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N-Methylformamide
Names
	Preferred IUPAC name N-Methylformamide
	Systematic IUPAC name N-Methylmethanamide
	Other names Methylformide; NMF
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]

Structure and properties

Because of slow rotation about the N-C(O) bond, NMF exists as two rotamers that can be distinguished by NMR spectroscopy. The two principal resonance structures for one of these rotamers is shown:

Principal resonance structures for one rotamer of NMF

This description highlights the partial double bond that exists between the carbonyl carbon and nitrogen, which raises the rotational barrier. Thus, the molecule is not able to freely rotate around its main axis and the (E)-configuration is preferred due to steric repulsion of the larger substituents.^[2]

This molecule has been tentatively identified in interstellar space by the ALMA radio telescope. It may have formed on dust grains. This could prove to be a key molecule for interstellar pre-biotic chemistry due to its peptide bond.^[3]

Preparation

NMF is typically prepared by allowing methylamine to react with methyl formate:^[1]

CH₃NH₂ + HCOOCH₃ → HCONHCH₃ + CH₃OH

A less common alternative to this process is transamidation involving formamide:^[1]

HCONH₂ + CH₃NH₂ → HCONHCH₃ + NH₃

Uses

NMF is a specialized solvent in oil refineries. It is a precursor in specialized amidation reactions where formamide would not be suitable. These reactions can generally be categorized by the following equation:

R-Lg + CH₃NHCHO → R-NCH₃CHO + H-Lg (where Lg is a leaving group).^[1]

Formothion is an insecticide prepared from N-methylformamide.

Laboratory uses

NMF is the precursor to methyl isocyanide, a ligand in coordination chemistry.^[4] NMF is used as a solvent in Aluminum Electrolytic Capacitors.

References

^ ^a ^b ^c ^d ^e ^f Bipp, H.; Kieczka, H. "Formamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_001. ISBN 978-3527306732.
^ . doi:10.1002/bip.360360405. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
^ Belloche, A.; et al. (May 2017). "Rotational spectroscopy, tentative interstellar detection, and chemical modeling of N-methylformamide". Astronomy & Astrophysics. 601: 41. arXiv:1701.04640. Bibcode:2017A&A...601A..49B. doi:10.1051/0004-6361/201629724. A49.
^ Schuster, R. E.; Scott, J. E.; Casanova, J. Jr. (1966). "Methyl Isocyanide". Organic Syntheses. 46: 75; Collected Volumes, vol. 5, p. 772.