Dimethylformamide



Dimethylformamide
IUPAC name N,N-dimethylmethanamide
Other names DMF, dimethylformide, N,N-dimethylformide, DMFA
Identifiers
CAS number 68-12-2
RTECS number LQ2100000
SMILES O=CN(C)C
Properties
Molecular formula C3H7NO
Molar mass 73.09 g/mol
Appearance Clear liquid
Density 0.944 g/cm3, liquid
Melting point

-61 °C (212 K)

Boiling point

153 °C (426 K)

Solubility in water Miscible
Refractive index (nD) 1.4305 (20 °C), εr = 36.71 (25°C)
Viscosity 0.92 cP at 20 °C
Structure
Dipole moment 3.86 D D (25 °C)
Hazards
MSDS ScienceLab.com
Main hazards flammable
R-phrases 61-20/21-36
S-phrases 53-45
Flash point 58 °C
Related Compounds
Related amides hexamethylphosphoramide
Related compounds acetonitrile
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Dimethylformamide is the formic acid.

Dimethylformamide is a hydrolyzed back into formic acid and dimethylamine, especially at elevated temperatures.

Structure and properties

Due to the contribution of the two possible resonance structures of an amide, the bond order of the proton NMR spectrum.

 

Applications

The primary use of dimethylformamide is as a solvent with low evaporation rate. Dimethylformamide is used in the production of acrylic fibers and pesticides, and in the manufacture of adhesives, synthetic leathers, fibers, films, and surface coatings.[2]

It is used as a reagent in the aldehydes.

DMF penetrates most paint strippers.

It is also used in the manufacturing of solvent dyes as an important raw material. It is consumed during reaction.

Production

Dimethyl formamide is produced with catalyzed reaction of dimethyl amine and carbon monoxide at low pressure and temperature. It may also be prepared on a laboratory scale by reacting dimethylamine with formic acid.

Precautions

Reaction with pilot plant scale, on the other hand, several accidents have been reported.

Toxicity

DMF has been linked to cancer in humans, and it is thought to cause birth defects. In some sectors of industry women are banned from working with DMF. For many reactions, it can be replaced with carcinogen, although EPA does not consider it a cancer risk.

References

  1. ^ a b Spectral Database for Organic Compounds, Dimethylformamide, accessed 27 Jan 2007.
  2. ^ Redlich, C; Beckett, W. S.; Sparer, J.; Barwick, K. W.; Riely, C. A.; Miller, H.; Sigal, S. L.; Shalat, S. L.; and Cullen, M. R.; 1988. Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann. Intern. Med. 108:680-686. PMID 3358569
 
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