Chloroacetonitrile
Names
Preferred IUPAC name
Chloroacetonitrile
Other names
α-Chloroacetonitrile
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.153 Edit this at Wikidata
EC Number
  • 203-467-0
KEGG
RTECS number
  • AL8225000
UNII
UN number 2668
  • InChI=1S/C2H2ClN/c3-1-2-4/h1H2
    Key: RENMDAKOXSCIGH-UHFFFAOYSA-N
  • C(C#N)Cl
Properties
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:
GHS06: ToxicGHS09: Environmental hazard
Danger
H301, H311, H331, H411
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).

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 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

References

  1. ^ Reisner, D. B.; Horning, E. C. (1950). "Chloroacetonitrile". Organic Syntheses. 30: 22. doi:10.15227/orgsyn.030.0022.
  2. ^ Lebeuf, Raphaël; Berlande, Muriel; Robert, Frédéric; Landais, Yannick (2009). "Preparation of (3,5-Dimethoxy-1-Phenyl-Cyclohexa-2,5-Dienyl)-Acetonitrile Through Birch Reductive Alkylation (BRA)". Organic Syntheses. 86: 1. doi:10.15227/orgsyn.086.0001.
  3. ^ Rees, Charles W. (1992). "Polysulfur-Nitrogen Heterocyclic Chemistry". Journal of Heterocyclic Chemistry. 29 (3): 639–651. doi:10.1002/jhet.5570290306.
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