3-Chloropropionitrile

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]

3-Chloropropionitrile
Names
Preferred IUPAC name
3-Chloropropanenitrile
Other names
1-Chloro-2-cyanoethane; β-Chloropropionitrile
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.025
UNII
  • 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
  • ClCCC#N
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 labelling:
GHS06: Toxic GHS07: Exclamation mark
Danger
H227, H300, H315, H319
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

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). "Nitriles". 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: 2197–2205. doi:10.1021/ic034801p.
  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.


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.