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Reagent Guide8th Edition

Synthetic Organic Chemistry& Materials Chemistry

We have reviewed our product line-ups and organized them according to the research areas of synthetic organic chemistry and materials chemistry. 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 fi elds of your interest.

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

Synthetic Organic ChemistryTopicsCopper-free Click Reactions .......................................1Easily Accessible Crystalline CO Surrogate Reagents ......2Functional Group Transformation & Introducing ReactionOxidation ........................................................................3Reduction .......................................................................9Halogenation .............................................................. 17Trifl uoromethylation ................................................... 23Trifl uoromethylthiolation ............................................ 25Formylation ................................................................. 26Cyanation .................................................................... 29Amination .................................................................... 31Mitsunobu Reaction ................................................... 34Condensation & Active Esterifi cation ..................... 38Carbon-Carbon Bond Forming ReactionsCarbonyl Olefi nation .................................................. 44Cross-coupling Reaction Using Transition Metal Catalysts .................................................................. 52

Activation of Non-active Bonds ............................... 69Synthetic ReagentsMetal Reagents for Organic Synthesis ................... 76Stable Lewis Acids in Aqueous Media ................... 89Ligands ........................................................................ 91Asymmetric Organocatalysts .................................102Chiral Auxiliaries ......................................................108Chiral Phase-transfer Catalysts .............................110Optical Resolving Agents .......................................113Protection & Derivatization ....................................120Ionic Liquids .............................................................130Fluorous Solvents ....................................................135Polymer-supported Reagents .................................137Building BlocksBoronic Acids & Boronic Acid Derivatives ..........139Chiral Building Blocks .............................................156Terminal Acetylenes ................................................180Azide Compounds ....................................................186

Materials ChemistryNanocarbon MaterialsFullerenes .................................................................190Carbon Nanotubes ...................................................192Graphene & Graphene Oxide .................................194Nanodiamonds .........................................................196Nanocarbon Unit Structures ..................................198Electronic MaterialsReagents for Solar Cell Research .........................201Reagents for Secondary Battery ...........................206Organic Light-Emitting Diode Materials ...............213Organic Transistor Materials ..................................219Molecular Conductors .............................................223Building Blocks for Semiconducting Polymer .....230Building Blocks for Small Molecule Semiconductor ...238Ligands for Functional Metal Complex ................254Optically Functional MaterialsPhotochromic Compounds .....................................259Liquid Crystal Materials ..........................................262Building Blocks for Liquid Crystals .......................270Organic Nonlinear Optical Materials ....................274Materials for Near Infrared Absorption .................276

Magnetic MaterialsMagnetic Metal Complexes ...................................277Organic Radicals .....................................................281Magnetic Ionic Liquids ............................................283Functional Organic DyesCoumarin Dyes .........................................................284Porphyrin & Phthalocyanine Dyes ........................286Perylene Dyes ..........................................................289Cyanine & Squarylium Dyes ..................................291Dipyrromethene Dyes ..............................................293Xanthene Dyes .........................................................294DCM Dyes ................................................................296Quinacridone Dyes ..................................................297Organic-Inorganic Hybrid MaterialsMetal-Organic Frameworks (MOFs / PCPs) & Related Ligands .....................................................298

Organic-Inorganic Perovskite Precursors .............303Silane Coupling Agents ..........................................305Self-Assembled Monolayer (SAM) Forming Agents .....................................................313

Polymer Research ReagentsPolymers ...................................................................316Monomers .................................................................319Polymerization Inhibitors .........................................320Polymerization Initiators ..........................................321Polymerization Catalysts ........................................325Precise Polymerization Reagents .........................328Resin Additives ........................................................333Photopolymer Research Reagents ........................341Macrocycles for Host-Guest ChemistryMacrocycles for Host-Guest Chemistry ...............342Other ReagentsBuilding Blocks for Dendrimers .............................348Derivatizing Reagents for Solubility Improvement ...351

Abbreviations ................................................................360Pressure-Temperature Nomograph ...........................362The physical properties of the typical organic solvents / Freezing mixtures .....................................................363

Periodic Table of the Elements .................................364

INDEX ...........................................................................365

TCI International Offi ces .............................................376TCI Distributors ............................................................377

If you are looking for products in the field of Bioscience & Analytical Science, please see below.

Reagent Guide8th EditionBioscience & Analytical ScienceBioscienceExample :Antibodies / Sugars / Nucleosides / Amino Acids / Lipids / Terpenes / Steroids etc.Analytical ScienceExample :GC Derivatizing Reagents / Labeling Reagents for HPLC / Chromatography Columns for HPLC / Derivatization Reagents for Mass Spectrometry etc.

Contents

1This 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.

Copper-free Click Reactions

Among the click chemistry proposed by K. B. Sharpless in 2001, the Huisgen cyclization using azides and terminal alkynes has been widely used in various reseach fi elds such as chemical biology and material science due to its excellent chemoselectivity.1) Generally, the Huisgen cyclization requires some copper salts to promote the reactions. However, use of the copper salt-mediated click reactions for in vivo applications is often highly restricted owing to the toxicity of active oxygen in vivo generated by the copper salt. Therefore, the development of advanced click reactions without using any copper salt has been investigated. In the research fields using copper-free click reactions, a number of studies aimed for in vivo applications such as living cells and biological experiments on animals have been reported. To be suitable for such purposes, molecular design of alkyne derivatives has been performed mainly to improve two chemical properties of second order reactions, rate constant and lipophilicity (log P). In 2004, C. R. Bertozzi et al. have reported the copper-free click reaction using highly-strained cyclooctyl groups as reactants. These cyclooctyl compounds satisfy the above mentioned two requests and are widely used as a molecular tool to reveal the metabolic systems.2) Recently, they have been used to construct the microenvironment of hydrogels supporting the basis of regenerative medicine research. Because of that, Bertozzi et al. have suggested general and accessible experimental procedures for researchers who dont do major synthetic organic chemistry, and their practical examples can be referred to in the research article.3) Furthermore, van Delft et al. have developed more eff ective cyclooctyl compounds usable for in vivo bioorthogonal and 3D imaging.3) For instance, ADIBO-amine and BCN-amine are suitable molecules for the copper-free click reaction in biological research because they have low lipophilicity and high reactivity. Especially, ADIBO-amine is used for PEGylation of proteins and nuclear imaging by positron emission tomography (PET) using a fl uorine-18 [18F] radioisotope. As stated above, ADIBO-amine and BCN-amine are expected to be powerful versatile tools for the copper-free click reaction because they can also be used for surface refo