Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-13 11:49:34 UTC |
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Update Date | 2023-02-21 17:29:04 UTC |
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HMDB ID | HMDB0041950 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Nitrobenzene |
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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). |
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Structure | InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H |
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Synonyms | Value | Source |
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Nitrobenzol | ChEBI | Oil OF mirbane | ChEBI | 4-Hydroxynitrobenzene | HMDB | 4-Nitrophenol | HMDB | Essence OF mirbane | HMDB | Essence OF myrbane | HMDB | Hydroxy(phenyl)azane oxide (acd/name 4.0) | HMDB | Mirbane oil | HMDB | Niphen | HMDB | Nitro-benzene | HMDB | Nitrobenzeen | HMDB | Nitrobenzen | HMDB | Nitrobenzol, liquid(dot) | HMDB | Oil OF myrbane | HMDB | p-Nitrophenol | HMDB | PNP | HMDB | PNP, p-Nitrophenol | HMDB | Rcra waste number u169 | HMDB |
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Chemical Formula | C6H5NO2 |
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Average Molecular Weight | 123.1094 |
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Monoisotopic Molecular Weight | 123.032028409 |
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IUPAC Name | nitrobenzene |
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Traditional Name | nitrobenzene |
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CAS Registry Number | 98-95-3 |
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SMILES | O=N(=O)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H |
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InChI Key | LQNUZADURLCDLV-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Nitrobenzenes |
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Direct Parent | Nitrobenzenes |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 5.7 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 2.09 mg/mL at 25 °C | Not Available | LogP | 1.85 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized) | splash10-0fb9-9000000000-cb5343370bc7b8d5540d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized) | splash10-0fi0-9200000000-940028739887fc7d3811 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized) | splash10-0fi0-9200000000-01d576e409b4cc0d4a11 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized) | splash10-0fi0-9200000000-913bbd87a6a1c495c53f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized) | splash10-0fb9-9000000000-cb5343370bc7b8d5540d | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized) | splash10-0fi0-9200000000-940028739887fc7d3811 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized) | splash10-0fi0-9200000000-01d576e409b4cc0d4a11 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nitrobenzene EI-B (Non-derivatized) | splash10-0fi0-9200000000-913bbd87a6a1c495c53f | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nitrobenzene GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dj-9400000000-a663b64f823c48e33092 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nitrobenzene GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nitrobenzene GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0fi0-9200000000-322385ed4a00b7c5fe02 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 10V, Positive-QTOF | splash10-00di-0900000000-7cb7381e7a13bf020273 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 20V, Positive-QTOF | splash10-03di-3900000000-617850731979c7ac52f5 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 40V, Positive-QTOF | splash10-03k9-9800000000-da6675b3e8755f1e2df7 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 10V, Negative-QTOF | splash10-00di-0900000000-64d5321b824d98a92b6e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 20V, Negative-QTOF | splash10-00di-0900000000-df2108c699830ae3492b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 40V, Negative-QTOF | splash10-0229-5900000000-1deb5a18d01251d41c4e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 10V, Positive-QTOF | splash10-00di-0900000000-a40838813cb50c62518e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 20V, Positive-QTOF | splash10-00di-0900000000-a40838813cb50c62518e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 40V, Positive-QTOF | splash10-0udi-9000000000-7b8dd26abd6fe153a4dc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 10V, Negative-QTOF | splash10-00di-0900000000-9c9fc313e5315679a8f9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 20V, Negative-QTOF | splash10-00di-0900000000-9c9fc313e5315679a8f9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nitrobenzene 40V, Negative-QTOF | splash10-0002-9000000000-9bdf09f4f521493796ac | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 7138 |
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KEGG Compound ID | C06813 |
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BioCyc ID | BENZENE-NO2 |
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BiGG ID | Not Available |
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Wikipedia Link | Nitrobenzene |
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METLIN ID | Not Available |
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PubChem Compound | 7416 |
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PDB ID | Not Available |
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ChEBI ID | 27798 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:8937894 ]
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