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Bulk Order (Pyridin-4-yl)boronic acid丨CAS 1692-15-5
(Pyridin-4-yl)boronic acid (CAS 1692-15-5), also known as 4-pyridylboronic acid or pyridine-4-boronic acid, is a heteroaromatic organoboron compound featuring a boronic acid group attached to the 4-position of a pyridine ring. Its structure combines the synthetic versatility of boronic acid functionality with the nitrogen-containing heteroaromatic framework of pyridine. This combination makes it a valuable building block in organic synthesis, particularly for preparing pyridyl-substituted aromatic and heteroaromatic compounds through palladium-catalyzed cross-coupling reactions. The pyridine nitrogen also provides an additional site for coordination and functional interactions, expanding its potential applications in medicinal chemistry, materials research, and coordination chemistry.
Chemical Identifiers
| InChI | 1S/C5H6BNO2/c8-6(9)5-1-3-7-4-2-5/h1-4,8-9H |
| InChI Key | QLULGIRFKAWHOJ-UHFFFAOYSA-N |
| Smiles | C1=C(C=CN=C1)B(O)O |
| EC No. | 671-679-4 |
| MDL No. | MFCD01074545 |
| PubChem CID | 2734379 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
(Pyridin-4-yl)boronic acid is useful in medicinal chemistry for introducing a pyridin-4-yl group into complex molecular structures. Pyridine rings are common features in pharmaceutical research compounds because their nitrogen atom can influence basicity, polarity, hydrogen-bonding interactions, and aqueous solubility. Through suitable Suzuki–Miyaura coupling reactions, this compound can be used to prepare pyridyl-substituted biaryl and heteroaryl intermediates. These structures support compound library development, lead optimization, and structure–activity relationship studies. Its application is particularly relevant when researchers seek to incorporate a nitrogen-containing aromatic ring into a target molecule.
Applications in Suzuki–Miyaura Cross-Coupling Reactions
A principal application of (Pyridin-4-yl)boronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling with compatible aryl or heteroaryl halides and pseudohalides. This reaction enables the formation of carbon–carbon bonds between the pyridyl group and other aromatic fragments, providing access to substituted bipyridines, pyridyl biaryls, and more complex heteroaromatic structures. The pyridine nitrogen may coordinate with transition-metal catalysts and influence reaction performance, so catalyst, ligand, base, and solvent selection can be important when optimizing the coupling process.
Applications in Heterocyclic Compound Synthesis
The pyridine ring makes this compound particularly valuable in the preparation of nitrogen-containing heterocyclic molecules. Cross-coupling reactions can connect the pyridyl fragment to other heteroaromatic systems, enabling the synthesis of diverse molecular frameworks containing multiple nitrogen atoms. Such compounds are investigated in pharmaceutical chemistry, agrochemical research, and specialty chemical development. The para-positioned boronic acid group provides a defined attachment point, supporting the preparation of structurally varied pyridine derivatives.
Applications in Coordination Chemistry and Functional Materials
The pyridine nitrogen can act as a coordination site for suitable metal centers, making (Pyridin-4-yl)boronic acid relevant to research involving metal–ligand interactions and functional coordination compounds. Its boronic acid group provides an additional chemical handle for molecular modification and incorporation into larger structures. Pyridyl-containing aromatic compounds are also investigated in the development of organic electronic materials, luminescent systems, and supramolecular architectures. Through appropriate coupling and functionalization strategies, this compound can contribute to the preparation of extended nitrogen-containing aromatic structures.
