Duroquinone

Duroquinone
Names
	Preferred IUPAC name 2,3,5,6-Tetramethylcyclohexa-2,5-diene-1,4-dione
	Other names 2,3,5,6-Tetramethyl-1,4-benzoquinone; Tetramethyl-p-benzoquinone
Identifiers
CAS Number	527-17-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1909128
ChEBI	CHEBI:42023 ;
ChEMBL	ChEMBL151604 ;
ChemSpider	61539 ;
DrugBank	DB01927 ;
ECHA InfoCard	100.007.646
EC Number	208-409-8;
Gmelin Reference	279610
PubChem CID	68238;
UNII	X0Q8791R69 ;
CompTox Dashboard (EPA)	DTXSID50200659 ;
	InChI InChI=1S/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3 Key: WAMKWBHYPYBEJY-UHFFFAOYSA-N ; InChI=1/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3 Key: WAMKWBHYPYBEJY-UHFFFAOYAK;
	SMILES CC1=C(C(=O)C(=C(C1=O)C)C)C;
Properties
Chemical formula	C10H12O2
Molar mass	164.20408 g/mol
Melting point	109 to 114 °C (228 to 237 °F; 382 to 387 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[1]

The compound is produced via nitration of durene (1,2,4,5-tetramethylbenzene) followed reduction to the diamine and then oxidation.^[2]

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.^[3]

The molecule has been mentioned in the popular press as a component of a "nano brain".^[4]

Duroquinone was observed in a degradation products generated from pyrolysis of α-Tocopheryl acetate.^[5]

References

^ 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
^ Lee Irvin Smith. (1943). "Duronquinone". Organic Syntheses; Collected Volumes, vol. 2, p. 254.
^ 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
^ *Fildes, Jonathan (2008-03-11). "Chemical brain controls nanobots". British Broadcasting Corporation. Retrieved 2008-03-11.
^ Wu, Dan; O’Shea, Donal F. (2020-03-24). "Potential for release of pulmonary toxic ketene from vaping pyrolysis of vitamin E acetate". Proceedings of the National Academy of Sciences. 117 (12): 6349–6355. doi:10.1073/pnas.1920925117. ISSN 0027-8424. PMC 7104367. PMID 32156732.

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[Kochi-1] 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

[2] Lee Irvin Smith. (1943). "Duronquinone". Organic Syntheses; Collected Volumes, vol. 2, p. 254.

[3] 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

[4] *Fildes, Jonathan (2008-03-11). "Chemical brain controls nanobots". British Broadcasting Corporation. Retrieved 2008-03-11.

[5] Wu, Dan; O’Shea, Donal F. (2020-03-24). "Potential for release of pulmonary toxic ketene from vaping pyrolysis of vitamin E acetate". Proceedings of the National Academy of Sciences. 117 (12): 6349–6355. doi:10.1073/pnas.1920925117. ISSN 0027-8424. PMC 7104367. PMID 32156732.

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