N-Methylformamide (NMF) is a colorless, nearly odorless, organic compound 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.
|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||59.068 g·mol−1|
|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|
Refractive index (nD)
Heat capacity (C)
|125.2 J K−1 mol−1|
|GHS Signal word||Danger|
|Flash point||111 °C (232 °F; 384 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|4 g kg−1 (oral, rat)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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. 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).
Structure and propertiesEdit
This description highlights the partial double bond that exists between the carbonyl carbon and nitrogen, which gives rise to a high 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.
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.
- CH3NH2 + HCOOCH3 → CH3NHCHO + CH3OH
- HCONH2 + CH3NH2 → CH3NHCHO + NH3
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:
- Bipp, H.; Kieczka, H. "Formamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_001.CS1 maint: multiple names: authors list (link)
- 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.CS1 maint: multiple names: authors list (link); Collective Volume, 5, p. 772