Cas no 1820712-83-1 (5-Bromo-imidazo[1,2-a]pyridine HCl)

5-Bromo-imidazo[1,2-a]pyridine HCl is a halogenated heterocyclic compound featuring a fused imidazole-pyridine core. The bromo substitution at the 5-position enhances its reactivity, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. Its hydrochloride salt form improves solubility and stability, facilitating handling and storage. This compound is particularly useful in cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, due to the bromine's electrophilic character. Its rigid bicyclic structure also contributes to its utility in medicinal chemistry for developing bioactive molecules. High purity and consistent quality ensure reliable performance in research and industrial applications.
5-Bromo-imidazo[1,2-a]pyridine HCl structure
1820712-83-1 structure
Product Name:5-Bromo-imidazo[1,2-a]pyridine HCl
CAS No:1820712-83-1
MF:C7H6BrClN2
MW:233.492939472198
CID:5070923
Update Time:2025-06-09

5-Bromo-imidazo[1,2-a]pyridine HCl Chemical and Physical Properties

Names and Identifiers

    • 5-Bromo-imidazo[1,2-a]pyridine HCl
    • 5-Bromoimidazo[1,2-a]pyridine HCl
    • 5-bromoimidazo[1,2-a]pyridine;hydrochloride
    • Inchi: 1S/C7H5BrN2.ClH/c8-6-2-1-3-7-9-4-5-10(6)7;/h1-5H;1H
    • InChI Key: QEGSOUOCOJZCFU-UHFFFAOYSA-N
    • SMILES: BrC1=CC=CC2=NC=CN21.Cl

Computed Properties

  • Exact Mass: 231.94029 g/mol
  • Monoisotopic Mass: 231.94029 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 129
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 17.3
  • Molecular Weight: 233.49

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Additional information on 5-Bromo-imidazo[1,2-a]pyridine HCl

Introduction to 5-Bromo-imidazo[1,2-a]pyridine HCl (CAS No. 1820712-83-1)

5-Bromo-imidazo[1,2-a]pyridine HCl, identified by its Chemical Abstracts Service (CAS) number 1820712-83-1, is a significant compound in the realm of pharmaceutical and medicinal chemistry. This heterocyclic organic molecule has garnered attention due to its versatile structural framework, which makes it a valuable scaffold for the development of various bioactive agents. The presence of both bromine and imidazopyridine moieties enhances its potential as a key intermediate in synthetic chemistry, enabling modifications that can yield novel pharmacological entities.

The imidazo[1,2-a]pyridine core is a privileged structure in drug discovery, known for its ability to interact with multiple biological targets. Its fused ring system provides a rigid yet adaptable platform for functionalization, allowing chemists to tailor properties such as solubility, metabolic stability, and binding affinity. The introduction of a bromine atom at the 5-position further expands its utility by facilitating cross-coupling reactions, which are pivotal in modern medicinal chemistry. These reactions include Suzuki-Miyaura, Buchwald-Hartwig, and other palladium-catalyzed transformations that are widely employed in the synthesis of complex molecules.

In recent years, 5-Bromo-imidazo[1,2-a]pyridine HCl has been explored in the context of developing small-molecule inhibitors targeting various therapeutic areas. Notably, its derivatives have shown promise in inhibiting kinases and other enzymes implicated in cancer progression. The brominated imidazopyridine scaffold serves as an effective handle for generating libraries of compounds that can be screened for biological activity. High-throughput screening (HTS) campaigns and structure-activity relationship (SAR) studies have utilized this compound as a building block to identify lead candidates with improved pharmacokinetic profiles.

One of the most compelling aspects of 5-Bromo-imidazo[1,2-a]pyridine HCl is its role in the synthesis of molecules that modulate protein-protein interactions. By leveraging its reactive sites, researchers have designed inhibitors that disrupt aberrant signaling pathways involved in inflammatory diseases and neurodegenerative disorders. The ability to fine-tune the electronic and steric properties of the imidazopyridine ring allows for the creation of highly specific binders. This precision is critical for minimizing side effects and enhancing therapeutic efficacy.

The pharmaceutical industry has also recognized the potential of 5-Bromo-imidazo[1,2-a]pyridine HCl in addressing unmet medical needs. Its incorporation into drug candidates has led to several clinical trials where it was used as a key intermediate in the synthesis of novel therapeutics. The compound’s stability under various reaction conditions makes it an attractive choice for large-scale production processes. Additionally, its compatibility with green chemistry principles has been noted, as many synthetic routes involving this intermediate can be optimized to reduce waste and energy consumption.

Advances in computational chemistry have further accelerated the development of derivatives based on 5-Bromo-imidazo[1,2-a]pyridine HCl. Molecular modeling techniques allow researchers to predict how modifications to the core structure will influence biological activity. This predictive power has enabled the rapid design of optimized analogs with enhanced potency and selectivity. Such innovations underscore the importance of this compound as a cornerstone in modern drug discovery.

The future prospects for 5-Bromo-imidazo[1,2-a]pyridine HCl are promising, with ongoing research exploring its applications in emerging fields such as epigenetics and gene therapy. Its structural versatility ensures that it will remain a relevant intermediate for decades to come. As new synthetic methodologies are developed and our understanding of biological systems deepens, the utility of this compound is expected to expand even further.

In conclusion,5-Bromo-imidazo[1,2-a]pyridine HCl (CAS No. 1820712-83-1) stands as a testament to the power of heterocyclic chemistry in addressing complex biomedical challenges. Its unique structural features and reactivity make it an indispensable tool for medicinal chemists striving to develop next-generation therapeutics. As research continues to uncover new applications for this compound, its significance in pharmaceutical innovation will only grow.

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