxycyclohexanecarboxylate 4-Hydroxycyclohexanecarboxylic Acid (cis- and trans- mixture) cis-4-Hydroxycyclohexanecarboxylic Acid trans-4-Hydroxycyclohexanecarboxylic Acid

25g 25g 25g 25g 5g 5g 25g 5g 5g

H1175

O

Product No. Product Name E0838 H0960 H0980 H1175

1g 1g

Unit Size 25g 5g 5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

5g 250g 25g 25g

327

1,4-Disubstituted Cyclohexanes

B2986

B1136

4-Alkyl Substituted

B1285

B2631

O

O

O

O

C OH

C OH

C OH

C OH

CH3 C CH3

(CH2)3CH3

(CH2)3CH3

B3037

I0664

M1621

CH3 C CH3

CH3

M1783

CH3

P0944

O

O

O

O

O

C OH

C OH

C OH

C OH

C OH

CH3

CH3

CH3 C CH3

CH3

CH3

P1656

CH3

P0943

T2417

T2423

(CH2)4CH3

T2424

O

O

O

O

O

C OH

C OH

C OH

C OH

C OH

CH2CH2CH3

CH2CH2CH3

CF3

CF3

CF3

Product No. Product Name B2986 B1136 B1285 B2631 B3037 I0664 M1621 M1783 P0944 P1656 P0943 T2417 T2423 T2424

Unit Size

4-Butylcyclohexanecarboxylic Acid (cis- and trans- mixture) trans-4-Butylcyclohexanecarboxylic Acid 4-tert-Butylcyclohexanecarboxylic Acid (cis- and trans- mixture) cis-4-tert-Butylcyclohexanecarboxylic Acid trans-4-tert-Butylcyclohexanecarboxylic Acid trans-4-Isopropylcyclohexanecarboxylic Acid 4-Methylcyclohexanecarboxylic Acid (cis- and trans- mixture) trans-4-Methylcyclohexanecarboxylic Acid trans-4-Pentylcyclohexanecarboxylic Acid 4-Propylcyclohexanecarboxylic Acid (cis- and trans- mixture) trans-4-Propylcyclohexanecarboxylic Acid 4-(Trifluoromethyl)cyclohexanecarboxylic Acid (cis- and trans- mixture) cis-4-(Trifluoromethyl)cyclohexanecarboxylic Acid trans-4-(Trifluoromethyl)cyclohexanecarboxylic Acid A2121

A0236

5g 5g 5g 5g

25g 25g 25g 25g 5g 25g 25g 25g 25g 25g 25g 5g 5g 5g

5g 5g 5g 5g 5g 1g 1g

B3251

B3253

O

O

O

O

C OH

C OH

C OH

C OH

CH2NH2

CH2NH2

Miscellaneous CH2NH C OC(CH3)3

C0788

C0789

C0475

CH2NH C OC(CH3)3

O

D3768

O

D3639

O

O

O

O

O

C OH

C OH

C OH

C OCH2CH CH2

C OCH2CH3

C OH

C OH

C OH

C OCH2CH CH2

C OCH2CH3

O

O

O

O

O

C1154

H1015

H1242

H1243

M1988

O

O

O

O

O

C OCH3

C OH

C OH

C OH

C OCH3

CH2OH

CH2OH

CH2OH

CH2NH2

. HCl

C OCH3 O

328

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

1,4-Disubstituted Cyclohexanes

Product No. Product Name A2121 A0236 B3251 B3253 C0788 C0789 C0475 D3768 D3639 C1154 H1015 H1242 H1243 M1988

Unit Size

4-(Aminomethyl)cyclohexanecarboxylic Acid (cis- and trans- mixture) trans-4-(Aminomethyl)cyclohexanecarboxylic Acid 4-(tert-Butoxycarbonylaminomethyl)cyclohexanecarboxylic Acid (cis- and trans- mixture) trans-4-(tert-Butoxycarbonylaminomethyl)cyclohexanecarboxylic Acid 1,4-Cyclohexanedicarboxylic Acid (cis- and trans- mixture) cis-1,4-Cyclohexanedicarboxylic Acid trans-1,4-Cyclohexanedicarboxylic Acid Diallyl 1,4-Cyclohexanedicarboxylate (cis- and trans- mixture) Diethyl trans-1,4-Cyclohexanedicarboxylate Dimethyl 1,4-Cyclohexanedicarboxylate (cis- and trans- mixture) 4-(Hydroxymethyl)cyclohexanecarboxylic Acid (cis- and trans- mixture) cis-4-(Hydroxymethyl)cyclohexanecarboxylic Acid trans-4-(Hydroxymethyl)cyclohexanecarboxylic Acid Methyl trans-4-(Aminomethyl)cyclohexanecarboxylate Hydrochloride

A1278

4-Substituted Cyclohexylamines

A1656

M1985

4-Carboxy Substituted

5g 25g 25g 25g 25g 5g 25g 5g 5g 1g

A1448 O

O

C OH

C OH

NH2

NH2

M1986

O

O

O

C OH

C OCH3

C OCH3

NH2

NH2

. HCl

. HCl NH2

Product No. Product Name A1278 A1448 A1656 M1985 M1986

5g 25g 5g 25g 500g 100g 500g 250g 25g 500g 25g 25g 5g 5g

5g

Unit Size

4-Aminocyclohexanecarboxylic Acid (cis- and trans- mixture) cis-4-Aminocyclohexanecarboxylic Acid trans-4-Aminocyclohexanecarboxylic Acid Methyl cis-4-Aminocyclohexanecarboxylate Hydrochloride Methyl trans-4-Aminocyclohexanecarboxylate Hydrochloride

