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2924191000 CAS No.: 68-12-2 Molecular Formular: C3H7NO Molecular
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 than an unsubstituted C=O bond. Also, because of the partial double bond character, the rotation about the C-N axis is slow at room temperature, 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, instead of one singlet of 6 protons in the proton NMR spectrum.
The primary use of dimethylformamide is as a solvent with low evaporation rate. Dimethylformamide is used in the production of acrylic fibers and plastics. It is also used as a solvent in peptide coupling for pharmaceuticals, in the development and production of pesticides, and in the manufacture of adhesives, synthetic leathers, fibers, films, and surface coatings.
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.
DMF is very effective at separating and suspending carbon nanotubes, and is recommended by the NIST for use in Near infrared spectroscopy of such. It is also used in the manufacturing of solvent dyes as an important raw material. It is consumed during reaction.
Package and Storage:
Reactions including the use of sodium hydride in DMF as a solvent are somewhat hazardous; exothermic decompositions have 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.
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- Posted By: Chemland Group INC
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Published date: September 6, 2012 -
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