N-Methylformamide

N-Methylformamide
Names
	Preferred IUPAC name N-Methylformamide
	Other names Methylformide; NMF; N-methylmethanamide
Identifiers
CAS Number	123-39-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1098352
ChEBI	CHEBI:7438 ;
ChEMBL	ChEMBL9240 ;
ChemSpider	28994 ;
ECHA InfoCard	100.004.205
EC Number	204-624-6;
KEGG	C11489 ;
MeSH	methylformamide
PubChem CID	31254;
RTECS number	LQ3000000;
UNII	XPE4G7Y986 ;
CompTox Dashboard (EPA)	DTXSID0025608 ;
	InChI InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4) Key: ATHHXGZTWNVVOU-UHFFFAOYSA-N ;
	SMILES CNC=O;
Properties
Chemical formula	C2H5NO
Molar mass	59.068 g·mol−1
Appearance	Colourless liquid
Odor	fishy, ammoniacal
Density	1.011 g mL−1
Melting point	−4 °C (25 °F; 269 K)
Boiling point	182.6 °C; 360.6 °F; 455.7 K
Solubility in water	Miscible
Refractive index (nD)	1.432
Thermochemistry
Heat capacity (C)	125.2 J K−1 mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H312, H360
Precautionary statements	P280, P308+P313
Flash point	111 °C (232 °F; 384 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	4 g kg−1 (oral, rat)
Related compounds
Related alkanamides	Dimethylformamide; dimethylacetamide; formamide;
	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

N-Methylformamide (NMF) is a colorless, nearly odorless, organic compound and secondary amide with molecular formula CH₃NHCHO, which is a liquid at room temperature. NMF is mainly used as a reagent in various organic syntheses with limited applications as a highly polar solvent.^[1]

NMF is closely related to other formamides, notably formamide and dimethylformamide (DMF). However, industrial use and production of NMF are far less than for either of these other formamides. DMF is favored over NMF as a solvent due to its greater stability.^[1] Annual production of NMF can be assumed to be significantly less than the production of either formamide (100,000 tons) or DMF (500,000 tons).^[1]

^ ^a ^b ^c Bipp, H.; Kieczka, H. "Formamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_001. ISBN 978-3527306732.

[NMF-1] Bipp, H.; Kieczka, H. "Formamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_001. ISBN 978-3527306732.

[1]

Names


Preferred IUPAC name N-Methylformamide
Other names Methylformide NMF N-methylmethanamide
Identifiers
CAS Number	123-39-7^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1098352
ChEBI	CHEBI:7438^N
ChEMBL	ChEMBL9240^Y
ChemSpider	28994^Y
ECHA InfoCard	100.004.205
EC Number	204-624-6
KEGG	C11489^Y
MeSH	methylformamide
PubChem CID	31254
RTECS number	LQ3000000
UNII	XPE4G7Y986^Y
CompTox Dashboard (EPA)	DTXSID0025608
InChI InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)^Y Key: ATHHXGZTWNVVOU-UHFFFAOYSA-N^Y
SMILES CNC=O
Properties
Chemical formula	C₂H₅NO
Molar mass	59.068 g·mol⁻¹
Appearance	Colourless liquid
Odor	fishy, ammoniacal
Density	1.011 g mL⁻¹
Melting point	−4 °C (25 °F; 269 K)
Boiling point	182.6 °C; 360.6 °F; 455.7 K
Solubility in water	Miscible
Refractive index (n_D)	1.432
Thermochemistry
Heat capacity (C)	125.2 J K⁻¹ mol⁻¹
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H312, H360
Precautionary statements	P280, P308+P313
Flash point	111 °C (232 °F; 384 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	4 g kg⁻¹ (oral, rat)
Related compounds
Related alkanamides	Dimethylformamide dimethylacetamide formamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references