Cas no 790262-70-3 (2-chloro-5-(1H-imidazol-4-yl)pyridine)

2-Chloro-5-(1H-imidazol-4-yl)pyridine is a heterocyclic compound featuring both pyridine and imidazole moieties, making it a versatile intermediate in organic synthesis and pharmaceutical research. Its distinct structure allows for selective functionalization at the chloro and imidazole positions, enabling applications in the development of biologically active molecules, particularly in medicinal chemistry. The compound's stability and reactivity under controlled conditions make it suitable for cross-coupling reactions and as a building block for ligands or small-molecule inhibitors. Its well-defined chemical properties facilitate reproducible results in synthetic workflows, supporting its use in high-value research and industrial applications.
2-chloro-5-(1H-imidazol-4-yl)pyridine structure
790262-70-3 structure
Product Name:2-chloro-5-(1H-imidazol-4-yl)pyridine
CAS No:790262-70-3
MF:C8H6ClN3
MW:179.606339931488
MDL:MFCD14583907
CID:555137
PubChem ID:11528450
Update Time:2025-10-30

2-chloro-5-(1H-imidazol-4-yl)pyridine Chemical and Physical Properties

Names and Identifiers

    • Pyridine,2-chloro-5-(1H-imidazol-5-yl)-
    • Pyridine,2-chloro-5-(1H-imidazol-4-yl)- (9CI)
    • 2-chloro-5-(1H-imidazol-4-yl)pyridine
    • Pyridine, 2-chloro-5-(1H-imidazol-4-yl)-
    • EN300-1984258
    • 5-(1H-imidazol-4-yl)-2-chloro-pyridine
    • 790262-70-3
    • GXVMWONQPKKCDF-UHFFFAOYSA-N
    • SCHEMBL4868679
    • MDL: MFCD14583907
    • Inchi: 1S/C8H6ClN3/c9-8-2-1-6(3-11-8)7-4-10-5-12-7/h1-5H,(H,10,12)
    • InChI Key: GXVMWONQPKKCDF-UHFFFAOYSA-N
    • SMILES: ClC1=CC=C(C=N1)C1=CN=CN1

Computed Properties

  • Exact Mass: 179.0250249g/mol
  • Monoisotopic Mass: 179.0250249g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 153
  • 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
  • XLogP3: 1.6
  • Topological Polar Surface Area: 41.6?2

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Additional information on 2-chloro-5-(1H-imidazol-4-yl)pyridine

Recent Advances in the Study of 2-chloro-5-(1H-imidazol-4-yl)pyridine (CAS: 790262-70-3) in Chemical Biology and Pharmaceutical Research

The compound 2-chloro-5-(1H-imidazol-4-yl)pyridine (CAS: 790262-70-3) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This heterocyclic compound, featuring both imidazole and pyridine rings, serves as a versatile scaffold for drug discovery, particularly in the development of kinase inhibitors and other small-molecule therapeutics. Recent studies have explored its role in modulating key biological pathways, making it a promising candidate for further investigation.

One of the most notable applications of 2-chloro-5-(1H-imidazol-4-yl)pyridine is its use as an intermediate in the synthesis of kinase inhibitors. Kinases play a critical role in cellular signaling, and their dysregulation is often implicated in diseases such as cancer and inflammatory disorders. Researchers have successfully incorporated this compound into the design of novel inhibitors targeting specific kinases, such as JAK2 and EGFR, which are known to drive tumorigenesis. The chloro and imidazole substituents on the pyridine ring provide optimal binding interactions with the kinase active sites, enhancing both potency and selectivity.

In addition to its role in kinase inhibition, recent studies have highlighted the potential of 2-chloro-5-(1H-imidazol-4-yl)pyridine in the development of antimicrobial agents. The imidazole moiety is a well-known pharmacophore in antifungal and antibacterial drugs, and its incorporation into this compound has shown promising activity against resistant strains of bacteria and fungi. Preliminary in vitro assays indicate that derivatives of this compound exhibit broad-spectrum antimicrobial activity, with minimal cytotoxicity to mammalian cells, suggesting its potential for further optimization.

Another area of interest is the compound's utility in chemical biology as a probe for studying protein-protein interactions. The unique electronic properties of the pyridine and imidazole rings make it an excellent candidate for photoaffinity labeling and other bioconjugation techniques. Recent work has demonstrated its effectiveness in cross-linking studies, enabling researchers to map interaction networks within complex biological systems. This application is particularly valuable for understanding the mechanisms of drug action and identifying new therapeutic targets.

Despite these promising findings, challenges remain in the optimization of 2-chloro-5-(1H-imidazol-4-yl)pyridine for clinical use. Issues such as metabolic stability, bioavailability, and off-target effects need to be addressed through further structural modifications and preclinical studies. However, the compound's versatility and demonstrated efficacy in multiple therapeutic areas underscore its potential as a valuable tool in drug discovery and chemical biology. Continued research in this direction is expected to yield novel therapeutics with improved efficacy and safety profiles.

In conclusion, 2-chloro-5-(1H-imidazol-4-yl)pyridine (CAS: 790262-70-3) represents a compelling case study in the intersection of chemical biology and pharmaceutical research. Its diverse applications, from kinase inhibition to antimicrobial activity and chemical probing, highlight its significance in modern drug discovery. As researchers continue to explore its potential, this compound is poised to play a pivotal role in the development of next-generation therapeutics.

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