Dimethylformamide
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| Dimethylformamide | |
|---|---|
| |
| |
| IUPAC name | N,N-dimethylmethanamide |
| Other names | DMF, dimethylformide, N,N-dimethylformide, DMFA |
| Identifiers | |
| CAS number | |
| RTECS number | LQ2100000 |
| SMILES | O=CN(C)C |
| 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) |
| Boiling point |
153 °C (426 K) |
| Solubility in water | Miscible |
| 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 D (25 °C) |
| Hazards | |
| MSDS | ScienceLab.com |
| Main hazards | flammable |
| R-phrases | 61-20/21-36 |
| S-phrases | 53-45 |
| Flash point | 58 °C |
| Related Compounds | |
| Related amides | Acetamide, Formamide, hexamethylphosphoramide |
| Related compounds | Dimethylsulfoxide, acetonitrile |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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Overview
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.
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 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.
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.
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.[1]
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.
Production
Dimethyl formamide is produced with catalyzed reaction of dimethyl amine and carbon monoxide at low pressure and temperature.
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 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.
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)
References
de:Dimethylformamid fr:Diméthylformamide it:Dimetilformammide nl:Dimethylformamide ja:N,N-ジメチルホルムアミドsv:Dimetylformamid
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
