U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=C(N)C=CC=C1

InChI

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

HIDE SMILES / InChI
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

Sources: DOI: 10.1002/cber.18730060146

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Fluorimetric determination of total ascorbic acid by a stopped-flow mixing technique.
2001 Aug
News on the Maillard reaction of oligomeric carbohydrates: a survey.
2001 Jun
Chitooligosaccharide-induced activation of o-phenylenediamine oxidation by wheat seedlings in the presence of oxalic acid.
2001 Mar
Capacitive detection of glucose using molecularly imprinted polymers.
2001 May
Measurement of pyruvate in blood by high-performance liquid chromatography with fluorescence detection.
2001 Sep
Sensitive detection and quantitation of mouse eosinophils in tissues using an enzymatic eosinophil peroxidase assay: its use to rapidly measure pulmonary eosinophilia during experimental respiratory syncytial virus infection of mice.
2002 Apr 1
Quantitative reaction cascades of ninhydrin in the solid state.
2002 Feb 2
[The study on reaction kinetics based on a new system of the horseradish peroxidase catalyting the oxidation of o-phenylenediamine by H2O2].
2002 Jun
2-Aminoanilinium phosphite.
2002 Oct
Modified carbon paste electrodes for flow injection amperometric determination of isocitrate dehydrogenase activity in serum.
2002 Sep 15
Characterization in vitro and in vivo of the oxygen dependence of an enzyme/polymer biosensor for monitoring brain glucose.
2002 Sep 30
[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
Amperometric biosensors based on recombinant laccases for phenols determination.
2003 Mar
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
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
Waste-free and facile solid-state protection of diamines, anthranilic acid, diols, and polyols with phenylboronic acid.
2003 Sep 5
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
Zn2+-chelating motif-tethered short-chain fatty acids as a novel class of histone deacetylase inhibitors.
2004 Jan 15
Biosensor for the determination of sorbitol based on molecularly imprinted electrosynthesized polymers.
2004 Jun 15
A bowl-shaped fullerene encapsulates a water into the cage.
2004 Mar 10
Combinatorial synthesis of biheterocyclic benzimidazoles by microwave irradiation.
2004 May
[The effect of tetrazole and its amino derivatives on the kinetics of peroxidase oxidation of chromogenic substrates].
2004 May-Jun
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
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
O-PHENYLENEDIAMINE
HSDB   MI  
Common 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
ORTHAMINE
Brand 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 Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY
FDA UNII
8B713N8Q0F
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID3025881
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY
NSC
5354
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY
CAS
95-54-5
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY
MERCK INDEX
m8666
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY Merck Index
MESH
C034193
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-430-6
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY
CHEBI
34043
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY
WIKIPEDIA
O-PHENYLENEDIAMINE
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY
HSDB
2893
Created by admin on Fri Dec 15 18:09:34 GMT 2023 , Edited by admin on Fri Dec 15 18:09:34 GMT 2023
PRIMARY