43. Acetamide

Nomenclature

CAS number: 60-35-5
Acetic acid amide.
C2H5NO; mol wt 59.07.
C 40.67%, H 8.53%, N 23.71%, O 27.09%.

Description and references

Prepd by fractional distillation of ammonium acetate: Coleman, Alvarado, Org. Synth. coll. vol. I, 3 (2nd ed., 1941); Gattermann-Wieland, Praxis des Organischen Chemikers (40th ed., 1961) p 118; Vogel, Practical Organic Chemistry (3rd ed., 1959) p 401. Prepn from methyl acetate, W. P. Munro et al., US 2106697 (1936 to Calco Chem.); from ethyl acetate, Vogel, op. cit., p 403. Studies of acetamide as an ionizing solvent: Jauder, Winkler, J. Inorg. Nucl. Chem. 9, 24, 32, 39 (1959) DOI. Toxicological study: Weisburger et al., Toxicol. Appl. Pharmacol. 14, 163 (1969) DOI PubMed.

Chemical structure

Properties

Deliquescent hexagonal crystals. Odorless when pure, but frequently has a mousy odor. d420 1.159. mp 81°. bp760 222°; bp100 158°; bp40 136°; bp20 120°; bp10 105°; bp5 92°. nD78 1.4274. Neutral reaction. pKb (25°): 14.51. One gram dissolves in 0.5 ml water, 2 ml alcohol, 6 ml pyridine. Sol in chloroform, glycerol, hot benzene.

Use

Solvent; molten acetamide is an excellent solvent for many organic and inorganic compounds. Solubilizer; renders sparingly soluble substances more soluble in water by mere addition or by fusion. Plasticizer; stabilizer. Manuf methylamine, denaturing alcohol. In organic syntheses.