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Selected 1,1'-Biphenyl-4-yl-boronic acid丨CAS 5122-94-1
1,1'-Biphenyl-4-yl-boronic acid (CAS 5122-94-1), also known as 4-biphenylboronic acid or [1,1'-biphenyl]-4-ylboronic acid, is an arylboronic acid featuring a biphenyl structure with a boronic acid group attached at the para position of one phenyl ring. Its extended aromatic framework and reactive boronic acid functionality make it a valuable building block for constructing larger conjugated molecules and complex biaryl structures. It is particularly useful in Suzuki–Miyaura cross-coupling reactions, enabling the introduction of a biphenyl unit into aromatic and heteroaromatic compounds. Its applications span pharmaceutical research, organic electronics, functional materials, and advanced organic synthesis.
Chemical Identifiers
| InChI | 1S/C12H11BO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,14-15H |
| InChI Key | XPEIJWZLPWNNOK-UHFFFAOYSA-N |
| Smiles | C2=C(C1=CC=CC=C1)C=CC(=C2)B(O)O |
| EC No. | 675-084-0 |
| MDL No. | MFCD00093311 |
| PubChem CID | 151253 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
1,1'-Biphenyl-4-yl-boronic acid is used to introduce a biphenyl structural motif into pharmaceutical intermediates and research compounds. Through palladium-catalyzed Suzuki–Miyaura coupling with suitable aryl or heteroaryl halides, it enables the formation of new carbon–carbon bonds and the preparation of structurally diverse biaryl and heterobiaryl molecules. Biphenyl frameworks are frequently explored in medicinal chemistry because their aromatic surfaces and conformational characteristics can influence molecular interactions and physicochemical properties. This reagent supports the synthesis of candidate structures, intermediate diversification, and structure–activity relationship studies during drug discovery and development.
Applications in Organic Synthesis and Cross-Coupling Reactions
A principal application of 1,1'-Biphenyl-4-yl-boronic acid is Suzuki–Miyaura cross-coupling. In the presence of a suitable palladium catalyst and base, its biphenyl group can be transferred to an organic coupling partner, such as an aryl or heteroaryl halide. This provides an efficient route to terphenyl derivatives, extended biaryl compounds, and other polyaromatic structures. The reaction offers flexibility in combining different aromatic building blocks, allowing chemists to construct complex molecular frameworks with controlled substitution patterns. The compound is therefore useful in multi-step synthesis, catalyst development, and the preparation of advanced aromatic intermediates.
Applications in Organic Electronics and Optoelectronic Materials
Extended aromatic structures are important in organic electronic and optoelectronic research because their conjugated systems can influence charge transport, light absorption, and emission characteristics. 1,1'-Biphenyl-4-yl-boronic acid provides a practical route to incorporating biphenyl units into larger molecular architectures through cross-coupling chemistry. The resulting compounds may be investigated as building blocks or intermediates for organic light-emitting diode (OLED) materials, organic semiconductors, conjugated oligomers, and other functional electronic materials. By coupling this reagent with different aromatic or heteroaromatic partners, researchers can modify molecular conjugation and explore structure–property relationships.
Applications in Liquid Crystal and Advanced Functional Materials Research
Biphenyl-based structures are widely investigated in liquid crystal and functional material chemistry because their aromatic frameworks can contribute to molecular rigidity and anisotropic properties. 1,1'-Biphenyl-4-yl-boronic acid can be used to prepare extended aromatic compounds for evaluating molecular shape, substitution effects, and phase behavior. Its cross-coupling functionality also enables the introduction of different aromatic groups, supporting the design of structurally varied molecules for liquid crystal research and other advanced material applications.
