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(3-Bromo-2-fluorophenyl)boronic acid (CAS 352535-97-8) is a halogenated aromatic boronic acid containing a bromine atom at the 3-position, a fluorine atom at the 2-position, and a boronic acid group attached to the benzene ring. This combination of functional groups makes it a versatile building block for organic synthesis, medicinal chemistry, pharmaceutical intermediate development, and specialty chemical research. The boronic acid functionality is particularly useful in carbon–carbon bond-forming reactions, while the bromine and fluorine substituents provide additional opportunities for molecular modification and structure–activity relationship studies.
Chemical Identifiers
| InChI | InChI=1S/C6H5BBrFO2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,10-11H |
| InChI Key | QCLOSORNRRMFIA-UHFFFAOYSA-N |
| Smiles | FC1=C(Br)C=CC=C1B(O)O |
| EC No. | 833-561-2 |
| MDL No. | MFCD05664228 |
| PubChem CID | 16217170 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(3-Bromo-2-fluorophenyl)boronic acid can be used in Suzuki–Miyaura cross-coupling reactions to construct substituted biaryl compounds and other complex aromatic structures. Under suitable palladium-catalyzed conditions, the boronic acid group can react with compatible organic halides or pseudohalides to form new carbon–carbon bonds. The bromine substituent may be retained for subsequent functionalization when appropriate reaction conditions and coupling partners are selected. This makes the compound useful for multistep synthetic strategies requiring controlled aromatic substitution and sequential bond formation.
Applications in Medicinal Chemistry
In medicinal chemistry, (3-Bromo-2-fluorophenyl)boronic acid serves as a building block for synthesizing halogenated aromatic compounds and exploring molecular structure–activity relationships. The fluorine atom can influence electronic properties, lipophilicity, and metabolic behavior depending on the overall molecular structure, while the bromine substituent provides an additional functional handle for chemical diversification. Researchers may use this compound in lead optimization, analog synthesis, and the preparation of molecular libraries containing substituted aromatic frameworks.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs involving the preparation of complex aromatic intermediates. Its boronic acid group facilitates the introduction of a bromofluorophenyl fragment into suitable target molecules through cross-coupling chemistry. The presence of both bromine and fluorine substituents enables researchers to investigate different synthetic pathways and substitution patterns during intermediate development. It may be particularly useful in routes requiring a defined halogenated aromatic structure for further chemical transformation.
Applications in Specialty Organic Synthesis
Beyond pharmaceutical research, (3-Bromo-2-fluorophenyl)boronic acid can be used in specialty organic synthesis involving multifunctional aromatic building blocks. Its combination of boronic acid, bromine, and fluorine functionalities offers opportunities for preparing substituted biaryls, heteroaryl-containing compounds, and other structurally complex molecules. Depending on reaction selectivity and functional-group compatibility, the bromine substituent can provide an additional site for subsequent cross-coupling or other transformations.