1g 1g

5g 5g 5g 1g

25g 25g 25g 5g 5g

A1160 OH

4-Hydroxy Substituted

NH2

Product No. Product Name A1160

Unit Size

trans-4-Aminocyclohexanol

B1084

M1117 NH2

4-Alkyl Substituted

25g

M1780 NH2

500g

M0957 NH2

NH2

. HCl CH3 C CH3 CH3

CH3

CH3

CH3

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

329

1,4-Disubstituted Cyclohexanes

Product No. Product Name

Unit Size

B1084 M1117 M1780 M0957

25ml

4-tert-Butylcyclohexylamine (cis- and trans- mixture) 4-Methylcyclohexylamine (cis- and trans- mixture) trans-4-Methylcyclohexylamine 4-Methylcyclohexylamine Hydrochloride

A2288

C0814

5g

C1798

250ml 25ml 25g 25g

C1426

CH2CH2OH

NH2

NH2

NH2

NH2

NH2

NH2

NH2

Miscellaneous

Product No. Product Name A2288 C0814 C1798 C1426

Unit Size

4-Aminocyclohexaneethanol (cis- and trans- mixture) 1,4-Cyclohexanediamine (cis- and trans- mixture) cis-1,4-Cyclohexanediamine trans-1,4-Cyclohexanediamine

1g 5ml 5g 5g

E0838

4-Substituted Cyclohexanols

H0980

4-Carboxy Substituted

H0960 O

O

C OCH2CH3

C OH

OH

OH

H1175 O

O

C OH

C OH

OH

OH

Product No. Product Name E0838 H0960 H0980 H1175

Unit Size

Ethyl trans-4-Hydroxycyclohexanecarboxylate 4-Hydroxycyclohexanecarboxylic Acid (cis- and trans- mixture) cis-4-Hydroxycyclohexanecarboxylic Acid trans-4-Hydroxycyclohexanecarboxylic Acid

A1617

A1162 OH

4-Amino Substituted

NH

C CH3 O

330

25g 5g 5g

A1160 OH

NH

C CH3 O

4-Acetamidocyclohexanol (cis- and trans- mixture) trans-4-Acetamidocyclohexanol trans-4-Aminocyclohexanol trans-4-(tert-Butoxycarbonylamino)cyclohexanol

5g 250g 25g 25g

B3564 OH

Product No. Product Name A1617 A1162 A1160 B3564

5g 25ml 25g 25g

NH2

OH

NH C OC(CH3)3 O

Unit Size 25g 1g

25g 25g 500g 5g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

1,4-Disubstituted Cyclohexanes

A1926

A2315

4-Alkyl Substituted B1270

OH

OH

CH2(CH2)3CH3

CH2(CH2)3CH3

(CH2)3CH3

B1271

E0366 OH

CH3 C CH3

CH3

CH3

I0782

M0196

CH3

P1882

E0768

OH

CH3 C CH3 CH3

I0780

OH

OH

CH2CH3

CH2CH3

M0353

OH

CH3

B0383

OH

OH

CH3 C CH3

B1930

M0354

OH

CH3

CH3

P1874

OH

OH

OH

OH

CH3

CH3

CH3

CH2CH2CH3

T2706 OH

OH

CH2CH2CH3

CF3

Product No. Product Name A1926 A2315 B1930 B0383 B1270 B1271 E0366 E0768 I0780 I0782 M0196 M0353 M0354 P1874 P1882 T2706

Unit Size

4-Amylcyclohexanol (cis- and trans- mixture) trans-4-Amylcyclohexanol 4-Butylcyclohexanol (cis- and trans- mixture) 4-tert-Butylcyclohexanol (cis- and trans- mixture) cis-4-tert-Butylcyclohexanol trans-4-tert-Butylcyclohexanol 4-Ethylcyclohexanol (cis- and trans- mixture) trans-4-Ethylcyclohexanol 4-Isopropylcyclohexanol (cis- and trans- mixture) trans-4-Isopropylcyclohexanol 4-Methylcyclohexanol (cis- and trans- mixture) cis-4-Methylcyclohexanol trans-4-Methylcyclohexanol 4-Propylcyclohexanol (cis- and trans- mixture) trans-4-Propylcyclohexanol 4-(Trifluoromethyl)cyclohexanol (cis- and trans- mixture)

A2266

C0482

5g 5g 25g 1g 1g

25ml

1g

C2319

25g 1g 25g 500g 5g 5g 25ml 5g 5g 1g 500ml 5ml 5ml 5g 1g 5g

C2320

OH

OH

OH

OH

CH2CH2NH2

OH

OH

OH

Miscellaneous

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

331

1,4-Disubstituted Cyclohexanes

H1253

H1257

H1258

OH

OH

OH

CH2CH2OH

CH2OH

CH2OH

Product No. Product Name A2266 C0482 C2319 C2320 H1253 H1257 H1258

Unit Size

4-(2-Aminoethyl)cyclohexanol (cis- and trans- mixture) 1,4-Cyclohexanediol (cis- and trans- mixture) cis-1,4-Cyclohexanediol trans-1,4-Cyclohexanediol 4-(2-Hydroxyethyl)cyclohexanol (cis- and trans- mixture) 4-(Hydroxymethyl)cyclohexanol (cis- and trans- mixture) trans-4-(Hydroxymethyl)cyclohexanol

