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1,3,5-Tribromobenzene

Names
IUPAC name 1,3,5-Tribromobenzene
Other names sym-Tribromobenzene
Identifiers
CAS Number	626-39-1
3D model (JSmol)	Interactive image
ChemSpider	11776
ECHA InfoCard	100.009.953
EC Number	210-947-3
PubChem CID	12279
UNII	O3TD0U1OAQ
CompTox Dashboard (EPA)	DTXSID3052307
InChI InChI=1S/C6H3Br3/c7-4-1-5(8)3-6(9)2-4/h1-3HKey: YWDUZLFWHVQCHY-UHFFFAOYSA-N
SMILES C1=C(C=C(C=C1Br)Br)Br
Properties
Chemical formula	C6H3Br3
Molar mass	314.802 g·mol
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 , 100 kPa). Infobox references

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

1. "1,3,5-Tribromobenzene". ChemSpider. Retrieved 25 December 2023.
2. ^ "1,3,5-Tribromobenzene". PubChem. Retrieved 25 December 2023.
3. ^ 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.

• Bromobenzenes