Duroquinone

{{chembox | Watchedfields = changed | verifiedrevid = 443715899 | ImageFileL1 = Duroquinone.png | ImageSizeL1 = 105 | ImageAltL1 = Structural formula of duroquinone | ImageFileR1 = Duroquinone 3D ball.png | ImageSizeR1 = 145 | ImageAltR1 = Ball-and-stick model of the duroquinone molecule | PIN = 2,3,5,6-Tetramethylcyclohexa-2,5-diene-1,4-dione | OtherNames = 2,3,5,6-Tetramethyl-1,4-benzoquinone<br />Tetramethyl-''p''-benzoquinone |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 61539 | InChI = 1/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3 | InChIKey = WAMKWBHYPYBEJY-UHFFFAOYAK | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 151604 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WAMKWBHYPYBEJY-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 527-17-3 | PubChem = 68238 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01927 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = X0Q8791R69 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 42023 | Beilstein = 1909128 | Gmelin = 279610 | EINECS = 208-409-8 | SMILES = CC1=C(C(=O)C(=C(C1=O)C)C)C }} |Section2={{Chembox Properties | Formula = C₁₀H₁₂O₂ | MolarMass = 164.20408 g/mol | Appearance = | Density = | MeltingPtC = 109 to 114 | MeltingPt_notes = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | 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}} }} }}

'''Duroquinone''' is an organic oxidant (C₆(CH₃)₄O₂). It is related to 1,4-benzoquinone by replacement of four H centres with methyl (Me) groups. The C₁₀O₂ core of this molecule is planar with two pairs of C=O and C=C bonds.<ref name=Kochi>J.-M. Lü, S. V. Rosokha, I. S. Neretin and J. K. Kochi, "Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs" Journal of the American Chemical Society 2006 128, 16708-16719.{{doi|10.1021/ja066471o}}</ref>

The compound is produced via nitration of durene (1,2,4,5-tetramethylbenzene) followed reduction to the diamine and then oxidation.<ref>{{OrgSynth|author=Lee Irvin Smith.|year=1943|title=Duronquinone|volume= |pages= |collvol=2|collvolpages=254|prep=CV2P0254}}</ref>

A derived organoiron compound (η²,η²-C₆(CH₃)₄O₂)Fe(CO)₃ is obtained by the carbonylation of 2-butyne in the presence of iron pentacarbonyl.<ref>H. W. Sternberg, R. Markby and I. Wender, "A Quinone Iron Tricarbonyl Complex and its Significance in Organic Synthesis", Journal of the American Chemical Society 1958 volume 80, pp. 1009-1010. {{doi|10.1021/ja01537a075}}</ref>

The molecule has been mentioned in the popular press as a component of a "nano brain".<ref>*{{cite news | first = Jonathan | last = Fildes | author = | title = Chemical brain controls nanobots | url = https://news.bbc.co.uk/1/hi/sci/tech/7288426.stm | format = | work = | publisher = British Broadcasting Corporation | location = | id = | pages = | page = | date = 2008-03-11 | access-date = 2008-03-11 | language = | quote = }}</ref>

Duroquinone was observed in a degradation products generated from pyrolysis of α-Tocopheryl acetate.<ref>{{Cite journal |last1=Wu |first1=Dan |last2=O’Shea |first2=Donal F. |date=2020-03-24 |title=Potential for release of pulmonary toxic ketene from vaping pyrolysis of vitamin E acetate |journal=Proceedings of the National Academy of Sciences |language=en |volume=117 |issue=12 |pages=6349–6355 |doi=10.1073/pnas.1920925117 |issn=0027-8424 |pmc=7104367 |pmid=32156732|doi-access=free }}</ref>

== References == {{reflist}}

Category:1,4-Benzoquinones

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