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N, N-Dimethylformamide is commonly used as a solvent. It is used as a reagent in Bouveault aldehyde synthesis and also in Vilsmeier-Haack reaction. It acts as a catalyst in the synthesis of acyl chlorides. It is used for separating and refining crude from olefin gas. DMF along with methylene chloride acts as a remover of varnish or lacquers. It is also used in the manufacture of adhesives, fibers and films.
Dipolar aprotic solvent, in which anions have enhanced nucleophilicity, compare Dimethyl sulfoxide, A13280. Effective solvent for a vast range of reactions.
CAUTION! Thermal runaway reactions can occur with NaH; see Sodium hydride, 13431.
In combination with POCl3, (COCl)2, etc., generates an iminium chloride intermediate for the formylation of reactive aromatic nuclei by the Vilsmeier reaction:
Compare also N-Methylformanilide, A11829, and preformed Vilsmeier reagent (Chloromethylene)dimethylammonium chloride, B24172. Monograph: Synthesis Using Vilsmeier Reagents, C. M. Marson, P. R. Giles, CRC Press, Boca Raton, FL (1994). Formylation can be extended to less active substrates, e.g. acenaphthene or mesitylene, with the DMF-triflic anhydride reagent: J. Chem. Soc., Chem. Commun., 1571 (1990). Under Vilsmeier conditions, electron-rich alkenes can be converted to ɑß-unsaturated aldehydes; see, e.g.: Synthesis, 752 (1976); and ketones to ß-chloroenals: Synthesis, 496 (1985); Org. Synth. Coll., 5, 215 (1973).
Vilsmeier conditions also promote dehydrations, e.g. in cyclodehydration of hydroxyphenols to give cyclic ethers, as an efficient alternative to the Mitsunobu reaction: J. Chem. Soc., Perkin 1, 2249 (1996); J. Org. Chem., 59, 4346 (1994):
DMF can also be used for formylation with alkyllithium or Grignard reagents: Synthesis, 228 (1984).
In aqueous DMF, tosylate esters undergo formolysis to formate esters: Synth. Commun., 26, 1031 (1996).
For the free-radical formylation of perfluoroalkyl iodides, see Zinc-copper couple, L09811.
Mahendra, N. R.; Pritam D.; Partha S. S. Physicochemical study of solution behaviour of alkali metal perchlorates prevailing in N,N-Dimethyl Formamide with the manifestation of ion Salvation consequences. J. Mol. Liq. 2015, 204, 243-247.
Wang, F.; Guo-zhu, J. The hydrogen bonding dynamics and cooperative Interactions in aqueous N,N-dimethyl formamide solution Studied by dielectric relaxation spectroscopy. Physica A 2014, 404, 315-322.
Hazard Statements: H226-H312-H332-H319-H360
Flammable liquid and vapour. Harmful in contact with skin. Harmful if inhaled. Causes serious eye irritation. May damage fertility or the unborn child.
Precautionary Statements: P210-P201-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.