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durene
Sign in to saveDurene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and isodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.
Chemical data
- Formula
- C10H14
- Molecular weight
- 134.22 g/mol
- IUPAC name
- 1,2,4,5-tetramethylbenzene
- SMILES
- CC1=CC(=C(C=C1C)C)C
- InChIKey
- SQNZJJAZBFDUTD-UHFFFAOYSA-N
- XLogP
- 4
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 134.11
Show 5 more facts
- melting point
- 79.3
- ionization energy
- 8.04
- boiling point
- 196.84
- chemical formula
- C₁₀H₁₄
- canonical SMILES
- CC1=CC(=C(C=C1C)C)C
via Wikidata · CC0
~2 min read
Article
4 sectionsContents
- Production
- Reactions and uses
- Safety
- References
Durene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and isodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.
==Production== It is a component of coal tar and was first prepared from pseudocumene in 1870. It is produced by methylation of other methylated benzene compounds such as p-xylene and pseudocumene. C6H4(CH3)2 + 2 CH3Cl → C6H2(CH3)4 + 2 HCl In industry, a mixture of xylenes and trimethylbenzenes is alkylated with methanol. Durene can be separated from its isomers by selective crystallization, exploiting its high melting point. The original synthesis of durene involved a similar reaction starting from toluene.