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Dimethylacetamide

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Dimethylacetamide
Names
IUPAC name
N,N-dimethylacetamide
Other names
DMAc, DMA, acetic acid-dimethylamide, Dimethylacetamide, acetyldimethylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.389 Edit this at Wikidata
RTECS number
  • AB7700000
UNII
  • InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3 checkY
    Key: FXHOOIRPVKKKFG-UHFFFAOYSA-N checkY
  • InChI=1/C4H9NO/c1-4(6)5(2)3/h1-3H3
    Key: FXHOOIRPVKKKFG-UHFFFAOYAE
  • O=C(N(C)C)C
Properties
C4H9NO
Molar mass 87.122 g·mol−1
Appearance Colorless liquid with
faint ammonia odor
Density 0.94 g/cm3
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 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
2
2
Flash point 63 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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)2NH2+Cl-

Dimethylacetamide is useful as a medium for strong bases such as sodium hydroxide.[1] 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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