Thioanisole is an organic compound with the formula CH<sub>3</sub>SC<sub>6</sub>H<sub>5</sub>. It is a colorless liquid that is soluble in organic solvents. It is the simplest alkylâÂÂaryl thioether. The name indicates that this compound is the sulfur analogueâÂÂthe thioether rather than the oxygen-centered etherâÂÂof anisole.
It can be prepared by methylation of thiophenol.
Alkyllithium reagents deprotonate thioanisole at the methyl group to afford C<sub>6</sub>H<sub>5</sub>SCH<sub>2</sub>Li, a strong nucleophile that can be alkylated to form more complex chains and structures. The resulting homologated thioether can be manipulated in a variety of ways.
Oxidation of sulfur via addition of a single oxygen atom gives methyl phenyl sulfoxide, a reaction useful for titration of oxidants such as dimethyldioxirane. Successive oxidation then leads to the sulfone.