Misplaced Pages

Phenanthrenequinone

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Not to be confused with Phanquinone.
Phenanthrenequinone
Names
Preferred IUPAC name Phenanthrene-9,10-dione
Other names 9,10-Phenanthrenequinone
Identifiers
CAS Number
ChEBI
ChemSpider
ECHA InfoCard 100.001.377 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula C14H8O2
Molar mass 208.216 g·mol
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)
Hazards
GHS labelling:
Pictograms GHS09: Environmental hazard GHS07: Exclamation mark
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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 , 100 kPa). Infobox references
Chemical compound

Phenanthrenedione is a quinone derivative of a polycyclic aromatic hydrocarbon. It is an orange, water-insoluble solid.

Laboratory synthesis and use

It has been prepared by oxidation of phenanthrene with chromic acid.

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

It is cytotoxic and potentially mutagenic.

Phenanthrenequinone is one of many contributors to harmful particulate emissions from diesel motor vehicles.

Related compounds

References

  1. " 84-11-7|Phenanthrenequinone|Toxnet|". nih.gov.
  2. 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.
  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.
  5. 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.
  6. 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.
Stub icon

This article about an organic compound is a stub. You can help Misplaced Pages by expanding it.

Categories: