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 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]

Related Research Articles

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Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure H−C(=O)−O−H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.

<span class="mw-page-title-main">Aromaticity</span> Phenomenon of chemical stability in resonance hybrids of cyclic organic compounds

In chemistry, aromaticity means a molecule has a cyclic (ring-shaped) structure with pi bonds in resonance. Aromatic rings give increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability. The term aromaticity with this meaning is historically related to the concept of having an aroma, but is a distinct property from that meaning.

<span class="mw-page-title-main">Electron ionization</span> Ionization technique

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4
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<span class="mw-page-title-main">Formate dehydrogenase</span>

Formate dehydrogenases are a set of enzymes that catalyse the oxidation of formate to carbon dioxide, donating the electrons to a second substrate, such as NAD+ in formate:NAD+ oxidoreductase (EC 1.17.1.9) or to a cytochrome in formate:ferricytochrome-b1 oxidoreductase (EC 1.2.2.1). This family of enzymes has attracted attention as inspiration or guidance on methods for the carbon dioxide fixation, relevant to global warming.

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<span class="mw-page-title-main">Aldehyde deformylating oxygenase</span> Enzyme family

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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. Bibcode:2013Chmsp..92.1442K. doi:10.1016/j.chemosphere.2013.03.054. PMID   23611246.