Pentamethylbenzene
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |||
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| Preferred IUPAC name
1,2,3,4,5-Pentamethylbenzene | |||
| Other names
Pentamethylbenzene, Pentzene | |||
| Identifiers | |||
3D model (JSmol) |
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| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.010.763 | ||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| 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 | |||
| 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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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]