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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.
there are two rotamers and two principal res structures
 
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{{DISPLAYTITLE:''N''-Methylformamide}}
{{DISPLAYTITLE:''N''-Methylformamide}}
{{chembox
{{chembox
| Verifiedfields = changed
| verifiedrevid = 402502907
| Watchedfields = changed
| Name = ''N''-Methylformamide
| verifiedrevid = 409137791
| ImageFileL1 = methylformamide.png
| Name = ''N''-Methylformamide
| ImageNameL1 = Structural formula
| ImageFileR1 = Methylformamide-3D-balls.png
| ImageFile = Methylformamide skeletal.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Ball-and-stick model
| ImageSize = 100
| IUPACName = ''N''-Methylformamide
| ImageName = Skeletal formula of N-methylformamide
| OtherNames = NMF, methylformide
| ImageFile1 = Methylformamide-3D-balls.png
| Section1 = {{Chembox Identifiers
| ImageFile1_Ref = {{chemboximage|correct|??}}
| SMILES = O=CNC
| ImageSize1 = 100
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ImageName1 = Ball and stick model of N-methylformamide
| ChemSpiderID = 28994
| PIN = ''N''-Methylformamide
| OtherNames = Methylformide<br />NMF<br />''N''-methylmethanamide
|Section1={{Chembox Identifiers
| CASNo = 123-39-7
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = XPE4G7Y986
| PubChem = 31254
| PubChem = 31254
| ChemSpiderID = 28994
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 204-624-6
| KEGG = C11489
| KEGG = C11489
| KEGG_Ref = {{keggcite|correct|kegg}}
| InChI = 1/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
| MeSHName = methylformamide
| InChIKey = ATHHXGZTWNVVOU-UHFFFAOYAO
| ChEBI = 7438
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 9240
| ChEMBL = 9240
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = LQ3000000
| Beilstein = 1098352
| SMILES = CNC=O
| StdInChI = 1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ATHHXGZTWNVVOU-UHFFFAOYSA-N
| StdInChIKey = ATHHXGZTWNVVOU-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| CASNo = 123-39-7
}}
| CASNo_Ref = {{cascite|correct|CAS}}
|Section2={{Chembox Properties
| RTECS = LQ3000000
| C=2 | H=5 | N=1 | O=1
}}
| Appearance = Colourless liquid
| Section2 = {{Chembox Properties
| Odor = fishy, ammoniacal
| Formula = C<sub>2</sub>H<sub>5</sub>NO
| MolarMass = 59.067 g/mol
| Density = 1.011 g mL<sup>−1</sup>
| MeltingPtC = -4
| Appearance = Clear liquid
| BoilingPtK = 455.7
| Density = 1.003 g/cm<sup>3</sup>, liquid
| Solubility = Miscible
| Solubility = Miscible
| MeltingPtC = -3
| RefractIndex = 1.432
}}
| BoilingPt = 198-200 °C (471-473 K)
|Section3={{Chembox Thermochemistry
| pKa =
| HeatCapacity = 125.2 J K<sup>−1</sup> mol<sup>−1</sup>
| pKb =
}}
| Viscosity =
|Section4={{Chembox Hazards
| RefractIndex = 1.432
| GHSPictograms = {{gHS exclamation mark}} {{gHS health hazard}}
}}
| GHSSignalWord = '''DANGER'''
| Section3 = {{Chembox Structure
| HPhrases = {{h-phrases|312|360}}
| Dipole =
| PPhrases = {{p-phrases|280|308+313}}
}}
| FlashPtC = 111
| Section7 = {{Chembox Hazards
| LD50 = 4 g kg<sup>−1</sup> <small>(oral, rat)</small>
| MainHazards =
}}
| FlashPt = 111 °C
|Section5={{Chembox Related
| RPhrases = 61-21
| OtherFunction_label = alkanamides
| SPhrases = 53-45
| OtherFunction = {{unbulleted list|[[Dimethylformamide]]|[[dimethylacetamide]]|[[formamide]]|}}
}}
| OtherCompounds =
| Section8 = {{Chembox Related
}}
| Function = [[amide]]s
| OtherFunctn =
| OtherCpds =
}}
}}
}}


'''''N''-Methylformamide''' (NMF) is a colorless, nearly odorless, [[organic compound]] with molecular formula CH<sub>3</sub>NHCHO, 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]].<ref name=NMF>Hansjörg Bipp and Heinz Kieczka "Formamides" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. {{DOI|10.1002/14356007.a12_001}}</ref>
'''''N''-Methylformamide''' (NMF) is a colorless, nearly odorless, [[organic compound]] and [[secondary amide]] with molecular formula CH<sub>3</sub>NHCHO, 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]].<ref name=NMF>{{ Ullmann | author = Bipp, H. | author2 = Kieczka, H. | title = Formamides | doi = 10.1002/14356007.a12_001 }}</ref>


