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1,3,5-Tribromobenzene

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1,3,5-Tribromobenzene[1][2]
Names
IUPAC name
1,3,5-Tribromobenzene
Other names
sym-Tribromobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.953 Edit this at Wikidata
EC Number
  • 210-947-3
UNII
  • InChI=1S/C6H3Br3/c7-4-1-5(8)3-6(9)2-4/h1-3H
    Key: YWDUZLFWHVQCHY-UHFFFAOYSA-N
  • C1=C(C=C(C=C1Br)Br)Br
Properties
C6H3Br3
Molar mass 314.802 g·mol−1
Appearance colorless solid
Melting point 122 °C (252 °F; 395 K)
Boiling point 271 °C (520 °F; 544 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Preparation

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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]

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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  1. ^ "1,3,5-Tribromobenzene". ChemSpider. Retrieved 25 December 2023.
  2. ^ a b "1,3,5-Tribromobenzene". PubChem. Retrieved 25 December 2023.
  3. ^ a b Coleman, G. H.; Talbot, William F. (1933). "sym.-Tribromobenzene". Organic Syntheses. 13: 96. doi:10.15227/orgsyn.013.0096.
  4. ^ Bunck, David N.; Dichtel, William R. (2013). "Bulk Synthesis of Exfoliated Two-Dimensional Polymers Using Hydrazone-Linked Covalent Organic Frameworks". Journal of the American Chemical Society. 135 (40): 14952–14955. doi:10.1021/ja408243n. PMID 24053107.