Dimethylformamide

Dimethylformamide
Ball and stick model of dimethylformamide	Spacefill model of dimethylformamide
Names
	Preferred IUPAC name N,N-Dimethylformamide
	Other names Dimethylformamide; N,N-Dimethylmethanamide; DMF
Identifiers
CAS Number	68-12-2 ;
3D model (JSmol)	Interactive image;
3DMet	B00545;
Beilstein Reference	605365
ChEBI	CHEBI:17741 ;
ChEMBL	ChEMBL268291 ;
ChemSpider	5993 ;
DrugBank	DB01844 ;
ECHA InfoCard	100.000.617
EC Number	200-679-5;
KEGG	C03134 ;
MeSH	Dimethylformamide
PubChem CID	6228;
RTECS number	LQ2100000;
UNII	8696NH0Y2X ;
UN number	2265
CompTox Dashboard (EPA)	DTXSID6020515 ;
	InChI InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3 Key: ZMXDDKWLCZADIW-UHFFFAOYSA-N ;
	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)
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 (ΔfH⦵298)	−239.4 ± 1.2 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	−1.9416 ± 0.0012 MJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H312, H319, H332, H360
Precautionary statements	P280, P305+P351+P338, P308+P313
NFPA 704 (fire diamond)	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)
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	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). verify (what is ?) Infobox references

Dimethylformamide is an organic compound with the chemical formula H C O N(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 S_N2 reactions.

^ N,N-Dimethylmethanamide, NIST web thermo tables
^ 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.
^ "Hazardous Substances Data Bank (HSDB) - N,N-DIMETHYLFORMAMIDE".
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0226". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "Dimethylformamide". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[1] N,N-Dimethylmethanamide, NIST web thermo tables

[iupac2013-2] 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".

[PGCH-4] NIOSH Pocket Guide to Chemical Hazards. "#0226". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-5] "Dimethylformamide". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

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