Everything about Dimethylformamide totally explained
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Dimethylformamide is the
organic compound with the
formula (
CH3)
2NC(O)H. Commonly abbreviated DMF, this colourless liquid is miscible with
water and the majority of organic liquids. DMF is a common
solvent for
chemical reactions. Pure dimethylformamide is odorless whereas technical grade or degraded dimethylformamide often has a fishy smell due to impurity of
dimethylamine. Its name is derived from the fact that it's a derivative of
formamide, the
amide of
formic acid.
Dimethylformamide is a
polar (
hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as
SN2 reactions. Dimethylformamide can be synthesized from formic acid and dimethylamine. Dimethylformamide isn't stable in the presence of strong bases like
sodium hydroxide or strong acids such as
hydrochloric acid or
sulfuric acid and is
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
carbonyl C=O bond is reduced, while that of the
carbon-nitrogen bond is increased. Thus the
infrared spectrum of DMF shows a lower C=O stretching frequency at 1675 cm
-1 than an unsubstituted C=O bond. Also, because of the partial double bond character, the rotation about the C-N axis is slow, making the two methyl groups inequivalent on the
NMR time scale, giving rise to two singlets of 3 protons each at δ 2.97 and 2.88,
It is used as a reagent in the
Bouveault aldehyde synthesis and in the
Vilsmeier-Haack reaction, another useful method of forming
aldehydes.
DMF penetrates most
plastics and makes them
swell. It therefore frequently occurs as a component of
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
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.
Toxicity
DMF has been linked to
cancer in humans, and it's 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
dimethyl sulfoxide. Most manufacturers of DMF list (Life) or (Chronic) as a health hazard in their MSDS since DMF isn't readily disposed of by the body. According to
IARC, DMF is a possible
carcinogen, although
EPA doesn't consider it a cancer risk.
Further Information
Get more info on 'Dimethylformamide'.
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