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High Purity 5-Chloropyridine-3-boronic acid丨CAS 872041-85-5
5-Chloropyridine-3-boronic acid (CAS 872041-85-5) is a nitrogen-containing heteroaromatic boronic acid featuring a chlorine atom at the 5-position and a boronic acid group at the 3-position of a pyridine ring. This compound combines the synthetic versatility of organoboron chemistry with the distinctive electronic properties of a chlorinated pyridine framework. The pyridine nitrogen atom contributes polarity and hydrogen-bond-accepting functionality, while the chlorine substituent provides an additional site for selected chemical transformations. These characteristics make 5-Chloropyridine-3-boronic acid a useful building block for medicinal chemistry, pharmaceutical intermediate development, agrochemical research, heterocyclic synthesis, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C5H5BClNO2/c7-5-1-4(6(9)10)2-8-3-5/h1-3,9-10H |
| InChI Key | NJXYBTMCTZAUEE-UHFFFAOYSA-N |
| Smiles | B(C1=CC(=CN=C1)Cl)(O)O |
| EC No. | 677-212-0 |
| MDL No. | MFCD06798243 |
| PubChem CID | 20111877 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
5-Chloropyridine-3-boronic acid can be used in Suzuki–Miyaura cross-coupling reactions to construct carbon–carbon bonds between pyridine and other aromatic or heteroaromatic fragments. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group may react with compatible aryl or heteroaryl halides and pseudohalides to form substituted pyridine derivatives. This transformation enables the introduction of a 5-chloropyridin-3-yl fragment into more complex molecular frameworks. The chlorine substituent may be retained for subsequent functionalization when suitable reaction conditions are selected, making the compound useful for sequential synthesis strategies. Reaction optimization may be necessary because heteroarylboronic acids can exhibit substrate-dependent stability and coupling efficiency.
Applications in Medicinal Chemistry
In medicinal chemistry, 5-Chloropyridine-3-boronic acid serves as a building block for preparing nitrogen-containing aromatic compounds and investigating structure–activity relationships. Pyridine rings are frequently incorporated into pharmaceutical research molecules because their nitrogen atoms can influence molecular polarity, solubility, and interactions with biological targets. The chlorine substituent introduces additional electronic and steric characteristics that may affect molecular recognition and physicochemical behavior. Through suitable coupling reactions, researchers can incorporate the 5-chloropyridin-3-yl fragment into candidate compounds for analog synthesis, lead optimization, and molecular library development.
Applications in Pharmaceutical Intermediate Synthesis
5-Chloropyridine-3-boronic acid may support pharmaceutical research programs requiring intermediates containing a chlorinated pyridine structural unit. Its boronic acid functionality provides a route for connecting the pyridine ring to compatible aromatic or heteroaromatic coupling partners. The resulting products can serve as intermediates for further chemical modification or incorporation into more complex molecular structures. Depending on the synthetic strategy, the chlorine substituent may provide an additional site for selected cross-coupling or substitution reactions. This combination of functional groups makes the compound useful for developing multistep synthetic pathways and preparing structurally diverse pharmaceutical research intermediates.
Applications in Heterocyclic Chemistry
This compound is particularly relevant to heterocyclic chemistry because it contains a pyridine ring with two different reactive substituents. The boronic acid group supports suitable carbon–carbon bond-forming reactions, while the chlorine substituent can provide opportunities for further functionalization. Researchers may use 5-Chloropyridine-3-boronic acid to prepare substituted pyridines, biheteroaryl compounds, and other nitrogen-containing aromatic structures. It may also support synthetic methodology studies focused on reaction selectivity, catalyst compatibility, and the behavior of halogenated heteroarylboronic acids.
