|Preferred IUPAC name
3D model (JSmol)
|Molar mass||124.20 g/mol|
|Odor||leek or garlic-like|
|Melting point||−30 °C (−22 °F; 243 K)|
|Boiling point||195 °C (383 °F; 468 K)|
|Solubility||very soluble in ethanol, ether
soluble in CS2
slightly soluble in CCl4
Refractive index (nD)
|1.5751 (20 °C)|
|Flash point||70 °C (158 °F; 343 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|493 mg/kg (rat, oral)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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
Use in organic synthesis
The compound has been 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 + CH3C6H5
Condensed tannins undergo acid-catalyzed cleavage in the presence of benzyl mercaptan.
Methoxy-substituted benzyl mercaptans have been developed that cleave easily, are recyclable, and are odourless.
- Takatoshi Tominaga, Guy Guimbertau and Denis Dubourdieu, "Contribution of Benzenemethanethiol to Smoky Aroma of Certain Vitis vinifera L. Wines", J Ag Food Chem, 51, 1373-1376(2003) doi:10.1021/jf020756c
- Norman Kharasch; Robert B. Langford (1973). "2,4-dinitro-Benzenesulfenyl chloride". Org. Synth.; Coll. Vol., 5, p. 474
- 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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