Phenanthrenequinone

Phenanthrenedione is a quinone derivative of a polycyclic aromatic hydrocarbon. It is an orange, water-insoluble solid.[2]

Not to be confused with Phanquinone.
Phenanthrenequinone
Names
Systematic IUPAC name
9,10-Phenanthrenequinone[1]
Identifiers
ChEBI
ChemSpider
ECHA InfoCard 100.001.377
UNII
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 External MSDS
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H315, H319, H400
P273, P264, P280, P305+351+338, P337+313, P302+352, P332+313, P362, P391, P501
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
1
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

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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 (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. doi:10.1016/j.chemosphere.2013.03.054. PMID 23611246.
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