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.; Collective Volume, 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.; Collective Volume, 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] 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.