Cas no 1417422-00-4 ([5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid)

[5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid is a boronic acid derivative featuring a chloro-substituted pyrrolopyridine core and a toluenesulfonyl protecting group. This compound is primarily utilized as a key intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of complex biaryl structures in medicinal chemistry and materials science. The boronic acid moiety facilitates selective coupling with aryl halides under mild conditions, while the sulfonyl group enhances stability during handling and storage. Its well-defined reactivity profile makes it valuable for constructing heterocyclic scaffolds in drug discovery, particularly for kinase inhibitors and other biologically active molecules. The product is typically characterized by HPLC, NMR, and mass spectrometry to ensure high purity (>95%) and batch consistency.
[5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid structure
1417422-00-4 structure
Product Name:[5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid
CAS No:1417422-00-4
MF:C14H12BClN2O4S
MW:350.585081100464
MDL:MFCD29918534
CID:4595715
Update Time:2025-10-28

[5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid Chemical and Physical Properties

Names and Identifiers

    • [5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid
    • (5-Chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)boronic acid
    • Boronic acid, B-[5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-
    • [5-chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronicacid
    • [5-chloro-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-3-yl]boronic acid
    • MDL: MFCD29918534
    • Inchi: 1S/C14H12BClN2O4S/c1-9-2-4-11(5-3-9)23(21,22)18-8-13(15(19)20)12-6-10(16)7-17-14(12)18/h2-8,19-20H,1H3
    • InChI Key: RBKQSKSGWGOASE-UHFFFAOYSA-N
    • SMILES: ClC1=CN=C2C(=C1)C(B(O)O)=CN2S(C1C=CC(C)=CC=1)(=O)=O

Computed Properties

  • Exact Mass: 350.0299359 g/mol
  • Monoisotopic Mass: 350.0299359 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 3
  • Complexity: 521
  • 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: 101
  • Molecular Weight: 350.6

[5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid Pricemore >>

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Additional information on [5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid

Comprehensive Overview of [5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid (CAS No. 1417422-00-4)

[5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid (CAS No. 1417422-00-4) is a highly specialized boronic acid derivative that has garnered significant attention in the field of medicinal chemistry and drug discovery. This compound, characterized by its unique pyrrolopyridine core and sulfonyl functional group, serves as a critical building block in the synthesis of various biologically active molecules. Its boronic acid moiety makes it particularly valuable for Suzuki-Miyaura cross-coupling reactions, a cornerstone in modern organic synthesis.

The structural complexity of [5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid allows it to interact with diverse biological targets, making it a focal point in the development of kinase inhibitors and anticancer agents. Researchers are increasingly exploring its potential in targeted therapy, especially in the context of precision medicine, where the demand for novel small-molecule drugs is rising. The compound's CAS No. 1417422-00-4 is frequently searched in academic and industrial databases, reflecting its growing relevance in pharmaceutical R&D.

One of the most compelling aspects of this compound is its role in proteolysis-targeting chimeras (PROTACs), a cutting-edge technology in drug development. PROTACs leverage the ubiquitin-proteasome system to degrade specific disease-causing proteins, and [5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid has shown promise as a key linker or warhead in these constructs. This aligns with the current trend in biopharma to develop next-generation therapeutics with enhanced specificity and fewer side effects.

From a synthetic perspective, the compound's boronic acid group facilitates efficient C-C bond formation, which is essential for constructing complex molecular architectures. Its pyrrolopyridine scaffold is also noteworthy, as this heterocyclic system is prevalent in many FDA-approved drugs. The combination of these features makes CAS No. 1417422-00-4 a versatile intermediate in the synthesis of heterocyclic compounds, which are central to modern drug design.

In addition to its pharmaceutical applications, [5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid is also being investigated for its potential in material science. Its ability to form stable covalent organic frameworks (COFs) and metal-organic frameworks (MOFs) has opened new avenues in the development of advanced materials for catalysis and sensing. This multidisciplinary utility underscores the compound's importance beyond traditional medicinal chemistry.

The growing interest in CAS No. 1417422-00-4 is evident from the increasing number of patent filings and scientific publications referencing this compound. Researchers are particularly keen on optimizing its synthetic routes to improve yield and scalability, addressing one of the key challenges in industrial-scale production. Furthermore, its structure-activity relationship (SAR) studies are providing valuable insights into the design of more potent and selective bioactive molecules.

As the demand for innovative therapeutics continues to rise, [5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid is poised to play a pivotal role in shaping the future of drug discovery. Its unique chemical properties and broad applicability make it a standout candidate for researchers exploring new chemical entities (NCEs) and lead optimization. With ongoing advancements in computational chemistry and high-throughput screening, the potential applications of this compound are expected to expand even further.

In summary, [5-Chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]boronic acid (CAS No. 1417422-00-4) represents a convergence of synthetic versatility and biological relevance. Its role in Suzuki-Miyaura couplings, PROTACs, and material science highlights its multifaceted utility. As research progresses, this compound is likely to remain a cornerstone in the development of next-generation drugs and advanced materials, solidifying its position as a critical tool in scientific innovation.

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