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Description
3,3'-Dibromo-4,4'-dihydroxybiphenyl is a non-heterocyclic building block constructed on a biphenyl framework carrying two bromine atoms and two hydroxyl groups arranged symmetrically across both rings. In the laboratory, this compound serves as a rigid, long-axis scaffold that supplies four reactive points at once. The bromine atoms act as handles for metal-catalysed coupling reactions, while the phenols can be protected, etherified, or used as directing groups. This combination makes the material a highly productive starting point for synthetic and materials chemists working on extended aromatic architectures.
The property that makes this building block stand out is the regularity of its structure. The C₂ symmetry of the molecule simplifies NMR spectra and reduces the likelihood of forming isomers that are difficult to separate. The carbon–bromine bonds, positioned ortho to the phenol groups, are ready to undergo Suzuki, Sonogashira, and Buchwald–Hartwig couplings, as well as halogen–metal exchange, allowing new groups to be installed in a controlled manner. Meanwhile, the two phenol groups permit the formation of polymers, macrocycles, or bidentate ligands with a fixed donor-to-donor spacing. The biphenyl core itself contributes rigidity and a useful conjugated system.
In Indonesian laboratories, this building block is typically used in university and institutional research groups engaged in organic synthesis, coordination chemistry, and materials development. It is generally handled at the bench scale during multi-step route development, where a symmetrical dihalogenated diphenol shortens the path to more elaborate targets. Research teams working on conjugated frameworks, ligand design, and polymer precursors commonly draw on this compound when a predictable, rigid two-ring core with defined substitution is required.
Laboratory Applications
- Suzuki–Miyaura cross-coupling: the two carbon–bromine bonds allow controlled installation of aryl and heteroaryl groups, extending the conjugated biphenyl core symmetrically in a single catalytic step.
- Sonogashira coupling for conjugated systems: the aryl bromide positions accept alkynyl partners, giving rigid, extended π-systems built directly on the long axis of the biphenyl framework.
- Buchwald–Hartwig amination: the bromine handles support carbon–nitrogen bond formation, enabling the preparation of diamino-substituted biphenyl diols for further functionalisation or ligand work.
- Bidentate ligand synthesis: the two phenol donors sit at a fixed separation on a rigid scaffold, giving coordination chemists predictable donor geometry for metal complex construction.
- Polymer and macrocycle precursors: the phenol groups can be etherified or polymerised while the halogen positions remain available, supporting stepwise assembly of macrocyclic and polymeric architectures.
Specifications
- Brand: TCI
- Catalogue reference: D3602
- CAS number: 189039-64-3
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard laboratory research pack sizes as supplied by the manufacturer
- Storage: store according to the manufacturer's stated conditions on the product label
Handling and Storage
Store the compound in its original tightly closed container, kept in a cool, dry, and well-ventilated area away from direct sunlight, moisture, and incompatible materials. Amber glass or the manufacturer's supplied packaging is suitable for limiting light exposure, and containers should be resealed promptly after each use to avoid moisture uptake. Handle the material in a fume hood using appropriate personal protective equipment, including safety glasses, gloves, and a laboratory coat. Avoid generating or inhaling dust, and avoid contact with skin and eyes. Always consult the manufacturer's Safety Data Sheet before handling, weighing, or disposing of this material, and follow institutional waste procedures for halogenated aromatic compounds.
![4,4'-[2-(4-Bromophenyl)-2-phenylethene-1,1-diyl]diphenol (CAS 936803-69-9) - TCI B6579 - AMI Scientific](http://amiscientific.com/cdn/shop/files/TCI2510B6579.jpg?v=1768204513&width=533)
