Duroquinone

Duroquinone is an organic compound (C4(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]

Duroquinone
Structural formula of duroquinone
Ball-and-stick model of the duroquinone molecule
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
3D model (JSmol)
1909128
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.646
EC Number
  • 208-409-8
279610
UNII
Properties
C10H12O2
Molar mass 164.20408 g/mol
Melting point 109 to 114 °C (228 to 237 °F; 382 to 387 K)
Hazards
GHS pictograms
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 (η22-C4(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]

References

  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, 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


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