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Chemical Supplier Quinoline-3-boronic acid丨CAS 191162-39-7
Quinoline-3-boronic acid (CAS 191162-39-7) is a heteroaromatic organoboron compound consisting of a quinoline ring system bearing a boronic acid group at the 3-position. The quinoline framework contains a fused benzene and pyridine ring, providing a nitrogen-containing aromatic structure widely used in medicinal chemistry and organic synthesis. The boronic acid functionality enables carbon–carbon bond formation through suitable cross-coupling reactions, making this compound a useful building block for constructing substituted quinoline derivatives. Its combination of a heteroaromatic nitrogen atom and a reactive boronic acid group makes it relevant to pharmaceutical intermediate development, heterocyclic chemistry, agrochemical research, and specialty organic synthesis.
Chemical Identifiers
| InChI |
1S/C9H8BNO2/c12-10(13)8-5-7-3-1-2-4-9(7)11-6-8/h1-6,12-13H |
| InChI Key | YGDICLRMNDWZAK-UHFFFAOYSA-N |
| Smiles | OB(C1=CC2=CC=CC=C2N=C1)O |
| EC No. | 640-162-5 |
| MDL No. | MFCD02183527 |
| PubChem CID | 2734663 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
Quinoline-3-boronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing 3-aryl- and 3-heteroaryl-substituted quinoline derivatives. Under optimized palladium-catalyzed conditions, the boronic acid group can react with suitable aryl or heteroaryl halides to form new carbon–carbon bonds. This approach enables the direct incorporation of the quinolin-3-yl fragment into larger molecular frameworks. Reaction conditions may require optimization because heteroaromatic nitrogen atoms can influence catalyst coordination, while certain heteroarylboronic acids may undergo competing decomposition or protodeboronation.
Applications in Medicinal Chemistry
Quinoline derivatives are widely investigated in medicinal chemistry because the nitrogen-containing fused aromatic framework can participate in diverse molecular interactions. Quinoline-3-boronic acid provides a building block for preparing substituted quinoline research compounds with different aromatic and heteroaromatic substituents. Researchers can use it to explore how structural modifications at the 3-position affect molecular properties and interactions with biological targets. These applications include lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
Quinoline-3-boronic acid may support pharmaceutical intermediate synthesis requiring substituted quinoline structures. Through suitable cross-coupling reactions, it can be connected to selected aromatic or heteroaromatic fragments to generate advanced intermediates. The quinoline nitrogen atom contributes to the electronic properties of the resulting molecules and may provide opportunities for subsequent chemical modification. This synthetic flexibility makes the compound relevant to the development of complex nitrogen-containing aromatic structures used in pharmaceutical research.
Applications in Heterocyclic Compound Synthesis
The compound is particularly useful in heterocyclic synthesis involving fused nitrogen-containing aromatic systems. Its boronic acid group enables coupling with suitable heteroaryl halides, allowing the construction of molecules containing quinoline and additional heterocyclic rings. Such transformations can produce linked heteroaromatic frameworks with varied electronic and structural characteristics. Researchers may use these compounds as intermediates for further functionalization or as components of molecular libraries for chemical and biological evaluation.
