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127-19-5 - N,N-Dimethylacetamide, 99% - DMA - A10924 - Alfa Aesar

A10924 N,N-Dimethylacetamide, 99%

CAS Number
127-19-5
Synonyms
DMA

Size Price ($) Quantity Availability
250ml 19.54
500ml 26.37
2500ml 84.98
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N,N-Dimethylacetamide, 99%

MDL
MFCD00008686
EINECS
204-826-4

Chemical Properties

Formula
C4H9NO
Formula Weight
87.12
Melting point
-20°
Boiling Point
165-166°
Flash Point
70°(158°F)
Density
0.940
Refractive Index
1.4385
Solubility
Miscible with water, benzene, alcohol, acetone, ether, esters and ketones.

Applications

N,N-Dimethylacetamide is used as a polar solvent in organic synthesis as well as in reactions involving strong bases such as sodium hydroxide. It is also used as a solvent for fibers like polyacrylonitrile, spandex, as an excipient in drugs viz. vumon, busulfex and in the adhesive industry. It finds application as a reaction medium in the production of pharmaceuticals, agrochemicals, dyes and plasticizers. It is widely used in polymer industry due to its high solving power for high molecular-weight polymers and synthetic resins. It plays an important role as a catalyst in various reactions viz. cyclization, halogenation, cynidation, alkylation and dehydrogenation and increases the yield of main products. It is also used as an extracting agent for oil and gases, in paint removers, in the production of photo-resist stripping compounds and as booster solvent in coatings.

Notes

Hygroscopic. Incompatible with strong oxidizing agents.

Literature References

Dipolar aprotic solvent, cf N,N-Dimethyl­formamide, A13547, Dimethyl­ sulfoxide, A13280, 1-Methyl-2-pyrrolidinone, A12260.

See also Sodium hydride, 13431, for warning.

Useful solvent in halex fluorinations of chloroarenes; compare Sulfolane, A13466.

Undergoes Vilsmeier-type reactions (compare DMF), with reactive substrates, introducing an acetyl group: Chem. Ber., 97, 616 (1964).

Reacts with alkyl and aryl Grignard reagents to give methyl ketones in good yields: Synthesis, 228 (1984).

In the presence of triflic anhydride and 2,4,6-collidine, forms a highly-reactive keteniminium triflate, which undergoes a [2+2] cycloaddition reaction with terminal alkenes to give, after hydrolysis a 3-alkylcyclobutanone: J. Am. Chem. Soc., 107, 2192 (1985); Org. Synth. Coll., 8, 306 (1993):

Messaadi, A.; Salhi, H.; Das, D.; Alzamil, N. O.; Alkhaldi, M. A.; Ouerfelli, N.; Hamzaoui, A. H. A novel approach to discuss the viscosity Arrhenius behaviour and to derive the partial molar properties in binary mixtures of N, N-dimethylacetamide with 2-methoxyethanol in the temperature interval (from 298.15 to 318.15) K. Phys. Chem. Liq. 2015, 53 (4), 506-517.

Shokouhi, M.; Farahani, H.; Jenab, M. H.; Jalili, A. H. Solubility of Hydrogen Sulfide in N-Methylacetamide and N, N-Dimethylacetamide: Experimental Measurement and Modeling. J. Chem. Eng. Data 2015, 60 (3), 499-508.

GHS Hazard and Precautionary Statements

Hazard Statements: H360-H312-H332-H227

May damage fertility or the unborn child. Harmful in contact with skin. Harmful if inhaled. Combustible liquid.

Precautionary Statements: P210-P201-P261-P280-P281-P304+P340-P312-P363-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,3227
Beilstein
1737614
Harmonized Tariff Code
2924.19
TSCA
Yes
RTECS
AB7700000

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