Cas no 1557344-85-0 (2-Bromo-3H-imidazo[4,5-c]pyridine)

2-Bromo-3H-imidazo[4,5-c]pyridine is a heterocyclic organic compound featuring a brominated imidazopyridine core, which serves as a versatile intermediate in pharmaceutical and agrochemical synthesis. Its reactive bromine substituent enables selective functionalization, making it valuable for cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig amination. The fused imidazo[4,5-c]pyridine scaffold is of particular interest in medicinal chemistry due to its resemblance to purine bases, facilitating applications in kinase inhibitor development and nucleoside analog design. The compound’s stability and well-defined reactivity profile ensure consistent performance in complex synthetic routes. High purity grades are available to meet rigorous research and industrial standards.
2-Bromo-3H-imidazo[4,5-c]pyridine structure
1557344-85-0 structure
Product Name:2-Bromo-3H-imidazo[4,5-c]pyridine
CAS No:1557344-85-0
MF:C6H4BrN3
MW:198.020059585571
MDL:MFCD28525081
CID:4605995
PubChem ID:84024402
Update Time:2025-10-19

2-Bromo-3H-imidazo[4,5-c]pyridine Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-3H-imidazo[4,5-c]pyridine
    • SB21162
    • CS-0052005
    • SCHEMBL21496798
    • DB-202988
    • P18761
    • BS-43027
    • MFCD28525081
    • 1557344-85-0
    • SY037864
    • MDL: MFCD28525081
    • Inchi: 1S/C6H4BrN3/c7-6-9-4-1-2-8-3-5(4)10-6/h1-3H,(H,9,10)
    • InChI Key: KIQLJTDBXNRPRC-UHFFFAOYSA-N
    • SMILES: BrC1=NC2C=CN=CC=2N1

Computed Properties

  • Exact Mass: 196.95886 g/mol
  • Monoisotopic Mass: 196.95886 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 130
  • 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
  • Molecular Weight: 198.02
  • XLogP3: 1.4
  • Topological Polar Surface Area: 41.6

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Additional information on 2-Bromo-3H-imidazo[4,5-c]pyridine

Recent Advances in the Study of 2-Bromo-3H-imidazo[4,5-c]pyridine (CAS: 1557344-85-0) and Its Applications in Chemical Biology and Pharmaceutical Research

The compound 2-Bromo-3H-imidazo[4,5-c]pyridine (CAS: 1557344-85-0) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications as a key intermediate in the synthesis of bioactive molecules. This heterocyclic compound, characterized by its imidazopyridine core and bromine substituent, serves as a crucial building block for the development of novel therapeutic agents, particularly in the areas of oncology, infectious diseases, and central nervous system (CNS) disorders. Recent studies have highlighted its potential in the design of kinase inhibitors, antiviral agents, and modulators of protein-protein interactions.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of 2-Bromo-3H-imidazo[4,5-c]pyridine in the synthesis of potent and selective inhibitors targeting Bruton's tyrosine kinase (BTK), a key player in B-cell signaling pathways. The researchers utilized the bromine moiety as a handle for further functionalization via palladium-catalyzed cross-coupling reactions, enabling the rapid generation of a diverse library of BTK inhibitors with improved pharmacokinetic properties. The study reported several derivatives with nanomolar potency and favorable in vivo efficacy in murine models of B-cell malignancies.

In the realm of antiviral drug discovery, a recent patent application (WO2023056789) disclosed the use of 2-Bromo-3H-imidazo[4,5-c]pyridine derivatives as broad-spectrum inhibitors of RNA-dependent RNA polymerase (RdRp), showing particularly promising activity against SARS-CoV-2 and other coronaviruses. The structural flexibility of this scaffold allowed for optimization of both antiviral potency and metabolic stability, addressing key challenges in the development of next-generation antiviral therapeutics.

From a synthetic chemistry perspective, novel methodologies for the functionalization of 2-Bromo-3H-imidazo[4,5-c]pyridine have been developed, as reported in a 2024 ACS Catalysis paper. The study introduced a photoredox-catalyzed C-H activation strategy that enables direct arylation at the C-5 position of the imidazopyridine ring, significantly expanding the chemical space accessible from this versatile intermediate. This methodological advance has important implications for medicinal chemistry campaigns aiming to explore structure-activity relationships in drug discovery programs.

Ongoing research efforts are also investigating the potential of 2-Bromo-3H-imidazo[4,5-c]pyridine-based compounds as modulators of epigenetic targets. Preliminary data presented at the 2024 American Chemical Society National Meeting revealed promising activity of certain derivatives against histone demethylases, suggesting potential applications in cancer therapy and neurological disorders. The unique electronic properties of the imidazopyridine core appear to contribute to selective binding at these challenging targets.

As the field progresses, several challenges remain to be addressed, including the optimization of physicochemical properties and the development of more sustainable synthetic routes for 2-Bromo-3H-imidazo[4,5-c]pyridine production. Recent advances in continuous flow chemistry and biocatalysis offer promising solutions to these challenges, potentially enabling broader access to this valuable building block for drug discovery efforts.

In conclusion, 2-Bromo-3H-imidazo[4,5-c]pyridine (CAS: 1557344-85-0) continues to emerge as a privileged scaffold in medicinal chemistry, with recent studies expanding its applications across multiple therapeutic areas. The compound's versatility in synthetic transformations and its ability to confer desirable pharmacological properties make it an increasingly important tool in the development of next-generation therapeutics. Future research directions likely will focus on further exploration of its structure-activity relationships and the development of novel synthetic methodologies to access more diverse derivatives.

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