Duroquinone
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Names | |||
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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)
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1909128 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.007.646 | ||
EC Number |
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279610 | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C10H12O2 | |||
Molar mass | 164.20408 g/mol | ||
Melting point | 109 to 114 °C (228 to 237 °F; 382 to 387 K) | ||
Hazards | |||
GHS labelling: | |||
Signal word
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Warning | ||
H315, H319, H335 | |||
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). | |||
what is ?) | (|||
Infobox references | |||
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]
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-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[]
- ^ 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, 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.
Categories:
- 1,4-Benzoquinones
- Ketone stubs