terephthalaldehyde

Terephthalaldehyde, or 1,4-benzenedicarbaldehyde, is an aromatic dialdehyde that serves as a versatile building block in organic synthesis. Its chemical formula is C8H6O2 and its molar mass is about 134.14 g/mol. It has two aldehyde functional groups attached to a para-substituted benzene ring, which gives it bifunctionality and a tendency to undergo condensation and imine-forming reactions.

Commercially, terephthalaldehyde is produced from para-xylene via oxidation to the corresponding dicarboxylic acid (terephthalic acid) and subsequent controlled reduction to the dialdehyde or via alternative routes. The compound is typically a colorless to white crystalline solid, with limited water solubility and higher solubility in organic solvents.

In terms of reactivity, the two aldehyde groups enable reactions with amines to form imines or Schiff bases, and with active methylene compounds in condensation reactions. This makes terephthalaldehyde a useful bifunctional crosslinker and building block in polymer chemistry. It is employed in the synthesis of resins, polyurethanes, cured epoxy systems, and functional materials. It can also serve as a precursor to ligands or dyes in coordination chemistry and materials science.

Safety: Terephthalaldehyde can be an irritant to skin, eyes, and the respiratory tract. Proper handling includes using gloves and eye protection, working in a well-ventilated area, and keeping away from sources of ignition and strong oxidizers. Store in a cool, dry place.