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High Quality 2-Fluoropyridine-5-boronic acid pinacol ester丨CAS 444120-95-0
2-Fluoropyridine-5-boronic acid pinacol ester (CAS 444120-95-0), also known as 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, is a fluorinated heteroaromatic organoboron compound featuring a fluorine atom at the 2-position and a pinacol boronate ester group at the 5-position of a pyridine ring. This compound combines the synthetic versatility of boronate esters with the electronic characteristics of a fluorinated nitrogen-containing heterocycle. The pyridine nitrogen contributes polarity and hydrogen-bond-accepting functionality, while the fluorine substituent influences the electronic properties and reactivity of the aromatic ring. These features make the compound a useful building block for medicinal chemistry, pharmaceutical intermediate development, agrochemical research, heterocyclic synthesis, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C11H15BFNO2/c1-10(2)11(3,4)16-12(15-10)8-5-6-9(13)14-7-8/h5-7H,1-4H3 |
| InChI Key | ZKSRQMCKFLGPQU-UHFFFAOYSA-N |
| Smiles | B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)F |
| EC No. | 626-822-5 |
| MDL No. | MFCD03412792 |
| PubChem CID | 12177222 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-Fluoropyridine-5-boronic acid pinacol ester is useful in Suzuki–Miyaura cross-coupling reactions for constructing substituted pyridine derivatives and other heteroaromatic compounds. Under appropriately optimized palladium-catalyzed conditions, the pinacol boronate group can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation enables the introduction of a 6-fluoropyridin-3-yl fragment, equivalently described as a 2-fluoropyridin-5-yl fragment, into more complex molecular frameworks. The fluorine substituent may remain intact under suitable coupling conditions, providing an additional site for subsequent chemical modification. Reaction optimization may be necessary because heteroarylboronate esters can exhibit substrate-dependent stability and coupling efficiency.
Applications in Medicinal Chemistry
In medicinal chemistry, 2-Fluoropyridine-5-boronic acid pinacol ester serves as a building block for preparing fluorinated nitrogen-containing aromatic compounds and exploring structure–activity relationships. Fluoropyridine fragments are frequently investigated in pharmaceutical discovery because the combination of an aromatic nitrogen atom and fluorine substitution can influence molecular polarity, electronic distribution, lipophilicity, and interactions with biological targets. The boronate ester functionality provides a convenient route for incorporating the fluoropyridine unit into diverse candidate molecules. Researchers may use this compound in lead optimization, analog synthesis, and molecular library development to investigate the effects of fluorinated heteroaromatic substitution.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring intermediates containing a fluorinated pyridine structural unit. Its boronate ester functionality enables carbon–carbon bond formation with compatible aromatic or heteroaromatic coupling partners. The resulting compounds can serve as intermediates for further chemical modification or incorporation into more complex research molecules. Because the fluorine atom is located adjacent to the pyridine nitrogen, it may participate in nucleophilic aromatic substitution under suitable conditions, allowing selected nitrogen-, oxygen-, or sulfur-containing substituents to be introduced. This combination of reactive sites provides flexibility for developing multistep synthetic routes and preparing structurally diverse pharmaceutical research intermediates.
Applications in Heterocyclic Chemistry
2-Fluoropyridine-5-boronic acid pinacol ester is particularly relevant to heterocyclic chemistry because it combines a functionalized pyridine ring with a reactive organoboron group. The pinacol boronate functionality supports selected carbon–carbon bond-forming reactions, while the fluorinated pyridine framework provides additional opportunities for molecular modification. Researchers may use this compound to prepare substituted pyridines, biheteroaryl derivatives, and other nitrogen-containing aromatic structures. It can also support synthetic methodology studies focused on catalyst compatibility, reaction selectivity, and the behavior of fluorinated heteroarylboronate esters under different reaction conditions.
