Acenaphthoquinone

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

Acenaphthoquinone

Names
Preferred IUPAC name Acenaphthylene-1,2-dione
Other names Acenaphthoquinone (no longer accepted even in general nomenclature[1]) Acenaphthenequinone 1,2-Acenaphthenequinone Acenaphthenedione 1,2-Acenaphthylenedione Acenaphthene-1,2-dione 1,2-Diketoacenaphthene
Identifiers
CAS Number	82-86-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15342 Y
ChEMBL	ChEMBL395653 Y
ChemSpider	6468 Y
ECHA InfoCard	100.001.311
EC Number	201-441-3
KEGG	C02807 Y
PubChem CID	6724
UNII	3950D6UEIQ Y
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 Y Key: AFPRJLBZLPBTPZ-UHFFFAOYSA-N Y 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). Y verify (what is YN ?) Infobox references

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]