Nomenclature
CAS number: 542-76-7
3-Chloropropanenitrile; 3-chloropropanonitrile.
C
3H
4ClN; mol wt 89.52.
C 40.25%, H 4.50%, Cl 39.60%, N 15.65%.
Description and references
Prepd from acrylonitrile and hydrogen chloride
or bromide: Moureu, Clarke, Bull. Soc. Chim.
Fr. [4] 27, 905 (1920); Stewart,
Clarke, J. Am. Chem. Soc. 69, 714 (1947); Shirley, Preparation
of Organic Intermediates (Wiley, New York, 1951) p 82.
Properties
Liquid. Acrid, characteristic odor. Poisonous. mp -51°. d425 1.1363. bp760 176° (dec); bp200 132° (dec); bp50 95.2°; bp5 46.0°. Flash pt 168°F (75.5°C). nD25 1.4341. Begins to dec when heated above
130° evolving HCl. Absorbs strongly in the infrared. Transparent
to uv above 220 nm. Soly in water at 25°: 4.5 g/100 ml. Soly of
water in β-chloropropionitrile at 25°: 2.2 ml/100 g. Miscible with
ethanol, ether, acetone, benzene, carbon tetrachloride. LD50 orally in mice,
rats: 9, 100 mg/kg, Fassett in Industrial Hygiene and Toxicology vol. 2,
F. A. Patty, Ed. (Interscience, New York, 2nd ed., 1962) pp 2025-2026.Caution
Exposure by any route should be
avoided. Somewhat less hazardous than acrylonitrile because of lower
vapor pressure. Readily penetrates skin to produce systemic cyanide
poisoning, death.Use
In pharmaceutical and polymer synthesis. Combines
the reactivity of a nitrile and an alkyl halide. Because of the cyano
group the chlorine atom is more reactive than in ordinary alkyl halides.