Pentamethylbenzene

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Pentamethylbenzene
Pentamethylbenzene.svg
Pentamethylbenzene-3D-balls.png
Names
Preferred IUPAC name
1,2,3,4,5-Pentamethylbenzene
Other names
Pentamethylbenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.763 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C11H16/c1-7-6-8(2)10(4)11(5)9(7)3/h6H,1-5H3
    Key: BEZDDPMMPIDMGJ-UHFFFAOYSA-N
  • InChI=1/C11H16/c1-7-6-8(2)10(4)11(5)9(7)3/h6H,1-5H3
    Key: BEZDDPMMPIDMGJ-UHFFFAOYAT
  • Cc1cc(C)c(C)c(C)c1C
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 solventssoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

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. Bibcode:1984JAChS.106.3968H. doi:10.1021/ja00326a014.
  2. 1 2 Smith, Lee Irvin (1930). "Durene". Organic Syntheses . 10: 32. doi:10.15227/orgsyn.010.0032 ; Collected Volumes, vol. 2, p. 248.
  3. ↑ Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2002). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN   978-3-527-30673-2.
  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.
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