What is N,N-Dimethylformamide?

N,N-Dimethylformamide, or dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging degraded samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is a derivative of formamide, the amide of formic acid. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions [1].

DMF was first prepared in 1893 by the French chemist Albert Verley (8 January 1867 – 27 November 1959), by distilling a mixture of dimethylamine hydrochloride and potassium formate. DMF is prepared by combining methyl formate and dimethylamine or by reaction of dimethylamine with carbon monoxide [2]. Although currently impractical, DMF can be prepared from supercritical carbon dioxide using ruthenium-based catalysts.

N,N-dimethylformamide is a member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups. It has a role as a polar aprotic solvent and a hepatotoxic agent. It is a volatile organic compound and a member of formamides [3]. DMF appears as a water-white liquid with a faint fishy odor. Flash point 136°F. Slightly less dense than water. Vapors heavier than air. Toxic by inhalation or skin absorption. May irritate eyes. It derives from a DMF is a polar aprotic solvent with a high boiling point (153 oC). DMF is also used as a reagent in some reactions. A closely related solvent is dimethylacetamide (DMA). DMF is flammable and its explosive limits are 2.2-16% v/v. At temperatures above 350 °C, thermal decomposition of DMF to form dimethylamine and carbon monoxide occurs.

The primary use of DMF is as a solvent with low evaporation rate. DMF is a clear liquid that has been widely used in industries as a solvent, an additive, or an intermediate because of its extensive miscibility with water and most common organic solvents. DMF 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 [4]. As a cheap and common reagent, DMF also has many uses in a research laboratory.

DMF is readily absorbed through the skin, inhaled, or ingested. DMF is a potent liver toxin. DMF may cause abdominal pain, constipation, nausea and vomiting, headache, weakness, dizziness, skin problems, and alcohol intolerance. Current evidence associating DMF with cancer in humans is not conclusive. Its health effects include hepatotoxicity and male reproductoxicity, possibly linked with mitochondrial DNA (mtDNA) alterations including mtDNA common deletion (delta-mtDNA4977) and mtDNA copy number; during the biotransformation of DMF in the body, free radicals are formed, including hydroxyl radicals. The world-wide consumption of DMF in 2001 was approximately 285, 000 metric tonnes and most of that was used as an industrial solvent. Overexposure to DMF could result in hepatotoxicity, alcohol intolerance, possible embryotoxicity and teratogenicity in humans and animals, and decline of human sperm motility. Based on its wide application and a wide range of toxic effects, DMF has been selected as one of the four priority compounds for human field studies by the National Toxicology Program (NTP) of the US National Institute of Environmental Health Sciences (NIEHS). The current permissible exposure limit for DMF in the working environment is 10 ppm in both USA and Taiwan. The concentrations of two major DMF metabolites in urine, N-methylformamide (U-NMF) of 15 mg/L and N-acetyl-S-(N-methylcarbamoyl) cysteine (U-AMCC) of 40 mg/L, were recommended as the biological exposure indices (BEIs) by the American Conference of Governmental Industrial Hygienists for DMF exposure in workplace.

References

[1] https://en.wikipedia.org/wiki/Dimethylformamide

[2] Weissermel, K.; Arpe, H.-J. (2003). Industrial Organic Chemistry: Important Raw Materials and Intermediates. Wiley-VCH. pp. 45–46. ISBN 3-527-30578-5.

[3] https://pubchem.ncbi.nlm.nih.gov/compound/dimethylformamide

[4] Bipp, H.; Kieczka, H. "Formamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_001.pub2.

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