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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:34 UTC
Update Date2023-02-21 17:29:04 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
Data?1677000544
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point5.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.09 mg/mL at 25 °CNot Available
LogP1.85Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.14 g/LALOGPS
logP1.89ALOGPS
logP1.91ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-8.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.38 m³·mol⁻¹ChemAxon
Polarizability11.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.85531661259
DarkChem[M-H]-120.90331661259
DeepCCS[M+H]+122.86830932474
DeepCCS[M-H]-120.03330932474
DeepCCS[M-2H]-156.64430932474
DeepCCS[M+Na]+131.89430932474
AllCCS[M+H]+124.232859911
AllCCS[M+H-H2O]+119.432859911
AllCCS[M+NH4]+128.732859911
AllCCS[M+Na]+130.032859911
AllCCS[M-H]-117.332859911
AllCCS[M+Na-2H]-119.232859911
AllCCS[M+HCOO]-121.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NitrobenzeneO=N(=O)C1=CC=CC=C11701.4Standard polar33892256
NitrobenzeneO=N(=O)C1=CC=CC=C11046.6Standard non polar33892256
NitrobenzeneO=N(=O)C1=CC=CC=C11095.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized)splash10-0fb9-9000000000-cb5343370bc7b8d5540d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized)splash10-0fi0-9200000000-940028739887fc7d38112017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized)splash10-0fi0-9200000000-01d576e409b4cc0d4a112017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized)splash10-0fi0-9200000000-913bbd87a6a1c495c53f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized)splash10-0fb9-9000000000-cb5343370bc7b8d5540d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized)splash10-0fi0-9200000000-940028739887fc7d38112018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized)splash10-0fi0-9200000000-01d576e409b4cc0d4a112018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized)splash10-0fi0-9200000000-913bbd87a6a1c495c53f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nitrobenzene GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-9400000000-a663b64f823c48e330922017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nitrobenzene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nitrobenzene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fi0-9200000000-322385ed4a00b7c5fe022014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 10V, Positive-QTOFsplash10-00di-0900000000-7cb7381e7a13bf0202732016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 20V, Positive-QTOFsplash10-03di-3900000000-617850731979c7ac52f52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 40V, Positive-QTOFsplash10-03k9-9800000000-da6675b3e8755f1e2df72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 10V, Negative-QTOFsplash10-00di-0900000000-64d5321b824d98a92b6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 20V, Negative-QTOFsplash10-00di-0900000000-df2108c699830ae3492b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 40V, Negative-QTOFsplash10-0229-5900000000-1deb5a18d01251d41c4e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 10V, Positive-QTOFsplash10-00di-0900000000-a40838813cb50c62518e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 20V, Positive-QTOFsplash10-00di-0900000000-a40838813cb50c62518e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 40V, Positive-QTOFsplash10-0udi-9000000000-7b8dd26abd6fe153a4dc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 10V, Negative-QTOFsplash10-00di-0900000000-9c9fc313e5315679a8f92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 20V, Negative-QTOFsplash10-00di-0900000000-9c9fc313e5315679a8f92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrobenzene 40V, Negative-QTOFsplash10-0002-9000000000-9bdf09f4f521493796ac2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7138
KEGG Compound IDC06813
BioCyc IDBENZENE-NO2
BiGG IDNot Available
Wikipedia LinkNitrobenzene
METLIN IDNot Available
PubChem Compound7416
PDB IDNot Available
ChEBI ID27798
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]