Showing Compound Card for Nitrobenzene (CDB000646)

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Record Information
Version1.0
Created at2020-03-19 00:48:41 UTC
Updated at2020-12-07 19:07:37 UTC
CannabisDB IDCDB000646
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNitrobenzene
DescriptionNitrobenzene, also known as nitrobenzol or oil of mirbane, 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. Approximately 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 hydrophobic pale-yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced at 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). Nitrobenzene has been reported as a volatile compound detected in cannabis samples obtained through police seizure (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight123.11
Monoisotopic Molecular Weight123.032
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
Disposition

Source:

Role

Biological role:

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point5.7 °CNot Available
Boiling Point210.9 °CWikipedia
Water Solubility2.09 mg/mL at 25 °CNot Available
logP1.85Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0fi0-9200000000-322385ed4a00b7c5fe022014-09-20View Spectrum
GC-MSNitrobenzene, non-derivatized, GC-MS Spectrumsplash10-0fb9-9000000000-cb5343370bc7b8d5540dSpectrum
GC-MSNitrobenzene, non-derivatized, GC-MS Spectrumsplash10-0fi0-9200000000-940028739887fc7d3811Spectrum
GC-MSNitrobenzene, non-derivatized, GC-MS Spectrumsplash10-0fi0-9200000000-01d576e409b4cc0d4a11Spectrum
GC-MSNitrobenzene, non-derivatized, GC-MS Spectrumsplash10-0fi0-9200000000-913bbd87a6a1c495c53fSpectrum
GC-MSNitrobenzene, non-derivatized, GC-MS Spectrumsplash10-0fb9-9000000000-cb5343370bc7b8d5540dSpectrum
GC-MSNitrobenzene, non-derivatized, GC-MS Spectrumsplash10-0fi0-9200000000-940028739887fc7d3811Spectrum
GC-MSNitrobenzene, non-derivatized, GC-MS Spectrumsplash10-0fi0-9200000000-01d576e409b4cc0d4a11Spectrum
GC-MSNitrobenzene, non-derivatized, GC-MS Spectrumsplash10-0fi0-9200000000-913bbd87a6a1c495c53fSpectrum
Predicted GC-MSNitrobenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dj-9400000000-a663b64f823c48e33092Spectrum
Predicted GC-MSNitrobenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNitrobenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-7cb7381e7a13bf0202732016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-617850731979c7ac52f52016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-9800000000-da6675b3e8755f1e2df72016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-64d5321b824d98a92b6e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-df2108c699830ae3492b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-5900000000-1deb5a18d01251d41c4e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-a40838813cb50c62518e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-a40838813cb50c62518e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-7b8dd26abd6fe153a4dc2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-9c9fc313e5315679a8f92021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-9c9fc313e5315679a8f92021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-9bdf09f4f521493796ac2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CCl4, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0041950
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 IDNot Available
ChEBI ID27798
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]