Dimethylformamide (DMF) is a clear liquid that is miscible with water and most organic solvents. It is a common solvent for chemical reactions. Pure dimethylformamide has a special odor, and industrial grade or deteriorated dimethylformamide has a fishy smell because it contains impurities of dimethylamine. The name is derived from the fact that it is a dimethyl substitution of formamide (an amide of formic acid) and both methyl groups are located on the N (nitrogen) atom. Dimethylformamide is a high boiling polar (hydrophilic) aprotic solvent that promotes the SN2 reaction mechanism. Dimethylformamide is made using methyl formate and dimethylamine. Dimethylformamide is unstable (especially at elevated temperatures) in the presence of a strong base such as sodium hydroxide or a strong acid such as hydrochloric acid or sulfuric acid and hydrolyzed to formic acid and dimethylamine. HCON(CH3)2+H2O → (CH3)2NH+HCOOH.
On October 27, 2017, the World Health Organization's International Agency for Research on Cancer published a preliminary list of carcinogens, dimethylformamide in the list of Class 2A carcinogens.
