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China Supplier (2-Bromophenyl)boronic acid丨CAS 244205-40-1
(2-Bromophenyl)boronic acid (CAS 244205-40-1), also known as 2-bromophenylboronic acid or o-bromophenylboronic acid, is a halogenated aromatic organoboron compound containing a bromine atom and a boronic acid group at adjacent positions on a benzene ring. Its structure combines the reactivity of an aryl bromide with the synthetic versatility of a boronic acid, providing two functional sites for chemical modification. This makes the compound a useful building block for medicinal chemistry, pharmaceutical intermediate development, cross-coupling chemistry, heterocyclic synthesis, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C6H6BBrO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H |
| InChI Key | PLVCYMZAEQRYHJ-UHFFFAOYSA-N |
| Smiles | C1=CC=CC(=C1B(O)O)Br |
| EC No. | 678-199-4 |
| MDL No. | MFCD01114672 |
| PubChem CID | 2773294 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(2-Bromophenyl)boronic acid is useful in Suzuki–Miyaura cross-coupling chemistry for constructing substituted biaryl and aryl–heteroaryl compounds. The boronic acid group can react with compatible organic halides under appropriately optimized palladium-catalyzed conditions to form carbon–carbon bonds. The bromine substituent may also serve as a coupling site in a separate reaction. Because both functionalities can participate in cross-coupling chemistry, controlling chemoselectivity is essential. Suitable catalyst systems, coupling partners, and reaction conditions can enable the preparation of complex aromatic structures through sequential transformations.
Applications in Medicinal Chemistry
In medicinal chemistry, (2-Bromophenyl)boronic acid serves as a building block for preparing substituted aromatic compounds and exploring structure–activity relationships. The ortho-brominated phenyl framework provides opportunities to modify molecular geometry, steric interactions, and aromatic substitution patterns. Researchers may use this compound to synthesize biaryl derivatives, functionalized aromatic intermediates, and molecular libraries for pharmaceutical discovery. Its two reactive functional groups offer flexibility when developing synthetic routes to structurally diverse research compounds.
Applications in Pharmaceutical Intermediate Synthesis
(2-Bromophenyl)boronic acid may support pharmaceutical intermediate synthesis involving multifunctional aromatic building blocks. The boronic acid group enables selected carbon–carbon bond-forming reactions, while the bromine atom provides an additional site for subsequent catalytic functionalization. This allows the preparation of aromatic intermediates containing different substituents at adjacent positions. Such structures can be useful in multistep synthesis, particularly when a target molecule requires controlled introduction of multiple aromatic fragments.
Applications in Functional Materials Research
(2-Bromophenyl)boronic acid may also be employed in the synthesis of aromatic intermediates for functional materials research. Its two reactive sites enable the construction of extended aromatic frameworks through selected coupling reactions. The resulting compounds may be investigated for electronic, optical, thermal, or structural properties, depending on their molecular architecture. Such synthetic flexibility is relevant to exploratory research involving organic electronic materials, conjugated compounds, and specialty molecular materials.
