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)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.311
EC Number
  • 201-441-3
KEGG
UNII
  • 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)
NFPA 704 four-colored diamond
2
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
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

  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.
  2. 1 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. ISBN 978-3527306732.
  3. ↑ Allen, C. F. H.; VanAllan, J. A. (1944). "Acenaphthenequinone". Org. Synth. 24: 1. doi:10.15227/orgsyn.024.0001.
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