beta-Chloropropionitrile

Title: b-Chloropropionitrile
CAS Registry Number: 542-76-7
CAS Name: 3-Chloropropanenitrile
Additional Names: 3-chloropropanonitrile
Molecular Formula: C3H4ClN
Molecular Weight: 89.52
Percent Composition: C 40.25%, H 4.50%, Cl 39.60%, N 15.65%
Line Formula: ClCH2CH2CN
Literature 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 b-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.
Melting point: mp -51°
Boiling point: bp760 176° (dec); bp200 132° (dec); bp50 95.2°; bp5 46.0°
Flash point: Flash pt 168°F (75.5°C)
Index of refraction: nD25 1.4341
Density: d425 1.1363
Toxicity data: 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.
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