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Dimethylacetamide

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Dimethylacetamide
Names
IUPAC name Dimethylacetamide
Other names DMAc, DMA, acetic acid-dimethylamide, N,N-dimethylacetamide, acetyldimethylamine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.389 Edit this at Wikidata
PubChem CID
RTECS number
  • AB7700000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3Key: FXHOOIRPVKKKFG-UHFFFAOYSA-N
  • InChI=1/C4H9NO/c1-4(6)5(2)3/h1-3H3Key: FXHOOIRPVKKKFG-UHFFFAOYAE
SMILES
  • O=C(N(C)C)C
Properties
Chemical formula C4H9NO
Molar mass 87.122 g·mol
Appearance Colorless liquid with
faint ammonia odor
Density 0.94 g/cm
Melting point −20 °C (−4 °F; 253 K)
Boiling point 164-166 °C
Viscosity 1.956 cP @ 25 °C

1.279 cP @ 50 °C
0.896 cP @ 75 °C
0.661 cP @ 100 °C

Hazards
Occupational safety and health (OHS/OSH):
Main hazards Toxic (T)
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazards (white): no code
2
Flash point 70 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Dimethylacetamide 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 chemistry. DMAc is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.

The chemical reactions of dimethylacetamide are typical of N,N-disubstituted amides. It will hydrolyze in the presence of acids:

CH3CON(CH3)2 + H2O + HCl → CH3COOH + (CH3)2NH2Cl

Dimethylacetamide is useful as a medium for strong bases such as sodium hydroxide. Dimethylacetamide is commonly used as a solvent for fibers or in the adhesive industry. It is also employed in the production of pharmaceuticals and plasticizers as a reaction medium.

References

  1. S. Zen and E. Kaji (1988). "Dimethyl nitrosuccinate". Organic Syntheses; Collected Volumes, vol. 6, p. 503.
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