4,4'-Methylenebis(2-chloroaniline) (CHEM000140)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (49)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:10 UTC
Update Date2026-03-27 00:17:38 UTC
Accession NumberCHEM000140
Identification
Common Name4,4'-Methylenebis(2-chloroaniline)
ClassSmall Molecule
Description4,4'-Methylenebis(2-chloroaniline) (MBOCA) is a synthetic chemical used primarily to make polyurethane products. It may be found in gears, gaskets, sport boots, roller skate wheels, shoe soles, rolls and belt drives in cameras, computers and copy machines, wheels and pulleys for escalators and elevators, components in home appliances, and various military applications. It is also used as a coating in chemical reactions to set glues, plastics, and adhesives. (3)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 1
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Methylenebis(chloroaniline)ChEBI
MOCAChEBI
3,3'-Dichloro-4,4'-diaminodiphenylmethaneHMDB
Methylene bis(chloroaniline)HMDB
MBOCAHMDB
Chemical FormulaC13H12Cl2N2
Average Molecular Mass267.154 g/mol
Monoisotopic Mass266.038 g/mol
CAS Registry Number101-14-4
IUPAC Name4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline
Traditional Namebis amine
SMILESNC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl
InChI IdentifierInChI=1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2
InChI KeyIBOFVQJTBBUKMU-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
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point110°C
Boiling PointNot Available
Solubility0.0139 mg/mL at 24 °C [VOORMAN,R & PENNER,D (1986A)]
Predicted Properties
PropertyValueSource
Water Solubility0.0046 g/LALOGPS
logP3.72ALOGPS
logP3.62ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.81 m³·mol⁻¹ChemAxon
Polarizability26.74 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-0890000000-d320fad1a29793ad1cd3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-ac6db8aa96928a715ff0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0390000000-5200973976fe40d343c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h93-0790000000-9bffe8b198bbfea28e82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-a39ca28199798c1d03b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-ea98e6716aef094aff27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-2590000000-6da5025dcc24706340adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-56429813ec6e144d5baaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-388bf1eeaceec6102241Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0950000000-0208d8e66ffecbcf4b9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3090000000-685f6029d831cae1342bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-6090000000-189ae8cf88e4d83e80f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9110000000-6f3606859a73a43fab2cSpectrum
MSMass Spectrum (Electron Ionization)splash10-0159-2690000000-cb107296d1f635b2a12aSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of ToxicityMBOCA's carcinogenicity is thought to be a result of its ability to bind to DNA, hemoglobin, and serum albumin. One metabolite in particular, N-hydroxy-N,N’-diacetyl MBOCA, is known to bind nucleic acids, forming DNA adducts. Other N-oxidized MBOCA metabolites, such as n-hydroxy MBOCA and mononitroso-MBOCA, have been shown to form hemoglobin adducts. (5, 3)
Metabolism4,4'-Methylenebis(2-chloroaniline) may be absorbed via oral, inhalation, or dermal exposure. It distributes throughout the body, concentrating in the liver, kidney, and adipose tissue. Metabolism involves N-acetylation, N-hydroxylation (which may be followed by n-oxidation), and ring hydroxylation. The mainy enzymes involves are phenobarbital-inducible cytochrome P-450 enzymes. MBOCA and its metabolites are excreted mainly in the urine. (3)
Toxicity ValuesLD50: >5 g/kg (Dermal, Rabbit) (6) LD50: 400 mg/kg (Oral, Guinea Pig) (6) LD50: 64 mg/kg (Intraperitoneal, Mouse) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (2)
Uses/Sources4,4'-Methylenebis(2-chloroaniline) is used primarily to make polyurethane products. It may be found in gears, gaskets, sport boots, roller skate wheels, shoe soles, rolls and belt drives in cameras, computers and copy machines, wheels and pulleys for escalators and elevators, components in home appliances, and various military applications. It is also used as a coating in chemical reactions to set glues, plastics, and adhesives. (3)
Minimum Risk LevelChronic Oral: 0.003 mg/kg/day (1)
Health Effects4,4'-Methylenebis(2-chloroaniline) is a known human carcinogen. It may also damage the liver and kidneys. (3)
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0244288
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link4,4'-Methylenebis(2-chloroaniline)
Chemspider ID7262
ChEBI ID28124
PubChem Compound IDNot Available
Kegg Compound IDC10999
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19447850
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21501672
3. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.