Cas no 1261365-71-2 (5-Chloro-2,3-diiodopyridine)

5-Chloro-2,3-diiodopyridine is a halogenated pyridine derivative with significant utility in organic synthesis and pharmaceutical research. Its structure, featuring chloro and iodo substituents at the 2, 3, and 5 positions, makes it a versatile intermediate for cross-coupling reactions, such as Suzuki or Sonogashira couplings, enabling the construction of complex heterocyclic frameworks. The electron-withdrawing effects of the halogens enhance reactivity in nucleophilic substitution and metal-catalyzed transformations. This compound is particularly valuable in medicinal chemistry for the development of bioactive molecules due to its ability to serve as a scaffold for further functionalization. High purity and stability under standard conditions ensure reliable performance in laboratory applications.
5-Chloro-2,3-diiodopyridine structure
5-Chloro-2,3-diiodopyridine structure
Product Name:5-Chloro-2,3-diiodopyridine
CAS No:1261365-71-2
MF:C5H2ClI2N
MW:365.338024616241
MDL:MFCD18374109
CID:1076273
PubChem ID:50988854
Update Time:2025-10-07

5-Chloro-2,3-diiodopyridine Chemical and Physical Properties

Names and Identifiers

    • 5-Chloro-2,3-diiodopyridine
    • MFCD18374109
    • 5-Chloro-2,3-diiodopyridine, AldrichCPR
    • DB-358830
    • 1261365-71-2
    • AKOS015849007
    • MDL: MFCD18374109
    • Inchi: 1S/C5H2ClI2N/c6-3-1-4(7)5(8)9-2-3/h1-2H
    • InChI Key: KHLVOIBFCQEXOO-UHFFFAOYSA-N
    • SMILES: IC1C(=NC=C(C=1)Cl)I

Computed Properties

  • Exact Mass: 364.79700
  • Monoisotopic Mass: 364.79652g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 0
  • Complexity: 101
  • 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: 2.8
  • Topological Polar Surface Area: 12.9?2

Experimental Properties

  • PSA: 12.89000
  • LogP: 2.94420

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Additional information on 5-Chloro-2,3-diiodopyridine

5-Chloro-2,3-Diiodopyridine: A Comprehensive Overview

5-Chloro-2,3-Diiodopyridine (CAS No. 1261365-71-2) is a unique organic compound that has garnered significant attention in the fields of chemistry and materials science. This compound belongs to the family of pyridine derivatives, which are widely studied for their versatile applications in drug design, electronic materials, and catalysis. The structure of 5-Chloro-2,3-Diiodopyridine is characterized by a pyridine ring with substituents at positions 2, 3, and 5. Specifically, the 2 and 3 positions are occupied by iodine atoms, while the 5 position bears a chlorine atom. This substitution pattern imparts unique electronic and steric properties to the molecule, making it a valuable compound for various research and industrial applications.

Recent advancements in synthetic chemistry have enabled the efficient synthesis of 5-Chloro-2,3-Diiodopyridine through a variety of methods. One prominent approach involves the iodination of chloropyridines using iodinating agents such as iodine monochloride (ICl) or other halogenation reagents. The reaction conditions are carefully optimized to ensure high yields and selectivity for the desired product. The synthesis of this compound is not only a testament to the ingenuity of modern chemical synthesis but also highlights the importance of understanding reaction mechanisms in achieving desired molecular architectures.

The electronic properties of 5-Chloro-2,3-Diiodopyridine make it an attractive candidate for applications in optoelectronics and photovoltaics. Recent studies have demonstrated that this compound can act as an effective sensitizer in dye-sensitized solar cells (DSSCs). The presence of iodine atoms at positions 2 and 3 significantly enhances the light-harvesting capabilities of the molecule by extending its absorption spectrum into the visible region. Furthermore, the chlorine substituent at position 5 contributes to the overall stability and electron transport properties of the compound. These findings underscore the potential of 5-Chloro-2,3-Diiodopyridine as a key component in next-generation solar energy technologies.

In addition to its role in energy-related applications, 5-Chloro-2,3-Diiodopyridine has also been explored for its potential in medicinal chemistry. Researchers have investigated its ability to act as a scaffold for drug design due to its unique combination of halogen substituents and aromaticity. For instance, studies have shown that this compound can serve as a template for designing inhibitors of certain enzymes or receptors involved in disease pathways. The ability to fine-tune the electronic properties of 5-Chloro-2,3-Diiodopyridine through substitution patterns opens up new avenues for drug discovery and development.

The structural versatility of 5-Chloro-2,3-Diiodopyridine also makes it an interesting subject for fundamental studies in coordination chemistry. Recent research has focused on its ability to coordinate with metal ions such as copper(II) or iron(III), forming stable metal complexes with unique magnetic and electronic properties. These complexes have potential applications in magnetic data storage devices or as catalysts in organic transformations. The coordination behavior of 5-Chloro-2,3-Diiodopyridine highlights its role as a versatile ligand capable of interacting with various metal centers under different conditions.

From an environmental perspective, understanding the fate and behavior of 5-Chloro-2,3-Diiodopyridine in natural systems is crucial for assessing its potential impact on ecosystems. Studies have shown that this compound exhibits moderate biodegradability under aerobic conditions, with microbial communities playing a significant role in its transformation. However, further research is needed to fully understand its persistence and toxicity under various environmental conditions.

In conclusion, 5-Chloro-2,3-Diiodopyridine (CAS No. 1261365-71-2) is a multifaceted compound with promising applications across diverse fields such as energy technology, medicinal chemistry, and materials science. Its unique structure and electronic properties continue to drive innovative research aimed at unlocking its full potential. As advancements in synthetic methods and characterization techniques unfold, we can expect even more groundbreaking discoveries related to this intriguing molecule.

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