1,3,5-Tribromobenzene
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| Names | |
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| IUPAC name
1,3,5-Tribromobenzene
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| Other names
sym-Tribromobenzene
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| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.009.953 |
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PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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1,3,5-Tribromobenzene is an aryl bromide and isomer of tribromobenzene, also known as sym-tribromobenzene.[2]
Preparation[edit]
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
Reactions and uses[edit]
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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[edit]
- ^ "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.