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Details

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

SHOW SMILES / InChI
Structure of O-PHENYLENEDIAMINE

SMILES

NC1=CC=CC=C1N

InChI

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

HIDE SMILES / InChI
Molecular Formula C6H8N2
Molecular Weight 108.1411
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
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

Zincke, T.|Sintenis, F.
2
Sources: DOI: 10.1002/cber.18730060146

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
511
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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.
2004-12-17
Immunochemical detection of 3-deoxyglucosone in serum.
2004-12-17
Traceless solid-phase synthesis of nitrogen-containing heterocycles and their biological evaluations as inhibitors of neuronal sodium channels.
2004-11-09
Photoinduced DNA cleavage and cellular damage in human dermal fibroblasts by 2,3-diaminophenazine.
2004-10-21
Simultaneous separation and on-line concentration of amitrole and benzimidazole pesticides by capillary electrophoresis with a volatile migration buffer applicable to mass spectrometric detection.
2004-10-08
[The effect of tetrazole and its amino derivatives on the kinetics of peroxidase oxidation of chromogenic substrates].
2004-09-04
Microchip capillary electrophoresis with a boron-doped diamond electrochemical detector for analysis of aromatic amines.
2004-09
The induction of eosinophil peroxidase release: improved methods of measurement and stimulation.
2004-08
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.
2004-08
Carbohydrate carbonyl mobility--the key process in the formation of alpha-dicarbonyl intermediates.
2004-06-22
Comparisons of platinum, gold, palladium and glassy carbon as electrode materials in the design of biosensors for glutamate.
2004-06-15
Biosensor for the determination of sorbitol based on molecularly imprinted electrosynthesized polymers.
2004-06-15
Homology building as a means to define antigenic epitopes on dihydrofolate reductase (DHFR) from Plasmodium falciparum.
2004-06-12
Chemical reversibility and stable low-potential NADH detection with nonconventional conducting polymer nanotubule modified glassy carbon electrodes.
2004-06-01
Comparative study of electron mediators used in the electrochemical oxidation of NADH.
2004-05-15
A novel packed-bed bioreactor operating under isothermal and non-isothermal conditions.
2004-05-05
Combinatorial synthesis of biheterocyclic benzimidazoles by microwave irradiation.
2004-05
Synthesis of highly substituted aniline and o-phenylenediamine derivatives containing various substitution patterns.
2004-04-30
Changes in IgE- and antigen-dependent histamine-release in peripheral blood of Schistosoma mansoni-infected Ugandan fishermen after treatment with praziquantel.
2004-04-21
Histogranin-like antinociceptive and anti-inflammatory derivatives of o-phenylenediamine and benzimidazole.
2004-04
Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe.
2004-03-17
A bowl-shaped fullerene encapsulates a water into the cage.
2004-03-10
Role of contact allergens in pompholyx.
2004-03
An enzyme-linked immunosorbent assay (ELISA) for detection of Marek's disease virus-specific antibodies and its application in an experimental vaccine trial.
2004-03
Role of phosphate and carboxylate ions in maillard browning.
2004-02-25
Calix[4]pyrrole Schiff base macrocycles. Novel binucleating ligands for mu-oxo iron complexes.
2004-02-23
Zn2+-chelating motif-tethered short-chain fatty acids as a novel class of histone deacetylase inhibitors.
2004-01-15
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
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.
2003-11-15
Synthesis of some new thiazole derivatives of pharmaceutical interest.
2003-11
Serologic evidence of dengue infection before onset of epidemic, Bangladesh.
2003-11
Unexpected reaction pathways in the reaction of alkoxyalkynylchromium(0) carbenes with aromatic dinucleophiles.
2003-10-17
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.
2003-10-13
[Inhibition of peroxidase oxidation of aromatic amines by substituted phenols].
2003-10-03
Paradoxical impact of antioxidants on post-Amadori glycoxidation: Counterintuitive increase in the yields of pentosidine and Nepsilon-carboxymethyllysine using a novel multifunctional pyridoxamine derivative.
2003-10-03
Soluble form of carbonic anhydrase IX (CA IX) in the serum and urine of renal carcinoma patients.
2003-09-15
Waste-free and facile solid-state protection of diamines, anthranilic acid, diols, and polyols with phenylboronic acid.
2003-09-05
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.
2003-05-22
Reaction of alpha-oxoketene-N,S-arylaminoacetals with Vilsmeier reagents: an efficient route to highly functionalized quinolines and their benzo/hetero-fused analogues.
2003-05-16
Human milk secretory antibodies against attaching and effacing Escherichia coli antigens.
2003-05
A novel electro-optical sensor format with generic applicability for exploitation with NAD(P) dependent enzymes.
2003-05
Differences in wound-induced changes in cell-wall peroxidase activities and isoform patterns between seedlings of Prosopis tamarugo and Prosopis chilensis.
2003-05
[Prevalence of paracoccidioidomycosis infection determined by sorologic test in donors' blood in the Northwest of Paraná, Brazil].
2003-04-26
Accumulation of methylglyoxal in the gingival crevicular fluid of chronic periodontitis patients.
2003-04
Electroanalytical and spectroscopic characterization of poly(o-phenylenediamine) grown on highly oriented pyrolytic graphite.
2003-03
Catalytic flow-injection determination of reactive iron in non-acidified water samples.
2003-03
Activation of peroxidase-catalyzed oxidation of aromatic amines with 2-aminothiazole and melamine.
2003-01
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
[The study on reaction kinetics based on a new system of the horseradish peroxidase catalyting the oxidation of o-phenylenediamine by H2O2].
2002-06
Patents

