Acenaphthoquinone
{{chembox
| Watchedfields = changed
| verifiedrevid = 477238198
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Acenaphthoquinone.png
| ImageSize = 140px
| ImageAlt = Skeletal formula
| ImageFile1 = Acenaphthoquinone-3D-balls.png
| ImageSize1 = 160
| ImageAlt1 = Ball-and-stick model
| PIN = Acenaphthylene-1,2-dione
| OtherNames = Acenaphthoquinone (no longer accepted even in general nomenclature{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 724 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}})
Acenaphthenequinone
1,2-Acenaphthenequinone
Acenaphthenedione
1,2-Acenaphthylenedione
Acenaphthene-1,2-dione
1,2-Diketoacenaphthene
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6468
| InChIKey = AFPRJLBZLPBTPZ-UHFFFAOYAC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 395653
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H6O2/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(11)14/h1-6H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AFPRJLBZLPBTPZ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 82-86-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3950D6UEIQ
| EINECS = 201-441-3
| PubChem = 6724
| SMILES = O=C3c2cccc1cccc(c12)C3=O
| InChI = 1/C12H6O2/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(11)14/h1-6H
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15342
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C02807
| 3DMet = B00505
}}
|Section2={{Chembox Properties
| C=12 | H=6 | O=2
| Appearance = Purple-yellow crystals to brown powder
| Density =
| MeltingPtC = 257 to 261
| MeltingPt_notes =
| BoilingPt =
| Solubility = Insoluble (90.1 mg/L)
}}
|Section3={{Chembox Hazards
| MainHazards = Irritating
| FlashPt =
| AutoignitionPt =
| NFPA-H = 2
| NFPA-F = 0
| NFPA-R = 0
| NFPA-S =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}}
}}
Acenaphthoquinone is a quinone derived from acenaphthene. It is a water-insoluble yellow solid. It is a precursor to some agrichemicals and dyes.{{Ullmann|doi=10.1002/14356007.a13_227|title=Hydrocarbons|year=2000|last1=Griesbaum|first1=Karl|last2=Behr|first2=Arno|last3=Biedenkapp|first3=Dieter|last4=Voges|first4=Heinz-Werner|last5=Garbe|first5=Dorothea|last6=Paetz|first6=Christian|last7=Collin|first7=Gerd|last8=Mayer|first8=Dieter|last9=Höke|first9=Hartmut|isbn=3527306730}}
Preparation
The compound is prepared in the laboratory by oxidation of acenaphthene with potassium dichromate.{{cite journal|title=Acenaphthenequinone|first1=C. F. H. |last1=Allen|first2=J. A.|last2=VanAllan|journal=Org. Synth.|year=1944|volume=24|page=1|doi=10.15227/orgsyn.024.0001}} Commercially, oxidation is effected with peroxide. Over-oxidation gives naphthalenedicarboxylic anhydride.
References
{{Reflist}}
External links
- [https://web.archive.org/web/20060518002254/http://www.npi.gov.au/database/substance-info/profiles/74.html National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet]
- [https://web.archive.org/web/20050414054720/http://wlapwww.gov.bc.ca/wat/wq/BCguidelines/pahs/pahs-01.htm PAHs - including structural diagrams]
- [https://archive.today/20121209043934/http://www.chemicalland21.com/arokorhi/specialtychem/finechem/1,2-ACENAPHTHYLENEDIONE.htm Entry at ChemicalLand21.com]
Category:Polycyclic aromatic compounds
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