B1083

25g

1g 100g 1g 1g 5g 1g

C0479

5g 500g 200mg 5g 5g 25g 5g

C2234

CH2NH2

CH2OH

CH2OH

CH2NH2

CH2OH

CH2OH

Others

C1133

C1135 O

CH2O C CH

O CH2O C CH

D0271

CH2CH3 (CH2)3CH3

CH2CH3 (CH2)3CH3

C1136 O

CH2O C CH2CH

O CH2O C CH2CH

E0424

CH3 CH3

D0700

CH2O C

CH3

O

CH3

CH2O C

(CH2)10CH3

(CH2)10CH3

I0284

CH3

CH2CH3

CH3

CH3

332

CH3

CH3

CH3

CH3

I0285

M1412 CH3

CH3

CH3

CH3

Product No. Product Name B1083 C0479 C2234 C1133 C1135 C1136 D0700 D1715 D0271 E0424 I0284 I0285 M1412

D1715

O

1,4-Bis(aminomethyl)cyclohexane (cis- and trans- mixture) 1,4-Cyclohexanedimethanol (cis- and trans- mixture) trans-1,4-Cyclohexanedimethanol 1,4-Cyclohexanedimethanol Bis(2-ethylhexanoate) 1,4-Cyclohexanedimethanol Diisovalerate 1,4-Cyclohexanedimethanol Dilaurate 1,4-Dimethylcyclohexane (cis- and trans- mixture) cis-1,4-Dimethylcyclohexane trans-1,4-Dimethylcyclohexane 1-Ethyl-4-methylcyclohexane (cis- and trans- mixture) cis-1-Isopropyl-4-methylcyclohexane trans-1-Isopropyl-4-methylcyclohexane 4-Methyl-1-cyclohexanemethanol (cis- and trans- mixture)

CH3

CH3

CH3

CH2OH

Unit Size 25g 5g

25ml 5ml 5ml

5g

25g 500g 25g 25g 1g 1g 500ml 25ml 25ml 1ml 5ml 1ml 25g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Monofunctional & α, ω-Bifunctional Alkanes

Monofunctional & α, ω-Bifunctional Alkanes Monofunctional Alkanes / H-(CH2)n-X x 

 n 1

―OH

―COOH

―NH2

―Br

―Cl

M0097

A2035

M0137

B1618

――

2

――

P0500

E0055

B0588

C0164

3

P0491

B0754

P0520

B0638

C0266

4

B0228

V0003

B0707

B0560

C0142

5

P0055

H0105

A0445

B0628

C0237

6

H0130

H0030

H0134

B0600

C0184

7

H0033

O0027

H0045

B0598

C0182

8

O0212

N0288

O0045

B0626

C0236

9

N0292

D0017

N0297

B0933

C0233

10

D0031

U0004

D0033

B0583

C0600

11

U0005

L0011

A0761

B0934

C0599

12

D0978

T0412

D0980

B0587

C0163

13

T0803

M0476

A0762

B0935

C2213

14

T0084

P0035

T0090

B0233

C0622

15

P0036

P0002

A0763

B0936

―― C0183

16

H0071

H0019

H0074

B0599

17

H0018

S0163

A0764

B0937

――

18

O0006

N0283

O0014

B0625

C0235

19

N0284

E0006

A0765

――

――

20

E0004

H0010

――

B0391

C0774

―NH2

―Br

―Cl

α,ω-Bifunctional Alkanes / X-(CH2)n-X x 

―OH

―COOH

1

――

M0028

――

D0192

D0529

2

E0105

S0100

E0077

D0180

D0310

3

P0486

G0069

D0114

D0202

D0399

4

B0680

A0161

D0239

D0176

D0349

 n

5

P0050

P0435

D0108

D0198

D0390

6

H0099

O0023

D0095

D0185

D0372

7

H0028

A1318

D0094

D2119

D1030

8

O0024

S0022

D0107

D1064

D1012

9

N0287

N0333

D0106

D1746

――

10

D0014

D0013

D0085

D0179

D0247

11

――

T0021

D2075

D2487

――

12

D0969

T0704

D0091

D1346

――

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

333

ω-Functional Alkanols, Carboxylic Acids, Amines & Halides

ω-Functional Alkanols, Carboxylic Acids, Amines & Halides X−(CH2)n−OH Product No. Product Name C0270 C0144 C0815 C0801 B0590 B0641 B1885 B1848 B1822 B1852 B1729 B1785 B1730 B1477 B1731 I0391

Unit Size

3-Chloro-1-propanol 4-Chloro-1-butanol (contains varying amounts of Tetrahydrofuran) 5-Chloro-1-pentanol 6-Chloro-1-hexanol 2-Bromoethanol 3-Bromo-1-propanol 4-Bromo-1-butanol (contains varying amounts of Tetrahydrofuran) 5-Bromo-1-pentanol 6-Bromo-1-hexanol 7-Bromo-1-heptanol 8-Bromo-1-octanol 9-Bromo-1-nonanol 10-Bromo-1-decanol 11-Bromo-1-undecanol 12-Bromo-1-dodecanol 2-Iodoethanol (stabilized with Copper chip)

