Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:40:16 UTC
Update Date2023-02-21 17:28:58 UTC
HMDB IDHMDB0041808
Secondary Accession Numbers
  • HMDB41808
Metabolite Identification
Common Name4,4'-Methylenedianiline
Description4,4’-Methylenedianiline (MDA) is an industrial chemical that is produced and used industrially as a precursor to polyamides, epoxy resins, and polyurethane foams (PMID: 20621954 ). It is a primary aromatic amine, belonging to the family of compounds known as Diphenylmethanes. Diphenylmethanes are compounds consisting of methane with two of the hydrogen atoms replaced by phenyl groups. MDA is used mainly as a precursor to 4,4 ́-methylene diphenyl diisocyanate (MDI), which is a precursor to many polyurethane foams. To generate MDI, which is a highly reactive isocyanate, MDA is treated with phosgene. Workers exposed to MDI may develop sensitization, leading to occupational asthma. MDI is metabolized in the body and secreted in the urine as MDA, Therefore MDA is a urinary biomarker of MDI exposure. On its own, MDA is a known animal carcinogen, and human hepatotoxin. MDA produces genotoxic effects by forming DNA adducts in the liver and inducing DNA damage to hepatocytes (PMID: 32038824 ). The Occupational Safety and Health Administration has set a permissible exposure limit at 0.01 ppm over an eight-hour time-weighted average, and a short-term exposure limit at 0.10 ppm.
Structure
Data?1677000537
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point92.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mL at 25 °CNot Available
LogP1.59Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.84731661259
DarkChem[M-H]-146.2631661259
DeepCCS[M+H]+148.92330932474
DeepCCS[M-H]-146.54430932474
DeepCCS[M-2H]-180.43830932474
DeepCCS[M+Na]+155.16430932474
AllCCS[M+H]+146.132859911
AllCCS[M+H-H2O]+141.832859911
AllCCS[M+NH4]+150.132859911
AllCCS[M+Na]+151.332859911
AllCCS[M-H]-149.032859911
AllCCS[M+Na-2H]-149.132859911
AllCCS[M+HCOO]-149.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,4'-MethylenedianilineNC1=CC=C(CC2=CC=C(N)C=C2)C=C13345.4Standard polar33892256
4,4'-MethylenedianilineNC1=CC=C(CC2=CC=C(N)C=C2)C=C12076.3Standard non polar33892256
4,4'-MethylenedianilineNC1=CC=C(CC2=CC=C(N)C=C2)C=C12132.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4,4'-Methylenedianiline,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C=C2)C=C12386.6Semi standard non polar33892256
4,4'-Methylenedianiline,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C=C2)C=C12226.9Standard non polar33892256
4,4'-Methylenedianiline,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C=C2)C=C12490.7Semi standard non polar33892256
4,4'-Methylenedianiline,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C=C2)C=C12262.0Standard non polar33892256
4,4'-Methylenedianiline,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C=C2)C=C1)[Si](C)(C)C2322.0Semi standard non polar33892256
4,4'-Methylenedianiline,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C=C2)C=C1)[Si](C)(C)C2256.0Standard non polar33892256
4,4'-Methylenedianiline,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C12470.4Semi standard non polar33892256
4,4'-Methylenedianiline,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C12254.6Standard non polar33892256
4,4'-Methylenedianiline,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C2414.2Semi standard non polar33892256
4,4'-Methylenedianiline,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C2342.2Standard non polar33892256
4,4'-Methylenedianiline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C=C2)C=C12630.6Semi standard non polar33892256
4,4'-Methylenedianiline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C=C2)C=C12448.2Standard non polar33892256
4,4'-Methylenedianiline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C12994.5Semi standard non polar33892256
4,4'-Methylenedianiline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C12715.4Standard non polar33892256
4,4'-Methylenedianiline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C2795.4Semi standard non polar33892256
4,4'-Methylenedianiline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C2678.3Standard non polar33892256
4,4'-Methylenedianiline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C13151.5Semi standard non polar33892256
4,4'-Methylenedianiline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C12848.9Standard non polar33892256
4,4'-Methylenedianiline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1)[Si](C)(C)C(C)(C)C3272.8Semi standard non polar33892256
4,4'-Methylenedianiline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1)[Si](C)(C)C(C)(C)C3044.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4,4'-Methylenedianiline GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-1900000000-a1316bc903c186c143182017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4'-Methylenedianiline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-1900000000-3ade5e930b45bb46e7462014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 10V, Positive-QTOFsplash10-000t-0900000000-4644a7dbb46f9d7b2ba12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 20V, Positive-QTOFsplash10-000t-0900000000-a4548ac0cc34b55b07372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 40V, Positive-QTOFsplash10-0pe9-3900000000-4cb485ecb653179900c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 10V, Negative-QTOFsplash10-0002-0900000000-31a3645696c4f9d211ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 20V, Negative-QTOFsplash10-0002-0900000000-0e89f98c9bcf3071812e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 40V, Negative-QTOFsplash10-000w-4900000000-9cfc5d89ecd51b783c252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 10V, Positive-QTOFsplash10-0002-0900000000-d89ea9976ffd35a15c712021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 20V, Positive-QTOFsplash10-0002-2900000000-5ccfe3083b2af59df3532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 40V, Positive-QTOFsplash10-004l-7900000000-07b5c14a9b509e0f39222021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 10V, Negative-QTOFsplash10-0002-0900000000-d2d648aa4423d0c7a4552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 20V, Negative-QTOFsplash10-0002-0900000000-d2d648aa4423d0c7a4552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4'-Methylenedianiline 40V, Negative-QTOFsplash10-001i-1900000000-b08e84c052ca33f2d5b92021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1195131
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 ]
  4. Giouleme O, Karabatsou S, Hytiroglou P, Xanthis A, Tsiaousi E, Katsaros M, Koliouskas D: 4,4'-Methylenedianiline-induced hepatitis in an industrial worker: case report and review of the literature. Hum Exp Toxicol. 2011 Jul;30(7):762-7. doi: 10.1177/0960327110376549. Epub 2010 Jul 9. [PubMed:20621954 ]
  5. Oh JH, Yoon HJ, Lim JS, Park HJ, Cho JW, Kwon MS, Yoon S: Analysis of Gene Expression in 4,4'-Methylenedianiline-induced Acute Hepatotoxicity. Toxicol Res. 2009 Jun;25(2):85-92. doi: 10.5487/TR.2009.25.2.085. Epub 2009 Jun 1. [PubMed:32038824 ]