Cas no 1366482-40-7 (2,3-Difluoropyridine-5-boronic acid)

2,3-Difluoropyridine-5-boronic acid is a fluorinated pyridine boronic acid derivative commonly employed as a versatile building block in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. The presence of fluorine substituents enhances its reactivity and stability, making it valuable for constructing complex heterocyclic frameworks. The boronic acid functional group facilitates efficient coupling with aryl or vinyl halides, enabling the synthesis of biaryl or styrenyl compounds. Its structural features are advantageous in pharmaceutical and agrochemical research, where fluorinated pyridines are often key motifs. The compound is typically handled under inert conditions due to the sensitivity of the boronic acid moiety to protodeboronation.
2,3-Difluoropyridine-5-boronic acid structure
1366482-40-7 structure
Product Name:2,3-Difluoropyridine-5-boronic acid
CAS No:1366482-40-7
MF:C5H4BF2NO2
MW:158.898568153381
MDL:MFCD21609554
CID:1035441
PubChem ID:70699821
Update Time:2025-06-26

2,3-Difluoropyridine-5-boronic acid Chemical and Physical Properties

Names and Identifiers

    • (5,6-Difluoropyridin-3-yl)boronic acid
    • 2,3-Difluoropyridine-5-boronic acid
    • MDL: MFCD21609554
    • Inchi: 1S/C5H4BF2NO2/c7-4-1-3(6(10)11)2-9-5(4)8/h1-2,10-11H
    • InChI Key: DMQCLRPLFKDGQN-UHFFFAOYSA-N
    • SMILES: FC1=C(N=CC(B(O)O)=C1)F

Computed Properties

  • Exact Mass: 159.03000
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1

Experimental Properties

  • PSA: 53.35000
  • LogP: -0.96040

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Additional information on 2,3-Difluoropyridine-5-boronic acid

2,3-Difluoropyridine-5-boronic acid: A Versatile Building Block in Modern Pharmaceutical Synthesis

2,3-Difluoropyridine-5-boronic acid (CAS No. 1366482-40-7) is a highly versatile and valuable compound in the field of pharmaceutical and organic synthesis. This compound, characterized by its unique structural features, has gained significant attention due to its potential applications in the development of novel drugs and materials. The presence of both difluoro and boronic acid functionalities provides a rich platform for a wide range of chemical transformations, making it an essential reagent in modern synthetic chemistry.

The difluoro substitution on the pyridine ring imparts unique electronic and steric properties to the molecule, which can influence its reactivity and selectivity in various chemical reactions. The boronic acid group, on the other hand, is a well-known functional group that can participate in Suzuki-Miyaura coupling reactions, a widely used method for the formation of carbon-carbon bonds. This combination of functionalities makes 2,3-Difluoropyridine-5-boronic acid an ideal building block for the synthesis of complex molecules with diverse biological activities.

Recent research has highlighted the importance of 2,3-Difluoropyridine-5-boronic acid in the development of new pharmaceuticals. For instance, a study published in the Journal of Medicinal Chemistry demonstrated the use of this compound as a key intermediate in the synthesis of potent inhibitors of specific enzymes involved in various diseases. The ability to fine-tune the electronic properties of the pyridine ring through fluorination has been shown to enhance the potency and selectivity of these inhibitors, making them promising candidates for drug development.

In addition to its applications in medicinal chemistry, 2,3-Difluoropyridine-5-boronic acid has also found use in materials science. The boronic acid group can be readily converted into other functional groups through various chemical transformations, such as esterification or coupling reactions. This versatility has led to its use in the synthesis of advanced materials with tailored properties, including polymers and coordination complexes.

The synthesis of 2,3-Difluoropyridine-5-boronic acid typically involves a multi-step process that includes the formation of the difluoro pyridine ring followed by the introduction of the boronic acid functionality. One common approach involves the reaction of 2,3-difluoro-5-chloropyridine with boronic acid derivatives under appropriate conditions. The choice of reagents and reaction conditions is crucial for achieving high yields and purity levels, which are essential for downstream applications.

From a safety and handling perspective, 2,3-Difluoropyridine-5-boronic acid should be stored under dry conditions and handled with care to avoid exposure to moisture or air. The compound is generally stable under standard laboratory conditions but may require special precautions when used in large-scale processes or industrial settings.

In conclusion, 2,3-Difluoropyridine-5-boronic acid (CAS No. 1366482-40-7) is a powerful and flexible reagent that continues to play a crucial role in modern synthetic chemistry. Its unique combination of difluoro and boronic acid functionalities makes it an indispensable tool for researchers working on the development of new drugs and advanced materials. As research in this area progresses, it is likely that new applications and synthetic strategies will emerge, further expanding the utility and impact of this important compound.

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