9,10-phenanthrenequinone

Structural formula
General
Surname	9,10-phenanthrenequinone
other names	Phenanthrenequinone; Phenanthraquinone; Phenanthroquinone; 9,10-dihydro-9,10-dioxophenanthrene;
Molecular formula	C 14 H 8 O 2
Brief description	dark orange odorless solid, crystalline needles, platelets
External identifiers / databases
EC number	201-515-5
ECHA InfoCard	100.001.377
PubChem	6763
ChemSpider	6505
Wikidata	Q25103737
properties
Molar mass	208.22 g mol −1
Physical state	firmly
density	1.405 g cm −3
Melting point	203-206 ° C
boiling point	> 360 ° C
solubility	practically insoluble in water (7.5 mg l −1 at 25 ° C); slightly soluble in ethanol; soluble in diethyl ether, benzene, hot ethanol and boiling water;
safety instructions
H and P phrases	H: 319-400
	P: 262-273-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

9,10-phenanthrenequinone is a chemical compound from the group of ketones and polycyclic aromatic hydrocarbons . It is isomeric to anthraquinone .

Extraction and presentation

9,10-phenanthrenequinone can be obtained by liquid-phase oxidation of phenanthrene with chromates or with tert-butyl hydroperoxide , and via 9,10- phenanthrene oxide with nitric acid or hypochlorite . 9,10-phenanthrenequinone reacts like a typical α-diketone , e.g. B. When heated with aqueous alkaline solutions, it is subject to benzilic acid rearrangement with the formation of 9-hydroxyfluorene-9-carboxylic acid (flurenol).

Occurrence

9,10-phenanthrenequinone is found in coal tar , in tobacco and diesel soot .

properties

9,10-phenanthrenequinone is a flammable, hardly flammable, crystalline, dark orange, odorless solid that is practically insoluble in water. It is also easily sublimable .

use

9,10-phenanthrenequinone can be used for the passivation of silicon (100) surfaces. Like other quinones , it can also serve as a substrate for a variety of flavoenzymes . Also, in dyes, as curing agents for dentures , for the determination of copper by spectrophotometric methods for organic syntheses may be used. It is used as a printing chemical, and in paper finishing, 9,10-phenanthrenequinone is as new compositions for labeling aldehydes used, also it serves as a source of some polyannularer benzenoid systems by the Wittig reaction by means of phase transfer catalysis .

Individual evidence

↑ ^a ^b ^c ^d Werner Baumann, Herberg-Liedtke: Paper chemicals: data and facts on environmental protection , Springer-Verlag, 1993, ISBN 978-3-642-58040-6 , p. 605.
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 84-11-7 in the GESTIS substance database of the IFA , accessed on August 5, 2016(JavaScript required) .
↑ ^a ^b Data sheet 9,10-Phenanthrenequinone, 95% from AlfaAesar, accessed on August 6, 2016 ( PDF )(JavaScript required) .
↑ VK Ahluwalia, R. Aggarwal, VK Ahluwalia: Comprehensive Practical Organic Chemistry: Preparations And Quantitative Analysis. Universities Press, 2000, ISBN 978-81-7371-475-7 , p. 164.
↑ Amit Arora: Organic Chemistry: Aromatic, Alcohols Aldehydes & Acids. Discovery Publishing House, 2006, ISBN 978-81-8356-189-1 , p. 321.
↑ ^a ^b Entry on 9,10-phenanthrenequinone in the Hazardous Substances Data Bank , accessed on August 5, 2016.
↑ Phenanthrenchinon on Spektrum.de, accessed on August 5, 2016.
^ Heinz-Gerhard Franck, Jürgen W. Stadelhofer: Industrial Aromatic Chemistry , Springer Science & Business Media, 1988, ISBN 978-3-642-73432-8 , p. 363.
^ Heinz-Gerhard Franck, Gerd Collin: coal tar: chemistry, technology and use. Springer-Verlag, 1968, ISBN 978-3-642-88258-6 , p. 174.
↑ Alan Rodgman, Thomas A. Perfetti: The Chemical Components of Tobacco and Tobacco Smoke. Second Edition, CRC Press, April 19, 2016, ISBN 978-1-46651552-9 , p. 637.
↑ N. Kishikawa, M. Wada, Y. Ohba, K. Nakashima, N. Kuroda: Highly sensitive and selective determination of 9,10-phenanthrenequinone in airborne particulates using high-performance liquid chromatography with pre-column derivatization and fluorescence detection. In: Journal of Chromatography A . Volume 1057, Number 1-2, November 2004, pp. 83-88, PMID 15584225 .
↑ Friedrich Emich: Textbook of microchemistry. Springer-Verlag, 1926, ISBN 978-3-642-91506-2 , p. 257.
↑ Mahmoud El-Maghrabey, Naoya Kishikawa, Naotaka Kuroda: 9,10-Phenanthrenequinone as a Mass-Tagging Reagent for Ultra-Sensitive Liquid Chromatography Tandem Mass Spectrometry Assay of Aliphatic Aldehydes in Human Serum , In: Journal of Chromatography A. Elsevier, 29 July 2016, doi: 10.1016 / j.chroma.2016.07.082 .
↑ A. Minsky, M. Rabinovitz, A Facile Synthesis of Some Polycyclic Hydrocarbons: Application of Phase Transfer Catalysis in the Bis-Wittig Reaction. In: Synthesis . 1983, No. 6, pp. 497, 498, doi: 10.1055 / s-1983-30401 .

