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302066

Sigma-Aldrich

1,2-Dinitrobenzene

≥99%

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:
24858229
NACRES:
NA.22

assay

≥99%

form

solid

bp

319 °C/773 mmHg (lit.)

mp

114-117 °C (lit.)

solubility

chloroform: soluble 5%, clear, yellow-green

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

The electrochemistry of 1,2-dinitrobenzene in the presence of 1,3-diphenylurea was studied. The kinetics of the aromatic nucleophilic substitution reactions of 1,2-dinitrobenzene with butylamine and piperidine were investigated as a function of the amine concentration and temperature.

Application

1,2-Dinitrobenzene was used as internal standard for analysis of the explosives, TNT, RDX, and tetryl in sea water by vapor phase chromatography with the nickel-63 electron capture detector.

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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Comparative kinetic study of solvent effects in the reactions of 1, 2-dinitrobenzene with butylamine and piperidine.
Chiacchiera SM, et al.
Journal of Physical Organic Chemistry, 2(8), 631-645 (1989)
Analysis of explosives in sea water.
Hoffsommer JC and Rosen JM.
Bulletin of Environmental Contamination and Toxicology, 7(2-3), 177-181 (1972)
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
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
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
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