Benzyl mercaptan

Chemical properties

Cream to white, moist crystals; musty odor. Insoluble in water; soluble in alcohol or ether. There are three isomers with different boiling points.

Chemical properties

Benzyl mercaptan has repulsive, garlic-like odor. It oxidizes in air to dibenzyl disulfide.

Occurrence

Reported found in coffee.

The Uses of Benzyl mercaptan

Benzyl mercaptan can be used as:

• A nucleophilic reagent in the cleavage of proanthocyanidins into their constitutive subunits.
• A reactant in the synthesis of dithiocarboxylic esters in the presence of phosphorus pentasulfide as a catalyst.
• A modifier to functionalize the surface of CNT for enhanced interaction with Pt-nanoparticles.

The Uses of Benzyl mercaptan

Intermediate, bacteriostat.

What are the applications of Application

Benzyl mercaptan is a common laboratory alkylthiol, which can be used as a source of thiol function

Preparation

From benzyl chloride and potassium hydrosulfide.

Definition

ChEBI: Benzyl thiol is a thiol that is toluene in which one of the methyl hydrogens has been replaced by a sulfanyl group. It has a role as a plant metabolite. It is a thiol and a member of benzenes. It derives from a hydride of a toluene.

Aroma threshold values

Detection: 0.19 to 2.6 ppb.

Taste threshold values

Taste characteristics at 15 ppm: leek, horseradish, cabbage, green, tomato and coffee.

Synthesis Reference(s)

Canadian Journal of Chemistry, 53, p. 1480, 1975 DOI: 10.1139/v75-205
Synthesis, p. 498, 1984 DOI: 10.1055/s-1984-30880

Hazard

Skin irritant.

Safety Profile

Poison by inhalation and intraperitoneal routes. Moderately toxic by ingestion. An eye irritant. Questionable carcinogen with experimental tumorigenic data. Flammable when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fire, use foam, CO2, dry chemical, water spray, mist, fog. When heated to decomposition and on contact with acid or acid fumes it emits highly toxic fumes of SOx. See also SULFIDES and MERCAPTANS.

Purification Methods

Purify benzyl mercaptan via the mercury salt [see Kern J Am Chem Soc 75 1865 1953], which crystallises from *benzene as needles (m 121o), and then dissolve it in CHCl3. Pass H2S gas through the solution to regenerate the mercaptan. The HgS that precipitates is filtered off and washed thoroughly with CHCl3. The filtrate and washings are evaporated to remove CHCl3; then the residue is fractionally distilled under reduced pressure [Mackle & McClean, Trans Faraday Soc 58 895 1962]. [Beilstein 6 IV 2632.]