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Details

Stereochemistry ACHIRAL
Molecular Formula C6H8N2.2ClH
Molecular Weight 181.063
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,2-PHENYLENEDIAMINE DIHYDROCHLORIDE

SMILES

Cl.Cl.NC1=CC=CC=C1N

InChI

InChIKey=RIIWUGSYXOBDMC-UHFFFAOYSA-N
InChI=1S/C6H8N2.2ClH/c7-5-3-1-2-4-6(5)8;;/h1-4H,7-8H2;2*1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H8N2
Molecular Weight 108.1411
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

o-Phenylenediamine is a chemical intermediate used in the synthesis of fungicides, corrosion inhibitors, pigments, and pharmaceuticals. It is also used to remove elemental sulfur in mining ores, and to remove aldehyde color formers in polymeric products. o-Phenylenediamine is also a substrate of enzyme-catalyzed oxidation reactions. 2,3-Diaminophenazine was detected as a product of peroxidase-catalyzed oxidation of o-phenylenediamine dihydrochloride in ELISA procedures. o-Phenylenediamine is a methaemoglobin-producer. Oral administration of o-phenylenediamine led to significantly increased incidences of liver tumors in the rat and mouse.

Originator

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
Reduction of dioxygen by a dimanganese unit bonded inside a cavity provided by a pyrrole-based dinucleating ligand.
2001 Apr 1
o-Phenylenediamine-induced DNA damage and mutagenicity in tobacco seedlings is light-dependent.
2001 Aug 22
News on the Maillard reaction of oligomeric carbohydrates: a survey.
2001 Jun
Detection of alpha-dicarbonyl compounds in Maillard reaction systems and in vivo.
2001 Nov
Purification and characterization of a cationic isoperoxidase from scented-geranium.
2001 Nov
[Inhibition of peroxidase oxidation of 3,3',5,5'-tetramethylbenzidine and o-phenylenediamine by 1-amino-2-naphthol-4-sulfonic acid and its polysulfide].
2001 Nov-Dec
Comparison of electrochemical detection of acetylcholine-induced nitric oxide release (NO) and contractile force measurement of rabbit isolated carotid artery endothelium.
2002 Apr 15
Automatic flow system with voltammetric detection for diacetyl monitoring during brewing process.
2002 Jun 19
Extension of the color suite available for chemical enhancement of fingerprints in blood.
2002 Mar
Characterization of soluble oligomers produced by electrochemical oxidation of o-phenylenediamine by electrospray ionization sequential mass spectrometry.
2003
Effect of o-phenylenediamine on Cu adsorption and desorption in red soil and its uptake by paddy rice (Oryza sativa).
2003 Apr
Activation of peroxidase-catalyzed oxidation of aromatic amines with 2-aminothiazole and melamine.
2003 Jan
Relative quantification of N(epsilon)-(Carboxymethyl)lysine, imidazolone A, and the Amadori product in glycated lysozyme by MALDI-TOF mass spectrometry.
2003 Jan 1
[Noncompetitive activation of peroxidase oxidation of o-phenylenediamine by melamine].
2003 Jan-Feb
Amperometric biosensors based on recombinant laccases for phenols determination.
2003 Mar
L523S, an RNA-binding protein as a potential therapeutic target for lung cancer.
2003 Mar 24
DNA damage induced by indirect and direct acting mutagens in catalase-deficient transgenic tobacco. Cellular and acellular Comet assays.
2003 Mar 3
Site-specific quantitative evaluation of the protein glycation product N6-(2,3-dihydroxy-5,6-dioxohexyl)-L-lysinate by LC-(ESI)MS peptide mapping: evidence for its key role in AGE formation.
2003 May-Jun
Serologic evidence of dengue infection before onset of epidemic, Bangladesh.
2003 Nov
Unexpected reaction pathways in the reaction of alkoxyalkynylchromium(0) carbenes with aromatic dinucleophiles.
2003 Oct 17
Paradoxical impact of antioxidants on post-Amadori glycoxidation: Counterintuitive increase in the yields of pentosidine and Nepsilon-carboxymethyllysine using a novel multifunctional pyridoxamine derivative.
2003 Oct 3
