Hexamethylbenzene

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Hexamethylbenzene
IUPAC name

1,2,3,4,5,6-Hexamethylbenzene

Other names

Mellitene

Identifiers
CAS number 87-85-4 YesY
PubChem 6908
ChemSpider 6642
Jmol-3D images Image 1
Properties
Molecular formula C12H18
Molar mass 162.27 g mol−1
Appearance White crystalline powder
Melting point 165 °C; 329 °F; 438 K
Boiling point 265.2 °C; 509.4 °F; 538.3 K
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Hexamethylbenzene is white crystalline solid with chemical formula C6(CH3)6. It is a synthetic aromatic hydrocarbon with six methyl groups stemming from the carbon centres of the ring. Hexamethylbenzene has historical significance in the field of X-ray crystallography. In 1929, Kathleen Lonsdale first proved the shape of hexamethylbenzene and thus showed that the benzene ring is hexagonal and flat.[1]

Uses

Hexamethylbenzene has no significant commercial uses. The six methyl groups enhance the proton affinity of the central ring.[2] Because it is electron-rich, hexamethylbenzene can be used as a ligand in organometallic chemistry. Two examples from organoruthenium chemistry are the sandwich complexes Ru(ɳ4-C6(CH3)6)(ɳ6-C6(CH3)6) and the dication [Ru(ɳ6-C6(CH3)6)2]2+.[3]

Hexamethylbenzene has been used as a solvent for 3He NMR spectroscopy.[4]

Preparation

Hexamethylbenzene can be prepared by the reaction of phenol with methanol at 400 °C in the presence of an alumina catalyst.[5]

References

  1. ↑ "The Structure of the Benzene Ring in Hexamethylbenzene". Proceedings of the Royal Society 123A (494). 1929. 
  2. ↑ Earhart, H. W., and Andrew P. Komin "Polymethylbenzenes" Encyclopedia of Chemical Technology (2000)
  3. ↑ M. A. Bennett, T. N. Huang, T. W. Matheson, A. K. Smith (1982). "(η6-Hexamethylbenzene)Ruthenium Complexes". Inorganic Syntheses. Inorganic Syntheses 21: 74–78. doi:10.1002/9780470132524.ch16. ISBN 9780470132524. 
  4. ↑ Saunders, M.;Jimenez-Vazquez, H. A.; Khong, A. (1996). "NMR of3He Dissolved in Organic Solids". J. Phys. Chem. 100 (39): 15968–15971. doi:10.1021/jp9617783. 
  5. ↑ Landis, Phillip S.; Haag, Werner O. (1963). The Journal of Organic Chemistry 28 (2): 585. doi:10.1021/jo01037a517. 
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