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.<ref name=NMF/> 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).<ref name=NMF/>
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.<ref name=NMF/> 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).<ref name=NMF/>


==Structure and properties==
==Structure and properties==
Like DMF and formamide, each of the two [[rotamer]]s of NMF are described by two principal [[resonance structure]]s:
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 structure]]s for one of these rotamers is shown:
::[[Image:NMFresonanceStr's.png|220px|Principal resonance structures for one rotamer of NMF]]
::[[Image:NMFresonanceStr's.png|220px|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|date=December 2009}}
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|(''E'')-configuration]] is preferred due to [[steric repulsion]] of the larger substituents.<ref>{{cite journal |doi=10.1002/bip.360360405}}</ref>

This molecule has been tentatively identified in [[interstellar space]] by the [[Atacama Large Millimeter Array|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]].<ref name=Belloche2017/>


==Preparation==
==Preparation==
NMF is typically prepared by allowing [[methylamine]] to react with [[methyl formate]]:<ref name=NMF/>
NMF is typically prepared by allowing [[methylamine]] to react with [[methyl formate]]:<ref name=NMF/>
:CH<sub>3</sub>NH<sub>2</sub> + HCOOCH<sub>3</sub> → CH<sub>3</sub>NHCHO + CH<sub>3</sub>OH
:CH<sub>3</sub>NH<sub>2</sub> + HCOOCH<sub>3</sub> → HCONHCH<sub>3</sub> + CH<sub>3</sub>OH


A less common alternative to this process is [[transamidation]] involving [[formamide]]:<ref name=NMF/>
A less common alternative to this process is [[transamidation]] involving [[formamide]]:<ref name=NMF/>
:HCONH<sub>2</sub> + CH<sub>3</sub>NH<sub>2</sub> → CH<sub>3</sub>NHCHO + NH<sub>3</sub>
:HCONH<sub>2</sub> + CH<sub>3</sub>NH<sub>2</sub> → HCONHCH<sub>3</sub> + NH<sub>3</sub>


==Uses==
==Uses==
NMF is used in specialized amidation reactions where formamide would not be suitable. These reactions can generally be categorized by the following equation:
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 + CH<sub>3</sub>NHCHO → R-NCH<sub>3</sub>CHO + H-Lg (where Lg is a [[leaving group]])
:R-Lg + CH<sub>3</sub>NHCHO → R-NCH<sub>3</sub>CHO + H-Lg (where Lg is a [[leaving group]]).<ref name=NMF/>
[[Image:Formothion.svg|thumb|left|120px|[[Formothion]] is an insecticide prepared from N-methylformamide.]]
These reactions typically proceed in high yields.<ref name=NMF/>


===Laboratory uses===
NMF is the precursor to [[methyl isocyanide]], a ligand in [[coordination chemistry]] and an intermediate in the production of some pharmaceutical compounds.<ref>{{OrgSynth | author = R. E. Schuster, James E. Scott, and Joseph Casanova, Jr. | title = Methyl_Isocyanide | collvol = 5 | collvolpages = 772 | year =1973 | prep = CV5P0772}}</ref>
NMF is the precursor to [[methyl isocyanide]], a ligand in [[coordination chemistry]].<ref>{{ OrgSynth | author = Schuster, R. E. | author2 = Scott, J. E. | author3 = Casanova, J. Jr. | title = Methyl Isocyanide | year = 1966 | volume = 46 | page = 75 | collvol = 5 | collvolpages = 772 | prep = CV5P0772 }}</ref> NMF is used as a solvent in Aluminum Electrolytic Capacitors.


==References==
==References==
{{Reflist|refs=
{{reflist}}

<ref name=Belloche2017>{{cite journal
| title=Rotational spectroscopy, tentative interstellar detection, and chemical modeling of N-methylformamide
| display-authors=1 | last1=Belloche | first1=A.
| last2=Meshcheryakov | first2=A. A. | last3=Garrod | first3=R. T.
| last4=Ilyushin | first4=V. V. | last5=Alekseev | first5=E. A.
| last6=Motiyenko | first6=R. A. | last7=Margulès | first7=L.
| last8=Müller | first8=H. S. P. | last9=Menten | first9=K. M.
| journal=Astronomy & Astrophysics
| volume=601 | id=A49 | pages=41 | date=May 2017
| arxiv=1701.04640 | bibcode=2017A&A...601A..49B
| doi=10.1051/0004-6361/201629724 }}</ref>

}}

{{Authority control}}


{{DEFAULTSORT:Methylformamide, N-}}
{{DEFAULTSORT:Methylformamide, N-}}
[[Category:Amides]]
[[Category:Formamides]]
[[Category:Amide solvents]]
[[Category:Amide solvents]]
[[Category:Solvents]]
[[Category:Solvents]]

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