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N,N-Dimethylacetamide is used as a polar solvent in organic synthesis as well as in reactions involving strong bases such as sodium hydroxide. It is also used as a solvent for fibers like polyacrylonitrile, spandex, as an excipient in drugs viz. vumon, busulfex and in the adhesive industry. It finds application as a reaction medium in the production of pharmaceuticals, agrochemicals, dyes and plasticizers. It is widely used in polymer industry due to its high solving power for high molecular-weight polymers and synthetic resins. It plays an important role as a catalyst in various reactions viz. cyclization, halogenation, cynidation, alkylation and dehydrogenation and increases the yield of main products. It is also used as an extracting agent for oil and gases, in paint removers, in the production of photo-resist stripping compounds and as booster solvent in coatings.
See also Sodium hydride, 13431, for warning.
Useful solvent in halex fluorinations of chloroarenes; compare Sulfolane, A13466.
Undergoes Vilsmeier-type reactions (compare DMF), with reactive substrates, introducing an acetyl group: Chem. Ber., 97, 616 (1964).
Reacts with alkyl and aryl Grignard reagents to give methyl ketones in good yields: Synthesis, 228 (1984).
In the presence of triflic anhydride and 2,4,6-collidine, forms a highly-reactive keteniminium triflate, which undergoes a [2+2] cycloaddition reaction with terminal alkenes to give, after hydrolysis a 3-alkylcyclobutanone: J. Am. Chem. Soc., 107, 2192 (1985); Org. Synth. Coll., 8, 306 (1993):
Messaadi, A.; Salhi, H.; Das, D.; Alzamil, N. O.; Alkhaldi, M. A.; Ouerfelli, N.; Hamzaoui, A. H. A novel approach to discuss the viscosity Arrhenius behaviour and to derive the partial molar properties in binary mixtures of N, N-dimethylacetamide with 2-methoxyethanol in the temperature interval (from 298.15 to 318.15) K. Phys. Chem. Liq. 2015, 53 (4), 506-517.
Shokouhi, M.; Farahani, H.; Jenab, M. H.; Jalili, A. H. Solubility of Hydrogen Sulfide in N-Methylacetamide and N, N-Dimethylacetamide: Experimental Measurement and Modeling. J. Chem. Eng. Data 2015, 60 (3), 499-508.
Gefahrenhinweise (EU): H227-H312-H332-H360
Combustible liquid. Harmful in contact with skin. Harmful if inhaled. May damage fertility or the unborn child.
Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.