Cas no 1190423-61-0 ((5-(Benzyloxy)pyridin-3-yl)boronic acid)

(5-(Benzyloxy)pyridin-3-yl)boronic acid is a boronic acid derivative featuring a benzyloxy-substituted pyridine core, commonly employed as a versatile intermediate in Suzuki-Miyaura cross-coupling reactions. Its boronic acid functional group enables efficient palladium-catalyzed aryl-aryl bond formation, making it valuable in pharmaceutical and materials science research. The benzyloxy group enhances solubility and stability while allowing further functionalization under mild conditions. This compound is particularly useful in constructing complex heterocyclic frameworks due to its compatibility with diverse reaction conditions. Careful handling under inert atmospheres is recommended to prevent boronic acid degradation. Its well-defined reactivity profile and synthetic flexibility make it a reliable choice for targeted organic synthesis applications.
(5-(Benzyloxy)pyridin-3-yl)boronic acid structure
1190423-61-0 structure
Product Name:(5-(Benzyloxy)pyridin-3-yl)boronic acid
CAS No:1190423-61-0
MF:C12H12BNO3
MW:229.039583206177
MDL:MFCD07375003
CID:1026292
PubChem ID:53398533
Update Time:2025-05-21

(5-(Benzyloxy)pyridin-3-yl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • (5-(Benzyloxy)pyridin-3-yl)boronic acid
    • 5-Benzyloxypyridine-3-boronic acid
    • (5-phenylmethoxypyridin-3-yl)boronic acid
    • 3-Benzyloxy-pyridine-5-boronic acid
    • 5-(Benzyloxy)pyridine-3-boronic acid
    • 5-BENZYLOXY-3-PYRIDINYLBORONIC ACID
    • 5-Benzyloxy-3-pyridinylboronicacid
    • A892675
    • [5-(benzyloxy)pyridin-3-yl]boronic acid
    • MFCD07375003
    • SY224119
    • CS-0174876
    • IGKYPUBWQHKLLC-UHFFFAOYSA-N
    • AB40922
    • AKOS013526879
    • DTXSID00694488
    • PS-12948
    • SCHEMBL2182223
    • 1190423-61-0
    • CHEMBL3417360
    • (5-BENZYLOXY-3-PYRIDYL)BORONIC ACID
    • FD10206
    • FT-0768514
    • Boronic acid, B-[5-(phenylmethoxy)-3-pyridinyl]-
    • 5-(BENZYLOXY)PYRIDIN-3-YLBORONIC ACID
    • DB-061513
    • MDL: MFCD07375003
    • Inchi: 1S/C12H12BNO3/c15-13(16)11-6-12(8-14-7-11)17-9-10-4-2-1-3-5-10/h1-8,15-16H,9H2
    • InChI Key: IGKYPUBWQHKLLC-UHFFFAOYSA-N
    • SMILES: O(C1C=NC=C(B(O)O)C=1)CC1C=CC=CC=1

Computed Properties

  • Exact Mass: 229.09100
  • Monoisotopic Mass: 229.0910234g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 4
  • Complexity: 222
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 62.6?2

Experimental Properties

  • PSA: 62.58000
  • LogP: 0.34040

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Additional information on (5-(Benzyloxy)pyridin-3-yl)boronic acid

Introduction to (5-(Benzyloxy)pyridin-3-yl)boronic acid (CAS No. 1190423-61-0)

(5-(Benzyloxy)pyridin-3-yl)boronic acid (CAS No. 1190423-61-0) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound is characterized by its unique structural features, which include a pyridine ring substituted with a benzyloxy group and a boronic acid moiety. These features endow the compound with a range of chemical properties that make it valuable for various applications, particularly in the development of new pharmaceuticals and advanced materials.

The benzyloxy substituent on the pyridine ring imparts enhanced solubility and stability to the molecule, making it suitable for use in aqueous environments. The boronic acid group, on the other hand, is known for its ability to form stable complexes with various functional groups, including alcohols, amines, and carboxylic acids. This property is particularly useful in cross-coupling reactions, where (5-(Benzyloxy)pyridin-3-yl)boronic acid can serve as a valuable building block for the synthesis of complex organic molecules.

Recent advancements in synthetic methodologies have further expanded the utility of (5-(Benzyloxy)pyridin-3-yl)boronic acid. For instance, a study published in the *Journal of Organic Chemistry* demonstrated the efficient synthesis of this compound using palladium-catalyzed reactions. The researchers reported high yields and excellent selectivity, highlighting the potential of this method for large-scale production. This development is particularly significant for pharmaceutical companies that require large quantities of high-purity intermediates for drug discovery and development.

In the context of medicinal chemistry, (5-(Benzyloxy)pyridin-3-yl)boronic acid has shown promise as a lead compound for the development of novel therapeutic agents. Its structural features make it an attractive candidate for targeting specific biological pathways. For example, a recent study published in *Bioorganic & Medicinal Chemistry* explored the use of this compound as a scaffold for designing inhibitors of protein-protein interactions (PPIs). The researchers found that derivatives of (5-(Benzyloxy)pyridin-3-yl)boronic acid exhibited potent inhibitory activity against several PPIs involved in cancer progression and inflammatory diseases.

Moreover, (5-(Benzyloxy)pyridin-3-yl)boronic acid has been investigated for its potential applications in materials science. Its ability to form stable complexes with various functional groups makes it an excellent candidate for the synthesis of functional polymers and nanomaterials. A study published in *Advanced Materials* reported the successful preparation of polymeric nanoparticles using (5-(Benzyloxy)pyridin-3-yl)boronic acid as a cross-linking agent. These nanoparticles exhibited enhanced stability and biocompatibility, making them suitable for drug delivery and imaging applications.

The environmental impact of (5-(Benzyloxy)pyridin-3-yl)boronic acid has also been studied to ensure its safe use in various applications. Research published in *Environmental Science & Technology* evaluated the biodegradability and toxicity of this compound. The results indicated that (5-(Benzyloxy)pyridin-3-yl)boronic acid is biodegradable under aerobic conditions and exhibits low toxicity to aquatic organisms, making it an environmentally friendly choice for industrial processes.

In conclusion, (5-(Benzyloxy)pyridin-3-yl)boronic acid (CAS No. 1190423-61-0) is a multifaceted compound with significant potential in medicinal chemistry and materials science. Its unique structural features and chemical properties make it a valuable intermediate for the synthesis of complex organic molecules, therapeutic agents, and functional materials. Ongoing research continues to uncover new applications and optimize synthetic methodologies, further solidifying its importance in these fields.

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