Durene

Durene

Names
IUPAC name 1,2,4,5-tetramethylbenzene
Other names Durol
Identifiers
CAS Number	95-93-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:38978 Y
ChemSpider	6999 Y
ECHA InfoCard	100.002.242
KEGG	C14534 Y
PubChem CID	7269
UNII	181426CFYB Y
InChI InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3 Y Key: SQNZJJAZBFDUTD-UHFFFAOYSA-N Y InChI=1/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3 Key: SQNZJJAZBFDUTD-UHFFFAOYAJ
SMILES c1c(c(cc(c1C)C)C)C
Properties
Chemical formula	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
Magnetic susceptibility (χ)	-101.2·10−6 cm3/mol
Hazards
Main hazards	Flammable
Flash point	73.9 °C (165.0 °F; 347.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox 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, m.p. −6.2 °C) and isodurene (1,2,3,5-tetramethylbenzene, m.p. −23.7 °C). Durene has an unusually high melting point, reflecting its high molecular symmetry.

It is a component of coal tar. It is produced by methylation of other methylated benzene compounds such as p-xylene and pseudocumene.

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.

Durene is a significant byproduct of the production of gasoline from methanol via the "MTG (Methanol to Gasoline) process".

Durene is an electron-rich arene, exhibiting nucleophilicity comparable to that of phenol. It is readily halogenated on the ring for example. Nitration gives the dinitro derivative, a precursor to duroquinone. In industry, it is the precursor to pyromellitic 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) and cross-linking agent for alkyd resins.