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Quality Supplier Biphenyl-2-boronic acid丨CAS 4688-76-0
Biphenyl-2-boronic acid (CAS 4688-76-0) is an aromatic organoboron compound featuring a boronic acid group attached to the 2-position of a biphenyl structure. Its molecular framework combines two linked benzene rings with a reactive boronic acid functionality, making it a useful building block in organic synthesis. The boronic acid group can participate in palladium-catalyzed cross-coupling reactions, particularly Suzuki–Miyaura coupling, enabling the formation of new carbon–carbon bonds. Its ortho-substituted biphenyl structure also provides a valuable structural motif for developing complex aromatic compounds and functional materials.
Chemical Identifiers
| InChI | 1S/C12H11BO2/c14-13(15)12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,14-15H |
| InChI Key | HYCYKHYFIWHGEX-UHFFFAOYSA-N |
| Smiles | C1=C(C(=CC=C1)B(O)O)C2=CC=CC=C2 |
| EC No. | 670-315-1 |
| MDL No. | MFCD00136929 |
| PubChem CID | 4589187 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
Biphenyl-2-boronic acid can be used as an intermediate in the preparation of biaryl compounds relevant to pharmaceutical research and medicinal chemistry. Through Suzuki–Miyaura coupling with suitable aryl or heteroaryl halides, it enables the introduction of a biphenyl unit into molecular structures. This approach supports the synthesis of compound libraries for structure–activity relationship studies, lead optimization, and the development of new pharmaceutical intermediates. Its specific ortho-substitution pattern can also influence molecular conformation and steric properties, making it useful when researchers need to investigate how aromatic geometry affects biological activity.
Applications in Organic Synthesis and Cross-Coupling Reactions
One of the principal applications of Biphenyl-2-boronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling. It can react with aryl halides or other suitable electrophilic coupling partners to produce extended biaryl structures. The reaction is widely used in modern organic synthesis because it offers a practical route to carbon–carbon bond formation under a range of reaction conditions. The resulting products can serve as intermediates for further functionalization, including halogenation, oxidation, substitution, and the introduction of additional aromatic or heteroaromatic groups.
Applications in Functional Materials Research
The biphenyl framework is an important structural element in the design of organic functional materials. Biphenyl-2-boronic acid provides a route to compounds with extended aromatic systems that may be explored in organic electronics, optoelectronic materials, and advanced polymers. Researchers can use it to introduce biphenyl units into molecular architectures and investigate their effects on conjugation, molecular packing, thermal behavior, and material properties. Its boronic acid functionality offers a convenient synthetic handle for building more complex aromatic structures.
Applications in Chemical Research and Method Development
Biphenyl-2-boronic acid is also useful in academic and industrial research focused on developing new catalytic systems and synthetic methodologies. Its ortho-substituted structure provides a useful substrate for studying steric effects, catalyst performance, and reaction selectivity in cross-coupling chemistry. It can support investigations into reaction optimization, ligand selection, solvent effects, and the preparation of structurally diverse biaryl compounds.