Patents

06476041
3
JP1043544A
2
JP2000083697A
2
JP2000212153A
4
JP2001014640A
2
JP2003136837A
2
JP2003530385A
2
JP2006028098A
2
JP2006299196A
2
JP2006512436A
4
JP2007093764A
2
JP2009045821A
2
JP2009263324A
5
JP2009501243A
3
JP2011514266A
2
JP2011529983A
2
JP3856833B2
8
JP4820369B2
7
JP5364395B2
2
JPH01102071A
2
JPH01152146A
2
JPH01187099A
2
JPH01198638A
2
JPH01215860A
2
JPH01230543A
2
JPH01234405A
3
JPH01252673A
2
JPH01278549A
3
JPH02120737A
2
JPH02147676A
2
JPH02178088A
2
JPH0225750A
2
JPH0260955A
2
JPH03111425A
2
JPH03112946A
5
JPH03127762A
5
JPH03212427A
2
JPH03285953A
2
JPH04134056A
2
JPH04229862A
2
JPH04275347A
2
JPH04330026A
2
JPH05202049A
2
JPH05287210A
2
JPH0585995A
2
JPH06172571A
2
JPH06207169A
2
JPH06345902A
2
JPH0649475A
2
JPH07101969A
2
JPH07138274A
2
JPH07215920A
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:05:45 GMT 2025
Edited
by admin
on Mon Mar 31 19:05:45 GMT 2025
Record UNII
8B713N8Q0F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
O-PHENYLENEDIAMINE
HSDB   MI  
Common Name English
ORTHAMINE
Preferred Name English
O-PHENYLENEDIAMINE [MI]
Common Name English
O-AMINOANILINE
Common Name English
IK 3
Code English
C.I. 76010
Common Name English
O-DIAMINOBENZENE
Common Name English
O-PHENYLENEDIAMINE [HSDB]
Common Name English
SQ 15500
Code English
1,2-PHENYLENEDIAMINE
Systematic Name English
1,2-BENZENEDIAMINE
Systematic Name English
TIABENDAZOLE IMPURITY A [EP IMPURITY]
Common Name English
O-AMINOPHENYLAMINE
Common Name English
CI 76010
Common Name English
C.I. OXIDATION BASE 16
Common Name English
1,2-DIAMINOBENZENE
Systematic Name English
O-BENZENEDIAMINE
Common Name English
EK 1700
Code English
NSC-5354
Code English
2-AMINOANILINE
Systematic Name English
Code System Code Type Description
PUBCHEM
7243
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
FDA UNII
8B713N8Q0F
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID3025881
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
SMS_ID
300000053582
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
NSC
5354
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
CAS
95-54-5
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
MERCK INDEX
m8666
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY Merck Index
MESH
C034193
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-430-6
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
CHEBI
34043
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
WIKIPEDIA
O-PHENYLENEDIAMINE
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
HSDB
2893
Created by admin on Mon Mar 31 19:05:45 GMT 2025 , Edited by admin on Mon Mar 31 19:05:45 GMT 2025
PRIMARY
Related Record Type Details
Structure of 1,2-PHENYLENEDIAMINE DIHYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of THIABENDAZOLE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of O-PHENYLENEDIAMINE
ACTIVE MOIETY
NIH
NCATS
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