Cas no 2172496-15-8 (6-iodo-3,5-dimethylimidazo1,2-apyridine)

6-Iodo-3,5-dimethylimidazo[1,2-a]pyridine is a heterocyclic compound featuring an imidazopyridine core substituted with iodine at the 6-position and methyl groups at the 3- and 5-positions. This structure imparts reactivity suitable for cross-coupling reactions, making it valuable in pharmaceutical and agrochemical synthesis. The iodine substituent enables versatile functionalization via palladium-catalyzed couplings, while the dimethyl groups enhance stability and influence electronic properties. Its well-defined crystalline form ensures consistent purity, critical for precision applications. This compound serves as a key intermediate in the development of bioactive molecules, particularly in medicinal chemistry, where its scaffold is leveraged for target-oriented derivatization.
6-iodo-3,5-dimethylimidazo1,2-apyridine structure
2172496-15-8 structure
Product Name:6-iodo-3,5-dimethylimidazo1,2-apyridine
CAS No:2172496-15-8
MF:C9H9IN2
MW:272.085633993149
CID:6429505
PubChem ID:165795336
Update Time:2025-05-21

6-iodo-3,5-dimethylimidazo1,2-apyridine Chemical and Physical Properties

Names and Identifiers

    • 6-iodo-3,5-dimethylimidazo1,2-apyridine
    • 6-iodo-3,5-dimethylimidazo[1,2-a]pyridine
    • Imidazo[1,2-a]pyridine, 6-iodo-3,5-dimethyl-
    • 2172496-15-8
    • EN300-1591769
    • Inchi: 1S/C9H9IN2/c1-6-5-11-9-4-3-8(10)7(2)12(6)9/h3-5H,1-2H3
    • InChI Key: XETFDVYVSDPHQN-UHFFFAOYSA-N
    • SMILES: CC1=C(C=CC2=NC=C(C)N12)I

Computed Properties

  • Exact Mass: 271.98105g/mol
  • Monoisotopic Mass: 271.98105g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 174
  • 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: 3.2
  • Topological Polar Surface Area: 17.3?2

Experimental Properties

  • Density: 1.79±0.1 g/cm3(Predicted)
  • pka: 6.44±0.50(Predicted)

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Additional information on 6-iodo-3,5-dimethylimidazo1,2-apyridine

6-Iodo-3,5-Dimethylimidazo[1,2-a]pyridine: A Comprehensive Overview

6-Iodo-3,5-Dimethylimidazo[1,2-a]pyridine (CAS No. 2172496-15-8) is a structurally unique compound belonging to the imidazo[1,2-a]pyridine family. This compound has garnered significant attention in recent years due to its potential applications in various fields, including pharmacology and materials science. The imidazo[1,2-a]pyridine core is a bicyclic structure that combines the properties of both imidazole and pyridine rings, making it a versatile scaffold for chemical modifications. The presence of an iodo group at the 6-position and two methyl groups at the 3 and 5 positions further enhances its chemical reactivity and biological activity.

Recent studies have highlighted the importance of 6-Iodo-3,5-Dimethylimidazo[1,2-a]pyridine in drug discovery. Its ability to act as a precursor for more complex molecules has been exploited in the synthesis of novel pharmaceutical agents. For instance, researchers have demonstrated that this compound can undergo various substitution reactions to yield derivatives with enhanced bioavailability and selectivity. The iodo group serves as an excellent leaving group, enabling the formation of diverse functionalized products that can target specific biological pathways.

The synthesis of 6-Iodo-3,5-Dimethylimidazo[1,2-a]pyridine involves a multi-step process that typically begins with the preparation of the imidazo[1,2-a]pyridine core. This is followed by iodination at the 6-position and methylation at the 3 and 5 positions. The reaction conditions are carefully optimized to ensure high yields and purity. Recent advancements in catalytic methods have further streamlined this process, making it more efficient and scalable for industrial applications.

In terms of pharmacological activity, 6-Iodo-3,5-Dimethylimidazo[1,2-a]pyridine has shown promise as a lead compound for anti-inflammatory and anti-cancer therapies. Its ability to modulate key enzymes involved in inflammatory responses has been extensively studied. Additionally, its role as a potential anticancer agent has been explored through in vitro assays that demonstrate its ability to inhibit tumor cell proliferation while sparing normal cells.

The structural versatility of 6-Iodo-3,5-Dimethylimidazo[1,2-a]pyridine also makes it a valuable component in materials science. Its application as a building block for advanced materials such as conductive polymers and metal-organic frameworks (MOFs) has been reported in recent literature. The methyl groups provide steric hindrance that can influence the electronic properties of these materials, making them suitable for energy storage applications.

Furthermore, the use of 6-Iodo-3,5-Dimethylimidazo[1,2-a]pyridine in analytical chemistry has been documented. Its ability to act as a chelating agent for metal ions has been leveraged in the development of sensors for heavy metal detection. This application underscores its potential in environmental monitoring and quality control processes.

In conclusion, 6-Iodo-3,5-Dimethylimidazo[1,2-a]pyridine (CAS No. 2172496-15-8) is a multifaceted compound with a wide range of applications across different scientific disciplines. Its unique structure and reactivity make it an invaluable tool in drug discovery, materials science, and analytical chemistry. As research continues to uncover new avenues for its utilization, this compound is poised to play an increasingly important role in advancing scientific innovation.

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