Thioanisole

Description

Thioanisole is a chiral organosulfide with a wide range of uses in the chemical, pharmaceutical, flavour and fragrance and food industries. Its use in combination with biocatalysts in immobilised cells eliminates the 2-day preparation phase and results in complete bioconversion of thioanisole within 24 hours. Degradative halogenation of thioanisoles by iodine at temperatures between 100 and 150°C produces diphenyl sulfide, diphenyl disulfide, thianthrene and trimethylsulfonium iodide, as well as small amounts of hydrogen sulfide, hydrogen iodide, iodomethane and dimethyl sulfide.

Chemical properties

Colorless to yellow liquid

Chemical properties

Methyl phenyl sulfide has an unpleasant odor.

Occurrence

Reported found in coffee.

The Uses of Thioanisole

Thioanisole is used in oxidative biotransformations.

The Uses of Thioanisole

Intermediate, solvent for polymeric systems.

Definition

ChEBI: Thioanisole is an aryl sulfide that is thiophenol in which the hydrogen of the thiol group has been replaced by a methyl group. It is an aryl sulfide and a member of benzenes. It is functionally related to a thiophenol.

Aroma threshold values

Aroma characteristics at 0.1% EtoH: toluene solvent, spicy, pungent, woody sawdust.

Taste threshold values

Taste characteristics at .02 to 0.5 ppm: solventy, woody, roasted coffee.

Synthesis Reference(s)

Journal of the American Chemical Society, 112, p. 186, 1990 DOI: 10.1021/ja00157a030
The Journal of Organic Chemistry, 33, p. 4290, 1968 DOI: 10.1021/jo01275a070

Flammability and Explosibility

Non flammable