N-Methylformamide 1

N-Methylformamide
N-Methylformamide

Identifiers

CAS number [1]

123-39-7  

PubChem [2]
31254

ChemSpider [3]
28994  

EC number [4]
204-624-6

KEGG [5]
C11489  

MeSH [6]
methylformamide

ChEBI [7]
CHEBI:7438  

ChEMBL [8]
CHEMBL9240  

RTECS number LQ3000000

Beilstein Reference 1098352

Jmol-3D images [9]

Image 1
[10]
Image 2

Properties

Molecular formula 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

Solubility in water Miscible

Refractive index (nD) 1.432

Thermochemistry
N-Methylformamide 2

Specific 125.2 J K−1 mol−1

heat capacity C

Hazards

GHS pictograms

GHS hazard statements H312, H360

GHS precautionary statements P280, P308+313

EU Index 616-056-00-X

EU classification

T
R-phrases R61, R21

S-phrases S45

Flash point 111 °C (232 °F; 384 K)

LD50 4 g kg−1 (oral, rat)

Related compounds

Related alkanamides • Dimethylformamide

• dimethylacetamide
• formamide

Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

[11]
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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.
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

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

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]
N-Methylformamide 3

Preparation
NMF is typically prepared by allowing methylamine to react with methyl formate:
CH3NH2 + HCOOCH3 → CH3NHCHO + CH3OH
A less common alternative to this process is transamidation involving formamide:
HCONH2 + CH3NH2 → CH3NHCHO + 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).

Laboratory uses
NMF is the precursor to methyl isocyanide, a ligand in coordination chemistry.
NMF is used as a solvent in Aluminum Electrolytic Capacitors.
Formothion is an insecticide
prepared from
N-methylformamide.

References
[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=123-39-7
[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=31254
[3] http:/ / www. chemspider. com/ Chemical-Structure. 28994. html
[4] http:/ / esis. jrc. ec. europa. eu/ lib/ einecs_IS_reponse. php?genre=ECNO& entree=204-624-6
[5] http:/ / www. kegg. jp/ entry/ C11489
[6] http:/ / www. nlm. nih. gov/ cgi/ mesh/ 2007/ MB_cgi?mode=& term=methylformamide
[7] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=7438
[8] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL9240
[9] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=C%5BnH%5D%3Ac%3A%5Bo%5D
[10] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CNC%3DO
[11] http:/ / en. wikipedia. org/ w/ index. php?title=Special:ComparePages& rev1=409137791& page2=N-Methylformamide
Article Sources and Contributors 4

Article Sources and Contributors

N-Methylformamide  Source: http://en.wikipedia.org/w/index.php?oldid=586467318  Contributors: Beetstra, Bennomoehlman, Chem-awb, DePiep, Edgar181, Grigola2, JohnSRoberts99, Jynto,
Plasmic Physics, Quasar1826, Shanata, Smokefoot, Stone, V8rik, Vchorozopoulos, 5 anonymous edits

Image Sources, Licenses and Contributors

File:Methylformamide skeletal.png  Source: http://en.wikipedia.org/w/index.php?title=File:Methylformamide_skeletal.png  License: Public Domain  Contributors: Edgar181
File:Methylformamide-3D-balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Methylformamide-3D-balls.png  License: Public Domain  Contributors: Ben Mills and Jynto
File:Yes check.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Yes_check.svg  License: Public Domain  Contributors: Anomie
File:X mark.svg  Source: http://en.wikipedia.org/w/index.php?title=File:X_mark.svg  License: Public Domain  Contributors: User:Gmaxwell
Image:GHS-pictogram-exclam.svg  Source: http://en.wikipedia.org/w/index.php?title=File:GHS-pictogram-exclam.svg  License: Public Domain  Contributors: Torsten Henning
Image:GHS-pictogram-silhouete.svg  Source: http://en.wikipedia.org/w/index.php?title=File:GHS-pictogram-silhouete.svg  License: Public Domain  Contributors: Torsten Henning
Image:Hazard_T.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Hazard_T.svg  License: Public Domain  Contributors: BLueFiSH.as, Boweruk, Cäsium137, Ies, KES47,
MarianSigler, Matthias M., Maxima m, Natr, Phrood, Túrelio, W!B:, 13 anonymous edits
Image:NMFresonanceStr's.png  Source: http://en.wikipedia.org/w/index.php?title=File:NMFresonanceStr's.png  License: Public Domain  Contributors: Smokefoot
Image:Formothion.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Formothion.svg  License: Public Domain  Contributors: Ed (Edgar181)

License
Creative Commons Attribution-Share Alike 3.0
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