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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-H319-H332-H335-H336-H350-H360D
Flammable liquid and vapour. Harmful in contact with skin. Causes serious eye irritation. Harmful if inhaled. May cause respiratory irritation. May cause drowsiness or dizziness. May cause cancer. May damage the unborn child.
Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P264b-P271-P280-P281-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P312-P337+P313-P363-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. Call a POISON CENTER or doctor/physician if you feel unwell. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant