1,2-Naphthoquinone
Chemical compound
From Wikipedia, the free encyclopedia
1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C
10H
6O
2. It is classified as a 1,2-diketone as well as an ortho-quinone. More specifically, it is one of several naphthoquinones.[1]
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| Names | |
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| Preferred IUPAC name
Naphthalene-1,2-dione | |
| Other names
o-Naphthoquinone, β-naphthoquinone | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.602 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C10H6O2 | |
| Molar mass | 158.156 g·molâ1 |
| Appearance | yellow solid |
| Melting point | 145 to 147 °C (293 to 297 °F; 418 to 420 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and occurrence
1,2-Naphthoquinone is produced commercially by air-oxidation of 1-naphthol in the presence of copper catalyst.[1] A laboratory route involved oxidation of 1-amino-2-hydroxynaphthalene with ferric chloride.[2]
It is a metabolite of naphthalene. It arises from the naphthalene-1,2-oxide.[3]
It is also found in diesel exhaust particles. The accumulation of 1,2-naphthoquinone has been shown to damage the eyes of rats.[4]
See also
- 1,4-Naphthoquinone, an isomer of 1,2-naphthoquinone
- Diazonaphthoquinone, a diazo derivative of 1,2-naphthoquinone