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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
J V Barbo et al.
Journal of immunology (Baltimore, Md. : 1950), 154(4), 1551-1559 (1995-02-15)
A population of CD8+ T cells from dinitrobenzene sulfonate-primed mice produce soluble effector molecules that down-regulate the magnitude of dinitrophenol-specific contact hypersensitivity reactions. These soluble molecules express the binding specificity and serologic determinants of alpha/beta TCR. To examine the requirement
P A Cossum et al.
Drug metabolism and disposition: the biological fate of chemicals, 13(6), 664-668 (1985-11-01)
The metabolism of radiolabeled dinitrobenzene (DNB) isomers was compared in hepatocytes and hepatic subcellular fractions isolated from male Fischer-344 rats. Under aerobic conditions, reduction was the major metabolic pathway for m- and p- DNB in hepatocytes with m- and p-nitroaniline
Tomoko Andoh et al.
FEBS letters, 525(1-3), 131-134 (2002-08-07)
In Saccharomyces cerevisiae, the overexpression of ROD1 confers resistance to o-dinitrobenzene (o-DNB), a representative of target drugs of glutathione S-transferase. The roles of Rod1 in drug resistance have remained to be determined. We isolated the rog3 mutation as a suppressor
H Tamaki et al.
Journal of bacteriology, 181(9), 2958-2962 (1999-04-28)
Glutathione S-transferases (GSTs) Y-1 and Y-2 from the yeast Issatchenkia orientalis were purified by passage through a glutathione-agarose column, and the cDNA for GST Y-1 was cloned and sequenced. The deduced amino acid sequence consisted of 188 residues with a
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