Record Information
Version1.0
Creation date2010-04-08 22:06:22 UTC
Update date2019-11-26 03:00:11 UTC
Primary IDFDB004724
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN,N-Dimethylformamide
DescriptionDimethylformamide is a polar (hydrophilic) Aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions. Dimethylformamide can be synthesized from methyl formate and dimethyl amine or reaction of dimethyl amine and carbon monoxide. Dimethylformamide is not stable in the presence of strong bases like sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid and is hydrolyzed back into formic acid and dimethylamine, especially at elevated temperatures.; Dimethylformamide is the organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated DMF (though this acronym is sometimes used for dimethylfuran), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Pure dimethylformamide is odorless whereas technical grade or degraded dimethylformamide often has a fishy smell due to impurity of dimethylamine. Its name is derived from the fact that it is a derivative of formamide, the amide of formic acid.; N,N-Dimethylformamide (DMF) is a clear liquid that has been widely used in industries as a solvent, an additive, or an intermediate because of its extensive miscibility with water and most common organic solvents. Its health effects include hepatotoxicity and male reproductoxicity, possibly linked with mitochondrial DNA (mtDNA) alterations including mtDNA common deletion (delta-mtDNA4977) and mtDNA copy number; during the biotransformation of DMF in the body, free radicals are formed, including hydroxyl radicals.; The world-wide consumption of DMF in 2001 was approximately 285,000 metric tonnes and most of that was used as an industrial solvent. Overexposure to DMF could result in hepatotoxicity, alcohol intolerance, possible embryotoxicity and teratogenicity in humans and animals, and decline of human sperm motility. Based on its wide application and a wide range of toxic effects, DMF has been selected as one of the four priority compounds for human field studies by the National Toxicology Program (NTP) of the US National Institute of Environmental Health Sciences (NIEHS). The current permissible exposure limit for DMF in the working environment is 10 ppm in both USA and Taiwan. The concentrations of two major DMF metabolites in urine, N-methylformamide (U-NMF) of 15 mg/L and N-acetyl-S-(N-methylcarbamoyl) cysteine (U-AMCC) of 40 mg/L, were recommended as the biological exposure indices (BEIs) by the American Conference of Governmental Industrial Hygienists for DMF exposure in workplace. (PMID: 17254560). N,N-Dimethylformamide is found in papaya.
CAS Number68-12-2
Structure
Thumb
Synonyms
SynonymSource
DimethylformamideChEBI
DMFChEBI
N,N-DimethylmethanamideChEBI
N-FormyldimethylamineChEBI
Dimethyl formamideHMDB
Dimethyl-formamideHMDB
Dimethylamid kyseliny mravenciHMDB
DimethylforamideHMDB
DimethylformamidHMDB
DimetilformamideHMDB
DimetylformamiduHMDB
DwumetyloformamidHMDB
FormyldimethylamineHMDB
N,N- Dimethyl formamideHMDB
N,N- DimethylformamideHMDB
N,N-Dimethyl-formamideHMDB
N,N DimethylformamideHMDB
Dimethylformamid (german)biospider
DMF (amide)biospider
DMF (dimethylformamide)biospider
DMF (van)biospider
DMFAbiospider
Dynasolve 100biospider
Formamide, dimethyl-biospider
Formamide, n,n-dimethyl-biospider
Formic acid, amide, n,n-dimethyl-biospider
Formin acid,amide,n,n-dimethylbiospider
HCON(CH3)2biospider
HSDB 78biospider
N-formyldimethylaminebiospider
N, n-dimethylmethanamidebiospider
N,n- dimethyl formamidebiospider
N,n- dimethylformamidebiospider
N,n-dimethyl formamidebiospider
N,n-dimethylformamidebiospider
N,N-Dimethylformamide [UN2265] [Flammable liquid]biospider
N,n-dimethylmethanamidebiospider
N,n-dimetilformamidabiospider
Predicted Properties
PropertyValueSource
Water Solubility725 g/LALOGPS
logP-0.77ALOGPS
logP-0.63ChemAxon
logS1ALOGPS
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.77 m³·mol⁻¹ChemAxon
Polarizability7.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC3H7NO
IUPAC nameN,N-dimethylformamide
InChI IdentifierInChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
InChI KeyZMXDDKWLCZADIW-UHFFFAOYSA-N
Isomeric SMILESCN(C)C=O
Average Molecular Weight73.0938
Monoisotopic Molecular Weight73.052763851
Classification
Description Belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentTertiary carboxylic acid amides
Alternative Parents
Substituents
  • Tertiary carboxylic acid amide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point-60.4 oC
Boiling PointNot Available
Experimental Water Solubility1000 mg/mL at 25 oCISHOW (NA--) @2ND
Experimental logP-1.01HANSCH,C ET AL. (1995)
Experimental pKa-0.3
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-006x-9000000000-039511887fde37138176Spectrum
Predicted GC-MSN,N-Dimethylformamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9000000000-34e0d5dce52ab7332a48Spectrum
Predicted GC-MSN,N-Dimethylformamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-2fc3e0f8da9a647359faSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001l-9000000000-f4fe42c25bc21b32c720Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000x-9000000000-c16bd85f59063ed223cdSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-9000000000-cc68a0ecc7c49de9adf0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00di-9000000000-9f91c0e4ecf9323c5268Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-9000000000-cc68a0ecc7c49de9adf0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-9000000000-9f91c0e4ecf9323c5268Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-006y-9000000000-5543ffa660a73e2f60aeSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-9000000000-9f91c0e4ecf9323c5268Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-7021cfe3ddcd7eead969Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-ceda884adf62fcbbade6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-dfa16f4b703eedcce213Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-20383304fc1b3341c39dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-4add65e7ea3604d5d1fcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-a05f660af113d947481eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-bc974757d0839ce6b57cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-bc974757d0839ce6b57cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-33646a67bc59fe05be54Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-ca67ae001025b0816d1cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9000000000-c1637e5f95671002e1bcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-78ef7927403f69155f40Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID5993
ChEMBL IDCHEMBL268291
KEGG Compound IDC03134
Pubchem Compound ID6228
Pubchem Substance IDNot Available
ChEBI ID17741
Phenol-Explorer IDNot Available
DrugBank IDDB01844
HMDB IDHMDB01888
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDN,N-DIMETHYL-FORMAMIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDDMF
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDN,N-Dimethylformamide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).