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Supply Bulk 2-Methylpyridine-4-boronic acid丨CAS 579476-63-4
2-Methylpyridine-4-boronic acid (CAS 579476-63-4), also known as 2-methylpyridin-4-ylboronic acid, is a nitrogen-containing heteroaromatic boronic acid featuring a methyl group 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 substituted pyridine framework. The pyridine nitrogen atom contributes polarity and hydrogen-bond-accepting functionality, while the methyl substituent influences the steric and electronic environment of the aromatic ring. These features make 2-Methylpyridine-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/C6H8BNO2/c1-5-4-6(7(9)10)2-3-8-5/h2-4,9-10H,1H3 |
| InChI Key | UFYBTLOLWSABAU-UHFFFAOYSA-N |
| Smiles | CC1=NC=CC(B(O)O)=C1 |
| EC No. | 640-238-8 |
| MDL No. | MFCD03095364 |
| PubChem CID | 4192664 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-Methylpyridine-4-boronic acid can be used in Suzuki–Miyaura cross-coupling reactions to prepare 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-methylpyridin-4-yl fragment into complex molecular frameworks. Such reactions are useful for preparing biaryl, arylpyridine, and biheteroaryl compounds. Because heteroarylboronic acids can exhibit substrate-dependent stability and coupling efficiency, careful selection of the catalyst, base, solvent, and reaction conditions may be necessary.
Applications in Medicinal Chemistry
In medicinal chemistry, 2-Methylpyridine-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 methyl substituent at the 2-position introduces an additional structural feature that may affect lipophilicity, steric interactions, and molecular conformation. Researchers may incorporate the 2-methylpyridin-4-yl fragment into suitable 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-methylpyridine 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 can serve as intermediates for further chemical modification or incorporation into more complex molecular structures. The combination of a pyridine nitrogen atom and a methyl substituent provides a defined framework for exploring synthetic routes and preparing structurally diverse pharmaceutical research intermediates.
Applications in Heterocyclic Chemistry
2-Methylpyridine-4-boronic acid is particularly relevant to heterocyclic chemistry because it contains a functionalized pyridine ring suitable for further molecular elaboration. The boronic acid group supports selected carbon–carbon bond-forming reactions, while the pyridine nitrogen contributes distinctive electronic characteristics to the aromatic system. Researchers may use this compound to prepare substituted pyridines, biheteroaryl derivatives, and other nitrogen-containing aromatic molecules. It may also support synthetic methodology studies involving heteroarylboronic acid stability, catalyst compatibility, and reaction selectivity.
