Chloroacetonitrile is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula ClCH₂CN. A colorless liquid, it is derived from

acetonitrile Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not clas ...

(CH₃CN) by replacement of one H with Cl. In practice, it is produced by dehydration of

chloroacetamide Chloroacetamide (2-chloroacetamide) is a chlorinated organic compound with the molecular formula ClCH2CONH2. Chloroacetamide is a colorless solid although older samples appear yellow. It has a characteristic odor and is readily soluble in water. ...

. The compound is an

alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

, and as such is handled cautiously. Chloroacetonitrile is also generated in situ by the reaction of

with

sulfur monochloride Disulfur dichloride is the inorganic compound of sulfur and chlorine with the formula S2Cl2. Some alternative names for this compound are ''sulfur monochloride'' (the name implied by its empirical formula, SCl), ''disulphur dichloride'' (British ...

. A second chlorination gives dichloro

, which undergoes cycloaddition with sulfur monochloride to give 4,5-dichloro-1,2,3-dithiazolium chloride:{{cite journal , doi=10.1002/jhet.5570290306, title=Polysulfur-Nitrogen Heterocyclic Chemistry, year=1992, last1=Rees, first1=Charles W., journal=Journal of Heterocyclic Chemistry, volume=29, issue=3, pages=639–651 :Cl₂CHCN + S₂Cl₂ → ₂NC₂Cl₂l + HCl

References

Nitriles