M-DINITROBENZENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H4N2O4
Molecular Weight	168.107
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)C1=CC(=CC=C1)[N+]([O-])=O

InChI

InChIKey=WDCYWAQPCXBPJA-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.atsdr.cdc.gov/toxprofiles/tp.asp?id=842&tid=164 | https://www.ncbi.nlm.nih.gov/pubmed/13016137

m-Dinitrobenzene (1,3-DBN) is a synthetic compound used in manufacture of explosives. 1,3-DNB has been used as a camphor substitute in nitrocellulose, a compound used in explosives and propellants.1,3-DNB was manufactured during both world wars as a component in the explosive roburite. Commercially, 1,3-DNB has been used extensively as an organic intermediate for m-phenylenediamine, a chemical used in the synthesis of aramid fibers and spandex. 1,3-DNB is an industrial chemical used in organic synthesis and dyes. In medicine, 1,3-DNB was used for colorimetric determination of 17-ketosteroids.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Weibull modeling of the Fenton's oxidation process.	2001	11381782
Mitochondrial adaptation to in vivo polyunsaturated fatty acid deficiency: increase in phosphorylation efficiency.	2001 Feb	11460926
Evaluation of effects of 1,3-dinitrobenzene on sperm motility of hamster using computer assisted semen analysis (CASA).	2001 Jun	11404794
Chemistry of the diazeniumdiolates. 3. Photoreactivity.	2001 Jun 13	11389628
The reproducibility of tolerance to lower-body negative pressure and its quantification.	2001 May	11417436
The Egyptian mongoose, Herpestes ichneumon, is a possible reservoir host of visceral leishmaniasis in eastern Sudan.	2001 May	11393826
Suppression of arylamine toxicity in the Fischer-344 rat following ingestion of a complex mixture.	2001 May-Jun	11442020
Thyroxine reversibly inhibits the uncoupling action of protonophores on energy production in rat thymus lymphocytes.	2002 Apr	11996661
Inhibition of transthyretin amyloid fibril formation by 2,4-dinitrophenol through tetramer stabilization.	2002 Apr 1	11913969
Two-dimensional (13)C-(13)C correlation spectroscopy with magic angle spinning and dynamic nuclear polarization.	2002 Apr 3	11916398
The influence of Sacoglottis gabonensis stem bark extract and its isolate bergenin, Nigerian alcoholic beverage additives, on the metabolic and haematological side effects of 2,4-dinitrophenyl hydrazine-induced tissue damage.	2002 Dec	14567070
Atomic thermal motions studied by variable-temperature X-ray diffraction and related to non-linear optical properties of crystalline meta-dinitrobenzene.	2002 Dec	12456978
Solution-state dynamic nuclear polarization at high magnetic field.	2002 Jul 31	12137529
Frequent chromosome 9p losses in histologically normal nasopharyngeal epithelia from southern Chinese.	2002 Nov 20	12397655
Oligomycin, inhibitor of the F0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis.	2002 Nov 21	12444550
The response of adult rat sertoli cells, immortalized by a temperature-sensitive mutant of SV40, to 1,2-dinitrobenzene, 1,3-dinitrobenzene, 2,4-dinitrotoluene, 3,4-dinitrotoluene, and cadmium.	2003 Apr	12776928
Dynamic nuclear polarization at 9T using a novel 250GHz gyrotron microwave source.	2003 Feb	12615147
Peroxynitrite generated in the rat spinal cord induces oxidation and nitration of proteins: reduction by Mn (III) tetrakis (4-benzoic acid) porphyrin.	2003 Jan 15	12503084
Continuous biotransformation and removal of nitrophenols under denitrifying conditions.	2003 Jul	12767298
Influence of pH on the toxicity of nitrophenols to Microtox and Spirotox tests.	2003 Jul	12729708
1,3-Dinitrobenzene inhibits mitochondrial complex II in rat and mouse brainstem and cortical astrocytes.	2003 Jun	12782105
Energization of Comamonas testosteroni ATCC 17454 for indicating toxic effects of chlorophenoxy herbicides.	2003 Oct	14674583
p38gamma MAPK regulation of glucose transporter expression and glucose uptake in L6 myotubes and mouse skeletal muscle.	2004 Feb	14592936
Alterations in the natriuretic hormone system related to cardiopulmonary bypass in infants with congestive heart failure.	2004 Jul-Aug	14735254

Patents

Sample Use Guides

In Vivo Use Guide

In, animals, 1,3-DNB is rapidly absorbed by the oral route; data from one study indicate that at least 70% of a single oral dose was absorbed. In animals, depending on the vehicle, 1,3-DNB can also be readily absorbed through the skin.

Route of Administration: Other

In Vitro Use Guide

For colorimetric determination of 17-ketosteroids, into the calorimeter tube were accurately measured 0.2 cc. of a test solution, 0.2 cc. of m-dinitrobenzene solution, and 0.2 cc. of KOH solution. The tubes were then corked, gently shaken, and placed in a water bath for 45 minutes at 25°. At the end of 45 minutes the solution was diluted with 10.0 cc. of redistilled 95 per cent EtOH from a 10 cc. Koch burette. After the outside of the tube was dried and polished, it was placed in a rack for 3 minutes and read in the photoelectric calorimeter previously adjusted to 100 by means of the resistances with the blank in place.

Name

Type

Language

M-DINITROBENZENE

Systematic Name

English

1,3-DINITROBENZENE

Systematic Name

English

BENZENE, 1,3-DINITRO-

Systematic Name

English

DINITROBENZENE, M-

Systematic Name

English

M-DINITROBENZENE [MI]

Common Name

English

1,3-DINITROBENZENE [HSDB]

Common Name

English

META-DINITROBENZENE

Systematic Name

English

DINITROBENZENE

Systematic Name

English

BENZINUM DINITRICUM

Common Name

English

NSC-7189

Code

English

BENZINUM DINITRICUM [HPUS]

Common Name

English

Code System Code Type Description

PUBCHEM

7452