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126632

Sigma-Aldrich

1,2-Dinitrobenzene

97%

Synonym(s):

o-Dinitrobenzene

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About This Item

Linear Formula:
C6H4(NO2)2
CAS Number:
528-29-0
Molecular Weight:
168.11
Beilstein/REAXYS Number:
642224
EC Number:
208-431-8
MDL number:
MFCD00007093
UNSPSC Code:
12352100
PubChem Substance ID:
24847736
NACRES:
NA.22

assay

97%

form

solid

bp

319 °C/773 mmHg (lit.)

mp

114-117 °C (lit.)

SMILES string

[O-][N+](=O)c1ccccc1[N+]([O-])=O

InChI

1S/C6H4N2O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H

InChI key

IZUKQUVSCNEFMJ-UHFFFAOYSA-N

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General description

1,2-Dinitrobenzene (o-Dinitrobenzene) is one of the nitroaromatic compounds present in urine which has been studied using gas chromatography-mass spectrometry-selected ion monitoring methods†. The electrochemistry of 1,2-dinitrobenzene (o-Dinitrobenzene) is strongly affected by 1,3-diphenylurea.

Application

  • A highly divergent Pictet-Spengler approach for pyrrolo quinoxalines from aryl amine using 1,2-dinitrobenzene as an oxidant: Discusses the utility of 1,2-dinitrobenzene as an oxidant in organic synthesis, relevant for developing novel pharmaceuticals (Pardeshi et al., 2019).

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

302.0 °F - closed cup

flash_point_c

150 °C - closed cup

Certificates of Analysis (COA)

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Cindy Chan-Leonor et al.
The Journal of organic chemistry, 70(26), 10817-10822 (2005-12-17)
[reaction: see text] The electrochemistry of 1,2-dinitrobenzene (1,2-DNB), 1,3-dinitrobenzene (1,3-DNB), and 1,4-dinitrobenzene (1,4-DNB) is strongly affected by the presence of 1,3-diphenylurea. In DMF, the second reduction potential of all three DNBs shifts substantially positive in the presence of the urea
K Asaoka et al.
Journal of biochemistry, 94(5), 1685-1688 (1983-11-01)
Conditions have been examined for the use of o-dinitrobenzene as a substrate for colorimetric assay of glutathione S-transferases. Activities can be determined by measuring nitrite released enzymatically from the substrate using a diazo-coupling method with N-(1-naphthyl)ethylenediamine dihydrochloride and sulfanilamide. The
A L Wu et al.
The Journal of biological chemistry, 271(6), 2914-2920 (1996-02-09)
Glutathione-dependent detoxification reactions are catalyzed by the enzyme glutathione S-transferase and are important in drug resistance in organisms ranging from bacteria to humans. The yeast Issatchenkia orientalis expresses a glutathione S-transferase (GST) protein that is induced when the GST substrate
G V Gonzalez-Stawinski et al.
Clinical immunology (Orlando, Fla.), 98(2), 175-179 (2001-02-13)
Blocking the elicited humoral immune response has proven useful in treating individuals with autoimmune disorders or those who are at risk of developing antibodies which might be pathologic, e.g., transplant patients. Unfortunately, humoral immunity has evaded efforts at ablation and
Junro Shinoda et al.
Biochemical and biophysical research communications, 364(2), 258-263 (2007-10-24)
Metazoan arrestin proteins bind to seven-transmembrane proteins, mediate their internalization and play central roles in the subsequent signal transduction pathway. In Saccharomyces cerevisiae, there are several arrestin-related proteins. One of those proteins, Rod1, has been identified to have the ability
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