Nitrobenzene
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Basic Info
| Common Name | Nitrobenzene(F05288) |
| 2D Structure | |
| 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). |
| FRCD ID | F05288 |
| CAS Number | 98-95-3 |
| PubChem CID | 7416 |
| Formula | C6H5NO2 |
| IUPAC Name | nitrobenzene |
| InChI Key | LQNUZADURLCDLV-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H |
| Canonical SMILES | C1=CC=C(C=C1)[N+](=O)[O-] |
| Isomeric SMILES | C1=CC=C(C=C1)[N+](=O)[O-] |
| Wikipedia | Nitrobenzene |
| Synonyms |
Oil of myrbane
NITROBENZENE
Nitrobenzol
98-95-3
Benzene, nitro-
Oil of mirbane
Mirbane oil
Essence of mirbane
nitro-Benzene
Nitrobenzeen
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Nitrobenzenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Nitrobenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 123.111 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 102 |
| Monoisotopic Mass | 123.032 |
| Exact Mass | 123.032 |
| XLogP | 1.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Computational identification of structural factors affecting the mutagenicpotential of aromatic amines: study design and experimental validation. | Arch Toxicol | 2018 Jul | 29779177 |
| Persulfate activation by naturally occurring trace minerals. | J Hazard Mater | 2011 Nov 30 | 21968122 |
| Acute toxicity and mutagenesis of three metabolites mixture of nitrobenzene inmice. | Toxicol Ind Health | 2011 Mar | 20858646 |
| Dynamics of glutathione-S-transferases in Mytilus galloprovincialis exposed to toxic Microcystis aeruginosa cells, extracts and pure toxins. | Toxicon | 2007 Nov | 17675203 |
| Photodegradation of metolachlor applying UV and UV/H2O2. | J Agric Food Chem | 2007 May 16 | 17447786 |
| Dietary toxicity of decomposed arborescent leaf litter against larval mosquito: involvement of a lignin-polypeptidic complex. | J Agric Food Chem | 2002 Oct 23 | 12381120 |
| The effects of T-2 toxin exposure on liver drug metabolizing enzymes in rabbit. | Food Addit Contam | 2000 Dec | 11271836 |
| Excised Barley root uptake of several (14)C labeled organic compounds. | Environ Monit Assess | 1985 Dec | 24258104 |
Targets
- 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
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 ]