Nomenclature
CAS number: 75-05-8
Methyl cyanide; cyanomethane; ethanenitrile.
C
2H
3N; mol wt 41.05.
C 58.52%, H 7.37%, N 34.12%.
CH
3CN.
Description and references
Small amounts occur in coal tar. Obtained
commercially as a byproduct in manuf of acrylonitrile, q.v. Prepn by dehydration of acetamide: H. Adkins,
B. H. Nissen, J. Am. Chem. Soc. 46, 130 (1924); A. I. Vogel, Practical Organic Chemistry (Longmans, London, 3rd ed.,
1959) p 407; Gattermann-Wieland, Praxis des
Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961)
p 125; or from acetylene and ammonia: DE 365432; Chem. Zentralbl. 1924 I, 2398; 1925 II, 1563. Review of purification methods: Techniques of Chemistry vol. II, entitled “Organic Solvents”, J. A. Riddick, W. B. Bunger, Eds.
(Wiley-Interscience, New York, 3rd ed., 1970) pp 798-805. Purification
and use as a solvent for inorganic fluorides: J. M. Winfield, J. Fluorine Chem. 25, 91 (1984).
Properties
Liquid. Ether-like odor. Poisonous, flammable, combustible. Burns with a luminous
flame. mp 45.7°. bp760 81.6°. Flash pt, open cup: 6°C (42°F). d415 0.78745; d430 0.77125. nD15 1.34604, nD30 1.33934. Dielectric constant at 25°
= 37.5. Surface tension at 20° = 29.04 dynes/cm. Misc with water,
methanol, methyl acetate, ethyl acetate, acetone, ether, acetamide
solutions, chloroform, carbon tetrachloride, ethylene chloride and
many unsaturated hydrocarbons. Immiscible with many saturated hydrocarbons
(petroleum fractions). Constant boiling mixture with water contains
16% H2O and bp 76°. Log P (octanol/water): 0.34. Vapor pressure
(20°): 74 mmHg. pKa: 25. LD50 orally in rats: 3800 mg/kg. See: H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol. 30, 63 (1968).Caution
Potential symptoms of overexposure
are irritation of nose, throat; asphyxia; nausea, vomiting; chest
pain; weakness; stupor, convulsions. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH
97-140, 1997) p 4.Use
In organic synthesis as starting material for acetophenone, α-naphthaleneacetic
acid, thiamine, acetamidine. To remove tars, phenols, and coloring
matter from petroleum hydrocarbons. To extract fatty acids from fish
liver oils and other animal and vegetable oils. Polar solvent in
non-aqueous titrations; non-aqueous solvent for inorganic salts.
In HPLC, UV, and electrochemistry applications. Facilitates reactions
between organic substrates and inorganic materials.