25g 25g 5ml 25g 25g 25g 5g 5g 5g 1g 5g 5g 5g 5g 5g

500g 500g 25ml 500g 500g 250g 25g 25g 25g 5g 25g 25g 25g 25g 25g 25g

CH2=CH(CH2)n−OH Product No. Product Name A0218 B0236 P1243 H0653 H0949 O0280 N0650 D1892 U0047

Allyl Alcohol 3-Buten-1-ol 4-Penten-1-ol 5-Hexen-1-ol 6-Hepten-1-ol 7-Octen-1-ol 8-Nonen-1-ol 9-Decen-1-ol 10-Undecen-1-ol

Unit Size 10ml 10ml

25ml 25ml 25ml 25ml 5g 5ml 5g 25ml 25ml

500ml 500ml 250ml 250ml 25g 25ml 25g 500ml 500ml

H2N−(CH2)n−OH Product No. Product Name A0297 A0298 A0438 A0407 A1013 A0875 A1027 A1522 A1523 A1524

334

2-Aminoethanol 2-Aminoethanol Hydrochloride 3-Amino-1-propanol 3-Amino-1-propanol Hydrochloride 4-Amino-1-butanol 5-Amino-1-pentanol 6-Amino-1-hexanol 8-Amino-1-octanol 10-Amino-1-decanol 12-Amino-1-dodecanol

Unit Size 25g 25g 25g 5g 25g 5g 1g 1g 1g

500g 500g 500g 25g 25g 250g 25g 5g 5g 5g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

ω-Functional Alkanols, Carboxylic Acids, Amines & Halides

X−(CH2)n−COOH Product No. Product Name C2123 C0276 C0651 C0309 C1507 B0531 B0645 B1279 B1169 B1290 B3671 B1675 B2323 B2264 B0389 I0071

Unit Size

Chloroacetic Acid 3-Chloropropionic Acid 4-Chlorobutyric Acid 5-Chlorovaleric Acid 6-Chlorohexanoic Acid Bromoacetic Acid 3-Bromopropionic Acid 4-Bromobutyric Acid 5-Bromovaleric Acid 6-Bromohexanoic Acid 7-Bromoheptanoic Acid 8-Bromooctanoic Acid 9-Bromononanoic Acid 10-Bromodecanoic Acid 11-Bromoundecanoic Acid 3-Iodopropionic Acid

25g 25g 25g 5g 25g 25g 10g 25g 10g 1g 5g 25g 5g

500g 500g 500g 25g 25g 500g 500g 25g 25g 250g 5g 25g 5g 25g 500g 25g

CH2=CH(CH2)n−COOH Product No. Product Name A0141 B0694 P0645 H0875 D1932 U0007 T1211

Unit Size

Acrylic Acid (stabilized with MEHQ) 3-Butenoic Acid 4-Pentenoic Acid 5-Hexenoic Acid 9-Decenoic Acid 10-Undecenoic Acid 22-Tricosenoic Acid

25g 25g 5g 5ml 25g 100mg

500g 250g 25ml 25g 25ml 500g 1g

H2N−(CH2)n−COOH Product No. Product Name G0099 G0103 A0180 A0282 A0663 A0436 A0312 A0311 A0932

Glycine Glycine Hydrochloride β-Alanine 4-Aminobutyric Acid 5-Aminovaleric Acid 5-Aminovaleric Acid Hydrochloride 6-Aminohexanoic Acid 7-Aminoheptanoic Acid 12-Aminolauric Acid

Unit Size 25g 25g 25g 25g 5g

1g

25g 5g 25g

500g 500g 500g 500g 25g 1g 500g 25g 500g

HO−(CH2)n−COOH Product No. Product Name

Unit Size

G0110 G0196 H0297

Glycolic Acid (ca. 70% in Water, ca. 12mol/L) Glycolic Acid 3-Hydroxypropionic Acid (contains varying amounts of 3,3'-Oxydipropionic Acid)

25g 25g

500g 500g

(ca. 30% in Water, ca. 3.6mol/L)

H0676 H0675

15-Hydroxypentadecanoic Acid 16-Hydroxyhexadecanoic Acid

10g 1g 1g

25g 5g 5g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

335

ω-Functional Alkanols, Carboxylic Acids, Amines & Halides

X−(CH2)n−NH2 Product No. Product Name C0851 C1062 B0591 B1263

Unit Size

2-Chloroethylamine Hydrochloride 3-Chloropropylamine Hydrochloride 2-Bromoethylamine Hydrobromide 3-Bromopropylamine Hydrobromide

25g 25g 25g 25g

500g 500g 500g 500g

CH2=CH(CH2)n−NH2 Product No. Product Name

Unit Size

A0219 A0226

25ml 25g

Allylamine Allylamine Hydrochloride

500ml 500g

X−(CH2)n−Cl Product No. Product Name B0573 B0572 B0575 B1345 B1476 B1998 B3537 C1179 C1190 C1037

Unit Size

Bromochloromethane 1-Bromo-2-chloroethane 1-Bromo-3-chloropropane 1-Bromo-4-chlorobutane 1-Bromo-5-chloropentane 1-Bromo-6-chlorohexane 1-Bromo-7-chloroheptane Chloroiodomethane (stabilized with Copper chip) 1-Chloro-2-iodoethane (stabilized with Copper chip) 1-Chloro-3-iodopropane (stabilized with Copper chip)

25g 25g 25g 25g 25g 25g 1g

500g 500g 500g 500g 25g 500g 5g 100g 5g 25g

CH2=CH(CH2)n−X Product No. Product Name C0274 V0032 B0643 B0920 B1474 B2106 B2849 B3576 B2816 I0070

336

Allyl Chloride Vinyl Bromide (stabilized with MEHQ) Allyl Bromide 4-Bromo-1-butene 5-Bromo-1-pentene 6-Bromo-1-hexene 10-Bromo-1-decene 11-Bromo-1-undecene 18-Bromo-1-octadecene Allyl Iodide (stabilized with Copper chip)

Unit Size 25ml

10g

25g 25g 5g 5g 1g 1g

500ml 100g 500g 250g 25g 25g 5g 5g 5g 25g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Quaternary Ammonium Compounds

Quaternary Ammonium Compounds R1 R2 N R4 R

X

3

X=F, Cl, Br, I, OH, etc.

