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Bulk Supplier 8-Quinolineboronic acid丨CAS 86-58-8
8-Quinolineboronic acid (CAS 86-58-8) is a heteroaromatic organoboron compound featuring a boronic acid group attached to the 8-position of a quinoline ring system. Its molecular structure combines the reactivity of boronic acid functionality with the fused nitrogen-containing aromatic framework of quinoline. This makes it a useful building block in organic synthesis, particularly for preparing quinoline-substituted biaryl and heteroaryl compounds through suitable transition-metal-catalyzed coupling reactions. The quinoline nitrogen also provides a potential coordination site, adding further interest to this compound in medicinal chemistry, coordination chemistry, and functional materials research.
Chemical Identifiers
| InChI | 1S/C9H8BNO2/c12-10(13)8-5-1-3-7-4-2-6-11-9(7)8/h1-6,12-13H |
| InChI Key | KXJJSKYICDAICD-UHFFFAOYSA-N |
| Smiles | OB(C1=C2N=CC=CC2=CC=C1)O |
| EC No. | 626-756-7 |
| MDL No. | MFCD01114698 |
| PubChem CID | 2734380 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
8-Quinolineboronic acid can be used to introduce a quinolin-8-yl fragment into complex molecular structures. Quinoline is an important heterocyclic scaffold in medicinal chemistry and pharmaceutical research because its fused aromatic framework and nitrogen atom offer opportunities to explore molecular recognition, electronic properties, and biological activity. Through suitable Suzuki–Miyaura cross-coupling reactions with compatible aryl or heteroaryl electrophiles, this compound can support the preparation of quinoline-containing intermediates and research compounds. These products may be used in lead optimization, structure–activity relationship studies, and the development of structurally diverse pharmaceutical candidates.
Applications in Suzuki–Miyaura Cross-Coupling Reactions
A key synthetic application of 8-Quinolineboronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling. Its boronic acid group can react with suitable aryl or heteroaryl halides and pseudohalides to form carbon–carbon bonds, enabling the preparation of substituted quinoline derivatives and extended aromatic structures. The quinoline nitrogen may coordinate with transition-metal catalysts and influence reaction performance, making catalyst, ligand, base, and solvent selection important during optimization. This compound provides a useful route for incorporating a quinoline unit into biaryl and heteroaryl molecular frameworks.
Applications in Heterocyclic Compound Synthesis
The fused quinoline structure makes this compound particularly relevant to the synthesis of complex nitrogen-containing aromatic molecules. Cross-coupling reactions can connect the quinoline fragment with other aromatic or heteroaromatic groups, enabling the preparation of compounds with extended conjugation and diverse structural features. Such molecules are investigated in pharmaceutical chemistry, agrochemical research, and specialty chemical development. The defined attachment point at the 8-position also provides a useful basis for designing quinoline derivatives with different substitution patterns.
Applications in Coordination Chemistry and Functional Materials
The nitrogen atom in the quinoline ring can participate in coordination with suitable metal centers, making quinoline-containing compounds useful in coordination chemistry and metal–ligand research. 8-Quinolineboronic acid offers an additional boronic acid functionality for molecular modification and incorporation into more complex structures. Its derivatives may be explored in the development of metal complexes, luminescent systems, molecular sensors, and functional organic materials. The combination of a coordinating nitrogen atom and a reactive boronic acid group provides flexibility for designing multifunctional molecular architectures.
