3-Chloropropionitrile

3-Chloropropionitrile
Names
	Preferred IUPAC name 3-Chloropropanenitrile
	Other names 1-Chloro-2-cyanoethane; β-Chloropropionitrile
Identifiers
CAS Number	542-76-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	10498;
ECHA InfoCard	100.008.025
PubChem CID	10963;
UNII	61N7S4SZ2Q ;
CompTox Dashboard (EPA)	DTXSID4030336 ;
	InChI InChI=1S/C3H4ClN/c4-2-1-3-5/h1-2H2 Key: GNHMRTZZNHZDDM-UHFFFAOYSA-N; InChI=1/C3H4ClN/c4-2-1-3-5/h1-2H2 Key: GNHMRTZZNHZDDM-UHFFFAOYAG;
	SMILES ClCCC#N;
Properties
Chemical formula	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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H227, H300, H315, H319
Precautionary statements	P210, P264, P270, P280, P301+P310+P330, P302+P352, P305+P351+P338, P332+P313, P337+P313, P370+P378, P403+P235, 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

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

^ Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN 3527306730.
^ 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.
^ 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.

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[1] Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN 3527306730.

[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.

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