Phenanthrenequinone
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| Names | |
|---|---|
| Preferred IUPAC name
Phenanthrene-9,10-dione | |
| Other names
9,10-Phenanthrenequinone[1]
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| Identifiers | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.377 |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
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|
| Properties | |
| C14H8O2 | |
| Molar mass | 208.216 g·mol−1 |
| Appearance | Orange solid |
| Odor | Odorless |
| Melting point | 209 °C (408 °F; 482 K) |
| Boiling point | 360 °C (680 °F; 633 K) |
| Slightly soluble (7.5 mg L−1) | |
| Hazards | |
| GHS labelling: | |
 
| |
| Warning | |
| H315, H319, H400 | |
| P264, P273, P280, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362, P391, P501 | |
| NFPA 704 (fire diamond) | |
| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phenanthrenedione is a quinone derivative of a polycyclic aromatic hydrocarbon. It is an orange, water-insoluble solid.[2]
Laboratory synthesis and use
[edit]It has been prepared by oxidation of phenanthrene with chromic acid.[3]
It is used as an artificial mediator for electron acceptor/donor in Mo/W containing formate dehydrogenase reduction of carbon dioxide to formate and vice versa. It is a better electron acceptor than the natural nicotinamide adenine dinucleotide (NAD+).
Safety
[edit]It is cytotoxic[4] and potentially mutagenic.[5]
Phenanthrenequinone is one of many contributors to harmful particulate emissions from diesel motor vehicles.[6]
Related compounds
[edit]References
[edit]- ^ " 84-11-7|Phenanthrenequinone|Toxnet|". nih.gov.
- ^ Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN 978-3527306732.
- ^ Wendland, Ray; LaLonde, John (1954). "Phenanthrenequinone". Org. Synth. 34: 76. doi:10.15227/orgsyn.034.0076.
- ^ Robert A. Kanaly; Natsuko Hamamura (September 2013). "9,10-Phenanthrenedione biodegradation by a soil bacterium and identification of transformation products by LC/ESI-MS/MS". Chemosphere. 92 (11): 1442–1449. Bibcode:2013Chmsp..92.1442K. doi:10.1016/j.chemosphere.2013.03.054. PMID 23611246.
- ^ Durant, John L.; Busby, William F.; Lafleur, Arthur L.; Penman, Bruce W.; Crespi, Charles L. (1996). "Human cell mutagenicity of oxygenated, nitrated and unsubstituted polycyclic aromatic hydrocarbons associated with urban aerosols". Mutation Research/Genetic Toxicology. 371 (3–4): 123–157. doi:10.1016/s0165-1218(96)90103-2. PMID 9008716.
- ^ Rogge, Wolfgang F.; Hildemann, Lynn M.; Mazurek, Monica A.; Cass, Glen R.; Simoneit, Bernd R. T. (1993). "Sources of fine organic aerosol. 2. Noncatalyst and catalyst-equipped automobiles and heavy-duty diesel trucks". Environmental Science & Technology. 27 (4): 636–651. doi:10.1021/es00041a007.
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