Dimethylformamide

Dimethylformamide
Skeletal formula of dimethylformamide with one explicit hydrogen added
Ball and stick model of dimethylformamide
Ball and stick model of dimethylformamide
Spacefill model of dimethylformamide
Spacefill model of dimethylformamide
Names
Preferred IUPAC name
N,N-Dimethylformamide[2]
Other names
Dimethylformamide
N,N-Dimethylmethanamide[1]
DMF
Identifiers
3D model (JSmol)
3DMet
605365
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.617 Edit this at Wikidata
EC Number
  • 200-679-5
KEGG
MeSH Dimethylformamide
RTECS number
  • LQ2100000
UNII
UN number 2265
  • InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3 checkY
    Key: ZMXDDKWLCZADIW-UHFFFAOYSA-N checkY
  • CN(C)C=O
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)[3]
UV-vismax) 270 nm
Absorbance 1.00
1.4305 (at 20 °C)
Viscosity 0.92 mPa·s (at 20 °C)
Structure
3.86 D
Thermochemistry
146.05 J/(K·mol)
−239.4 ± 1.2 kJ/mol
−1.9416 ± 0.0012 MJ/mol
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark GHS08: Health hazard
Danger
H226, H312, H319, H332, H360
P280, P305+P351+P338, P308+P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 58 °C (136 °F; 331 K)
445 °C (833 °F; 718 K)
Explosive limits 2.2–15.2%
30 mg/m3 (TWA)
Lethal dose or concentration (LD, LC):
  • 1.5 g/kg (rabbit, dermal)
  • 2.8 g/kg (rat, oral)
  • 3.7 g/kg (mouse, oral)
  • 3.5 g/kg (rat, oral)
3092 ppm (mouse, 2 h)[5]
5000 ppm (rat, 6 h)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 10 ppm (30 mg/m3) [skin][4]
REL (Recommended)
TWA 10 ppm (30 mg/m3) [skin][4]
IDLH (Immediate danger)
500 ppm[4]
Related compounds
Related alkanamides
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dimethylformamide, DMF is an organic compound with the chemical formula HCON(CH3)2. Its structure is HC(=O)−N(−CH3)2. 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.

  1. ^ N,N-Dimethylmethanamide, NIST web thermo tables
  2. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 841, 844. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The traditional name 'formamide' is retained for HCO-NH2 and is the preferred IUPAC name. Substitution is permitted on the –NH2 group.
  3. ^ "Hazardous Substances Data Bank (HSDB) - N,N-DIMETHYLFORMAMIDE".
  4. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0226". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ a b "Dimethylformamide". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).