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|Section2= |Section3= }} Benzyl mercaptan is an organosulfur compound with the formula C6H5CH2SH. It is a common laboratory alkylthiol and occurs in trace amounts naturally. Condensed tannins can undergo acid-catalyzed cleavage in the presence of a nucleophile like benzyl mercaptan. Benzyl mercaptan has been identified in boxwood (''Buxus sempervirens'' L.) and is known to contribute to the smoky aroma of certain wines.〔(Contribution of benzenemethanethiol to smoky aroma of certain Vitis vinifera L. wines. Tominaga, Takatoshi; Guimbertau, Guy; Dubourdieu, Denis, 2003 )〕 It also occurs naturally in coffee. It is created by the reaction of benzyl chloride and sodium hydrosulfide. ==Use in organic synthesis== The compound is used as a source of the thiol functional group in organic synthesis. It is introduced by S-alkylation to give alkyl benzylthioethers. Debenzylation is effected by dissolving metal reduction taking advantage of the weakened S-benzyl bond: :RSCH2C6H5 + 2 "H" → RSH + CH3C6H5 Methoxy-substituted derivatives of benzyl mercaptan have been developed, which cleave easily, are recyclable, and are odourless.〔M. Matoba, T. Kajimoto, M. Node "Development of a Novel Benzyl Mercaptan as a Recyclable Odorless Substitute of Hydrogen Sulfide" Synlett 2007, pp. 1930-4. 〕 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「Benzyl mercaptan」の詳細全文を読む スポンサード リンク
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