title: Thioanisole
text: # Thioanisole
  
  Thioanisole is an organic compound with the formula $CH_3SC_6H_5.$ 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 oxygen-centered ether—of anisole.
  
  It can be prepared by methylation of thiophenol.
  
  ## Reactions
  
  Alkyllithium reagents deprotonate thioanisole at the methyl group to afford $C_6H_5SCH_2Li,$ 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.
  
  