Formula C7H8S Density 1.06 g/cm³ Appearance colourless liquid | Molar mass 124.2 g/mol Boiling point 195 °C | |
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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 the nucleophilic benzyl mercaptan. Benzyl mercaptan has been identified in boxwood (Buxus sempervirens L.) and is known to contribute to the smoky aroma of certain wines. 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, which attacks the weakened S-benzyl bond:
RSCH2C6H5 + 2 "H" → RSH + CH3C6H5Methoxy-substituted derivatives of benzyl mercaptan have been developed that cleave easily, are recyclable, and are odourless.