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Bulk Inquiry 2-Chloropyridine-4-boronic acid丨CAS 458532-96-2
2-Chloropyridine-4-boronic acid (CAS 458532-96-2), also known as 2-chloropyridin-4-ylboronic acid, is a nitrogen-containing heteroaromatic boronic acid featuring a chlorine atom at the 2-position and a boronic acid group at the 4-position of a pyridine ring. This compound combines the synthetic versatility of organoboron chemistry with the distinctive electronic and structural characteristics of a chlorinated pyridine framework. The pyridine nitrogen atom contributes molecular polarity and hydrogen-bond-accepting functionality, while the chlorine substituent provides an additional reactive position for selected chemical transformations. These features make 2-Chloropyridine-4-boronic acid a useful building block for medicinal chemistry, pharmaceutical intermediate development, heterocyclic synthesis, agrochemical research, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C5H5BClNO2/c7-5-3-4(6(9)10)1-2-8-5/h1-3,9-10H |
| InChI Key | WJYRVVDXJMJLTN-UHFFFAOYSA-N |
| Smiles | C1=C(Cl)N=CC=C1B(O)O |
| EC No. | 628-060-9 |
| MDL No. | MFCD03788416 |
| PubChem CID | 5151595 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-Chloropyridine-4-boronic acid can be used in Suzuki–Miyaura cross-coupling reactions to construct substituted pyridine derivatives and other heteroaromatic compounds. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group may react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation enables the introduction of a 2-chloropyridin-4-yl fragment into complex molecular frameworks. The chlorine substituent at the 2-position may be retained for subsequent functionalization when suitable reaction conditions are selected. However, because activated heteroaryl chlorides can also participate in certain catalytic transformations, reaction selectivity should be evaluated carefully.
Applications in Medicinal Chemistry
In medicinal chemistry, 2-Chloropyridine-4-boronic acid serves as a building block for preparing nitrogen-containing aromatic compounds and investigating structure–activity relationships. Pyridine rings are widely used in pharmaceutical research because their nitrogen atoms can influence molecular polarity, hydrogen-bonding interactions, and biological target recognition. The chlorine substituent introduces additional electronic and steric characteristics that may affect molecular properties and provide opportunities for further modification. Researchers may incorporate the 2-chloropyridin-4-yl fragment into candidate molecules during lead optimization, analog synthesis, and compound library development.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring intermediates containing a 2-chloropyridine structural unit. Its boronic acid functionality provides a route for connecting the substituted pyridine ring to compatible aromatic or heteroaromatic coupling partners. The resulting compounds may undergo further chemical transformations depending on the desired target structure. In particular, the chlorine substituent adjacent to the pyridine nitrogen can be susceptible to nucleophilic aromatic substitution under suitable conditions, allowing the introduction of selected nitrogen-, oxygen-, or sulfur-containing groups. This combination of functional groups makes the compound useful for developing multistep synthetic routes and preparing structurally diverse pharmaceutical research intermediates.
Applications in Heterocyclic Chemistry
2-Chloropyridine-4-boronic acid is particularly relevant to heterocyclic chemistry because it contains a pyridine ring with two different functional groups that can support complementary synthetic transformations. The boronic acid group enables selected carbon–carbon bond-forming reactions, while the chlorine substituent provides an additional site for chemical modification. Researchers may use this compound to prepare substituted pyridines, biheteroaryl compounds, and other nitrogen-containing aromatic structures. It may also support synthetic methodology studies focused on chemoselectivity, catalyst compatibility, and the stability of chlorinated heteroarylboronic acids.
