Benzyl mercaptan
| Skeletal formula benzyl mercaptan | |
| Ball-and-stick model of the benzyl mercaptan molecule | |
| Names | |
|---|---|
| IUPAC name
phenylmethanethiol
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| Other names
alpha-Toluenethiol
Phenylmethanethiol Benzylthiol Thiobenzyl alcohol Benzyl mercaptan alpha-Toluolthiol Benzylhydrosulfide Benzyl hydrosulfide |
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| Identifiers | |
100-53-8  |
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| ChEMBL | ChEMBL1224557 |
| ChemSpider | 13851383 |
| Jmol 3D model | Interactive image |
| PubChem | 7509 |
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| Properties | |
| C7H8S | |
| Molar mass | 124.20 g/mol |
| Appearance | colourless liquid |
| Odor | leek or garlic-like |
| Density | 1.058 g/mL |
| Melting point | −30 °C (−22 °F; 243 K) |
| Boiling point | 195 °C (383 °F; 468 K) |
| low | |
| Solubility | very soluble in ethanol, ether soluble in CS2 slightly soluble in CCl4 |
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Refractive index (nD)
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1.5751 (20 °C) |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.[1] 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:[2]
- RSCH2C6H5 + 2 "H" → RSH + CH3C6H5
Methoxy-substituted derivatives of benzyl mercaptan have been developed, which cleave easily, are recyclable, and are odourless.[3]
References
- ↑ Contribution of benzenemethanethiol to smoky aroma of certain Vitis vinifera L. wines. Tominaga, Takatoshi; Guimbertau, Guy; Dubourdieu, Denis, 2003
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- ↑ 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. doi:10.1055/s-2007-984524
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