CAS Registry Number: 107-13-1
CAS Name: 2-Propenenitrile
Additional Names: vinyl cyanide; cyanoethylene
Molecular Formula: C3H3N
Molecular Weight: 53.06
Percent Composition: C 67.91%, H 5.70%, N 26.40%
Line Formula: CH2=CHCN
Literature References: Prepn by dehydration of ethylene cyanohydrin or acrylamide: Moureu, Ann. Chem. Phys.  2, 186 (1893). Manuf by ammoxidation of propylene: Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 46-49. Toxicity: H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol. 30, 63 (1948). Causes acute and chronic adrenocortical insufficiency: S. Szabo et al., Lab. Invest. 42, 533 (1980); eidem, J. Appl. Toxicol. 4, 131 (1984). Review of carcinogenic risk: IARC Monographs 19, 73-133 (1979); of toxicology and human exposure: Toxicological Profile for Acrylonitrile (PB91-180489, 1990) 136 p. Comprehensive review: The Chemistry of Acrylonitrile (Am. Cyanamid, New York, 2nd ed., 1959) 272 pp; J. F. Brazdil in Kirk-Othmer Encyclopedia of Chemical Technology vol. 1 (John Wiley & Sons, New York, 4th ed., 1991) pp 352-369.
Properties: Volatile liquid. Flammable and combustible. Should be stored and used in closed systems whenever possible. Work areas should be adequately ventilated, and should be free from open lights, flames, and equipment that is not explosion-proof. Handle in hood. May polymerize spontaneously, particularly in the absence of oxygen or on exposure to visible light. Polymerizes violently in the presence of concentrated alkali. On standing may slowly develop a yellow color particularly after excessive exposure to light. bp760 77.3°; bp500 64.7°; bp250 45.5°; bp100 23.6°; bp50 8.7°. mp -83.55°. d420 0.8060; d425 0.8004. nD25 1.3888. Flash pt, open cup: 32°F (0°C). Explosive mixtures in air at 25°: 3.05% low limit; 17.0% upper limit. At 20° 7.35 parts dissolve in 100 parts water and 3.1 parts water dissolve in 100 parts acrylonitrile. Miscible with most organic solvents. LD50 orally in rats: 0.093 g/kg (Smyth, Carpenter).
Melting point: mp -83.55°
Boiling point: bp760 77.3°; bp500 64.7°; bp250 45.5°; bp100 23.6°; bp50 8.7°
Flash point: Flash pt, open cup: 32°F (0°C)
Index of refraction: nD25 1.3888
Density: d420 0.8060; d425 0.8004
Toxicity data: LD50 orally in rats: 0.093 g/kg (Smyth, Carpenter)
CAUTION: Potential symptoms of overexposure are asphyxia; irritation of eyes and skin; headache; sneezing; nausea, vomiting; weakness, lightheadedness; skin vesiculation; scaling dermatitis. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 8. See also Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 215. This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-6.
Use: Manufacture of acrylic fibers. In the plastics, surface coatings, and adhesives industries. As a chemical intermediate in the synthesis of antioxidants, pharmaceuticals, dyes, surface-active agents, etc. In organic synthesis to introduce a cyanoethyl group. As a modifier for natural polymers. As a pesticide fumigant for stored grain. Experimentally to induce adrenal hemorrhagic necrosis in rats.