Duroquinone

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Duroquinone

IUPAC name 2,3,5,6-Tetramethyl-1,4-benzoquinone
Other names Tetramethyl-p-benzoquinone
Identifiers
CAS number	527-17-3^Y
ChemSpider	61539^Y
UNII	X0Q8791R69^Y
DrugBank	DB01927
ChEBI	CHEBI:42023^Y
ChEMBL	CHEMBL151604^Y
Jmol-3D images	Image 1
SMILES CC1=C(C(=O)C(=C(C1=O)C)C)C
InChI InChI=1S/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3^Y Key: WAMKWBHYPYBEJY-UHFFFAOYSA-N^Y InChI=1/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3 Key: WAMKWBHYPYBEJY-UHFFFAOYAK
Properties
Molecular formula	C₁₀H₁₂O₂
Molar mass	164.20408 g/mol
Melting point	109 - 114 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Duroquinone is the organic compound with the formula 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", Org. Synth. ; Coll. Vol. 2: 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.

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