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Benzyl mercaptan

Benzylthiol Thiobenzyl alcohol Benzyl mercaptan alpha-Toluolthiol Benzylhydrosulfide Benzyl hydrosulfide soluble in CS2 slightly soluble in CCl4 | NFPA-H = 2 | NFPA-F = 2 | NFPA-R = 0 Benzyl mercaptan is an organosulfur compound with the formula C6H5CH2SH. It is a common laboratory 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 salt must be subjected to alkaline hydrolysis to obtain the thiol.

It 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.

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.

References

References

  1. (2016). "CRC Handbook of Chemistry and Physics". [[CRC Press]].
  2. (2003). "Contribution of Benzenemethanethiol to Smoky Aroma of Certain Vitis vinifera L. Wines". Journal of Agricultural and Food Chemistry.
  3. Norman Kharasch. (1964). "2,4-Dinitrobenzenesulfenyl Chloride". Org. Synth..
  4. (2014). "Greene's Protective Groups in Organic Synthesis". Wiley.
  5. (2007). "Development of a Novel Benzyl Mercaptan as a Recyclable Odorless Substitute of Hydrogen Sulfide". Synlett.
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