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Dimethylacetamide

Dimethylacetamide
Skeletal formula of dimethylacetamide
Ball and stick model of dimethylacetamide
Names
IUPAC name
N,N-Dimethylacetamide
Identifiers
3D model (Jmol)
Abbreviations DMA, DMAC, DMAc
1737614
ChEBI
ChemSpider
ECHA InfoCard 100.004.389
EC Number 204-826-4
MeSH dimethylacetamide
PubChem CID
RTECS number AB7700000
UNII
Properties
C4H9NO
Molar mass 87.12 g·mol−1
Appearance Colorless liquid
Odor Ammoniacal
Density 0.937 g mL−1
Melting point −20 °C (−4 °F; 253 K)
Boiling point 165.1 °C; 329.1 °F; 438.2 K
Miscible
log P −0.253
Vapor pressure 300 Pa
UV-vis (λmax) 270 nm
Absorbance 1.00
1.4375
Viscosity 0.945 mPa s
Thermochemistry
178.2 J K−1 mol−1
−300.1 kJ mol−1
−2.5835–−2.5805 MJ mol−1
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H312, H319, H332, H360
P280, P308+313
Toxic T
R-phrases R61, R20/21
S-phrases S45
NFPA 704
Flammability code 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 fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 63 °C (145 °F; 336 K)
490 °C (914 °F; 763 K)
Explosive limits 1.8–11.5%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 2.24 g kg−1(dermal, rabbit)
4.3 g kg−1(oral, rat)
4.8 g/kg (oral, rat)
4.62 g/kg (oral, mouse)
2475 ppm (rat, 1 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 10 ppm (35 mg/m3) [skin]
REL (Recommended)
 TWA 10 ppm (35 mg/m3) [skin]
IDLH (Immediate danger)
 300 ppm
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.

DMA is prepared by the reaction of dimethylamine with acetic anhydride and esters of 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.

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.


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