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|Section2= |Section7= |Section8= }} Sodium cyanoborohydride is the chemical compound with the formula NaBH3CN. It is a colourless salt, but commercial samples can appear tan. It is widely used in organic synthesis for the reduction of imines. The salt tolerates aqueous conditions.〔Robert O. Hutchins, MaryGail K. Hutchins, Matthew L. Crawley "Sodium Cyanoborohydride" Encyclopedia of Reagents for Organic Synthesis, 2007 John Wiley & Sons. 〕 ==Use== Owing to the presence of the electron-withdrawing cyanide substituent, ()− is far less reducing than is ()−, as found in sodium borohydride.〔Ellen W. Baxter, Allen B. Reitz Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents in Organic Reactions, 2002, John Wiley and Sons. 〕 As a mild reducing agent, it is especially used to convert imines to amines. It is especially favored for reductive aminations, wherein aldehydes or ketones are treated with an amine in the presence of this reagent: : R2CO + R'NH2 + NaBH3CN + CH3OH → R2CH-NHR' + "NaCH3OBH2CN" The reagent is typically used in excess. Selectivity is achieved at mildly basic solutions (pH 7-10). The reagent is ideal for reductive aminations ("Borch Reaction"). In conjunction with tosylhydrazine, sodium cyanoborohydride is used in the reductive deoxygenation of ketones.〔 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Sodium cyanoborohydride」の詳細全文を読む スポンサード リンク
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