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Dimethylformamide information


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
CAS Number
  • 68-12-2 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B00545
Beilstein Reference
605365
ChEBI
  • CHEBI:17741 checkY
ChEMBL
  • ChEMBL268291 checkY
ChemSpider
  • 5993 checkY
DrugBank
  • DB01844 checkY
ECHA InfoCard 100.000.617 Edit this at Wikidata
EC Number
  • 200-679-5
KEGG
  • C03134 checkY
MeSH Dimethylformamide
PubChem CID
  • 6228
RTECS number
  • LQ2100000
UNII
  • 8696NH0Y2X checkY
UN number 2265
CompTox Dashboard (EPA)
  • DTXSID6020515 Edit this at Wikidata
InChI
  • InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3 checkY
    Key: ZMXDDKWLCZADIW-UHFFFAOYSA-N checkY
SMILES
  • CN(C)C=O
Properties
Chemical formula
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)
Solubility in water
Miscible
log P −0.829
Vapor pressure 516 Pa
Acidity (pKa) −0.3 (for the conjugate acid) (H2O)[3]
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
Dipole moment
3.86 D
Thermochemistry
Heat capacity (C)
146.05 J/(K·mol)
Std enthalpy of
formation fH298)
−239.4 ± 1.2 kJ/mol
Std enthalpy of
combustion cH298)
−1.9416 ± 0.0012 MJ/mol
Hazards
GHS labelling:
Pictograms
GHS02: Flammable GHS07: Exclamation mark GHS08: Health hazard
Signal word
Danger
Hazard statements
H226, H312, H319, H332, H360
Precautionary statements
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)
Autoignition
temperature
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)
  • 1.5 g/kg (rabbit, dermal)
  • 2.8 g/kg (rat, oral)
  • 3.7 g/kg (mouse, oral)
  • 3.5 g/kg (rat, oral)
LC50 (median concentration)
3092 ppm (mouse, 2 h)[5]
LCLo (lowest published)
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
  • N-Methylformamide
  • Diethylformamide
  • Deuterated DMF
Related compounds
  • N-Nitroso-N-methylurea
  • ENU
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dimethylformamide 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).

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Dimethylformamide

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Dimethylformamide is an organic compound with the chemical formula HCON(CH3)2. Its structure is HC(=O)−N(−CH3)2. Commonly abbreviated as DMF (although...

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Amide

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Swern oxidation. Oxalyl chloride is mainly used together with a N,N-dimethylformamide catalyst in organic synthesis for the preparation of acyl chlorides...

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Water

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Deuterated dimethylformamide ((CD3)2NCOD), also known as deuterated DMF, is an isotopologue of DMF ((CH3)2NCOH) in which the hydrogen atom ("H") is replaced...

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Methylammonium lead halide

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from 0.8 g/mL at 20 °C to 0.3 g/mL at 80 °C for [CH3NH3]PbBr3 in dimethylformamide. This property is used in the growth of MALH single crystals and films...

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Solvation

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to right: 1. Water, 2. Methanol, 3. Ethanol, 4. Acetonitrile, 5. Dimethylformamide, 6. Acetone, 7. Ethylacetate, 8. Dichlormethane 9. n-Hexane, 10....

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Potassium chloride

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41 Methanol 5.3 Ethanol 0.37 Formic acid 192 Sulfolane 0.04 Acetonitrile 0.024 Acetone 0.00091 Formamide 62 Acetamide 24.5 Dimethylformamide 0.17–0.5...

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Fluxional molecule

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the four CO ligands. A classic example of a fluxional molecule is dimethylformamide (DMF). At temperatures near 100 °C, the 500 MHz 1H NMR spectrum of...

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Triamcinolone

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20 {\displaystyle [\alpha ]_{D}^{20}} +65° to +72° cm3/dm·g (1% in dimethylformamide). In 2010, Teva and Perrigo launched the first generic inhalable triamcinolone...

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Polar aprotic solvent

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dichloromethane CH2Cl2 39.6 °C 9.08 1.3266 g/cm3 1.6 low boiling point dimethylformamide (CH3)2NCHO 153 °C 36.7 0.95 g/cm3 3.86 reacts with strong bases...

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Formamide

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Formamides are compounds of the type RR′NCHO. One important formamide is dimethylformamide, (CH3)2NCHO. In the past, formamide was produced by treating formic...

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DMF

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DMF may refer to: Dimethylformamide, a common solvent Dimethyl fumarate, a small molecule anti-inflammatory human medicine 2,5-Dimethylfuran, a liquid...

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Dihydrolevoglucosenone

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dipolar solvent. It is an environmentally friendly alternative to dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP). Dihydrolevoglucosenone can...

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Cornforth reagent

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pyridinium cations. The Cornforth reagent is readily soluble in water, dimethylformamide and dimethyl sulfoxide (DMSO). It is poorly soluble in acetone and...

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Polyacrylonitrile

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created at the Buna Werke Schkopau (Polyacrylonitrile) and Leuna works (Dimethylformamide). In the same year, the collective was awarded the GDR's National...

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Vilsmeier reagent

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Vilsmeier reaction or Vilsmeier-Haack reaction that use mixtures of dimethylformamide and phosphorus oxychloride to generate the Vilsmeier reagent, which...

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Reference electrode

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Dichloromethane CH2Cl2 0.46, 0.475 Tetrahydrofuran THF 0.56, 0.547 Dimethylformamide DMF 0.45, 0.470 Acetone (CH3)2C=O 0.48 Dimethylsulfoxide DMSO 0.435...

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softening cured cyanoacrylate. Other solvents include nitromethane, dimethylformamide, dimethyl sulfoxide, and methylene chloride. Another viable solvent...

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Dimethylamine

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the substance which then need to be further purified. The solvents dimethylformamide and dimethylacetamide are derived from dimethylamine. It is raw material...

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Alcohol intolerance

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Kazunori; Watanabe, Takao; Ikeda, Masayuki (1992-01-01). "Occupational dimethylformamide exposure". International Archives of Occupational and Environmental...

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