Benzyl mercaptan is an organosulfur compound with the formula C₆H₅CH₂SH. It is a common laboratory thiol, alkylthiol that occurs in trace amounts naturally. It is a colorless, malodorous liquid.

Preparation and occurrence

Benzyl mercaptan can be prepared by the reaction of benzyl chloride and thiourea. The initially formed isothiouronium, isothiouronium salt must be subjected to alkaline hydrolysis to obtain the thiol. It has been identified in buxus, boxwood (''Buxus sempervirens'' L.) and is known to contribute to the smoky aroma of certain wines. It also occurs naturally in coffee.

Use in organic synthesis

Benzyl mercaptan is used for S-alkylation to give benzylthioethers. It has been used as a source of the thiol functional group in organic synthesis. Debenzylation can be effected by dissolving metal reduction: :RSCH₂C₆H₅ + 2 H⁺ + 2 e⁻ → RSH + CH₃C₆H₅ Condensed tannins undergo acid-catalyzed cleavage in the presence of benzyl mercaptan.

Related derivatives

Methoxy-substituted benzyl mercaptans have been developed that cleave easily, are recyclable, and are odorless.

References

{{reflist Thiols Benzyl compounds Foul-smelling chemicals