Dimethylformamide

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"DMF" redirects here. For other uses, see DMF (disambiguation).

Dimethylformamide

General
Systematic name	N, N-dimethylformamide
Other names	DMF, DMFA
Molecular formula	C₃H₇NO
SMILES	O=CN(C)C
Molar mass	73.09 g/mol
Appearance	Clear liquid
CAS number	68-12-2
Properties
Density and phase	0.944 g/cm³, liquid
Solubility in water	Miscible
Melting point	-61 °C (212 K)
Boiling point	153 °C (426 K)
Acidity (pK_a)	?
Basicity (pK_b)	?
Viscosity	? cP at ? °C
Structure
Dipole moment	? D
Dielectric Constant	36.70
Polarity Index	6.4
Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704	2 1 0
Flash point	58 °C
Auto-ignition temperature	445 °C
R/S statement	R: 61-20/21-36 S: 53-45
RTECS number	?
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related amides	Acetamide, Formamide
Related compounds	?
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Dimethylformamide (DMF, N,N-dimethylformamide) is a clear liquid, miscible with water and majority of organic solvents. It is a common solvent that is often used in chemical reactions. Pure dimethylformamide is odorless while technical grade or degraded dimethylformamide often has a fishy smell due to dimethylamine impurities. Its name is derived from the fact that it is formamide (the amide of formic acid) with two methyl group substitutions, both of them on the N (nitrogen) atom.

Dimethylformamide is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates the S_N2 reaction mechanism. Dimethylformamide is synthesized from formic acid and dimethylamine. Dimethylformamide is not stable in the presence of strong bases like sodium hydroxide or strong acids like hydrochloric acid or sulfuric acid and is hydrolyzed back into formic acid and dimethylamine, especially at elevated temperatures.

1 Uses
2 Production
3 Precautions
4 Toxicity
5 References
6 External links

[edit] Uses

The primary use of dimethylformamide is as a solvent with low evaporation rate. Dimethylformamide is used in the production of acrylic fibers and plastics. Additional usage includes ,its utilisation as a solvent in peptide coupling for pharmaceuticals ,use in the development and production of pesticides, and in the manufacture of adhesives, synthetic leathers, fibers, films, and surface coatings.^[1]

It is used as a reagent in the Bouveault aldehyde synthesis and in the Vilsmeier-Haack reaction, another useful method of forming aldehydes.

The proton NMR spectrum of DMF has two singlets for the methyl groups because the rate of rotation about the carbonyl carbon - nitrogen bond is slow on the NMR timescale. The carbonyl carbon - nitrogen bond has a bond order greater than one while the amide carbon oxygen bond has a bond order lower than two. The infra-red spectra of amides normally has a C=O band lower than 1700 cm-1 because the C=O bond is weakened by donation of electron density from the nitrogen to the oxygen.

DMF penetrates most plastics and makes them swell. It therefore frequently occurs as a component of paint strippers.

[edit] Production

Dimethyl formamide is produced with catalyzed reaction of dimethyl amine and carbon monoxide at low pressure and temperature.

[edit] Precautions

Reaction with sodium hydride in DMF as a solvent are somewhat hazardous; exothermic decomposition has been reported at temperatures as low as 26 °C. On a laboratory scale any thermal runaway is (usually) quickly noticed and brought under control with an ice bath and this remains a popular combination of reagents. On a pilot plant scale, on the other hand, several accidents have been reported.

[edit] 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. It is an irksome solvent to use which is viscous and hard to evaporate. For many reactions it can be replaced with dimethyl sulfoxide. Most producers list DMF as (Life) or (Chronic) as a health hazard in their MSDS, as DMF is not readily disposed of by the body.

According to IARC, DMF may be a possible carcinogen, though EPA does not consider it a cancer risk.

[edit] References

↑ 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.