Phenanthrenequinone
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Names | |
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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
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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 | |
Safety data sheet (SDS) | External MSDS |
GHS labelling: | |
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Signal word
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Warning |
H315, H319, H400 | |
P264, P273, P280, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362, P391, P501 | |
NFPA 704 (fire diamond) | ![]()
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Phenanthrenedione is a quinone derivative of a polycyclic aromatic hydrocarbon. It is an orange, water-insoluble solid.[2]
Laboratory synthesis and use[]
It has been prepared by oxidation of phenanthrene with chromic acid.[3]
It is used as a 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 Nicodinamide adenosine dinucleotide(NAD+).
Safety[]
It is a cytotoxic.[4]
References[]
- ^ " 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 (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.
- ^ 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.
Categories:
- Quinones
- Phenanthrenes
- Enones
- Organic compound stubs