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Benzo[b]furan-2-boronic acid (CAS 98437-24-2), also known as benzofuran-2-boronic acid, is a heteroaromatic organoboron compound featuring a boronic acid group attached to the 2-position of a benzofuran ring. Its fused aromatic structure contains an oxygen heteroatom and provides a rigid, conjugated molecular framework. Combined with the versatile boronic acid functionality, this compound is a valuable building block for pharmaceutical intermediates, medicinal chemistry, heterocyclic synthesis, and functional organic materials research.
Chemical Identifiers
| InChI | 1S/C8H7BO3/c10-9(11)8-5-6-3-1-2-4-7(6)12-8/h1-5,10-11H |
| InChI Key |
PKRRNTJIHGOMRC-UHFFFAOYSA-N |
| Smiles | OB(C1=CC2=CC=CC=C2O1)O |
| EC No. | 671-849-8 |
| MDL No. | MFCD00236019 |
| PubChem CID | 2776266 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
Benzo[b]furan-2-boronic acid is a useful heteroaryl coupling partner in Suzuki–Miyaura cross-coupling reactions. Under suitable palladium-catalyzed conditions, it can react with compatible aryl or heteroaryl halides to form carbon–carbon bonds, enabling the preparation of substituted benzofuran derivatives and biheteroaryl compounds. These transformations provide an effective route for incorporating the benzofuran-2-yl fragment into complex molecular structures.
Applications in Pharmaceutical Intermediate Synthesis
Benzofuran derivatives are important structural motifs in pharmaceutical research and the development of bioactive compounds. Benzo[b]furan-2-boronic acid provides a convenient building block for introducing the benzofuran ring into aromatic and heteroaromatic frameworks. Its coupling functionality supports multistep synthesis and the preparation of advanced intermediates for pharmaceutical research.
Applications in Medicinal Chemistry
In medicinal chemistry, the benzofuran scaffold is valued for its rigid aromatic structure and potential to participate in diverse molecular interactions. Benzo[b]furan-2-boronic acid enables researchers to incorporate this oxygen-containing heterocyclic unit into candidate molecules through suitable cross-coupling reactions. It is relevant to analog synthesis, lead optimization, and structure–activity relationship studies involving benzofuran-containing compounds.
Applications in Heterocyclic Compound Synthesis
This compound is particularly useful for preparing substituted benzofurans and more complex heterocyclic structures. Its boronic acid group provides a versatile synthetic handle for connecting the benzofuran ring with other aromatic and heteroaromatic fragments. The resulting compounds can serve as intermediates for further functionalization, cyclization, and the construction of structurally diverse heterocyclic systems.