Fluoride Chloride Bromide

Iodide Hydroxide Others

Fluorides Product No. Product Name T1339 T1338 T1125

Tetrabutylammonium Fluoride (70-75% in Water) Tetrabutylammonium Fluoride (1mol/L in Tetrahydrofuran) Tetrabutylammonium Fluoride (1mol/L in Tetrahydrofuran) [for Catalyst of acylation, silylation

T1037

Tetrabutylammonium Fluoride Hydrate [for Catalyst of acylation, silylation and cleavage of

T0838 T2027 T2026

Tetraethylammonium Fluoride Hydrate Tetraethylammonium Fluoride Tetrahydrofluoride Tetraethylammonium Fluoride Trihydrofluoride

and cleavage of Silyl Ether] silyl ether]

Unit Size 25ml

25g 100ml

500g 500ml

25ml

100ml

25g 5g

250g 25g 10g 10g

Chlorides Product No. Product Name

Unit Size

A0084 A1493 B0414 B0044 B0107 B0237 B1683 B1689 B0416 B1297 A0208 A5160

25g 25ml 25g 25g

B1684 B1685 B1384 B0444 B0447 B3358 C0596 C0050 C0172 C1180 C0329 D1306 D2003 D1630 D1016 I0453

Acetylcholine Chloride (3-Acrylamidopropyl)trimethylammonium Chloride (74-76% in Water) (stabilized with MEHQ) Benzalkonium Chloride (50% in Water) Benzethonium Chloride Benzoylcholine Chloride Benzylcetyldimethylammonium Chloride Hydrate N-Benzylcinchonidinium Chloride [Chiral Phase-Transfer Catalyst] N-Benzylcinchoninium Chloride [Chiral Phase-Transfer Catalyst] Benzyldimethylphenylammonium Chloride Benzyldimethylstearylammonium Chloride Hydrate Benzyldimethyltetradecylammonium Chloride Hydrate Benzyldimethyltetradecylammonium Chloride Hydrate [Ion association reagent for extraction

25g

25g 25g

photometric analysis and sensitizer in photometric determination of metals] N-Benzylquinidinium Chloride [Chiral Phase-Transfer Catalyst] N-Benzylquininium Chloride [Chiral Phase-Transfer Catalyst]

Benzyltributylammonium Chloride Benzyltriethylammonium Chloride Benzyltrimethylammonium Chloride 1-Butyl-1-methylpyrrolidinium Chloride Carbamylcholine Chloride DL-Carnitine Hydrochloride Chlorocholine Chloride (3-Chloro-2-hydroxypropyl)trimethylammonium Chloride (ca. 50% in Water) Choline Chloride Decyltrimethylammonium Chloride Diallyldimethylammonium Chloride (60% in Water) Dimethyldistearylammonium Chloride Dodecyltrimethylammonium Chloride Dodecyltrimethylammonium Chloride [Reagent for Ion-Pair Chromatography]

25g 25g 25g 5g 10g 25g 25g 25ml 25g 25ml 25g 25g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

500g 500ml 500g 500g 25g 500g 10g 5g 25g 500g 500g 5g 5g 5g 500g 500g 500g 25g 25g 500g 500g 500ml 500g 25g 500ml 500g 500g 500g

337

Quaternary Ammonium Compounds

Product No. Product Name B0457 H0082 H0090 D0973 M0073 M0918 M0681 M1293 T1365 O0178 P0241 P0274 P0834 S0358 S0149 T1433 T0055 I0366 T0095 T0136 T2106 M0852 T1307 P0244 S0087 T0926 T2246 T0826

Girard's Reagent T Hexadecyltrimethylammonium Chloride Hexamethonium Chloride Dihydrate Lauroylcholine Chloride Methacholine Chloride Methacroylcholine Chloride (ca. 80% in Water) (stabilized with MEHQ) (2-Methoxyethoxymethyl)triethylammonium Chloride β-Methylcholine Chloride Methyltri-n-octylammonium Chloride n-Octyltrimethylammonium Chloride Phenyltriethylammonium Chloride Phosphocholine Chloride Calcium Salt Tetrahydrate Phosphocholine Chloride Sodium Salt Hydrate [for Cholinesterase Substrate] Stachydrine Hydrochloride Succinylcholine Chloride Dihydrate Tetraamylammonium Chloride Tetrabutylammonium Chloride Tetrabutylammonium Chloride [Reagent for Ion-Pair Chromatography] Tetraethylammonium Chloride Tetramethylammonium Chloride Tetrapropylammonium Chloride Triethylmethylammonium Chloride Trimethyl[2,3-(dioleyloxy)propyl]ammonium Chloride Trimethylphenylammonium Chloride Trimethylstearylammonium Chloride Trimethyltetradecylammonium Chloride Trimethyl[3-(triethoxysilyl)propyl]ammonium Chloride Trioctylmethylammonium Chloride (R=C6-C10) [Phase-transfer Catalyst]

