1,3,5-Tribromobenzene

1,3,5-Tribromobenzene^[1]^[2]
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/h1-3H Key: YWDUZLFWHVQCHY-UHFFFAOYSA-N;
	SMILES C1=C(C=C(C=C1Br)Br)Br;
Properties
Chemical formula	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). Infobox references

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

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

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]

^ "1,3,5-Tribromobenzene". ChemSpider. Retrieved 25 December 2023.
^ ^a ^b "1,3,5-Tribromobenzene". PubChem. Retrieved 25 December 2023.
^ ^a ^b Coleman, G. H.; Talbot, William F. (1933). "sym.-Tribromobenzene". Organic Syntheses. 13: 96. doi:10.15227/orgsyn.013.0096.
^ 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.