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

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|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)

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|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}}

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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

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