tetramethylbenzene

Tetramethylbenzene refers to a family of aromatic hydrocarbons derived from benzene by substituting four hydrogen atoms with methyl groups. The nominal molecular formula for all tetramethylbenzenes is C10H14, though the arrangement of methyl groups gives several distinct isomers.

The best-known member is 1,2,4,5-tetramethylbenzene, commonly called durene. Other isomers exist, differing in the positions of the four methyl substituents on the benzene ring.

Durene is a colorless crystalline solid at room temperature. It is insoluble in water and dissolves in most organic solvents. It is relatively chemically inert toward mild oxidants and reductions but can undergo oxidation or electrophilic substitution under strong conditions.

Production methods for tetramethylbenzenes are industrially varied. They are typically obtained in small quantities as byproducts of coal tar processing or by dedicated methylation routes using alkylation catalysts. Commercial samples are often mixtures of isomers.

Applications include use as chemical intermediates in the manufacture of dyes, resins, and specialty organic compounds. Durene also serves as a reference material in analytical chemistry and as a high-purity standard for calibration in some chromatographic techniques.

Safety and handling: tetramethylbenzenes are flammable and can irritate skin and eyes on contact. They should be stored in well-ventilated areas away from oxidizers and handled with gloves and eye protection.

See also: mesitylene, p-xylene, ethylbenzene.