| Benzyl mercaptan | |
|---|---|
|
phenylmethanethiol |
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Other names
alpha-Toluenethiol |
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| Identifiers | |
| CAS number | 100-53-8 |
| PubChem | 7509 |
| ChemSpider | 13851383 |
| ChEMBL | CHEMBL1224557 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C7H8S |
| Molar mass | 124.20 g/mol |
| Appearance | colourless liquid with a leek or garlic-like odour[1] |
| Density | 1.058 g/mL |
| Boiling point |
195 °C |
| Solubility in water | low |
| Hazards | |
| Main hazards | stench |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.[2]
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:[3]
Methoxy-substituted derivatives of benzyl mercaptan have been developed, which cleave easily, are recyclable, and are odourless.[4]