Increased AP-1 and NF-kappaB activation and recruitment with the combination of the proinflammatory cytokines IL-1beta, tumor necrosis factor alpha and IL-17 in rheumatoid synoviocytes.
2004
Changes in IgE- and antigen-dependent histamine-release in peripheral blood of Schistosoma mansoni-infected Ugandan fishermen after treatment with praziquantel.
2004 Apr 21
The induction of eosinophil peroxidase release: improved methods of measurement and stimulation.
2004 Aug
Chemical polymerization of m-phenylenediamine, in the presence of glucose oxidase, produces an enzyme-retaining electrooxidisable polymer used to produce a biosensor for amperometric detection of glucose from brain dialysate.
2004 Aug
Molecular and electronic structure of four- and five-coordinate cobalt complexes containing two o-phenylenediamine- or two o-aminophenol-type ligands at various oxidation levels: an experimental, density functional, and correlated ab initio study.
2004 Dec 17
Immunochemical detection of 3-deoxyglucosone in serum.
2004 Dec 17
Calix[4]pyrrole Schiff base macrocycles. Novel binucleating ligands for mu-oxo iron complexes.
2004 Feb 23
Role of phosphate and carboxylate ions in maillard browning.
2004 Feb 25
Zn2+-chelating motif-tethered short-chain fatty acids as a novel class of histone deacetylase inhibitors.
2004 Jan 15
Chemical reversibility and stable low-potential NADH detection with nonconventional conducting polymer nanotubule modified glassy carbon electrodes.
2004 Jun 1
Biosensor for the determination of sorbitol based on molecularly imprinted electrosynthesized polymers.
2004 Jun 15
Combinatorial synthesis of biheterocyclic benzimidazoles by microwave irradiation.
2004 May
Comparative study of electron mediators used in the electrochemical oxidation of NADH.
2004 May 15
A novel packed-bed bioreactor operating under isothermal and non-isothermal conditions.
2004 May 5
[The effect of tetrazole and its amino derivatives on the kinetics of peroxidase oxidation of chromogenic substrates].
2004 May-Jun
Traceless solid-phase synthesis of nitrogen-containing heterocycles and their biological evaluations as inhibitors of neuronal sodium channels.
2004 Nov-Dec
Simultaneous separation and on-line concentration of amitrole and benzimidazole pesticides by capillary electrophoresis with a volatile migration buffer applicable to mass spectrometric detection.
2004 Oct 8
Microchip capillary electrophoresis with a boron-doped diamond electrochemical detector for analysis of aromatic amines.
2004 Sep
Photoinduced DNA cleavage and cellular damage in human dermal fibroblasts by 2,3-diaminophenazine.
2005 Jan-Feb
Patents
Substance Class Chemical
Created
by admin
on Tue Oct 22 13:36:28 UTC 2019
Edited
by admin
on Tue Oct 22 13:36:28 UTC 2019
Record UNII
Z16252Z50J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,2-PHENYLENEDIAMINE DIHYDROCHLORIDE
Systematic Name English
1,2-BENZENEDIAMINE, DIHYDROCHLORIDE
Common Name English
O-PHENYLENEDIAMINE, DIHYDROCHLORIDE
Common Name English
1,2-BENZENEDIAMINE, HYDROCHLORIDE (1:2)
Systematic Name English
1,2-DIAMINOBENZENE DIHYDROCHLORIDE
Systematic Name English
1,2-BENZENEDIAMINE DIHYDROCHLORIDE [HSDB]
Common Name English
Code System Code Type Description
CAS
615-28-1
Created by admin on Tue Oct 22 13:36:28 UTC 2019 , Edited by admin on Tue Oct 22 13:36:28 UTC 2019
PRIMARY
PUBCHEM
11990
Created by admin on Tue Oct 22 13:36:28 UTC 2019 , Edited by admin on Tue Oct 22 13:36:28 UTC 2019
PRIMARY
ECHA (EC/EINECS)
210-418-7
Created by admin on Tue Oct 22 13:36:28 UTC 2019 , Edited by admin on Tue Oct 22 13:36:28 UTC 2019
PRIMARY
EPA CompTox
615-28-1
Created by admin on Tue Oct 22 13:36:28 UTC 2019 , Edited by admin on Tue Oct 22 13:36:28 UTC 2019
PRIMARY
MESH
C034193
Created by admin on Tue Oct 22 13:36:28 UTC 2019 , Edited by admin on Tue Oct 22 13:36:28 UTC 2019
PRIMARY
HSDB
615-28-1
Created by admin on Tue Oct 22 13:36:28 UTC 2019 , Edited by admin on Tue Oct 22 13:36:28 UTC 2019
PRIMARY
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