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.^[1] The compound is an alkylating agent,^[2] and as such is handled cautiously.

Chloroacetonitrile

Names
Preferred IUPAC name Chloroacetonitrile
Other names α-Chloroacetonitrile
Identifiers
CAS Number	107-14-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82416
ChEMBL	ChEMBL3187297
ChemSpider	7568
ECHA InfoCard	100.003.153
EC Number	203-467-0
KEGG	C19360
PubChem CID	7856
RTECS number	AL8225000
UNII	CN524K9DXD
UN number	2668
CompTox Dashboard (EPA)	DTXSID7021524
InChI InChI=1S/C2H2ClN/c3-1-2-4/h1H2 Key: RENMDAKOXSCIGH-UHFFFAOYSA-N
SMILES C(C#N)Cl
Properties
Chemical formula	C2H2ClN
Molar mass	75.50 g·mol−1
Appearance	colorless liquid
Density	1.193 g·cm−3
Boiling point	123–124 °C (253–255 °F; 396–397 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H331, H411
Precautionary statements	P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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:^[3]

Cl₂CHCN + S₂Cl₂ → [S₂NC₂Cl₂]Cl + HCl

See also

• halogenation