1,3,5-Tribromobenzene

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.