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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:40:16 UTC
Update Date2019-07-23 06:35:05 UTC
HMDB IDHMDB0041808
Secondary Accession Numbers
  • HMDB41808
Metabolite Identification
Common Name4,4'-Methylenedianiline
Description4,4'-Methylenedianiline, also known as bis(4-aminophenyl)methane or DDM, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. The liver and thyroid are the targets of 4,4'-methylenedianiline in animals. The N-N-acetylation of the compound leads to the formation of some toxic derivatives. 4,4'-Methylenedianiline is a strong basic compound (based on its pKa). 4,4'-Methylenedianiline is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. After 4,4'-Methylenedianiline enters to our body, it is transported in the blood or stored in tissues.
Structure
Data?1563863705
Synonyms
ValueSource
4,4'-DiphenylmethanediamineChEBI
4,4'-Methylenebis(benzeneamine)ChEBI
4-(4-Aminobenzyl)anilineChEBI
alpha-(p-Aminophenyl)-p-toluidineChEBI
Bis(4-aminophenyl)methaneChEBI
Bis(p-aminophenyl)methaneChEBI
Bis-p-aminophenylmethaneChEBI
DADPMChEBI
DAPMChEBI
DDMChEBI
Di-(4-aminophenyl)methaneChEBI
Di-(p-aminophenyl)methaneChEBI
DianilinomethaneChEBI
p,P'-diaminodiphenylmethaneChEBI
p,P'-methylenedianilineChEBI
4,4'-DiaminodiphenylmethaneKegg
a-(p-Aminophenyl)-p-toluidineGenerator
Α-(p-aminophenyl)-p-toluidineGenerator
4, 4'-DiphenylmethanediamineHMDB
4, 4'-Methylenebis(aniline)HMDB
4,4'-DiaminodiphenylmethanHMDB
4,4'-Methylene(bisaniline)HMDB
4,4'-Methylene-dianilineHMDB
4,4'-Methylenebis-benzenamineHMDB
4,4'-Methylenebis[aniline]HMDB
4,4'-Methylenedi-anilineHMDB
4,4'-MethylenedibenzenamineHMDB
4,4-MethylenedianilineHMDB
4-(4-Aminobenzyl)phenylamine (acd/name 4.0)HMDB
Ancamine TLHMDB
Araldite hardener 972HMDB
Bis(aminophenyl)methaneHMDB
Bis-p-aminofenylmethanHMDB
CurithaneHMDB
Di(4-aminophenyl)methaneHMDB
DiaminodiphenylmethaneHMDB
DianilinemethaneHMDB
Epicure DDMHMDB
Epikure DDMHMDB
Jeffamine ap-20HMDB
MDAHMDB
Methylenebis(aniline)HMDB
Methylenebis[aniline]HMDB
MethylenedianilineHMDB
p, P'-methylenedianilineHMDB
p,P'-diaminodifenylmethanHMDB
Sumicure mHMDB
TonoxHMDB
4,4'-Diaminodiphenylmethane, sodium chloride (3:1)HMDB
4,4'-Diaminodiphenylmethane dihydrochlorideHMDB
4,4'-Methylene dianilineHMDB
4,4'-MethylenebisanilineHMDB
4,4'-MDAHMDB
4,4'-MethylenedianilineChEBI
Chemical FormulaC13H14N2
Average Molecular Weight198.2637
Monoisotopic Molecular Weight198.115698458
IUPAC Name4-[(4-aminophenyl)methyl]aniline
Traditional Name4,4'-diaminodiphenylmethane
CAS Registry Number101-77-9
SMILES
NC1=CC=C(CC2=CC=C(N)C=C2)C=C1
InChI Identifier
InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2
InChI KeyYBRVSVVVWCFQMG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Role

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point92.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mL at 25 °CNot Available
LogP1.59Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.061 g/LALOGPS
logP2.04ALOGPS
logP2.41ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)4.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.2 m³·mol⁻¹ChemAxon
Polarizability22.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-1900000000-a1316bc903c186c14318Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-4644a7dbb46f9d7b2ba1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0900000000-a4548ac0cc34b55b0737Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pe9-3900000000-4cb485ecb653179900c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-31a3645696c4f9d211baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-0e89f98c9bcf3071812eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000w-4900000000-9cfc5d89ecd51b783c25Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-1900000000-3ade5e930b45bb46e746Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7296
KEGG Compound IDC14288
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4,4'-Methylenedianiline
METLIN IDNot Available
PubChem Compound7577
PDB IDNot Available
ChEBI ID32506
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pludro G, Karlowski K, Mankowska M, Woggon H, Uhde WJ: [Toxicological and chemical studies of some epoxy resins and hardeners. I. Study of acute and subacute toxicity of phthalic acid anhydride, 4,4'diaminodiphenylmethane and epoxy resin Epilox EG-34]. Acta Pol Pharm. 1969;26(4):353-8. [PubMed:5349261 ]
  2. Yasuda SK: Determination of 3,3'-dichloro-4,4'-diaminodiphenylmethane in air. J Chromatogr. 1975 Feb 12;104(2):283-90. [PubMed:1150762 ]
  3. Manis MO, Braselton WE Jr: Structure elucidation and in vitro reactivity of the major metabolite of 4,4'-methylenebis(2-chloroaniline) (MBOCA) in canine urine. Fundam Appl Toxicol. 1984 Dec;4(6):1000-8. [PubMed:6549168 ]