| Record Information |
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| Version | 2.0 |
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| Creation Date | 2014-08-29 05:53:42 UTC |
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| Update Date | 2014-12-24 20:26:42 UTC |
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| Accession Number | T3D4216 |
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| Identification |
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| Common Name | Nitrobenzene |
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| Class | Small Molecule |
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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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| Compound Type | - Cigarette Toxin
- Dye
- Explosive Agent
- Industrial/Workplace Toxin
- Metabolite
- Organic Compound
- Pesticide
- Pollutant
- Solvent
- Synthetic Compound
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| Chemical Structure | |
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| 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 |
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| Chemical Formula | C6H5NO2 |
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| Average Molecular Mass | 123.109 g/mol |
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| Monoisotopic Mass | 123.032 g/mol |
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| CAS Registry Number | 98-95-3 |
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| IUPAC Name | nitrobenzene |
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| Traditional Name | nitrobenzene |
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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 | InChIKey=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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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Liquid |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | 5.7°C | | Boiling Point | 210.8°C (411.4°F) | | Solubility | 2.09 mg/mL at 25°C | | LogP | 1.85 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fb9-9000000000-cb5343370bc7b8d5540d | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fi0-9200000000-940028739887fc7d3811 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fi0-9200000000-01d576e409b4cc0d4a11 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fi0-9200000000-913bbd87a6a1c495c53f | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fb9-9000000000-cb5343370bc7b8d5540d | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fi0-9200000000-940028739887fc7d3811 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fi0-9200000000-01d576e409b4cc0d4a11 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fi0-9200000000-913bbd87a6a1c495c53f | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dj-9400000000-a663b64f823c48e33092 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-7cb7381e7a13bf020273 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-3900000000-617850731979c7ac52f5 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03k9-9800000000-da6675b3e8755f1e2df7 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-64d5321b824d98a92b6e | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-df2108c699830ae3492b | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0229-5900000000-1deb5a18d01251d41c4e | JSpectraViewer | | MS | Mass Spectrum (Electron Ionization) | splash10-0fi0-9200000000-322385ed4a00b7c5fe02 | JSpectraViewer | MoNA | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | 2B, possibly carcinogenic to humans. (5) |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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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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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB41950 |
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| PubChem Compound ID | 7416 |
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| ChEMBL ID | CHEMBL15750 |
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| ChemSpider ID | 7138 |
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| KEGG ID | C06813 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 27798 |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | NBZ |
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| ACToR ID | Not Available |
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| Wikipedia Link | nitrobenzene |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Link |
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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. [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]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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