| N,N-Dimethylformamide | |
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N,N-Dimethylmethanamide |
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Other names
DMF; Dimethylformamide; N,N-Dimethylformamide; DMFA |
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| Identifiers | |
| CAS number | 68-12-2 |
| PubChem | 6228 |
| ChemSpider | 5993 |
| UNII | 8696NH0Y2X |
| DrugBank | DB01844 |
| KEGG | C03134 |
| ChEBI | CHEBI:17741 |
| ChEMBL | CHEMBL268291 |
| RTECS number | LQ2100000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C3H7NO |
| Molar mass | 73.09 g/mol |
| Appearance | Clear liquid |
| Density | 0.944 g/cm3, liquid |
| Melting point |
-61 °C, 212 K, -78 °F |
| Boiling point |
153 °C, 426 K, 307 °F |
| Solubility in water | Miscible |
| Vapor pressure | 0.3 kPa (@ 20°C) |
| Refractive index (nD) | 1.4305 (20 °C), εr = 36.71 (25°C) |
| Viscosity | 0.92 cP at 20 °C |
| Structure | |
| Dipole moment | 3.86 D (25 °C) |
| Hazards | |
| MSDS | MSDS |
| R-phrases | R61 R20/21 R36 |
| S-phrases | S53 S45 |
| Main hazards | flammable |
| NFPA 704 |
2
1
0
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| Flash point | 58 °C |
| Threshold Limit Value | 10 ppm[1] (TWA) |
| Related compounds | |
| Related amides | Acetamide, Formamide, hexamethylphosphoramide |
| Related compounds | Dimethyl sulfoxide, acetonitrile, N-Methylformamide |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (though this acronym is sometimes used for dimethylfuran), 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 is 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 methyl formate and dimethylamine or by reaction of dimethylamine with carbon monoxide.[2] 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.
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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[3] 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,[3] instead of one singlet of 6 protons in the proton NMR spectrum.
N,N-Dimethylformamide (DMF) is miscible with water in all proportions.[4] The vapour pressure at 20°C is 3.5hPa.[5] A Henry's law constant of 7.47×10−5 hPa·m3/mol can be deduced from an experimentally determined equilibrium constant at 25 °C.[6] The partition coefficient logPOW is measured to –0.85.[7] Since the density of DMF (0.95 g/cm3 at 20 °C[4]) is very similar to that of water, significant flotation or stratification in surface waters in case of accidental losses is not expected.
Dimethyl formamide is produced either via catalyzed reaction of dimethylamine and carbon monoxide in methanol or via the reaction of methyl formate with dimethylamine.[2] It may also be prepared on a laboratory scale by reacting dimethylamine with formic acid.
The primary use of dimethylformamide is as a solvent with low evaporation rate. 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.[8]
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.[11]
DMF has been linked to cancer in humans, and it is thought to cause birth defects.[12] 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 is a possible carcinogen, although EPA does not consider it a cancer risk.