Dimethylformamide
Dimethylformamide is an organic compound with the formula (CH3)2N−C(=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 samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.
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| Names | |||
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| Preferred IUPAC name
N,N-Dimethylformamide | |||
| Other names
Dimethylformamide N,N-Dimethylmethanamide DMF | |||
| Identifiers | |||
3D model (JSmol) |
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| 3DMet | |||
| 605365 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.000.617 | ||
| EC Number |
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| KEGG | |||
| MeSH | Dimethylformamide | ||
PubChem CID |
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| RTECS number |
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| UNII | |||
| UN number | 2265 | ||
CompTox Dashboard (EPA) |
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| Properties | |||
| C3H7NO | |||
| Molar mass | 73.095 g·mol−1 | ||
| Appearance | Colourless liquid | ||
| Odor | Odorless, fishy if impure | ||
| Density | 0.948 g/mL | ||
| Melting point | −61 °C (−78 °F; 212 K) | ||
| Boiling point | 153 °C (307 °F; 426 K) | ||
| Miscible | |||
| log P | −0.829 | ||
| Vapor pressure | 516 Pa | ||
| Acidity (pKa) | −0.3 (for the conjugate acid) (H2O) | ||
| UV-vis (λmax) | 270 nm | ||
| Absorbance | 1.00 | ||
Refractive index (nD) |
1.4305 (at 20 °C) | ||
| Viscosity | 0.92 mPa·s (at 20 °C) | ||
| Structure | |||
| 3.86 D | |||
| Thermochemistry | |||
Heat capacity (C) |
146.05 J/(K·mol) | ||
Std enthalpy of formation (ΔfH⦵298) |
−239.4 ± 1.2 kJ/mol | ||
Std enthalpy of combustion (ΔcH⦵298) |
−1.9416 ± 0.0012 MJ/mol | ||
| Hazards | |||
| GHS labelling: | |||
| Danger | |||
| H226, H312, H319, H332, H360 | |||
| P280, P305+P351+P338, P308+P313 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 58 °C (136 °F; 331 K) | ||
| 445 °C (833 °F; 718 K) | |||
| Explosive limits | 2.2–15.2% | ||
Threshold limit value (TLV) |
30 mg/m3 (TWA) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
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LC50 (median concentration) |
3092 ppm (mouse, 2 h) | ||
LCLo (lowest published) |
5000 ppm (rat, 6 h) | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) |
TWA 10 ppm (30 mg/m3) [skin] | ||
REL (Recommended) |
TWA 10 ppm (30 mg/m3) [skin] | ||
IDLH (Immediate danger) |
500 ppm | ||
| Related compounds | |||
Related alkanamides |
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Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |||