Chloroacetonitrile

Chloroacetonitrile is the organic compound with the formula ClCH₂CN. A colorless liquid, it is derived from acetonitrile (CH₃CN) by replacement of one H with Cl. In practice, it is produced by dehydration of chloroacetamide. The compound is an alkylating agent, and as such is handled cautiously.

Chloroacetonitrile is also generated in situ by the reaction of acetonitrile with sulfur monochloride. A second chlorination gives dichloroacetonitrile, which undergoes cycloaddition with sulfur monochloride to give 4,5-dichloro-1,2,3-dithiazolium chloride:

Cl₂CHCN + S₂Cl₂ → [S₂NC₂Cl₂]Cl + HCl

References

See also

• halogenation