Unit Size 25g 25g 25g 25g 25g

25g

1g 5g 5g 5g 5g 25g 25g 25g 100mg 25g 25g 25g 5g 25g

500g 500g 500g 1g 500g 500g 5g 25g 500g 25g 25g 25g 5g 10mg 25g 25g 25g 25g 500g 500g 25g 500g 1g 500g 500g 500g 25g 500g

Bromides Product No. Product Name A0083 B0106 B1217 B0443 B2980 B0577 B2754 B3424 C0328 D1314 D3269 D1467 D2363 D1974 D2355 D1975 D2754 D2354 D1468 D0721 F0286 F0166 H0081 H0481 H0989 H0534 H0448 M0072 N0358 O0163 P0243 S0231 T1432 T0054

338

Acetylcholine Bromide Benzoylcholine Bromide Benzyltributylammonium Bromide Benzyltriethylammonium Bromide Benzyltrimethylammonium Bromide Bromocholine Bromide 1,1'-(Butane-1,4-diyl)bis[4-aza-1-azoniabicyclo[2.2.2]octane] Dibromide 1-Butyl-1-methylpiperidinium Bromide Choline Bromide Decamethonium Bromide 1,1'-(Decane-1,10-diyl)bis[4-aza-1-azoniabicyclo[2.2.2]octane] Dibromide Decyltrimethylammonium Bromide Didecyldimethylammonium Bromide Dilauryldimethylammonium Bromide Dimethyldimyristylammonium Bromide Dimethyldioctadecylammonium Bromide Dimethyldioctylammonium Bromide Dimethyldipalmitylammonium Bromide Dodecyltrimethylammonium Bromide Ethylhexadecyldimethylammonium Bromide (Ferrocenylmethyl)dodecyldimethylammonium Bromide (Ferrocenylmethyl)trimethylammonium Bromide Hexadecyltrimethylammonium Bromide Hexamethonium Bromide Hexyldimethyloctylammonium Bromide Hexyltrimethylammonium Bromide Homatropine Methyl Bromide Methacholine Bromide Neostigmine Bromide n-Octyltrimethylammonium Bromide Phenyltrimethylammonium Bromide Scopolamine Methyl Bromide Tetraamylammonium Bromide Tetrabutylammonium Bromide

Unit Size 25g 25g 25g 25g

5g 25g 5g 25g 25g 25g 25g 5g 25g 25g 25g 1g 25g 25g 5g 25g 5g 5g 25g 25g 5g 25g

25g 500g 500g 500g 250g 25g 1g 25g 500g 25g 1g 500g 5g 500g 500g 250g 25g 500g 500g 500g 5g 5g 500g 500g 25g 500g 25g 25g 25g 500g 500g 1g 25g 500g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Quaternary Ammonium Compounds

Product No. Product Name I0365 T1142 T0906 T0094 T1602 T1599 T0135 T1603 T0694 T1036 S0364 T0494 V0063

Unit Size

Tetrabutylammonium Bromide [Reagent for Ion-Pair Chromatography] Tetra(decyl)ammonium Bromide Tetradecyltrimethylammonium Bromide Tetraethylammonium Bromide Tetraheptylammonium Bromide Tetrahexylammonium Bromide Tetramethylammonium Bromide Tetra-n-octylammonium Bromide Tetrapropylammonium Bromide 3-(Trifluoromethyl)phenyltrimethylammonium Bromide Trimethylstearylammonium Bromide Trimethylvinylammonium Bromide Valethamate Bromide

25g 25g 25g 5g 25g 10g 25g

1g

500g 25g 500g 500g 25g 25g 500g 25g 500g 25g 25g 10g 25g

Iodides Product No. Product Name A0085 A0116 B0108 B0307 B0446 B0772 B0775 D1315 D1343 E0190 E0191 F0167 H0407 M0598 C0037 P0242 T1011 T0057 T0097 T1396 T1010 T0139 T1155 T0172 T1014 P0246 T2625

Acetylcholine Iodide Acetylthiocholine Iodide Benzoylcholine Iodide Benzoylthiocholine Iodide Benzyltriethylammonium Iodide Butyrylcholine Iodide Butyrylthiocholine Iodide Decamethonium Iodide 1,1-Dimethyl-4-phenylpiperazinium Iodide Ethyltrimethylammonium Iodide Ethyltripropylammonium Iodide (Ferrocenylmethyl)trimethylammonium Iodide (2-Hydroxyethyl)triethylammonium Iodide β-Methylcholine Iodide O-β-Naphthyloxycarbonylcholine Iodide [for Determination of Serum Cholinesterase] Phenyltriethylammonium Iodide Tetraamylammonium Iodide Tetrabutylammonium Iodide Tetraethylammonium Iodide Tetraheptylammonium Iodide Tetrahexylammonium Iodide Tetramethylammonium Iodide Tetra-n-octylammonium Iodide Tetrapropylammonium Iodide 3-(Trifluoromethyl)phenyltrimethylammonium Iodide Trimethylphenylammonium Iodide Trimethyl[2-[(trimethylsilyl)methyl]benzyl]ammonium Iodide

