Dimethylformamide is the organic compound with the formula (CH₃)₂NC(O)H. Commonly abbreviated DMF, this colourless liquid is miscible with water and 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 is a derivative of formamide, the amide of formic acid. Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... For other uses, see Viscosity (disambiguation). ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... This page meets Wikipedias criteria for speedy deletion. ... The examples and perspective in this article or section may not represent a worldwide view. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... acetamide Acetamide (or Acetic acid amide or Ацетамид) CH3CONH2, the amide of acetic acid, is a white crystalline solid in pure form. ... Formamide, also known as Methanamide (IUPAC) and Carbamaldehyde, formula HCONH2 is an amide derived from formic acid. ... Hexamethylphosphoramide (abbreviated HMPA) is a colorless organic liquid with the formula [(CH3)2N]3PO. HMPA is the oxide of the highly basic tertiary phosphine P(NMe2)3. ... Dimethyl sulfoxide (DMSO) is the chemical compound with the formula (CH3)2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. ... Acetonitrile is an organic molecule, often used as a solvent, with the chemical formula of CH3CN. Also known as methyl cyanide, it is the simplest of the organic nitriles. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... H2O and HOH redirect here. ... For other uses, see Solvent (disambiguation). ... For other uses, see Chemical reaction (disambiguation). ... Safety (MSDS) data for dimethylamine General Synonyms: N-methyl-methanamine Molecular formula: C2H7N CAS No: 124-40-3 EINECS No: 204-697-4 EC index no: 612-001-00-9 Physical data Appearance: colourless gas with strong ammonia-like smell Melting point: -92 C Boiling point: 7. ... Formamide, also known as Methanamide (IUPAC) and Carbamaldehyde, formula HCONH2 is an amide derived from formic acid. ... Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. ...

Dimethylformamide is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as S_N2 reactions. Dimethylformamide can be synthesized from formic acid and dimethylamine.^{[citation needed]} Dimethylformamide is not 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. A commonly-used example of a polar compound is water (H2O). ... The adjective hydrophilic describes something that likes water (from Greek hydros = water; philos = friend). ... In chemistry, nucleophilic subsitution is a type of chemical reaction in which one nucleophile (electron donor) replaces another as a covalent substituent of some atom. ... Flash point Non-flammable. ... R-phrases , S-phrases , , Flash point Non-flammable. ... R-phrases S-phrases , , , Flash point Non-flammable Related Compounds Related strong acids Selenic acid Hydrochloric acid Nitric acid Related compounds Hydrogen sulfide Sulfurous acid Peroxymonosulfuric acid Sulfur trioxide Oleum Supplementary data page Structure and properties n, εr, etc. ... Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water. ...

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[1] than an unsubstuted 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,^[1] instead of one singlet of 6 protons in the proton NMR spectrum. Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e. ... A carbon-nitrogen bond is a covalent bond between carbon and nitrogen and one of the most abundant in organic chemistry and biochemistry [1]. Nitrogen has five valence electrons and in simple amines it is trivalent with two remaining electrons forming a lone pair. ... Infrared spectroscopy (IR spectroscopy) is the subset of spectroscopy that deals with the infrared region of the electromagnetic spectrum. ... NMR redirects here. ... Pacific Northwest National Laboratorys high magnetic field (800 MHz, 18. ...

The two resonance forms of DMF

Image File history File links Size of this preview: 800 × 250 pixelsFull resolution‎ (3,242 × 1,012 pixels, file size: 20 KB, MIME type: image/png) Resonance forms of an en:amide bond (en:dimethylformamide). ... Image File history File links Size of this preview: 800 × 250 pixelsFull resolution‎ (3,242 × 1,012 pixels, file size: 20 KB, MIME type: image/png) Resonance forms of an en:amide bond (en:dimethylformamide). ...

Applications

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.^[2] Acrylic fibers are synthetic fibers made from a polymer with a weight average molecular weight of ~100,000. ... For other uses, see Plastic (disambiguation). ... A cropduster spreading pesticide. ... For the band, see Adhesive (band). ... For people named Leather, see Leather (surname). ...

It is used as a reagent in the Bouveault aldehyde synthesis and in the Vilsmeier-Haack reaction, another useful method of forming aldehydes. The Bouveault aldehyde synthesis is a one-pot chemical reaction that converts a primary alkyl halide to an aldehyde one carbon longer. ... The Vilsmeier-Haack reaction or Vilsmeier reaction is an organic reaction between a substituted amide and a activated arene in the presence of phosphorus oxychloride. ... An aldehyde. ...

DMF penetrates most plastics and makes them swell. It therefore frequently occurs as a component of paint strippers. For other uses, see Plastic (disambiguation). ... Edema (BE: oedema, formerly known as dropsy) is swelling of any organ or tissue due to accumulation of excess fluid. ... Paint stripper, or paint remover, is the generic name given to solvent mixtures designed to removed paint and clean the underlying surface. ...

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. Dimethylamine or N-methylmethanamine or DMA is an organic compound and an amine. ... Carbon monoxide, with the chemical formula CO, is a colorless, odorless, and tasteless gas. ...

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. Sodium hydride is a highly flammable, and corrosive chemical compound with formula NaH and CAS number 7646-69-7. ... A pilot plant is a small chemical processing system which is operated to generate information about the behavior of the system for use in design of larger facilities. ...

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 dimethyl sulfoxide. Most manufacturers of DMF list (Life) or (Chronic) as a health hazard in their MSDS since DMF is not readily disposed of by the body. According to IARC, DMF may be a possible carcinogen, although EPA does not consider it a cancer risk. Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ... A congenital disorder is a medical condition or defect that is present at or before birth (for example, congenital heart disease). ... Dimethyl sulfoxide (DMSO) is the chemical compound with the formula (CH3)2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. ... The International Agency for Research on Cancer (IARC, or CIRC in its French acronym) is an intergovernmental agency forming part of the World Health Organisation of the United Nations. ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... EPA redirects here. ...

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

Year 1988 (MCMLXXXVIII) was a leap year starting on Friday (link displays 1988 Gregorian calendar). ...

External links

• International Chemical Safety Card 0457
• NIOSH Pocket Guide to Chemical Hazards 0226
• Dimethylformamide usage on Organic Syntheses
• Concise International Chemical Assessment Document 31: N,N-Dimethylformamide
• Material Safety Data Sheet for DMF
• DMF Chronic Toxicity Summary (PDF)