5711. Malononitrile

Nomenclature

CAS number: 109-77-3
Propanedinitrile; methylene cyanide; dicyanomethane; cyanoacetonitrile.
C3H2N2; mol wt 66.06.
C 54.54%, H 3.05%, N 42.41%.

Description and references

Prepn: Henri, Compt. Rend. 102, 1394 (1886); B. B. Corson et al., Org. Synth. coll. vol. 2, 379 (1943); A. R. Surrey, J. Am. Chem. Soc. 65, 2471 (1943); idem, US 2389217 (1945 to Winthrop); idem, Org. Synth. coll. vol. 3, 535 (1955). Toxicity study: G. R. N. Jones, M. S. Israel, Nature 228, 1315 (1970). Reviews: F. Freeman, Chem. Rev. 69, 591-624 (1969); A. J. Fatiadi, Synthesis 1978, 165-204, 241-282.

Chemical structure

Properties

Colorless solid, mp 32°. bp760 218-219°, bp20 109°. d420 1.1910; nD34 1.4146. Poisonous. Very sol in alc, ether; sol in water, acetone, benzene. LD50 i.p. in mice: 12.9 mg/kg (Jones, Israel).

Caution

Potential symptoms of overexposure are irritation of eyes, skin, nose, throat; headache, dizziness, weakness, giddiness, confusion, convulsions; dyspnea; abdominal pain, nausea, vomiting. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 190.

Use

In organic synthesis.