Structural Formula Vector Image
Title: Acetonitrile
CAS Registry Number: 75-05-8
Additional Names: Methyl cyanide; cyanomethane; ethanenitrile
Molecular Formula: C2H3N
Molecular Weight: 41.05
Percent Composition: C 58.52%, H 7.37%, N 34.12%
Line Formula: CH3CN
Literature References: Small amounts occur in coal tar. Obtained commercially as a byproduct in manuf of acrylonitrile, q.v.: R. A. Smiley in Kirk-Othmer Encyclopedia of Chemical Technology vol. 15 (Wiley-Interscience, New York, 3rd ed., 1978) p 896. Prepn by dehydration of acetamide: Adkins, Nissen, J. Am. Chem. Soc. 46, 143 (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. Toxicity: H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol. 30, 63 (1968).
Properties: Liquid. Ether-like odor. Poisonous! Burns with a luminous flame. mp -45°. bp760 81.6°. Flash pt 12.8°C (55°F). d415 0.78745; d430 0.77125. nD15 1.34604, nD30 1.33934. Dielectric constant at 20° = 38.8. 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). Dissolves some in organic salts, e.g., silver nitrate, lithium nitrate, magnesium bromide. Constant boiling mixture with water contains 16% H2O and bp 76°. LD50 orally in rats: 3800 mg/kg (Smyth).
Melting point: mp -45°
Boiling point: bp760 81.6°; bp 76°
Flash point: Flash pt 12.8°C (55°F)
Index of refraction: nD15 1.34604; nD30 1.33934
Density: d415 0.78745; d430 0.77125
Toxicity data: LD50 orally in rats: 3800 mg/kg (Smyth)
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, a-naphthaleneacetic acid, thiamine, acetamidine. To remove tars, phenols, and coloring matter from petroleum hydrocarbons which are not soluble in acetonitrile. To extract fatty acids from fish liver oils and other animal and vegetable oils. Can be used to recrystallize steroids. As an indifferent medium in physicochemical investigations. Wherever a polar solvent having a rather high dielectric constant is required. As medium for promoting reactions involving ionization. As a solvent in non-aqueous titrations. As a non-aqueous solvent for inorganic salts.

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