1,3,5-Tribromobenzene is an aryl bromide and isomer of tribromobenzene, also known as sym-tribromobenzene.
Preparation Brominating aniline with elemental bromine gives 2,4,6-tribromoaniline. This is then diazotized, then reacted with ethanol to replace the diazonium group with hydrogen, forming 1,3,5-tribromobenzene.
It has also been prepared by these methods: replacement of the amino group of 3,5-dibromoaniline with bromine the action of light on bromoacetylene, effecting an alkyne trimerisation to 1,3,5-tribromobenzene decomposition of 2,4,6-tribromophenylhydrazine reduction of 2,4,6-tribromobenzenediazonium sulfate a side product in the preparation of 2,4,6-tribromobenzonitrile
Reactions and uses
1,3,5-Tribromobenzene is a precursor to C3-symmetric molecules. It undergoes a Suzuki reaction with three equivalents of 4-formylphenylboronic acid to form 1,3,5-tris(4-formylphenyl)benzene (TFPB), a monomer for covalent organic frameworks.
References