Synthesis of azo compounds
Synthesis of diazonium salts
Azo coupling is the most widely used industrial reaction in the production of dyes, lakes and pigments. Aromatic diazonium ions acts as electrophiles in coupling reactions with activated aromatics such as anilines or phenols. The substitution normally occurs at the para position, except when this position is already occupied, in which case ortho position is favoured. The pH of solution is quite important; it must be mildly acidic or neutral, since no reaction takes place if the pH is too low.
Mechanism of Azo Coupling
Synthesis and properties of bis(hetaryl)azo dyes
M. Wang, K. Funabiki, M. Matsui, Dyes and Pigments, 2003, 57, 77-86.