Unit Size 1g 1g

5g 1g 5g 5g 1g

5g 25g 25g

25g

5g 100g 25g 25g

25g 25g 25g 25g 25g 25g 25g 25g 5g 25g 25g 5g 10g 25g 100mg 25g 25g 500g 500g 25g 25g 500g 5g 500g 25g 500g 5g

Hydroxides Product No. Product Name B0445 B0448 B1071 B0378 B1070 B0428 C0326 H0083 H0974 S0070 T0056 T1948 T0717 T0041 T1685 T0955

Benzyltriethylammonium Hydroxide (10% in Water) Benzyltrimethylammonium Hydroxide (40% in Methanol) Benzyltrimethylammonium Hydroxide (40% in Water) Benzyltrimethylammonium Hydroxide (40% in Water) Benzyltrimethylammonium Hydroxide (10% in Water) Benzyltrimethylammonium Hydroxide (10% in Water) Choline (48-50% in Water) Hexadecyltrimethylammonium Hydroxide (25% in Methanol) Hexadecyltrimethylammonium Hydroxide (10% in Water) Sphingomyelin from Bovine Brain Tetrabutylammonium Hydroxide (10% in Isopropyl Alcohol) Tetrabutylammonium Hydroxide (37% in Methanol) Tetrabutylammonium Hydroxide (10% in Methanol) Tetrabutylammonium Hydroxide (10% in Methanol) [for non-aqueous titration] Tetrabutylammonium Hydroxide (40% in Water) Tetrabutylammonium Hydroxide (10% in Water)

Unit Size 25ml 500ml 500ml 25ml 25ml 500ml 25ml 25g 500g 25ml 500ml 25ml 500ml Price on request 25g 25ml 500ml 25ml 500ml 25ml 500ml 25g 500g 25ml 500ml 25ml 25ml

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

339

Quaternary Ammonium Compounds

Product No. Product Name T0216 I0364 T2589 T0096 I0363 T1134 T0676 T1201 T1460 T0138 T1404 T1565 T1020 T0171 T0964 T0961

Tetrabutylammonium Hydroxide (10% in Water) Tetrabutylammonium Hydroxide (10% in Water) [Reagent for Ion-Pair Chromatography] Tetraethylammonium Hydroxide (35% in Water) Tetraethylammonium Hydroxide (10% in Water) Tetraethylammonium Hydroxide (10% in Water) [Reagent for Ion-Pair Chromatography] Tetrahexylammonium Hydroxide (10% in Methanol) Tetramethylammonium Hydroxide (10% in Methanol) Tetramethylammonium Hydroxide (10% in Methanol) [for Photoresist Research] Tetramethylammonium Hydroxide (ca. 25% in Water) Tetramethylammonium Hydroxide (10% in Water) Tetramethylammonium Hydroxide Pentahydrate Tetrapropylammonium Hydroxide (ca. 40% in Water) Tetrapropylammonium Hydroxide (20-25% in Water) Tetrapropylammonium Hydroxide (10% in Water) Tetrapropylammonium Hydroxide (10% in Water) 3-(Trifluoromethyl)phenyltrimethylammonium Hydroxide (5% in Methanol)

Unit Size 25ml 25ml

25ml

25g

25ml 25ml 100g 25ml 25ml 25ml

[for Transesterification of Glyceride]

P0878 P0245 T2192

Trimethylphenylammonium Hydroxide (20-25% in Methanol) Trimethylphenylammonium Hydroxide (20-25% in Methanol) [for On-Column Methylation] Tris(2-hydroxyethyl)methylammonium Hydroxide (45-50% in Water)

25ml

25g 25ml 500ml 500ml 25ml 5g 500ml 25ml 500ml 500ml 500g 25g 500ml 500ml 500ml 25ml 500ml 25ml 25g

(stabilized with MEHQ)

Others Product No. Product Name A0998 A2274 B3128 B1604 B1543 T1382 B0455 B0458 B1123 B1466 B2851 C0049 C1578 C0553 C0793

Acetylcholine Perchlorate Amyltriethylammonium Bis(trifluoromethanesulfonyl)imide Benzyltriethylammonium Borohydride Benzyltrimethylammonium Dichloroiodate Benzyltrimethylammonium Tetrachloroiodate [Chlorinating Reagent] Benzyltrimethylammonium Tribromide [Brominating Reagent] Betaine Anhydrous Betaine Hydrochloride Bis(tetrabutylammonium) Dichromate [Oxidizing Reagent] Bis(tetrabutylammonium) Tetracyanodiphenoquinodimethanide 1-Butyl-1-methylpyrrolidinium Bis(trifluoromethanesulfonyl)imide L-Carnitine 3-[(3-Cholamidopropyl)dimethylammonio]-1-propanesulfonate Choline Bitartrate 1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide Metho-p-toluenesulfonate

C1966 D2124 D2332 F0358 H1283

Cyclohexyltrimethylammonium Bis(trifluoromethanesulfonyl)imide Denatonium Benzoate Dodecyldimethyl(3-sulfopropyl)ammonium Hydroxide Inner Salt N-Fluoro-N '-(chloromethyl)triethylenediamine Bis(tetrafluoroborate) Hexadecyldimethyl(3-sulfopropyl)ammonium Hydroxide Inner Salt [for Biochemical

