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
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
| Molecular Formula | C6H4N2O4 |
| Molecular Weight | 168.107 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| p38gamma MAPK regulation of glucose transporter expression and glucose uptake in L6 myotubes and mouse skeletal muscle. | 2004-02 |
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| Alterations in the natriuretic hormone system related to cardiopulmonary bypass in infants with congestive heart failure. | 2004-01-22 |
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| Diagnostic value of sural nerve matrix metalloproteinase-9 in diabetic patients with CIDP. | 2003-12-09 |
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| One-tube semi-nested PCR-ELISA for the detection of human cytomegalovirus DNA sequences; comparison with hybridization-based and semi-nested-based PCR-ELISA procedures. | 2003-12 |
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| High-frequency dynamic nuclear polarization in MAS spectra of membrane and soluble proteins. | 2003-11-12 |
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| Highly effective poly(ethylene glycol) architectures for specific inhibition of immune receptor activation. | 2003-11-11 |
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| Immunoglobulin E is not required for but enhances airway inflammation and hyperresponsiveness. | 2003-11 |
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| Preparation of 6-thioguanosine phosphoramidite for oligoribonucleotide synthesis. | 2003-10-21 |
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| Energization of Comamonas testosteroni ATCC 17454 for indicating toxic effects of chlorophenoxy herbicides. | 2003-10 |
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| The specificity of cross-reactivity: promiscuous antibody binding involves specific hydrogen bonds rather than nonspecific hydrophobic stickiness. | 2003-10 |
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| Reactions of bis(2,4-dinitrophenyl) phosphate with hydroxylamine. | 2003-09-05 |
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| Metal binding characteristics of a laterally nonsymmetric aza cryptand upon functionalization with a pi-acceptor group. | 2003-08-11 |
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| Enhanced detection of nitroaromatic explosive vapors combining solid-phase extraction-air sampling, supercritical fluid extraction, and large-volume injection-GC. | 2003-07-01 |
|
| Human recombinant endopeptidase PHEX has a strict S1' specificity for acidic residues and cleaves peptides derived from fibroblast growth factor-23 and matrix extracellular phosphoglycoprotein. | 2003-07-01 |
|
| Trace analysis of explosives in soil: pressurized fluid extraction and gas and liquid chromatography-mass spectrometry. | 2003-07 |
|
| Quantification and aging of the post-blast residue of TNT landmines. | 2003-07 |
|
| Continuous biotransformation and removal of nitrophenols under denitrifying conditions. | 2003-07 |
|
| Influence of pH on the toxicity of nitrophenols to Microtox and Spirotox tests. | 2003-07 |
|
| Regioselectivity and the nature of the reaction mechanism in nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with primary amines. | 2003-06-27 |
|
| A unique autocatalytic process and evidence for a concerted-stepwise mechanism transition in the dissociative electron-transfer reduction of aryl thiocyanates. | 2003-06-18 |
|
| 1,3-Dinitrobenzene inhibits mitochondrial complex II in rat and mouse brainstem and cortical astrocytes. | 2003-06 |
|
| Kinetics and mechanism of the benzenethiolysis of 2,4-dinitrophenyl and 2,4,6-trinitrophenyl methyl carbonates and S-(2,4-dinitrophenyl) and S-(2,4,6-trinitrophenyl) ethyl thiolcarbonates. | 2003-05-02 |
|
| A fluorimetric method for the determination of pepsin activity. | 2003-05-01 |
|
| 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. | 2003-04 |
|
| Homogeneous immunoassay for detection of TNT and its analogues on a microfabricated capillary electrophoresis chip. | 2003-03-01 |
|
| Nitrophenyl derivatives of pyrrole 2,5-diamides: structural behaviour, anion binding and colour change signalled deprotonation. | 2003-02-21 |
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| Microchip capillary electrophoresis coupled with a boron-doped diamond electrode-based electrochemical detector. | 2003-02-15 |
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| Dynamic nuclear polarization at 9T using a novel 250GHz gyrotron microwave source. | 2003-02 |
|
| Peroxynitrite generated in the rat spinal cord induces oxidation and nitration of proteins: reduction by Mn (III) tetrakis (4-benzoic acid) porphyrin. | 2003-01-15 |
|
| Micro-HPLC and standard-size HPLC for the separation of peptide stereoisomers employing an ion-exchange principle. | 2003-01-15 |
|
| Cardiovascular effects of natriuretic peptides and their interrelation with endothelin-1. | 2003-01 |
|
| Responses of thalamic neurons to input from the male genitalia. | 2003-01 |
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| 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. | 2002-12 |
|
| Biosorption of nitrophenols on anaerobic granular sludge. | 2002-12 |
|
| Atomic thermal motions studied by variable-temperature X-ray diffraction and related to non-linear optical properties of crystalline meta-dinitrobenzene. | 2002-12 |
|
| Oligomycin, inhibitor of the F0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis. | 2002-11-21 |
|
| Frequent chromosome 9p losses in histologically normal nasopharyngeal epithelia from southern Chinese. | 2002-11-20 |
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| [Biosensor of the reactor type based on Rhodococcus erythropolis HL TM-1 cells for determining 2,4-dinitrophenol]. | 2002-10-24 |
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| A highly selective aerobic oxidation process catalyzed by electron-deficient nitroarenes via single electron transfer processes. | 2002-10-18 |
|
| Vapor phase transport of unexploded ordnance compounds through soils. | 2002-10 |
|
| Enhanced Dendroaspis natriuretic peptide immunoreactivity in experimental ureteral obstruction. | 2002-10 |
|
| Natriuretic peptide receptors and neutral endopeptidase in mediating the renal actions of a new therapeutic synthetic natriuretic peptide dendroaspis natriuretic peptide. | 2002-09-18 |
|
| Brain natriuretic peptide: role in cardiovascular and volume homeostasis. | 2002-09 |
|
| Solution-state dynamic nuclear polarization at high magnetic field. | 2002-07-31 |
|
| The effect of Sacoglottis gabonensis stem bark extract, a Nigerian alcoholic beverage additive, on the natural antioxidant defences during 2,4-dinitrophenyl hydrazine-induced membrane peroxidation in vivo. | 2002-07 |
|
| Enzymological aspects of bioconversion of m-dinitrobenzene. | 2002-07 |
|
| Entacapone does not induce conformational changes in liver mitochondria or skeletal muscle in vivo. | 2002-07 |
|
| Effects of alternative carbon sources on biological transformation of nitrophenols. | 2002 |
|
| Immune-mediated fever in the dog. Occurrence of antinuclear antibodies, rheumatoid factor, tumor necrosis factor and interleukin-6 in serum. | 2002 |
|
| An assessment of ammonia emissions from dairy facilities in Pennsylvania. | 2001-10-26 |
Sample Use Guides
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
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:28:56 GMT 2025
by
admin
on
Mon Mar 31 18:28:56 GMT 2025
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| Record UNII |
DK8B627BU0
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| Record Status |
Validated (UNII)
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| Record Version |
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7452
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1,3-Dinitrobenzene
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C017906
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DK8B627BU0
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m4569
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