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Record Information
Version2.0
Creation Date2014-08-29 05:53:42 UTC
Update Date2014-12-24 20:26:42 UTC
Accession NumberT3D4216
Identification
Common NameNitrobenzene
ClassSmall Molecule
DescriptionApproximately 95% of nitrobenzene is consumed in the production of aniline, which is a precursor to rubber chemicals, pesticides, dyes, explosives, and pharmaceuticals. Nitrobenzene is an organic compound with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents. Nitrobenzene is prepared by nitration of benzene with a mixture of concentrated sulfuric acid, water, and nitric acid. This mixture is sometimes called 'mixed acid.' The production of nitrobenzene is one of the most dangerous processes conducted in the chemical industry because of the exothermicity of the reaction ( delta H = 117 kJ/mol).
Compound Type
  • Cigarette Toxin
  • Dye
  • Explosive Agent
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pesticide
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
4-Hydroxynitrobenzene
Essence of Mirbane
Essence of Myrbane
Hydroxy(phenyl)azane oxide
Mirbane oil
Niphen
Nitro-Benzene
Nitrobenzeen
Nitrobenzen
Nitrobenzol
Nitrobenzol, liquid(DOT)
Oil of Mirbane
Oil of Myrbane
p-Nitrophenol
PNP
Pnp, p-nitrophenol
Rcra waste number U169
Chemical FormulaC6H5NO2
Average Molecular Mass123.109 g/mol
Monoisotopic Mass123.032 g/mol
CAS Registry Number98-95-3
IUPAC Namenitrobenzene
Traditional Namenitrobenzene
SMILESO=N(=O)C1=CC=CC=C1
InChI IdentifierInChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H
InChI KeyInChIKey=LQNUZADURLCDLV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitroaromatic compound
  • Organic nitro compound
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point5.7°C
Boiling Point210.8°C (411.4°F)
Solubility2.09 mg/mL at 25°C
LogP1.85
Predicted Properties
PropertyValueSource
Water Solubility1.14 mg/mLALOGPS
logP1.89ALOGPS
logP1.91ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area45.82 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.38 m3·mol-1ChemAxon
Polarizability11.22 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-00dj-9400000000-a663b64f823c48e33092View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0fb9-9000000000-cb5343370bc7b8d5540dView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0fi0-9200000000-940028739887fc7d3811View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0fi0-9200000000-01d576e409b4cc0d4a11View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0fi0-9200000000-913bbd87a6a1c495c53fView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0fb9-9000000000-cb5343370bc7b8d5540dView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0fi0-9200000000-940028739887fc7d3811View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0fi0-9200000000-01d576e409b4cc0d4a11View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0fi0-9200000000-913bbd87a6a1c495c53fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-7cb7381e7a13bf020273View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-617850731979c7ac52f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-9800000000-da6675b3e8755f1e2df7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-64d5321b824d98a92b6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-df2108c699830ae3492bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-5900000000-1deb5a18d01251d41c4eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0fi0-9200000000-322385ed4a00b7c5fe02View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB41950
PubChem Compound ID7416
ChEMBL IDCHEMBL15750
ChemSpider ID7138
KEGG IDC06813
UniProt IDNot Available
OMIM ID
ChEBI ID27798
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNBZ
ACToR IDNot Available
Wikipedia Linknitrobenzene
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Sierra-Santoyo A, Hernandez M, Albores A, Cebrian ME: Sex-dependent regulation of hepatic cytochrome P-450 by DDT. Toxicol Sci. 2000 Mar;54(1):81-7. [10746934 ]
  2. Lee KJ, Woo ER, Choi CY, Shin DW, Lee DG, You HJ, Jeong HG: Protective effect of acteoside on carbon tetrachloride-induced hepatotoxicity. Life Sci. 2004 Jan 9;74(8):1051-64. [14672760 ]
  3. Ying ST, Huang WF, Tian LY, Shen XY: [Effects of Pb(NO3)2 and cetylpyridinium chloride on sorption of p-nitrophenol by sediment]. Huan Jing Ke Xue. 2006 Jul;27(7):1373-6. [16881312 ]
  4. Wueweera JB, Gandolfi AJ, Badger DA, Sipes IG, Brendel K: Vitamin A potentiation of vinylidene chloride hepatotoxicity in rats and precision-cut rat liver slices. Fundam Appl Toxicol. 1996 Nov;34(1):73-83. [8937894 ]
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Nadp binding
Specific Function:
Maintains high levels of reduced glutathione in the cytosol.
Gene Name:
GSR
Uniprot ID:
P00390
Molecular Weight:
56256.565 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory274.1 uMNot AvailableBindingDB 50352162
IC50546.8 uMNot AvailableBindingDB 50352162
References
  1. Cakmak R, Durdagi S, Ekinci D, Senturk M, Topal G: Design, synthesis and biological evaluation of novel nitroaromatic compounds as potent glutathione reductase inhibitors. Bioorg Med Chem Lett. 2011 Sep 15;21(18):5398-402. doi: 10.1016/j.bmcl.2011.07.002. Epub 2011 Jul 13. [21795044 ]