Chemistry:3-Chloropropionitrile

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3-Chloropropionitrile
3-Chloropropionitrile.svg
Names
Preferred IUPAC name
3-Chloropropanenitrile
Other names
1-Chloro-2-cyanoethane; β-Chloropropionitrile
Identifiers
3D model (JSmol)
ChemSpider
UNII
Properties
C3H4ClN
Molar mass 89.52 g·mol−1
Appearance colorless liquid
Density 1.1573 g/cm3
Melting point −51 °C (−60 °F; 222 K)
Boiling point 175–176 °C (347–349 °F; 448–449 K)
Hazards
GHS pictograms GHS06: Toxic GHS07: Harmful
GHS Signal word Danger
H227, H300, H315, H319
P210, P264, P270, P280, P301+310+330Script error: No such module "Preview warning".Category:GHS errors, P302+352, P305+351+338, P332+313, P337+313, P370+378, P403+235, P405, P501
Related compounds
Related compounds
4-Chlorobutyronitrile
Propionitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

3-Chloropropionitrile is an organic compound with the formula ClCH2CH2CN. A colorless liquid, it is prepared by the reaction of hydrogen chloride with acrylonitrile. It is used commercially as a precursor to the drug famotidine.[1]

It is an alkylating agent, as illustrated by its reaction with imidazoles to give the cyanoethylated imidazolium salts.[2] Similarly, it alkylates thiourea, en route to 3-mercaptopropionitrile.[3]

References

  1. Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. 
  2. Zhao, Dongbin; Fei, Zhaofu; Scopelliti, Rosario; Dyson, Paul J. (2004). "Synthesis and Characterization of Ionic Liquids Incorporating the Nitrile Functionality". Inorganic Chemistry 43 (6): 2197–2205. doi:10.1021/ic034801p. PMID 15018545. 
  3. R. Eric Gerber; Carlos Hasbun; Larisa G. Dubenko; Mei Fong King; Donald E. Bierer (2000). "β-Mercaptopropionitrile". Organic Syntheses 77: 186. doi:10.15227/orgsyn.077.0186.