Duroquinone

Names

IUPAC name

2,3,5,6-Tetramethyl-1,4-benzoquinone

Other names

Tetramethyl-p-benzoquinone

Identifiers

CAS Number

527-17-3^Y

3D model (Jmol)

CHEBI:42023^Y

61539^Y

DB01927^Y

ECHA InfoCard

100.007.646

UNII

X0Q8791R69^Y

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

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)

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

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". Org. Synth. ; Coll. 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.

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