T3DB: Nitrobenzene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (1)XML

Targets (1)

Record Information

Version

2.0

Creation Date

2014-08-29 05:53:42 UTC

Update Date

2014-12-24 20:26:42 UTC

Accession Number

T3D4216

Identification

Common Name

Nitrobenzene

Class

Small 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).

Compound Type

Cigarette Toxin
Dye
Explosive Agent
Industrial/Workplace Toxin
Metabolite
Organic Compound
Pesticide
Pollutant
Solvent
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

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 Formula

C₆H₅NO₂

Average Molecular Mass

123.109 g/mol

Monoisotopic Mass

123.032 g/mol

CAS Registry Number

98-95-3

IUPAC Name

nitrobenzene

Traditional Name

nitrobenzene

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 Key

InChIKey=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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Nitrobenzenes

Direct Parent

Nitrobenzenes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

nitroarene (CHEBI:27798 )
nitrobenzenes (CHEBI:27798 )
an aromatic compound (BENZENE-NO2 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	5.7°C
Boiling Point	210.8°C (411.4°F)
Solubility	2.09 mg/mL at 25°C
LogP	1.85

Predicted Properties

Property	Value	Source
Water Solubility	1.14 g/L	ALOGPS
logP	1.89	ALOGPS
logP	1.91	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	-8.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.38 m³·mol⁻¹	ChemAxon
Polarizability	11.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fb9-9000000000-cb5343370bc7b8d5540d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fi0-9200000000-940028739887fc7d3811	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fi0-9200000000-01d576e409b4cc0d4a11	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fi0-9200000000-913bbd87a6a1c495c53f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fb9-9000000000-cb5343370bc7b8d5540d	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fi0-9200000000-940028739887fc7d3811	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fi0-9200000000-01d576e409b4cc0d4a11	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fi0-9200000000-913bbd87a6a1c495c53f	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-9400000000-a663b64f823c48e33092	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-7cb7381e7a13bf020273	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3900000000-617850731979c7ac52f5	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03k9-9800000000-da6675b3e8755f1e2df7	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-64d5321b824d98a92b6e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-df2108c699830ae3492b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0229-5900000000-1deb5a18d01251d41c4e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-a40838813cb50c62518e	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-a40838813cb50c62518e	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-7b8dd26abd6fe153a4dc	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-9c9fc313e5315679a8f9	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-9c9fc313e5315679a8f9	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-9bdf09f4f521493796ac	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fi0-9200000000-322385ed4a00b7c5fe02	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CCl₄, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (5)

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

27798

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

NBZ

ACToR ID

Not Available

Wikipedia Link

nitrobenzene

References

Synthesis Reference

Not Available

MSDS

Link

General References

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 ]
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 ]
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 ]
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 ]
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Glutathione reductase, mitochondrial

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

Type	Value	Assay Type	Assay Source
Inhibitory	274.1 uM	Not Available	BindingDB 50352162
IC50	546.8 uM	Not Available	BindingDB 50352162

References

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 ]

Nitrobenzene (T3D4216)

Structure for T3D4216: Nitrobenzene

Targets

Binding/Activity Constants

References