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Phenanthrenequinone

Basic information Description Uses Preparation Reactions Safety Related Supplier
Phenanthrenequinone Basic information
Phenanthrenequinone Chemical Properties
  • Melting point:209-212 °C(lit.)
  • Boiling point:360 °C
  • Density 1.405
  • refractive index 1.5681 (estimate)
  • Flash point:245 °C
  • storage temp. 2-8°C
  • solubility 7.5mg/l
  • form Powder
  • color Orange-brownish
  • Water Solubility Insoluble in water.
  • Merck 14,7213
  • BRN 608838
  • Stability:Stable. Incompatible with strong oxidizing agents.
  • CAS DataBase Reference84-11-7(CAS DataBase Reference)
  • NIST Chemistry Reference9,10-Phenanthroquinone(84-11-7)
  • EPA Substance Registry System9,10-Phenanthrenedione (84-11-7)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38
  • Safety Statements 26-36-24/25-22
  • RIDADR UN3077
  • WGK Germany 3
  • RTECS SF7875000
  • Autoignition Temperature630 °C DIN 51794
  • TSCA Yes
  • HazardClass 9
  • PackingGroup III
  • HS Code 29146990
  • Hazardous Substances Data84-11-7(Hazardous Substances Data)
  • ToxicityLD50 orally in Rabbit: > 16000 mg/kg
MSDS
Phenanthrenequinone Usage And Synthesis
  • Description9,10-phenanthrenequinone (9,10-PQ) is a quinone molecule found in air pollution abundantly in the diesel exhaust particles (DEP). This compound has studied extensively and has been shown to develop cytotoxic effects both in vitro and in vivo. 9, 10-PQ has been proposed to play a critical role in the development of cytotoxicity via generation of reactive oxygen species (ROS) through redox cycling. This compound also reduces expression of glutathione (GSH), which is critical in Phase II detoxification reactions.
  • Uses9,10-Phenanthrenequinon may be used for high quality passivation on silicon (100) surfaces. Quinones may serve as substrates for a variety of flavoenzymes.
    The quinones of polycyclic aromatic hydrocarbons are present in abundance in all burnt organic material. On being used to passivate silicon surfaces, it reacts with the dangling bonds on the surface via a heteroatomic Diels-Alder reaction. On account of the Π-electron conjugation, the semi conducting nature of the silicon is unaffected.
  • PreparationPhenanthrenequinone is obtained by the oxidation of the hydrocarbon phenanthrene C14H10. Upon reduction with sulphur dioxide, it yields phenanthrenehydroquinone which absorbs oxygen from the air forming a black quinhydrone. Upon further oxidation the phenanthrenequinone is again formed.
    9,10-Phenanthrenequinone is prepared by oxidation of phenanthrene with dihydroxy phenylselenonium benzenesulfonate in boiling dioxane-water. 9-methoxyphenanthrene is obtained when the reaction is carried out in methanol.
    https://www.tandfonline.com/doi/abs/10.1080/00397919708004809
  • Reactions9,10-Phenanthrenequinone (PQ) reacts with ketones under FeCl3 catalysis to furnish a variety of structurally diverse furan annulated products. While the reaction of PQ with acetone and cyclopentanone furnishes furan annulated ketals, its reaction with ethyl alkyl ketones provides 3-furaldehyde annulated products. In contrast to the reaction of PQ with cyclopentanone, its reaction with cyclohexanone furnishes a tetrahydrobenzofuran annulated secondary alcohol. The reactions of PQ with cycloheptanone and cyclooctanone take a different course to provide 7,8-dihydro-6H-cyclohepta[b]furan and 6,7,8,9-tetrahydrocycloocta[b]furan annulated products, respectively. Mechanistically, the above reactions go through aldol condensation, dehydration and cyclization to form furan-phenanthrene annulated products where in each step FeCl3 catalysis is involved.
    9,10-Phenanthrenequinone Reaction
    https://pubs.rsc.org/en/content/articlelanding/2012/ra/c2ra20499a
  • Chemical Propertiesburnt-orange powder
  • Synthesis Reference(s)The Journal of Organic Chemistry, 52, p. 3472, 1987 DOI: 10.1021/jo00391a065
  • Safety ProfilePoison by acute intraperitoneal route. Questionable carcinogen with experimental tumorigenic data by skin contact. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Purification MethodsCrystallise the quinone from dioxane or 95% EtOH and dry it under vacuum. [Beilstein 7 IV 2565.]
Phenanthrenequinone Preparation Products And Raw materials
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