Dimethylacetamide

Dimethylacetamide
IUPAC name N,N-dimethylacetamide
Other names DMAc, DMA, acetic acid-dimethylamide, Dimethylacetamide, acetyldimethylamine
Identifiers
CAS number	127-19-5 Y
PubChem	31374
ChemSpider	29107 Y
UNII	JCV5VDB3HY Y
ChEMBL	CHEMBL11873 Y
RTECS number	AB7700000
Jmol-3D images	Image 1
SMILES O=C(N(C)C)C
InChI InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3 Y Key: FXHOOIRPVKKKFG-UHFFFAOYSA-N Y InChI=1/C4H9NO/c1-4(6)5(2)3/h1-3H3 Key: FXHOOIRPVKKKFG-UHFFFAOYAE
Properties
Molecular formula	C4H9NO
Molar mass	87.12 g mol−1
Appearance	Colorless liquid with faint ammonia odor
Density	0.94 g/cm3
Melting point	-20 °C, 253 K, -4 °F
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
R-phrases	R61 R20/21
S-phrases	S53 S45
Main hazards	Toxic (T)
NFPA 704	0 2 0
Flash point	70 °C
Autoignition temperature	490 °C
Related compounds
Related Compounds	Acetic acid Dimethylamine Dimethylformamide
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV6P0503 ; Coll. Vol. 6: 503