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High Purity 4-(2-Naphthyl)phenylboronic Acid丨CAS 918655-03-5
4-(2-Naphthyl)phenylboronic acid (CAS 918655-03-5), also known as 4-(naphthalen-2-yl)phenylboronic acid, is an aromatic organoboron compound containing a naphthalene ring connected to a phenyl group bearing a boronic acid functionality at the para-position. Its extended aromatic framework combines the structural characteristics of naphthalene with the synthetic versatility of an arylboronic acid. This makes the compound a useful building block for preparing complex aromatic molecules, conjugated organic structures, and advanced chemical intermediates. It is particularly relevant to OLED materials research, organic semiconductor development, Suzuki–Miyaura cross-coupling chemistry, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C16H13BO2/c18-17(19)16-9-7-13(8-10-16)15-6-5-12-3-1-2-4-14(12)11-15/h1-11,18-19H |
| InChI Key | ICQAKBYFBIWELX-UHFFFAOYSA-N |
| Smiles | B(C1=CC=C(C=C1)C2=CC3=CC=CC=C3C=C2)(O)O |
| EC No. | 805-884-9 |
| MDL No. | MFCD09260454 |
| PubChem CID | 45382258 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
The boronic acid functionality of 4-(2-Naphthyl)phenylboronic acid enables its use in Suzuki–Miyaura cross-coupling reactions. Under appropriate palladium-catalyzed conditions, the compound can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation provides a practical route for introducing a naphthyl-substituted phenyl fragment into complex aromatic frameworks. The reaction is particularly useful for preparing extended biaryl and polyaryl systems, functionalized aromatic intermediates, and compounds designed for electronic materials research. Reaction conditions may require optimization depending on the coupling partner, solvent system, and solubility characteristics of the substrates.
Applications in OLED Materials Research
4-(2-Naphthyl)phenylboronic acid is a useful intermediate for synthesizing aromatic compounds investigated in organic light-emitting diode (OLED) technology. Naphthalene-containing structures are frequently explored in organic electronic materials because their aromatic frameworks can influence molecular rigidity, electronic properties, and intermolecular interactions. Through suitable cross-coupling reactions, this compound can be incorporated into larger molecular architectures containing additional aromatic or heteroaromatic units. Researchers may use the resulting derivatives to investigate their potential as host materials, charge-transport materials, or other functional components of OLED devices. Their suitability depends on the electronic structure, thermal properties, and experimentally measured performance of the final compounds.
Applications in Organic Semiconductor Research
4-(2-Naphthyl)phenylboronic acid may support the synthesis of organic semiconductor compounds containing extended aromatic structures. The naphthalene and phenyl units provide a defined molecular framework that can influence electronic interactions and solid-state organization when incorporated into larger molecules. Researchers may use this building block to prepare candidate materials for investigating charge transport, molecular packing, energy-level alignment, and other semiconductor-related characteristics. By connecting the naphthyl-substituted phenyl fragment with selected aromatic or heteroaromatic groups, different molecular architectures can be developed for systematic evaluation.
Applications in Photophysical and Luminescent Materials Research
This compound can serve as a synthetic precursor for preparing aromatic molecules intended for photophysical and luminescence studies. The naphthalene framework provides an aromatic chromophore that can influence absorption and emission behavior in appropriately designed compounds. Through suitable coupling reactions, 4-(2-Naphthyl)phenylboronic acid can be incorporated into larger conjugated structures containing electron-donating or electron-accepting substituents. Researchers may investigate the resulting derivatives for fluorescence characteristics, excited-state behavior, and other optical properties. Potential applications depend on the complete molecular structure and measured photophysical performance.
