Practical and Efficient Synthesis of Tris(4-formylphenyl)amine, a Key Building Block in Materials Chemistry

Abstract

A short, practical and efficient preparation of tris(4-formylphenyl)amine, a key building block in materials chemistry, is described. It involves a two-flask synthesis from triphenylamine, which requires shorter overall time than the direct one-flask threefold Vilsmeier-Haack formylation, while giving higher yields. The reaction levels off at the disubstitution stage, due to the deactivation of the bis-iminium intermediate, but hydrolysis of the latter into a less deactivated dialdehyde allows the third formylation to occur. The simple experimental protocol makes this method more convenient than the previously reported procedures.

Key words

materials chemistry - building block - aldehydes - electrophilic aromatic substitutions - Vilsmeier-Haack reaction

References

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This could explain why DMF is often used in larger amounts than POCl₃.²⁴ To overcome this problem, other authors tried to use high boiling chlorinated solvents, such as 1,2-dichloroethane, but the yields remained low.^19,26