Acenaphthoquinone

Acenaphthoquinone
Names
	Preferred IUPAC name Acenaphthylene-1,2-dione
	Other names Acenaphthoquinone (no longer accepted even in general nomenclature); Acenaphthenequinone; 1,2-Acenaphthenequinone; Acenaphthenedione; 1,2-Acenaphthylenedione; Acenaphthene-1,2-dione; 1,2-Diketoacenaphthene
Identifiers
CAS Number	82-86-0 ;
3D model (JSmol)	Interactive image;
3DMet	B00505;
ChEBI	CHEBI:15342 ;
ChEMBL	ChEMBL395653 ;
ChemSpider	6468 ;
ECHA InfoCard	100.001.311
EC Number	201-441-3;
KEGG	C02807 ;
PubChem CID	6724;
UNII	3950D6UEIQ ;
CompTox Dashboard (EPA)	DTXSID7049429 ;
	InChI InChI=1S/C12H6O2/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(11)14/h1-6H Key: AFPRJLBZLPBTPZ-UHFFFAOYSA-N ; InChI=1/C12H6O2/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(11)14/h1-6H Key: AFPRJLBZLPBTPZ-UHFFFAOYAC;
	SMILES O=C3c2cccc1cccc(c12)C3=O;
Properties
Chemical formula	C12H6O2
Molar mass	182.178 g·mol−1
Appearance	Purple-yellow crystals to brown powder
Melting point	257 to 261 °C (495 to 502 °F; 530 to 534 K)
Solubility in water	Insoluble (90.1 mg/L)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritating
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)	2 0 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Acenaphthoquinone is a quinone derived from acenaphthene. It is a water-insoluble yellow solid. It is a precursor to some agrichemicals and dyes.^[2]

Preparation

The compound is prepared in the laboratory by oxidation of acenaphthene with potassium dichromate.^[3] Commercially, oxidation is effected with peroxide. Over-oxidation gives naphthalenedicarboxylic anhydride.^[2]

References

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 724. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b 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 3527306730.
^ Allen, C. F. H.; VanAllan, J. A. (1944). "Acenaphthenequinone". Org. Synth. 24: 1. doi:10.15227/orgsyn.024.0001.

External links

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[IUPAC2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 724. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[Ull-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 3527306730.

[3] Allen, C. F. H.; VanAllan, J. A. (1944). "Acenaphthenequinone". Org. Synth. 24: 1. doi:10.15227/orgsyn.024.0001.

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