Phenanthrenequinone

Phenanthrenequinone
Names
	Preferred IUPAC name Phenanthrene-9,10-dione
	Other names 9,10-Phenanthrenequinone[1]
Identifiers
CAS Number	84-11-7;
ChEBI	CHEBI:37454;
ChemSpider	6505;
ECHA InfoCard	100.001.377
PubChem CID	6763;
UNII	42L7BZ8H74;
CompTox Dashboard (EPA)	DTXSID3058901 ;
Properties
Chemical formula	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)
Solubility in water	Slightly soluble (7.5 mg L−1)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H400
Precautionary statements	P264, P273, P280, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362, P391, P501
NFPA 704 (fire diamond)	1 1 1
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). 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 nicotinamide adenine dinucleotide (NAD⁺).

Safety

It is 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.

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[1] " 84-11-7|Phenanthrenequinone|Toxnet|". nih.gov.

[Ullmanns-2] 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.

[3] Wendland, Ray; LaLonde, John (1954). "Phenanthrenequinone". Org. Synth. 34: 76. doi:10.15227/orgsyn.034.0076.

[4] 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.