3243. N,N-Dimethylformamide

Nomenclature

CAS number: 68-12-2
DMF; DMFA.
C3H7NO; mol wt 73.09.
C 49.30%, H 9.65%, N 19.16%, O 21.89%.

Description and references

Prepd from dimethylamine and formic acid: Mitchell, Reid, J. Am. Chem. Soc. 53, 1879 (1931); Brown, J. Appl. Chem. 1, Suppl. Issue no. 2, S159 (1951); Campbell, US 3015674 (1962 to Commercial Solvents); Surman, US 3072725 (1963 to du Pont); from dimethylamine + HCN: Benneville et al., J. Org. Chem. 21, 772 (1956); from HCN + methanol: Fukuoka, Kominami, Chem. Tech. 1972 (Nov.), 640. Toxicity study: W. Bartsch et al., Arzneim.-Forsch. 26, 1581 (1976). Reviews of chemical uses: R. S. Kittila, Dimethylformamide Chemical Uses (du Pont, Wilmington, 1967) 264 pp and Suppl. (1973) 148 pp; J. S. Pizey, Synthetic Reagents Vol. 1 (John Wiley, New York, 1974) pp 4-99; C. L. Eberling in Kirk-Othmer Encyclopedia of Chemical Technology vol. 11 (Wiley-Interscience, New York, 3rd ed., 1980) pp 263-268. Review of carcinogenic risk: IARC Monographs 47, 171-197 (1989).

Chemical structure

Properties

Colorless to very slightly yellow liquid. Faint amine odor. mp -61°. bp760 153°; bp39 76°; bp3.7 25°. d425 0.9445. nD25 1.42803. Flash pt, open cup: 153°F (67°C). Misc with water and most common organic solvents. pH of 0.5 molar soln in H2O = 6.7. LD50 in mice, rats (ml/kg): 6.8, 7.6 orally; 6.2, 4.7 i.p. (Bartsch).

Caution

Potential symptoms of overexposure are irritation of eyes, skin and respiratory system; nausea, vomiting and colic; liver damage, hepatomegaly; high blood pressure; facial flush; dermatitis. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 114.

Use

Solvent for liqs and gases. In the synthesis of organic compounds. Solvent for Orlon and similar polyacrylic fibers. Wherever a solvent with a slow rate of evaporation is required. Has been termed the universal organic solvent.