Phenanthrenequinone

Last updated
Phenanthrenequinone
9,10-Phenanthrenequinone-2D-skeletal.svg
Names
Preferred IUPAC name
Phenanthrene-9,10-dione
Other names
9,10-Phenanthrenequinone [1]
Identifiers
ChEBI
ChemSpider
ECHA InfoCard 100.001.377 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
Properties
C14H8O2
Molar mass 208.216 g·mol−1
AppearanceOrange 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:
GHS-pictogram-pollu.svg GHS-pictogram-exclam.svg
Warning
H315, H319, H400
P264, P273, P280, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362, P391, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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
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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).

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

Contents

Laboratory synthesis and use

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

It is cytotoxic [4] and potentially mutagenic. [5]

Phenanthrenequinone is one of many contributors to harmful particulate emissions from diesel motor vehicles. [6]

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   978-3-527-30673-2.
  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.
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