[Werner-1] Werner Baumann, Herberg-Liedtke: Paper chemicals: data and facts on environmental protection , Springer-Verlag, 1993, ISBN 978-3-642-58040-6 , p. 605.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 84-11-7 in the GESTIS substance database of the IFA , accessed on August 5, 2016(JavaScript required) .

[Alfa-3] Data sheet 9,10-Phenanthrenequinone, 95% from AlfaAesar, accessed on August 6, 2016 ( PDF )(JavaScript required) .

[4] VK Ahluwalia, R. Aggarwal, VK Ahluwalia: Comprehensive Practical Organic Chemistry: Preparations And Quantitative Analysis. Universities Press, 2000, ISBN 978-81-7371-475-7 , p. 164.

[5] Amit Arora: Organic Chemistry: Aromatic, Alcohols Aldehydes & Acids. Discovery Publishing House, 2006, ISBN 978-81-8356-189-1 , p. 321.

[HSDB-6] Entry on 9,10-phenanthrenequinone in the Hazardous Substances Data Bank , accessed on August 5, 2016.

[7] Phenanthrenchinon on Spektrum.de, accessed on August 5, 2016.

[8] Heinz-Gerhard Franck, Jürgen W. Stadelhofer: Industrial Aromatic Chemistry , Springer Science & Business Media, 1988, ISBN 978-3-642-73432-8 , p. 363.

[9] Heinz-Gerhard Franck, Gerd Collin: coal tar: chemistry, technology and use. Springer-Verlag, 1968, ISBN 978-3-642-88258-6 , p. 174.

[10] Alan Rodgman, Thomas A. Perfetti: The Chemical Components of Tobacco and Tobacco Smoke. Second Edition, CRC Press, April 19, 2016, ISBN 978-1-46651552-9 , p. 637.

[11] N. Kishikawa, M. Wada, Y. Ohba, K. Nakashima, N. Kuroda: Highly sensitive and selective determination of 9,10-phenanthrenequinone in airborne particulates using high-performance liquid chromatography with pre-column derivatization and fluorescence detection. In: Journal of Chromatography A . Volume 1057, Number 1-2, November 2004, pp. 83-88, PMID 15584225 .

[12] Friedrich Emich: Textbook of microchemistry. Springer-Verlag, 1926, ISBN 978-3-642-91506-2 , p. 257.

[13] Mahmoud El-Maghrabey, Naoya Kishikawa, Naotaka Kuroda: 9,10-Phenanthrenequinone as a Mass-Tagging Reagent for Ultra-Sensitive Liquid Chromatography Tandem Mass Spectrometry Assay of Aliphatic Aldehydes in Human Serum , In: Journal of Chromatography A. Elsevier, 29 July 2016, doi: 10.1016 / j.chroma.2016.07.082 .

[14] A. Minsky, M. Rabinovitz, A Facile Synthesis of Some Polycyclic Hydrocarbons: Application of Phase Transfer Catalysis in the Bis-Wittig Reaction. In: Synthesis . 1983, No. 6, pp. 497, 498, doi: 10.1055 / s-1983-30401 .