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Thioanisole is used as an intermediate in the preparation of dyes, pharmaceuticals and agrochemicals. It is also used to prepare stable sulfonium salts, sulfoxides and sufones. It is utilized for the cleavage of methyl ethers in association with triflic acid. It acts as a flavoring agent or an adjuvant. It is an important starting material for the synthesis of 3-substituted benzo[b]thiophenes.
Monolithiation is thought to occur initially on the ring, but rearrangement then gives the more stable phenylthiomethyllithium: J. Org. Chem., 31, 4097 (1966); Tetrahedron Lett., 1961 (1977). Further metallation occurs at the ortho-position. See, e.g.: Tetrahedron, 46, 861 (1990). Demetallation and acylation is the basis of a route to 3-substituted benzo[b]thiophenes: Synthesis, 888 (1988):
Cation scavenger in the acidic deprotection of peptides; see, e.g.: Int. J. Pept. Prot. Res., 36, 255 (1990). See Appendix 6. The combination of the soft nucleophile thioanisole and the hard acid triflic acid has been used for the cleavage of methyl ethers, e.g. O-methyltyrosine, resistant to other methods: J. Chem. Soc., Chem. Commun., 971 (1979). The same conditions have been used for the cleavage of Cbz, Boc, benzyl and 4-methoxybenzyl protecting groups in peptide synthesis: Chem. Pharm. Bull., 28, 1214 (1980); 29, 600 (1981); J. Chem. Soc., Chem. Commun., 101 (1980); see also: Angew. Chem. Int. Ed., 33, 1729 (1994).
Trehoux, A.; Roux, Y.; Guillot, R.; Mahy, J. P.; Avenier, F. Catalytic oxidation of dibenzothiophene and thioanisole by a diiron(III) complex and hydrogen peroxide. J. Mol. Catal. A: Chem. 2015, 396, 40-46.
Li, S. L.; Xu, X.; Truhlar, D. G. Computational simulation and interpretation of the low-lying excited electronic states and electronic spectrum of thioanisole. Phys. Chem. Chem. Phys. 2015, 17 (31), 20093-20099.
Hazard Statements: H227-H302-H315-H319-H317
Combustible liquid. Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction.
Precautionary Statements: P210u-P261-P280a-P280a-P305+P351+P338-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Dispose of contents/container in accordance with local/regional/national/international regulations.