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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

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
[The study on reaction kinetics based on a new system of the horseradish peroxidase catalyting the oxidation of o-phenylenediamine by H2O2].
2002 Jun
Characterization of soluble oligomers produced by electrochemical oxidation of o-phenylenediamine by electrospray ionization sequential mass spectrometry.
2003
Advanced glycation end-product (AGE)-damaged IgG and IgM autoantibodies to IgG-AGE in patients with early synovitis.
2003
Accumulation of methylglyoxal in the gingival crevicular fluid of chronic periodontitis patients.
2003 Apr
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
[Prevalence of paracoccidioidomycosis infection determined by sorologic test in donors' blood in the Northwest of ParanĂ¡, Brazil].
2003 Jan-Feb
[Noncompetitive activation of peroxidase oxidation of o-phenylenediamine by melamine].
2003 Jan-Feb
[Inhibition of peroxidase oxidation of aromatic amines by substituted phenols].
2003 Jul-Aug
Electroanalytical and spectroscopic characterization of poly(o-phenylenediamine) grown on highly oriented pyrolytic graphite.
2003 Mar
Catalytic flow-injection determination of reactive iron in non-acidified water samples.
2003 Mar
Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers.
2003 Mar
Purification and characterization of a peroxidase from corn steep water.
2003 Mar 12
L523S, an RNA-binding protein as a potential therapeutic target for lung cancer.
2003 Mar 24
Human milk secretory antibodies against attaching and effacing Escherichia coli antigens.
2003 May
A novel electro-optical sensor format with generic applicability for exploitation with NAD(P) dependent enzymes.
2003 May
Differences in wound-induced changes in cell-wall peroxidase activities and isoform patterns between seedlings of Prosopis tamarugo and Prosopis chilensis.
2003 May
Reaction of alpha-oxoketene-N,S-arylaminoacetals with Vilsmeier reagents: an efficient route to highly functionalized quinolines and their benzo/hetero-fused analogues.
2003 May 16
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
A new assay format for electrochemical immunosensors: polyelectrolyte-based separation on membrane carriers combined with detection of peroxidase activity by pH-sensitive field-effect transistor.
2003 Nov 15
Alternative pathway for the formation of 4,5-dihydroxy-2,3-pentanedione, the proposed precursor of 4-hydroxy-5-methyl-3(2H)-furanone as well as autoinducer-2, and its detection as natural constituent of tomato fruit.
2003 Oct 13
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
Synthesis of highly substituted aniline and o-phenylenediamine derivatives containing various substitution patterns.
2004 Apr 30
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
Homology building as a means to define antigenic epitopes on dihydrofolate reductase (DHFR) from Plasmodium falciparum.
2004 Jun 12
Comparisons of platinum, gold, palladium and glassy carbon as electrode materials in the design of biosensors for glutamate.
2004 Jun 15
Biosensor for the determination of sorbitol based on molecularly imprinted electrosynthesized polymers.
2004 Jun 15
Carbohydrate carbonyl mobility--the key process in the formation of alpha-dicarbonyl intermediates.
2004 Jun 22
Role of contact allergens in pompholyx.
2004 Mar
An enzyme-linked immunosorbent assay (ELISA) for detection of Marek's disease virus-specific antibodies and its application in an experimental vaccine trial.
2004 Mar
Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe.
2004 Mar 17
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
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