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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.
Hazard Statements: H227-H312-H332-H360D
Combustible liquid. Harmful in contact with skin. Harmful if inhaled. May damage the unborn child.
Precautionary Statements: P201-P202-P210-P261-P271-P281-P302+P352-P304+P340-P308+P313-P312-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. Avoid breathing dust/fume/gas/mist/vapours/spray. Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF exposed or concerned: Get medical advice/attention. Call a POISON CENTER or doctor/physician if you feel unwell. 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