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 | |
| Names | |
|---|---|
| Preferred IUPAC name 1,2,4,5-Tetramethylbenzene | |
| Other names Durol | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
|
| ECHA InfoCard | 100.002.242 |
| KEGG |
|
| UNII | |
| |
| |
| Properties | |
| C10H14 | |
| Molar mass | 134.21816 |
| Density | 0.868 g/cm3 |
| Melting point | 79.2 °C (174.6 °F; 352.3 K) |
| Boiling point | 192 °C (378 °F; 465 K) at 760mmHg |
| −101.2·10−6 cm3/mol | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Flammable |
| Flash point | 73.9 °C (165.0 °F; 347.0 K) |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Durene, or1,2,4,5-tetramethylbenzene, is anorganic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as analkylbenzene. It is one of three isomers of tetramethylbenzene, the other two beingprehnitene (1,2,3,4-tetramethylbenzene) andisodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.
It is a component of coal tar and was first prepared frompseudocumene in 1870.[1] It is produced bymethylation of other methylated benzene compounds such asp-xylene and pseudocumene.[2]
In industry, a mixture ofxylenes and trimethylbenzenes is alkylated withmethanol. Durene can be separated from its isomers by selective crystallization, exploiting its high melting point.[3] The original synthesis of durene involved a similar reaction starting fromtoluene.[4]
Durene is a significant byproduct of the production of gasoline frommethanol via the"MTG (Methanol to Gasoline) process".[5]
It is a relatively easily oxidized benzene derivative, with E1/2 of 2.03 V vs NHE.[6] Its nucleophilicity is comparable to that ofphenol.[7] It is readily halogenated on the ring for example. Nitration gives the dinitro derivative, a precursor toduroquinone. In industry, it is the precursor topyromellitic dianhydride, which is used for manufacturing curing agents,adhesives, coating materials. It is used in the manufacture of some raw materials for engineering plastics (polyimides) andcross-linking agent foralkydresins.[8] It is also a suitable starting material for the synthesis ofhexamethylbenzene.[2]
With a simpleproton NMR spectrum comprising two signals due to the 2 aromatic hydrogens (2H) and four methyl groups (12H), durene is used as aninternal standard.[9]
Durene is not a skin irritant nor a skin sensitizer or eye irritant. Durene is only slightly toxic on an acute toxicologic basis and only poses an acute health hazard when ingested in excessive quantities.[10]
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