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Details

Stereochemistry ACHIRAL
Molecular Formula C13H12Cl2N2
Molecular Weight 267.154
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4,4'-METHYLENEBIS(2-CHLOROANILINE)

SMILES

NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl

InChI

InChIKey=IBOFVQJTBBUKMU-UHFFFAOYSA-N
InChI=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

HIDE SMILES / InChI

Molecular Formula C13H12Cl2N2
Molecular Weight 267.154
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Oxidative Stress Mechanisms Do Not Discriminate between Genotoxic and Nongenotoxic Liver Carcinogens.
2015-08-17
Cancer incidence and exposure to 4,4'-methylene-bis-ortho-chloroaniline (MbOCA).
2009-09
A survey of occupational exposure to 4,4'-methylene-bis (2-chloroaniline) (MbOCA) in the UK.
2009-07
Simultaneous analysis of urinary 4,4'-methylenebis(2-chloroaniline) and N-acetyl 4,4'-methylenebis(2-chloroaniline) using solid-phase extraction and liquid chromatography/tandem mass spectrometry.
2007
Identification and characterization of functional rat arylamine N-acetyltransferase 3: comparisons with rat arylamine N-acetyltransferases 1 and 2.
2006-10
Differential induction of micronuclei in peripheral lymphocytes and exfoliated urothelial cells of workers exposed to 4,4'-methylenebis-(2-chloroaniline) (MOCA) and bitumen fumes.
2005-12-13
Bladder cancer screening and monitoring of 4,4'-methylenebis(2-chloroaniline) exposure among workers in Taiwan.
2005-08
Occupational bladder cancer in a 4,4 -methylenebis(2-chloroaniline) (MBOCA)-exposed worker.
2005-06
Embryonic turkey liver: activities of biotransformation enzymes and activation of DNA-reactive carcinogens.
2004-10
Assessment of the performance of the Ames II assay: a collaborative study with 19 coded compounds.
2004-03-14
4,4'-Methylenebis(2-chloroaniline).
2004
Lack of DNA binding in the rat nasal mucosa and other tissues of the nasal toxicants roflumilast, a phosphodiesterase 4 inhibitor, and a metabolite, 4-amino-3,5-dichloropyridine, in contrast to the nasal carcinogen 2,6-dimethylaniline.
2002-02
4,4'-Methylenebis(2-chloroaniline).
2002
Carcinogen substrate specificity of human COX-1 and COX-2.
2001-01
Immunochemical, 32P-postlabeling, and GC/MS detection of 4-aminobiphenyl-DNA adducts in human peripheral lung in relation to metabolic activation pathways involving pulmonary N-oxidation, conjugation, and peroxidation.
1997-08-01
Contributions of human liver cytochrome P450 enzymes to the N-oxidation of 4,4'-methylene-bis(2-chloroaniline).
1992-02
4,4'-Methylenebis(2-chloroaniline) (MOCA): the effect of multiple oral administration, route, and phenobarbital induction on macromolecular adduct formation in the rat.
1991-01
Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4'-methylene-bis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases.
1989-01-01
Bladder tumors in two young males occupationally exposed to MBOCA.
1988
Determination of the tumorigenic potential of methylene-bis-orthochloroaniline.
1979-05-01
Urinary bladder tumors in dogs from 4,4'-methylene-bis (2-chloroaniline) (MOCA).
1978-09-01
Experimental neoplasia in rats from oral administration of 3,3'-dichlorobenzidine, 4,4'-methylene-bis-bis(2-chloroaniline), and 4,4'-methylene-bis(2-methylaniline).
1975-01
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:26:47 GMT 2025
Edited
by admin
on Mon Mar 31 19:26:47 GMT 2025
Record UNII
3L2W5VTT2A
Record Status Validated (UNII)
Record Version
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Name Type Language
4,4'-METHYLENEBIS(2-CHLOROANILINE)
MI  
Systematic Name English
NSC-52954
Preferred Name English
METHYLENEBIS(O-CHLOROANILINE)
Common Name English
4,4'-DIAMINO-3,3'-DICHLORODIPHENYLMETHANE
Common Name English
METHYLENEBIS(CHLOROANILINE) [HSDB]
Common Name English
DI-(4-AMINO-3-CHLOROPHENYL)METHANE
Systematic Name English
4,4'-METHYLENEBIS(2-CHLOROANILINE) [IARC]
Common Name English
4,4'-METHYLENEBIS(2-CHLOROBENZENAMINE)
Systematic Name English
4,4'-METHYLENEBIS(2-CHLOROANILINE) [MI]
Common Name English
BENZENAMINE, 4,4'-METHYLENEBIS(2-CHLORO-
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
202-918-9
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
PRIMARY
FDA UNII
3L2W5VTT2A
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
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MERCK INDEX
m7401
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
4,4'-Methylenebis(2-chloroaniline)
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
PRIMARY
CAS
101-14-4
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
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NCI_THESAURUS
C44319
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
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PUBCHEM
7543
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
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EPA CompTox
DTXSID5020865
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
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SMS_ID
300000053717
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
PRIMARY
HSDB
2629
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
PRIMARY
NSC
52954
Created by admin on Mon Mar 31 19:26:47 GMT 2025 , Edited by admin on Mon Mar 31 19:26:47 GMT 2025
PRIMARY