Thioanisole is an organic compound with the formula CH₃SC₆H₅. It is a colorless liquid that is soluble in organic solvents. It is the simplest alkyl-aryl thioether. The name indicates that this compound is the sulfur analogue, the thioether rather than the ether oxygen analogue; it is commonly used as a methylthio donor and as a model substrate in sulfoxidation and sulfone formation studies. Molecular weight is 124.21 g mol-1. Thioanisole undergoes oxidation at sulfur to give the corresponding sulfoxide and sulfone, and the aromatic ring participates in electrophilic aromatic substitution. In analytical and preparative contexts it displays a characteristic 1H NMR methyl singlet near 2.5 ppm and an aromatic multiplet in the 7.0 to 7.5 ppm region. Typical laboratory handling notes include sensitivity to strong oxidants and storage under inert atmosphere to limit formation of oxidation byproducts.
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