Cas no 1448866-17-8 ((3-chloropyridin-2-yl)boronic acid)

(3-Chloropyridin-2-yl)boronic acid is a versatile boronic acid derivative widely used in Suzuki-Miyaura cross-coupling reactions, a key method for forming carbon-carbon bonds in organic synthesis. The presence of both the boronic acid group and the chloropyridine moiety makes it a valuable intermediate in pharmaceutical and agrochemical research. Its stability and reactivity under mild conditions enable efficient functionalization of pyridine scaffolds. The compound is particularly useful for introducing chloropyridine motifs into complex molecules, aiding in the development of bioactive compounds. High purity grades ensure consistent performance in sensitive applications. Proper handling under inert conditions is recommended to preserve its integrity.
(3-chloropyridin-2-yl)boronic acid structure
1448866-17-8 structure
Product Name:(3-chloropyridin-2-yl)boronic acid
CAS No:1448866-17-8
MF:C5H5BClNO2
MW:157.362700223923
MDL:MFCD12401037
CID:5039927
PubChem ID:66866375
Update Time:2026-02-28

(3-chloropyridin-2-yl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • 3-Chloropyridine-2-boronic acid
    • (3-chloropyridin-2-yl)boronic acid
    • Boronic acid, B-(3-chloro-2-pyridinyl)-
    • BB 0261786
    • X2960
    • E76149
    • SCHEMBL982637
    • BS-49692
    • QBKWMNFYLXBEDV-UHFFFAOYSA-N
    • EN300-173404
    • 1448866-17-8
    • 3-Chloropyridine-2-boronic acid, 95%
    • CS-0162304
    • MFCD12401037
    • 3-CHLOROPYRIDIN-2-YLBORONIC ACID
    • DB-156937
    • B-(3-chloro-2-pyridinyl)boronic acid
    • MDL: MFCD12401037
    • Inchi: 1S/C5H5BClNO2/c7-4-2-1-3-8-5(4)6(9)10/h1-3,9-10H
    • InChI Key: QBKWMNFYLXBEDV-UHFFFAOYSA-N
    • SMILES: ClC1=CC=CN=C1B(O)O

Computed Properties

  • Exact Mass: 157.0101863g/mol
  • Monoisotopic Mass: 157.0101863g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 114
  • 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: 53.4

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Additional information on (3-chloropyridin-2-yl)boronic acid

Introduction to (3-chloropyridin-2-yl)boronic acid (CAS No. 1448866-17-8)

(3-chloropyridin-2-yl)boronic acid (CAS No. 1448866-17-8) is a versatile compound that has gained significant attention in the fields of organic synthesis, medicinal chemistry, and pharmaceutical research. This compound, also known as 3-chloro-2-pyridylboronic acid, is a boronic acid derivative of pyridine, characterized by its unique chemical structure and reactivity. The presence of a boronic acid group and a chloropyridine moiety makes it an attractive building block for various chemical transformations and biological applications.

The (3-chloropyridin-2-yl)boronic acid has been extensively studied for its potential in the synthesis of complex organic molecules, particularly in the development of new pharmaceuticals. Its reactivity is primarily driven by the boronic acid functionality, which can undergo various coupling reactions such as Suzuki-Miyaura coupling, which is widely used in the synthesis of biologically active compounds. The chloropyridine group, on the other hand, provides additional functionalization opportunities, making this compound a valuable intermediate in the synthesis of diverse chemical entities.

Recent advancements in the field have highlighted the importance of (3-chloropyridin-2-yl)boronic acid in the development of novel therapeutic agents. 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 a series of pyridine-based inhibitors targeting specific enzymes involved in cancer progression. The researchers reported that these inhibitors exhibited potent antiproliferative activity against various cancer cell lines, underscoring the potential of (3-chloropyridin-2-yl)boronic acid in drug discovery.

In addition to its applications in medicinal chemistry, (3-chloropyridin-2-yl)boronic acid has also found utility in materials science. The unique electronic properties of pyridine derivatives make them suitable for use in organic electronics and photovoltaic devices. A recent study published in *Advanced Materials* explored the use of (3-chloropyridin-2-yl)boronic acid as a building block for constructing conjugated polymers with enhanced charge transport properties. The results showed that these polymers exhibited excellent performance in organic solar cells, highlighting the compound's potential beyond traditional pharmaceutical applications.

The synthesis of (3-chloropyridin-2-yl)boronic acid typically involves several steps, including the formation of a boronate ester intermediate followed by hydrolysis to yield the boronic acid. Various synthetic routes have been reported in the literature, each with its own advantages and limitations. One common approach involves the reaction of 3-chloro-2-pyridine with diborane or borane complexes to form the corresponding boronate ester, which is then hydrolyzed under acidic conditions to produce (3-chloropyridin-2-yl)boronic acid. This method is known for its high yield and mild reaction conditions, making it suitable for large-scale production.

The stability and handling properties of (3-chloropyridin-2-yl)boronic acid are important considerations for both research and industrial applications. The compound is generally stable under ambient conditions but may degrade upon prolonged exposure to air and moisture. Therefore, it is recommended to store (3-chloropyridin-2-yl)boronic acid under inert atmosphere and at low temperatures to maintain its integrity. Additionally, care should be taken during handling to avoid contact with strong oxidizing agents or bases, which can lead to decomposition or unwanted side reactions.

In conclusion, (3-chloropyridin-2-yl)boronic acid (CAS No. 1448866-17-8) is a highly versatile compound with significant potential in various scientific and industrial fields. Its unique chemical structure and reactivity make it an invaluable tool for synthetic chemists and researchers working on new drug discovery and materials science applications. As ongoing research continues to uncover new uses and properties of this compound, it is likely to play an increasingly important role in advancing our understanding and capabilities in these areas.

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