|Jmol-3D images||Image 1
|Molar mass||59.07 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|
|Solubility in water||Miscible|
|Refractive index (nD)||1.432|
heat capacity C
|125.2 J K−1 mol−1|
|GHS hazard statements||H312, H360|
|GHS precautionary statements||P280, P308+313|
|Flash point||111 °C (232 °F; 384 K)|
|LD50||4 g kg−1 (oral, rat)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
N-Methylformamide (NMF) is a colorless, nearly odorless, organic compound with molecular formula CH3NHCHO, which is a liquid at room temperature. It is infinitely soluble in water. NMF is mainly used as a reagent in various organic syntheses with limited applications as a highly polar solvent.
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 properties
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.
- 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:
- "methylformamide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 29 April 2012.
- Bipp, H.; Kieczka, H. (2005), "Formamides", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a12_001
- Schuster, R. E.; Scott, J. E.; Casanova, J. Jr. (1966), "Methyl Isocyanide", Org. Synth. 46: 75; Coll. Vol. 5: 772