Acenaphthoquinone

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Acenaphthoquinone
Skeletal formula
Ball-and-stick model
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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EC Number
  • 201-441-3
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KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C12H6O2/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(11)14/h1-6H checkY
    Key: AFPRJLBZLPBTPZ-UHFFFAOYSA-N checkY
  • 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
  • O=C3c2cccc1cccc(c12)C3=O
Properties
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)
Insoluble (90.1 mg/L)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritating
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
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)

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2
0
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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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

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