Dimethylacetamide

Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons. Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons. Dimethylacetamide is produced industrially by the reaction of dimethylamine with methyl acetate at a temperature of 90–110 °C and a pressure of 12–25 bar in the presence of sodium methoxide in jet loop reactors. The separation and purification of the product is carried out by multistage distillation in rectification columns. DMA is obtained with 99% yield referred to methyl acetate. DMA may also be prepared by the reaction of dimethylamine with acetic anhydride or acetic acid. Dehydration of the salt of dimethylamine and acetic acid also furnishes this compound: The chemical reactions of dimethylacetamide are typical of N,N-disubstituted amides. It will hydrolyze in the presence of acids: It is however resistant to bases. For this reason DMA is useful solvent for reactions involving strong bases such as sodium hydroxide. Dimethylacetamide is commonly used as a solvent for fibers (e.g., polyacrylonitrile, spandex) or in the adhesive industry. It is also employed in the production of pharmaceuticals and plasticizers as a reaction medium. It is an important Lewis base used to establish the ECW model. Dimethylacetamide is also used as an excipient in drugs, e.g. in Vumon (teniposide), Busulfex (busulfan) or Amsidine (amsacrine). Dimethylacetamide is a medium potency reproductive toxicant (toxic for reproduction, category 1B) and may damage fertility or the unborn child. It is harmful in contact with skin or if inhaled, and causes serious eye irritation.