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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:34 UTC
Update Date2017-12-07 04:29:50 UTC
HMDB IDHMDB0041950
Secondary Accession Numbers
  • HMDB41950
Metabolite Identification
Common NameNitrobenzene
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).
Structure
Thumb
Synonyms
ValueSource
NitrobenzolChEBI
Oil OF mirbaneChEBI
4-HydroxynitrobenzeneHMDB
4-NitrophenolHMDB
Essence OF mirbaneHMDB
Essence OF myrbaneHMDB
Hydroxy(phenyl)azane oxide (acd/name 4.0)HMDB
Mirbane oilHMDB
NiphenHMDB
nitro-BenzeneHMDB
NitrobenzeenHMDB
NitrobenzenHMDB
Nitrobenzol, liquid(dot)HMDB
Oil OF myrbaneHMDB
P-NitrophenolHMDB
PNPHMDB
PNP, P-NitrophenolHMDB
Rcra waste number u169HMDB
Chemical FormulaC6H5NO2
Average Molecular Weight123.1094
Monoisotopic Molecular Weight123.032028409
IUPAC Namenitrobenzene
Traditional Namenitrobenzene
CAS Registry Number98-95-3
SMILES
O=N(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H
InChI KeyLQNUZADURLCDLV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitrobenzenes. These 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
Ontology
Disposition

Source:

Role

Biological role:

Environmental role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point5.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.09 mg/mL at 25 °CNot Available
LogP1.85Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.14 g/LALOGPS
logP1.89ALOGPS
logP1.91ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area45.82 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.38 m³·mol⁻¹ChemAxon
Polarizability11.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9000000000-cb5343370bc7b8d5540dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fi0-9200000000-940028739887fc7d3811View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fi0-9200000000-01d576e409b4cc0d4a11View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fi0-9200000000-913bbd87a6a1c495c53fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9000000000-cb5343370bc7b8d5540dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fi0-9200000000-940028739887fc7d3811View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fi0-9200000000-01d576e409b4cc0d4a11View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fi0-9200000000-913bbd87a6a1c495c53fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-9400000000-a663b64f823c48e33092View 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 AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7138
KEGG Compound IDC06813
BioCyc IDBENZENE-NO2
BiGG IDNot Available
Wikipedia LinkNitrobenzene
METLIN IDNot Available
PubChem Compound7416
PDB IDNBZ
ChEBI ID27798
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:8937894 ]