Pentamethylbenzene

Pentamethylbenzene is an organic compound with the formula C6H(CH3)5. It is a colourless solid with a sweet odor. The compound is classified as an aromatic hydrocarbon. It is a relatively easily oxidized benzene derivative, with E1/2 of 1.95 V vs NHE.[1]

Pentamethylbenzene
Names
IUPAC name
1,2,3,4,5-pentamethylbenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.763
UNII
Properties
C11H16
Molar mass 148.249 g·mol−1
Density 0.917 g/cm3
Melting point 54.4 °C (129.9 °F; 327.5 K)
Boiling point 232 °C (450 °F; 505 K)
Solubility in organic solvents soluble
Hazards
Main hazards Flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Synthesis and reactions

It is obtained as a minor product in the Friedel–Crafts methylation of xylene to durene (1,2,4,5-tetramethylbenzene).[2] Like durene, pentamethylbenzene is rather electron-rich and undergoes electrophilic substitution readily.[3] Indeed, it is used as a scavenger for carbocations.[4]

Pentamethylbenzene has been observed as an intermediate in the formation of hexamethylbenzene from phenol[5] and alkylation of durene or pentamethylbenzene has been reported as a suitable starting material for the synthesis of hexamethylbenzene.[2]

References
  1. Howell, J. O.; Goncalves, J. M.; Amatore, C.; Klasinc, L.; Wightman, R. M.; Kochi, J. K. (1984). "Electron transfer from aromatic hydrocarbons and their pi-complexes with metals. Comparison of the standard oxidation potentials and vertical ionization potentials". Journal of the American Chemical Society. 106 (14): 3968–3976. doi:10.1021/ja00326a014.
  2. Smith, Lee Irvin (1930). "Durene". Organic Syntheses. 10: 32. doi:10.15227/orgsyn.010.0032.; Collective Volume, 2, p. 248
  3. Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2002). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.
  4. Okaya, Shun; Okuyama, Keiichiro; Okano, Kentaro; Tokuyama, Hidetoshi (2016). "Trichloroboron-Promoted Deprotection of Phenolic Benzyl Ether Using Pentamethylbenzene as a Non Lewis-Basic Cation Scavenger". Organic Syntheses. 93: 63–74. doi:10.15227/orgsyn.093.0063.
  5. Landis, Phillip S.; Haag, Werner O. (1963). "Formation of Hexamethylbenzene from Phenol and Methanol". Journal of Organic Chemistry. 28 (2): 585. doi:10.1021/jo01037a517.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.