H0733 H0735 H0734 M2005 M1279 M2098 M1660 M1457 N0447 O0261 P0517 S0230 T2694 T0920 T1295 T0917 T1270 T1261 T1189 T1269

Hexadecyltrimethylammonium Hexafluorophosphate Hexadecyltrimethylammonium Perchlorate Hexadecyltrimethylammonium Tetrafluoroborate 2-(Methacryloyloxy)ethyl 2-(Trimethylammonio)ethyl Phosphate (Methoxycarbonylsulfamoyl)triethylammonium Hydroxide Inner Salt 1-Methyl-1-propylpyrrolidinium Bis(trifluoromethanesulfonyl)imide Methyltri-n-octylammonium Bis(trifluoromethanesulfonyl)imide Methyltri-n-octylammonium Hydrogen Sulfate Neostigmine Methyl Sulfate Octadecyldimethyl(3-sulfopropyl)ammonium Hydroxide Inner Salt Propionylcholine p-Toluenesulfonate Scopolamine Methyl Nitrate Tetrabutylammonium Acetate Tetrabutylammonium Azide Tetrabutylammonium Bifluoride Tetrabutylammonium Borohydride [Reducing Reagent] Tetrabutylammonium Bromodiiodide Tetrabutylammonium Dibromoaurate Tetrabutylammonium Dibromochloride Tetrabutylammonium Dibromoiodide

Unit Size 5g 5g 5g 25g 25g

5g 5g 1g 25g 5g

[for Peptide Synthesis]

5g 25g 5g

Research]

340

1g

5g 1g 1g 1g 1g 5g 5g 1g 5g 25g 1g 1g 25g 5g 5g 5g

1g

10g 5g 25g 25g 5g 25g 500g 500g 10g 100mg 25g 25g 5g 500g 25g 5g 25g 250g 25g 25g 25g 5g 5g 5g 25g 25g 5g 5g 25g 250g 25g 5g 500g 25g 25g 25g 1g 1g 25g 10g

Chemicals itemized in this TCI Reagent Guide are for testing or research purpose only. Therefore, please note those chemicals are not guaranteed in the user's favor relating to various problems under the Patent Law that might occur through their use.

Quaternary Ammonium Compounds

Product No. Product Name T1273 T1186 T1909 T1592 T1635 T1357 T1279 T0835 I0368 T2669 T0836 T1803 I0367 T1276 T0914 T2648 T1480 T1278 T1284 T1568 T1271 T2653

Tetrabutylammonium Dichloroaurate Tetrabutylammonium Dichlorobromide Tetrabutylammonium Difluorotriphenylsilicate Tetrabutylammonium Difluorotriphenylstannate Tetrabutylammonium Dihydrogen Trifluoride Tetrabutylammonium Diiodoaurate Tetrabutylammonium Hexafluorophosphate Tetrabutylammonium Hydrogen Sulfate Tetrabutylammonium Hydrogen Sulfate [Reagent for Ion-Pair Chromatography] Tetrabutylammonium p-Nitrophenoxide Tetrabutylammonium Perchlorate Tetrabutylammonium Perrhenate Tetrabutylammonium Phosphate (0.5mol/L in Water) [Reagent for Ion-Pair Chromatography] Tetrabutylammonium Salicylate Tetrabutylammonium Tetrafluoroborate Tetrabutylammonium Tetrafluoroborate Tetrabutylammonium Tetraphenylborate Tetrabutylammonium Thiocyanate Tetrabutylammonium Tribromide Tetrabutylammonium Trifluoromethanesulfonate Tetrabutylammonium Triiodide Tetradecyldimethyl(3-sulfopropyl)ammonium Hydroxide Inner Salt [for Biochemical

T0837 T0839 T0983 T0937 T1745 T1048 T1397 T0852 T1296 T0840 T0841 T1240 T0842 T0843 T1553 T1559 T2198 P0928

Tetraethylammonium Borohydride Tetraethylammonium Perchlorate Tetraethylammonium Tetrafluoroborate Tetraethylammonium p-Toluenesulfonate Tetraethylammonium Trifluoromethanesulfonate Tetramethylammonium Acetate Tetramethylammonium Acetate (ca. 15% in Water) Tetramethylammonium Borohydride [Reducing Reagent] Tetramethylammonium Hexafluorophosphate Tetramethylammonium Hydrogen Sulfate Tetramethylammonium Perchlorate Tetramethylammonium Sulfate Tetramethylammonium Tetrafluoroborate Tetramethylammonium p-Toluenesulfonate Tetramethylammonium Triacetoxyborohydride Tetrapropylammonium Perruthenate Triethylmethylammonium Tetrafluoroborate Trimethylphenylammonium Tribromide

Research]

Unit Size 5g 1g 5g 100mg 25g 25g 25g 5g 25g 1g 10ml 25g 1g 25g 25g 10g 1g 5g 5g

25g 5g

5g

5g 25g 5g 1g 25g

This TCI Reagent Guide is not an all inclusive guide of all the products available from us. Please refer to our catalog for further information or visit our web site.

100mg 25g 25g 5g 25g 1g 250g 500g 100g 25g 500g 5g 100ml 25g 500g 25g 5g 250g 500g 25g 25g 25g 25g 25g 25g 500g 25g 25g 25g 25g 25g 25g 25g 25g 500g 25g 25g 5g 25g 500g

341

Imidazolium Compounds

Imidazolium Compounds

D3611

B3159

B2473

B2474

B3028

(CH3)2CH

CH3

N

N N (CH3)2CH

CH(CH3)2

B2475

Cl

N

N

(CH2)3CH3

N

(CF3SO2)2N

N

CH3