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Purchase Bulk 4-Phenoxyphenylboronic acid丨CAS 51067-38-0
4-Phenoxyphenylboronic acid, CAS 51067-38-0, is an aromatic organoboron compound consisting of a phenylboronic acid group substituted with a phenoxy group at the para position. Its molecular structure combines two aromatic rings connected through an oxygen atom, together with a reactive boronic acid functionality. This combination makes it a versatile building block for organic synthesis, particularly in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions. The phenoxy substituent provides additional structural and electronic characteristics, making the compound useful in the preparation of biaryl compounds, pharmaceutical intermediates, specialty chemicals, and functional organic materials.
Chemical Identifiers
| InChI | 1S/C12H11BO3/c14-13(15)10-6-8-12(9-7-10)16-11-4-2-1-3-5-11/h1-9,14-15H |
| InChI Key | KFXUHRXGLWUOJT-UHFFFAOYSA-N |
| Smiles | OB(O)C1=CC=C(OC2=CC=CC=C2)C=C1 |
| EC No. | 687-755-5 |
| MDL No. | MFCD00093312 |
| PubChem CID | 2734377 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
4-Phenoxyphenylboronic acid is useful in medicinal chemistry for introducing a 4-phenoxyphenyl group into more complex molecular structures. Through Suzuki–Miyaura cross-coupling with suitable aryl or heteroaryl halides, it enables the formation of carbon–carbon bonds and the construction of diverse biaryl architectures. These structural motifs are frequently investigated in pharmaceutical research, where aromatic ring systems can influence molecular conformation, lipophilicity, and interactions with biological targets. The compound therefore serves as a valuable intermediate for drug discovery programs and the preparation of specialized pharmaceutical building blocks.
Applications in Biaryl and Heteroaryl Synthesis
The boronic acid group makes this compound suitable for cross-coupling reactions with a range of compatible organic electrophiles. By selecting different aryl or heteroaryl coupling partners, chemists can prepare compounds containing the 4-phenoxyphenyl structural unit. These products can be further modified to introduce additional functional groups or extend the aromatic framework. This versatility is valuable in synthetic chemistry, particularly for building structurally diverse molecular libraries and developing multi-step synthetic routes.
Applications in Functional Organic Materials
The two aromatic rings connected by an ether linkage provide a useful structural motif for the development of functional organic compounds. 4-Phenoxyphenylboronic acid can be used to introduce this motif into larger conjugated or aromatic molecular frameworks through cross-coupling chemistry. The resulting compounds may be explored in organic electronic materials, optical materials, and other advanced material research. Its ability to connect with different aromatic partners allows researchers to adjust molecular structure and investigate how substituent patterns affect material properties.
Applications in Specialty Chemical Development
This compound can also support the synthesis of specialty chemicals requiring substituted aromatic structures. The phenoxy group provides an ether-linked aromatic segment, while the boronic acid functionality offers a convenient route for carbon–carbon bond construction. These features make it useful for preparing customized intermediates, functional aromatic derivatives, and compounds intended for further chemical modification. Its role as a building block is particularly relevant when a synthetic target requires both an extended aromatic structure and a defined substitution pattern.
