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1,3,5-Tribromobenzene

Chemical compound From Wikipedia, the free encyclopedia

1,3,5-Tribromobenzene
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1,3,5-Tribromobenzene is an aryl bromide and isomer of tribromobenzene, also known as sym-tribromobenzene.[2]

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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.[3]

It has also been prepared by these methods:[3]

  • 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
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Reactions and uses

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1,3,5-tris(4-formylphenyl)benzene (TFPB)

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.[4]

References

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