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
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.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}}
The compound is produced via nitration of durene (1,2,4,5-tetramethylbenzene) followed reduction to the diamine and then oxidation.{{OrgSynth|author=Lee Irvin Smith.|year=1943|title=Duronquinone|volume= |pages= |collvol=2|collvolpages=254|prep=CV2P0254}}
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.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}}
The molecule has been mentioned in the popular press as a component of a "nano brain".*{{cite news
| first = Jonathan
| last = Fildes
| author =
| title = Chemical brain controls nanobots
| url = http://news.bbc.co.uk/1/hi/sci/tech/7288426.stm
| format =
| work =
| publisher = British Broadcasting Corporation
| location =
| id =
| pages =
| page =
| date = 2008-03-11
| accessdate = 2008-03-11
| language =
| quote =
| archiveurl =
}}
Duroquinone was observed in a degradation products generated from pyrolysis of α-Tocopheryl acetate.{{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 }}