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| | Pentamethylbenzene Basic information |
| Product Name: | Pentamethylbenzene | | Synonyms: | Benzene, 1,2,3,4,5-pentamethyl-;benzene,pentamethyl-;pentamethyl-benzen;Pentmethyl Benzene;Pentamethylbenzene~95%;1,2,3,4,5-PENTAMETHYLBENZENE;Pentamethyl phenyl;PENTAMETHYLBENZENE | | CAS: | 700-12-9 | | MF: | C11H16 | | MW: | 148.24 | | EINECS: | 211-837-8 | | Product Categories: | Building Blocks;Chemical Synthesis;Arenes;Building Blocks;Organic Building Blocks;Organic Building Blocks | | Mol File: | 700-12-9.mol |  |
| | Pentamethylbenzene Chemical Properties |
| Hazard Codes | F,Xi | | Risk Statements | 11-36/37/38 | | Safety Statements | 16-26-36 | | RIDADR | UN 1325 4.1/PG 2 | | WGK Germany | 3 | | TSCA | Yes | | HazardClass | 4.1 | | PackingGroup | III | | HS Code | 29029090 |
| | Pentamethylbenzene Usage And Synthesis |
| Chemical Properties | Pentamethylbenzene is a white to light yellow crystalline powder 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. | | Uses | Pentamethylbenzene was used to prepare a mixture of nitropentamethylbenzene and 2,3,4,5-tetramethylbenzyl nitrate. It was also used to prepare propene. | | Definition | ChEBI: Pentamethylbenzene is a methylbenzene that is benzene in which five of the hydrogens are replaced by methyl groups. | | Synthesis Reference(s) | Synthesis, p. 979, 1985 DOI: 10.1055/s-1985-31413 | | Synthesis | Pentamethylbenzene is obtained as a minor product in the Friedel–Crafts methylation of xylene to durene (1,2,4,5-tetramethylbenzene). Like durene, pentamethylbenzene is rather electron-rich and undergoes electrophilic substitution readily. Indeed, it is used as a scavenger for carbocations.
Pentamethylbenzene has been observed as an intermediate in the formation of hexamethylbenzene from phenol and alkylation of durene or pentamethylbenzene has been reported as a suitable starting material for the synthesis of hexamethylbenzene. | | Purification Methods | Successively crystallise it from absolute EtOH, aqueous EtOH, MeOH, toluene *C6H6, and dry it under vacuum. [Rader & Smith J Am Chem Soc 84 1443 1962.] It has also been sublimed. The 1,3,5-trinitrobenzene complex (1:1) has m 121o (EtOH). [Beilstein 5 H 443, 5 III 1010, 5 IV 1109.] | | Precautions | Incompatible with oxidizing agents. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. |
| | Pentamethylbenzene Preparation Products And Raw materials |
| Raw materials | Benzene, 1,2,3,4,5-pentamethyl-6-(trifluoromethyl)--->acetic acid: (2,3,4,5,6-pentamethylphenyl)mercury-->PENTAMETHYLBENZOIC ACID-->2',3',4',5',6'-PENTAMETHYLACETOPHENONE-->PENTAMETHYLIODOBENZENE-->ALLYL TOLUENE-4-SULFONATE-->2-Butyne | | Preparation Products | 2,3,4,5,6-PENTAMETHYLBENZYL ALCOHOL-->1-Butanone, 1-(2-methoxyphenyl)--->PENTAMETHYLBENZENESULFONYL CHLORIDE-->2,3,4,5,6-PENTAMETHYLBENZYL CHLORIDE-->BENZENEPENTACARBOXYLIC ACID-->2,4-DIMETHYLPENTANE |
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