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Showing NP-Card for N-Methylformamide (NP0086710)

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Record Information
Version1.0
Created at2022-05-11 16:28:50 UTC
Updated at2022-05-11 16:28:50 UTC
NP-MRD IDNP0086710
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Methylformamide
DescriptionN-Methylformamide, also known as HCONHCH3 or NMF, belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). N-Methylformamide is an extremely weak basic (essentially neutral) compound (based on its pKa). DMF is favored over NMF as a solvent due to its greater stability. 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. 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). NMF is typically prepared by allowing methylamine to react with methyl formate:CH3NH2 + HCOOCH3 → CH3NHCHO + CH3OHA less common alternative to this process is transamidation involving formamide:HCONH2 + CH3NH2 → CH3NHCHO + NH3NMF is a specialized solvent in oil refineries. These reactions can generally be categorized by the following equation:R-Lg + CH3NHCHO → R-NCH3CHO + H-Lg (where Lg is a leaving group). NMF is the precursor to methyl isocyanide, a ligand in coordination chemistry. NMF is used as a solvent in Aluminum Electrolytic Capacitors. N-Methylformamide (NMF) is a colorless, nearly odorless, organic compound with molecular formula CH3NHCHO, which is a liquid at room temperature. It was first documented in 1986 (PMID: 3712373). NMF is closely related to other formamides, notably formamide and dimethylformamide (DMF) (PMID: 17254560) (PMID: 16289959) (PMID: 19634900) (PMID: 24473177).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086710 (N-Methylformamide)


  Mrv0541 02231218562D          

  4  3  0  0  0  0            999 V2000
   14.3009   -5.3214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154   -5.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154   -6.5589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5864   -5.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  1  4  1  0  0  0  0
M  END
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3D MOL for NP0086710 (N-Methylformamide)

     RDKit          3D

  9  8  0  0  0  0  0  0  0  0999 V2000
    0.9650   -0.5363    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0513    0.5090   -0.3215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3108    0.4798    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7353   -0.4648    0.7492 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9541   -1.4042   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6322   -0.9842    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0218   -0.1627    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906    1.3009   -0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689    1.2625   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
M  END
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3D SDF for NP0086710 (N-Methylformamide)


  Mrv0541 02231218562D          

  4  3  0  0  0  0            999 V2000
   14.3009   -5.3214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154   -5.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154   -6.5589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5864   -5.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  1  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086710

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)

> <INCHI_KEY>
ATHHXGZTWNVVOU-UHFFFAOYSA-N

> <FORMULA>
C2H5NO

> <MOLECULAR_WEIGHT>
59.0672

> <EXACT_MASS>
59.037113787

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
5.75540955627049

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methylformamide

> <ALOGPS_LOGP>
-1.31

> <JCHEM_LOGP>
-0.8553109703333334

> <ALOGPS_LOGS>
0.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.54298091278144

> <JCHEM_PKA_STRONGEST_BASIC>
-0.842484936384209

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
14.8721

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylformamide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0086710 (N-Methylformamide)

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PDB for NP0086710 (N-Methylformamide)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      26.695  -9.933   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      28.029 -10.703   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      28.029 -12.243   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      25.361 -10.703   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END

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3D PDB for NP0086710 (N-Methylformamide)
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SMILES for NP0086710 (N-Methylformamide)
CNC=O
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INCHI for NP0086710 (N-Methylformamide)
InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
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View in JSmol
Synonyms
ValueSource
HCONHCH3ChEBI
MethylformamideChEBI
MonomethylformamideChEBI
N-Methyl-formamideChEBI
N-MonomethylformamideChEBI
NMFChEBI
N-MethylformamideKEGG
Chemical FormulaC2H5NO
Average Mass59.0672 Da
Monoisotopic Mass59.03711 Da
IUPAC NameN-methylformamide
Traditional Namemethylformamide
CAS Registry NumberNot Available
SMILES
CNC=O
InChI Identifier
InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
InChI KeyATHHXGZTWNVVOU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboximidic acids and derivatives  
Sub ClassCarboximidic acids  
Direct ParentCarboximidic acids  
Alternative Parents
Substituents
  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Carboximidic acid
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Imine
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.3ALOGPS
logP-0.86ChemAxon
logS0.83ALOGPS
pKa (Strongest Acidic)16.54ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.87 m³·mol⁻¹ChemAxon
Polarizability5.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001122  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022436  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11489  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Methylformamide  
METLIN IDNot Available
PubChem Compound31254  
PDB IDNot Available
ChEBI ID7438  
Good Scents IDNot Available
References
General References
  1. Shieh DB, Chen CC, Shih TS, Tai HM, Wei YH, Chang HY: Mitochondrial DNA alterations in blood of the humans exposed to N,N-dimethylformamide. Chem Biol Interact. 2007 Feb 20;165(3):211-9. Epub 2006 Dec 20. [PubMed:17254560  ] 
  2. Mraz J, Cimlova J, Stransky V, Nohova H, Kicova R, Simek P: N-Methylcarbamoyl-lysine adduct in globin: a new metabolic product and potential biomarker of N, N-dimethylformamide in humans. Toxicol Lett. 2006 Apr 10;162(2-3):211-8. doi: 10.1016/j.toxlet.2005.09.039. Epub 2005 Nov 14. [PubMed:16289959  ] 
  3. Frimpong K, Wzorek J, Lawlor C, Spencer K, Mitzel T: Use of N-methylformamide as a solvent in indium-promoted Barbier reactions en route to enediyne and epoxy diyne formation: comparison of rate and stereoselectivity in C-C bond-forming reactions with water. J Org Chem. 2009 Aug 21;74(16):5861-70. doi: 10.1021/jo900763u. [PubMed:19634900  ] 
  4. Kalyani D, Jyothi K, Sivaprakasam C, Nachiappan V: Spectroscopic and molecular modeling studies on the interactions of N-Methylformamide with superoxide dismutase. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 24;124:148-52. doi: 10.1016/j.saa.2014.01.013. Epub 2014 Jan 18. [PubMed:24473177  ] 
  5. Gate EN, Threadgill MD, Stevens MF, Chubb D, Vickers LM, Langdon SP, Hickman JA, Gescher A: Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide. J Med Chem. 1986 Jun;29(6):1046-52. doi: 10.1021/jm00156a024. [PubMed:3712373  ]