Benzyl mercaptan

Names
Preferred IUPAC name

Phenylmethanethiol

Other names

alpha-Toluenethiol
Benzylthiol
Thiobenzyl alcohol
Benzyl mercaptan
alpha-Toluolthiol
Benzylhydrosulfide
Benzyl hydrosulfide

Identifiers

CAS Number

* 100-53-8 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:137674

ChEMBL |

* ChEMBL1224557 Y

ChemSpider |

* 13851383 Y

PubChem CID

* 7509

UNII |

* OS34A21OBZ N

InChI

* InChI=1S/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2 Y

Key: UENWRTRMUIOCKN-UHFFFAOYSA-N Y

* InChI=1/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2

Key: UENWRTRMUIOCKN-UHFFFAOYAC

SMILES

* SCc1ccccc1

Properties

Chemical formula

| C7H8S
Molar mass | 124.20 g/mol
Appearance  | colourless liquid
Odor | Unpleasant 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)

Solubility in water

| low
Solubility | very soluble in ethanol, ether
soluble in CS2
slightly soluble in CCl4

Refractive index (nD)

| 1.5751 (20 °C)
Hazards
NFPA 704 (fire diamond)  |

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).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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.

## Contents

* 1 Preparation and occurrence
* 2 Use in organic synthesis
* 3 Related derivatives
* 4 References

## 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.[1] It also occurs naturally in coffee.

## Use in organic synthesis

Benzyl mercaptan is used for S-alkylation to give benzylthioethers.[2]

It has been used as a source of the thiol functional group in organic synthesis. Debenzylation can be effected by dissolving metal reduction:[3]

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.[4]

## References

1. ↑ Tominaga, Takatoshi; Guimbertau, Guy; Dubourdieu, Denis (2003). "Contribution of Benzenemethanethiol to Smoky Aroma of Certain Vitis vinifera L. Wines". Journal of Agricultural and Food Chemistry 51 (5): 1373–1376. doi:10.1021/jf020756c. PMID 12590483.
2. ↑ Norman Kharasch; Robert B. Langford (1964). "2,4-Dinitrobenzenesulfenyl Chloride". Org. Synth. 44: 47. doi:10.15227/orgsyn.044.0047.
3. ↑ Wuts, Peter G. M. (2014). Greene's Protective Groups in Organic Synthesis (5th ed.). Hoboken, NJ: Wiley. p. 842. ISBN 978-1-118-05748-3.
4. ↑ Matoba, Manabu; Kajimoto, Tetsuya; Node, Manabu (2007). "Development of a Novel Benzyl Mercaptan as a Recyclable Odorless Substitute of Hydrogen Sulfide". Synlett 2007 (12): 1930–1934. doi:10.1055/s-2007-984524.

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*[CID]: Compound ID