N-Methylformamide

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N-Methylformamide
Skeletal formula of N-methylformamide
Ball and stick model of N-methylformamide
Names
IUPAC name
N-Methylformamide[1]
Other names
Methylformide, NMF
Identifiers
123-39-7 YesY
1098352
ChEBI CHEBI:7438 N
ChEMBL ChEMBL9240 YesY
ChemSpider 28994 YesY
EC number 204-624-6
Jmol-3D images Image
Image
KEGG C11489 YesY
MeSH methylformamide
PubChem 31254
RTECS number LQ3000000
Properties
C2H5NO
Molar mass 59.07 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
Miscible
1.432
Thermochemistry
125.2 J K−1 mol−1
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
H312, H360
P280, P308+313
EU Index 616-056-00-X
EU classification Toxic T
R-phrases R61, R21
S-phrases S45
Flash point 111 °C (232 °F; 384 K)
Lethal dose or concentration (LD, LC):
4 g kg−1 (oral, rat)
Related compounds
Related alkanamides
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

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.[2]

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.[2] 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).[2]

Structure and properties[edit]

Like DMF and formamide, each of the two rotamers of NMF are described by two principal resonance structures:

Principal resonance structures for one rotamer of NMF

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.[citation needed]

Preparation[edit]

NMF is typically prepared by allowing methylamine to react with methyl formate:[2]

CH3NH2 + HCOOCH3 → CH3NHCHO + CH3OH

A less common alternative to this process is transamidation involving formamide:[2]

HCONH2 + CH3NH2 → CH3NHCHO + NH3

Uses[edit]

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).[2]
Formothion is an insecticide prepared from N-methylformamide.

Laboratory uses[edit]

NMF is the precursor to methyl isocyanide, a ligand in coordination chemistry.[3] NMF is used as a solvent in Aluminum Electrolytic Capacitors.

References[edit]

  1. ^ "methylformamide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 29 April 2012. 
  2. ^ a b c d e f Bipp, H.; Kieczka, H. (2005), "Formamides", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a12_001 
  3. ^ Schuster, R. E.; Scott, J. E.; Casanova, J. Jr. (1966). "Methyl Isocyanide". Org. Synth. 46: 75. ; Coll. Vol. 5, p. 772