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Details

Stereochemistry ACHIRAL
Molecular Formula C13H14N2.2ClH
Molecular Weight 271.186
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4,4'-METHYLENEDIANILINE DIHYDROCHLORIDE

SMILES

Cl.Cl.NC1=CC=C(CC2=CC=C(N)C=C2)C=C1

InChI

InChIKey=MXNNTNFLRICRPT-UHFFFAOYSA-N
InChI=1S/C13H14N2.2ClH/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11;;/h1-8H,9,14-15H2;2*1H

HIDE SMILES / InChI

Molecular Formula C13H14N2
Molecular Weight 198.2637
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Gene Expression Patterns Associated With Histopathology in Toxic Liver Fibrosis.
2016-01
4,4'-Methylenedianiline Alters Serotonergic Transport in a Novel, Sex-Specific Model of Pulmonary Arterial Hypertension in Rats.
2015-09
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.
2014
Expression of hepatocytic- and biliary-specific transcription factors in regenerating bile ducts during hepatocyte-to-biliary epithelial cell transdifferentiation.
2010-12-02
Determination of aromatic amines in aqueous extracts of polyurethane foam using hydrophilic interaction liquid chromatography and mass spectrometry.
2010-09-23
Primary aromatic amines (PAAs) in black nylon and other food-contact materials, 2004-2009.
2010-09
Ortho-rhom-bic modification of bis-[4-(3-pyridyl-methyl-idene-amino)-phen-yl]methane.
2010-08-18
A structural and spectroscopic investigation of the hydrochlorination of 4,4'-methylenedianiline.
2010-04-21
Curing and dynamic mechanical thermal properties of epoxy/clay nanocomposites.
2010-04
Validation of a liquid chromatography-mass spectrometry method for determining the migration of primary aromatic amines from cooking utensils and its application to actual samples.
2010-01
[Migration of monomers and primary aromatic amines from nylon products].
2010
The role of bridging ligands in determining DNA-binding ability and cross-linking patterns of dinuclear platinum(II) antitumour complexes.
2009-12-28
New isocyanate-specific albumin adducts of 4,4'-methylenediphenyl diisocyanate (MDI) in rats.
2009-12
Determination of aromatic amines in food products and composite food packaging bags by capillary electrophoresis coupled with transient isotachophoretic stacking.
2009-10-23
Identification of urinary biomarkers useful for distinguishing a difference in mechanism of toxicity in rat model of cholestasis.
2009-09
N,N'-(Methyl-enedi-p-phenyl-ene)dibenzamide.
2009-08-12
[Analysis of primary aromatic amines in paper products].
2009-08
Three cases of allergic contact dermatitis to 4,4'-diaminodiphenylmethane.
2009-06
Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation.
2009-03
Characterization of biliary conjugates of 4,4'-methylenedianiline in male versus female rats.
2008-10-15
Study of the infrared spectral features of an epoxy curing mechanism.
2008-10
Reactivity of in vitro activated human T lymphocytes to p-phenylenediamine and related substances.
2008-10
4,4'-Methyl-enedianilinium bis-(3-carb-oxy-4-hydroxy-benzene-sulfonate) monohydrate.
2008-09-17
Bis(1,2,3,4-tetra-hydro-quinolin-6-yl)methane.
2008-08-13
Contact sensitization to 4,4'-diaminodiphenylmethane and to isocyanates among general dermatology patients.
2008-08
Time- and dose-based gene expression profiles produced by a bile-duct-damaging chemical, 4,4'-methylene dianiline, in mouse liver in an acute phase.
2008-07
Organic-solvent extraction of model biomaterials for use in the in vitro chromosome aberration test.
2008-07
Percutaneous absorption of aromatic amines - a contribution for human health risk assessment.
2008-06
Liquid chromatography-electrospray tandem mass spectrometry investigations of fragmentation pathways of biliary 4,4'-methylenedianiline conjugates produced in rats.
2008-05
Validation of putative genomic biomarkers of nephrotoxicity in rats.
2008-04-18
Bis(4,4'-methyl-enedianilinium) naphthalene-1,5-disulfonate dihydrate.
2008-03-20
Bile duct destruction by 4,4'-diaminodiphenylmethane does not block the small hepatocyte-like progenitor cell response in retrorsine-exposed rats.
2007-11
How to optimize patch testing with diphenylmethane diisocyanate.
2007-09
Determination of isocyanate biomarkers in construction site workers.
2007-08-19
4,4'-Methylenedianiline and its dihydrochloride salt.
2004
Study on cross-reactivity to the para group.
1990
[The value of positive epicutaneous test reactions to 4,4'-diaminodiphenylmethane].
1989-01-01
Retinopathy from inhaling 4,4'-methylenedianiline aerosols.
1987-11
Sensitization to methylenedianiline and para-structures.
1987-05
Inhibition of neoplastic development in rat liver, kidney, oesophagus and forestomach by 4,4'-diaminodiphenylmethane administration.
1987-05
[Change in the allergen spectrum in contact eczema 1975-1984].
1987-01-01
Carcinogenesis studies of 4,4'-methylenedianiline dihydrochloride given in drinking water to F344/N rats and B6C3F1 mice.
1986
Yellow staining caused by 4,4'-methylenedianiline exposure. Occurrence among molded plastics workers.
1985-08
Methylene dianilene: a new toxic cause of visual failure with hepatitis.
1985-01
Occupational hepatitis caused by methylenedianiline.
1984-10-13
Neoplastic response of F344 rats and B6C3F1 mice to the polymer and dyestuff intermediates 4,4'-methylenebis(N,N-dimethyl)-benzenamine, 4,4'-oxydianiline, and 4,4'-methylenedianiline.
1984-06
4,4'-Diaminodiphenylmethane: promoting effect on the development of thyroid tumors in rats treated with N-bis(2-hydroxypropyl)nitrosamine.
1984-02
[Infrahepatic bile duct proliferation in the gestating rat treated with 4,4'-diaminodiphenylmethane (4,4DDPM)].
1983-12
Occupational photosensitivity to diaminodiphenylmethane.
1983-11
Effect of various factors on the induction of liver tumors in animals by quinoline.
1977-12
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
S0V6PBT14R
Record Status Validated (UNII)
Record Version
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Name Type Language
4,4'-METHYLENEDIANILINE DIHYDROCHLORIDE
Systematic Name English
ANILINE, 4,4'-METHYLENEDI-, DIHYDROCHLORIDE
Preferred Name English
BENZENAMINE,4,4'-METHYLENEBIS-, HYDROCHLORIDE (1:2)
Common Name English
METHYLENEDIANILINE DIHYDROCHLORIDE [HSDB]
Common Name English
Code System Code Type Description
HSDB
4347
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
EPA CompTox
DTXSID9020871
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
PUBCHEM
26108
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
13552-44-8
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
S0V6PBT14R
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
ECHA (EC/EINECS)
236-934-2
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
Related Record Type Details
PARENT -> SALT/SOLVATE