Nitrobenzene (CHEM003176)

Record Information
Version1.0
Creation Date2014-08-29 05:53:42 UTC
Update Date2026-08-23 11:48:02 UTC
Accession NumberCHEM003176
Identification
Common NameNitrobenzene
ClassSmall Molecule
Description
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 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).
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cigarette Toxin
  • Dye
  • Explosive Agent
  • Human Neurotoxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • PMT
  • Pesticide
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
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 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 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
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
Predicted 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
Spectra
Spectra
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
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0041950
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDBENZENE-NO2
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNitrobenzene
Chemspider ID7138
ChEBI ID27798
PubChem Compound ID7416
Kegg Compound IDC06813
YMDB IDNot Available
ECMDB IDM2MDB004932
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11304127
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12595155
3. 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.
4. 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.
5. 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.
6. 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.