3-Pyridylboronic acid(cas no: 1692-25-7)

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Pyridine-3-boronic acid is a boronic acid substance that can be used in Suzuki reactions, mainly in laboratory organic synthesis and chemical pharmaceutical research and development processes.

Product Name: 3-Pyridylboronic acid

CAS No.: 1692-25-7

3-Pyridylboronic Acid (CAS: 1692-25-7) is an important organoboron reagent, primarily used in pharmaceutical synthesis, materials science, and organic synthetic chemistry. Its main functions are as follows:

1. Core Application: Suzuki–Miyaura Coupling Reaction

• Function: Acts as a pyridine ring synthon to undergo palladium-catalyzed cross-coupling with aryl halides (or aryl sulfonates), efficiently constructing biaryl structures containing a pyridine ring.

• Advantage: The pyridine ring is a common nitrogen-containing heterocycle in drugs and materials. The 3‑pyridylboronic acid exhibits favorable reactivity due to its moderate steric hindrance and is widely used in the modular assembly of complex molecules.

2. Medicinal Chemistry and Intermediate Synthesis

• Pharmaceutical Building Block: Used in the synthesis of various active molecules, such as kinase inhibitors, antitumor agents, and neuroactive drugs (e.g., EGFR inhibitors, JAK inhibitors).

• Role: The pyridine ring can enhance a molecule’s water solubility, membrane permeability, and target‑binding affinity, making it a key fragment for optimizing pharmacokinetic properties in drug design.

3. Materials Science

• Functional Materials: Used to construct pyridine‑based ligands or conjugated units in organic light‑emitting diodes (OLEDs), fluorescent sensors, and metal‑organic frameworks (MOFs).

• Ligand Chemistry: Serves as a precursor for ligands that coordinate with metal ions (e.g., Pd, Ir, Pt) to prepare catalytic or luminescent metal complexes.

4. Chemical Properties and Precautions

• Stability: Moisture‑sensitive; should be stored sealed and protected from light (recommended: dry at 2–8 °C). The boronic acid group may undergo slow hydrolysis.

• Reactivity: The pyridine nitrogen may influence reaction conditions, requiring optimization of the base and catalyst system (commonly Pd(PPh₃)₄, K₂CO₃, etc.).

• Toxicity: Irritating to eyes and skin; appropriate personal protective equipment should be worn during handling.

5. Comparison with Related Analogues

• Positional Isomers:

  • 2‑Pyridylboronic acid: The boronic acid group is ortho to the nitrogen, which can lead to intramolecular hydrogen bonding and lower reactivity.

  • 4‑Pyridylboronic acid: Para‑substituted boronic acid; higher reactivity but potentially less stable.

• Advantage of the 3‑Isomer: Balances reactivity and stability, making it one of the most widely used pyridylboronic acid isomers.

Summary

3‑Pyridylboronic acid is a key reagent in nitrogen‑containing heterocycle synthesis. Through Suzuki coupling, it enables the precise introduction of a pyridine ring, playing an indispensable role in drug discovery (especially targeted therapies), the construction of functional materials, and the synthesis of fine chemicals. Its value lies in providing an efficient, modular strategy for aryl‑ring connection, significantly simplifying the synthesis of complex pyridine‑containing molecules.

This series of related compounds

I. Pyridylboronic Acids

II. Phenylboronic Acids

III. Heterocyclic Boronic Acids

IV. Protected Forms or Derivatives

V. Functionalized Boronic Acids (Special Functional Groups)

VI. Polyboronic Acids

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