4,4'-METHYLENEDIANILINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H14N2
Molecular Weight	198.2637
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=YBRVSVVVWCFQMG-UHFFFAOYSA-N

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

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

Approval Year

PubMed

Title	Date	PubMed
Gene Expression Patterns Associated With Histopathology in Toxic Liver Fibrosis.	2016-01	26396155
4,4'-Methylenedianiline Alters Serotonergic Transport in a Novel, Sex-Specific Model of Pulmonary Arterial Hypertension in Rats.	2015-09	26116029
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.	2014	25058030
Expression of hepatocytic- and biliary-specific transcription factors in regenerating bile ducts during hepatocyte-to-biliary epithelial cell transdifferentiation.	2010-12-02	21126359
Determination of aromatic amines in aqueous extracts of polyurethane foam using hydrophilic interaction liquid chromatography and mass spectrometry.	2010-09-23	20869512
Primary aromatic amines (PAAs) in black nylon and other food-contact materials, 2004-2009.	2010-09	20640962
Ortho-rhom-bic modification of bis-[4-(3-pyridyl-methyl-idene-amino)-phen-yl]methane.	2010-08-18	21588663
A structural and spectroscopic investigation of the hydrochlorination of 4,4'-methylenedianiline.	2010-04-21	20358076
Curing and dynamic mechanical thermal properties of epoxy/clay nanocomposites.	2010-04	20355516
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	19750402
[Migration of monomers and primary aromatic amines from nylon products].	2010	21071906
The role of bridging ligands in determining DNA-binding ability and cross-linking patterns of dinuclear platinum(II) antitumour complexes.	2009-12-28	20023919
New isocyanate-specific albumin adducts of 4,4'-methylenediphenyl diisocyanate (MDI) in rats.	2009-12	19928878
Determination of aromatic amines in food products and composite food packaging bags by capillary electrophoresis coupled with transient isotachophoretic stacking.	2009-10-23	19524248
Identification of urinary biomarkers useful for distinguishing a difference in mechanism of toxicity in rat model of cholestasis.	2009-09	19486331
N,N'-(Methyl-enedi-p-phenyl-ene)dibenzamide.	2009-08-12	21577550
[Analysis of primary aromatic amines in paper products].	2009-08	19745583
Three cases of allergic contact dermatitis to 4,4'-diaminodiphenylmethane.	2009-06	19489974
Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation.	2009-03	18563518
Characterization of biliary conjugates of 4,4'-methylenedianiline in male versus female rats.	2008-10-15	18692083
Study of the infrared spectral features of an epoxy curing mechanism.	2008-10	18926023
Reactivity of in vitro activated human T lymphocytes to p-phenylenediamine and related substances.	2008-10	18844695
4,4'-Methyl-enedianilinium bis-(3-carb-oxy-4-hydroxy-benzene-sulfonate) monohydrate.	2008-09-17	21201152
Bis(1,2,3,4-tetra-hydro-quinolin-6-yl)methane.	2008-08-13	21201729
Contact sensitization to 4,4'-diaminodiphenylmethane and to isocyanates among general dermatology patients.	2008-08	18759878
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	18648102
Organic-solvent extraction of model biomaterials for use in the in vitro chromosome aberration test.	2008-07	17941025
Percutaneous absorption of aromatic amines - a contribution for human health risk assessment.	2008-06	18343009
Liquid chromatography-electrospray tandem mass spectrometry investigations of fragmentation pathways of biliary 4,4'-methylenedianiline conjugates produced in rats.	2008-05	18373088
Validation of putative genomic biomarkers of nephrotoxicity in rats.	2008-04-18	18289764
Bis(4,4'-methyl-enedianilinium) naphthalene-1,5-disulfonate dihydrate.	2008-03-20	21202124
Bile duct destruction by 4,4'-diaminodiphenylmethane does not block the small hepatocyte-like progenitor cell response in retrorsine-exposed rats.	2007-11	17705295
How to optimize patch testing with diphenylmethane diisocyanate.	2007-09	17680861
Determination of isocyanate biomarkers in construction site workers.	2007-08-19	17701746
4,4'-Methylenedianiline and its dihydrochloride salt.	2004	21089905
Study on cross-reactivity to the para group.	1990	2242776
[The value of positive epicutaneous test reactions to 4,4'-diaminodiphenylmethane].	1989-01-01	2524372
Retinopathy from inhaling 4,4'-methylenedianiline aerosols.	1987-11	3692021
Sensitization to methylenedianiline and para-structures.	1987-05	3621924
Inhibition of neoplastic development in rat liver, kidney, oesophagus and forestomach by 4,4'-diaminodiphenylmethane administration.	1987-05	3581430
[Change in the allergen spectrum in contact eczema 1975-1984].	1987-01-01	2952479
Carcinogenesis studies of 4,4'-methylenedianiline dihydrochloride given in drinking water to F344/N rats and B6C3F1 mice.	1986	3712494
Yellow staining caused by 4,4'-methylenedianiline exposure. Occurrence among molded plastics workers.	1985-08	4026338
Methylene dianilene: a new toxic cause of visual failure with hepatitis.	1985-01	3988306
Occupational hepatitis caused by methylenedianiline.	1984-10-13	6482804
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	6587162
4,4'-Diaminodiphenylmethane: promoting effect on the development of thyroid tumors in rats treated with N-bis(2-hydroxypropyl)nitrosamine.	1984-02	6582329
[Infrahepatic bile duct proliferation in the gestating rat treated with 4,4'-diaminodiphenylmethane (4,4DDPM)].	1983-12	6679447
Occupational photosensitivity to diaminodiphenylmethane.	1983-11	6228378
Effect of various factors on the induction of liver tumors in animals by quinoline.	1977-12	598648

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:30:07 GMT 2025` Edited by `admin` on `Mon Mar 31 19:30:07 GMT 2025`
Record UNII	GG5LL7OBZC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-4709

Preferred Name

English

4,4'-METHYLENEDIANILINE

Systematic Name

English

4,4-DIPHENYLMETHANE DIAMINE

Common Name

English

4,4'-DIPHENYLMETHANE DIAMINE

Common Name

English

4,4-METHYLENEDIANILINE

Common Name

English

P,P'-DIAMINODIPHENYLMETHANE [MI]

Common Name

English

4,4'-METHYLENEDIANILINE [HSDB]

Common Name

English

METHYLENEDIANILINE-

Systematic Name

English

METHYLENEDIANILINE

Systematic Name

English

BIS(4-AMINOPHENYL)METHANE

Systematic Name

English

4,4'-METHYLENEDIANILINE [IARC]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45178