Cas no 1190313-54-2 (3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine)

3-Chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine is a heterocyclic compound featuring a fused pyrrolopyridine core with chloro and iodo substituents at the 3- and 4-positions, respectively. This structure serves as a versatile intermediate in organic synthesis, particularly in pharmaceutical and agrochemical research. The presence of both halogen atoms enhances its reactivity, enabling selective functionalization through cross-coupling reactions such as Suzuki or Buchwald-Hartwig couplings. Its rigid scaffold is valuable for constructing biologically active molecules, including kinase inhibitors and other therapeutic agents. The compound's stability and well-defined reactivity profile make it a practical choice for medicinal chemistry applications, offering precise control over molecular design and derivatization.
3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine structure
1190313-54-2 structure
Product Name:3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine
CAS No:1190313-54-2
MF:C7H4ClIN2
MW:278.47753238678
MDL:MFCD12962681
CID:4562140
PubChem ID:53412625
Update Time:2025-05-21

3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine Chemical and Physical Properties

Names and Identifiers

    • 3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine
    • 3-CHLORO-4-IODO-7-AZAINDOLE
    • SB14436
    • 1H-Pyrrolo[2,3-b]pyridine, 3-chloro-4-iodo-
    • MDL: MFCD12962681
    • Inchi: 1S/C7H4ClIN2/c8-4-3-11-7-6(4)5(9)1-2-10-7/h1-3H,(H,10,11)
    • InChI Key: AACCTCANGOIUGS-UHFFFAOYSA-N
    • SMILES: IC1C=CN=C2C=1C(=CN2)Cl

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 155
  • XLogP3: 2.6
  • Topological Polar Surface Area: 28.7

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Additional information on 3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine

3-Chloro-4-Iodo-1H-Pyrrolo[2,3-b]Pyridine: A Comprehensive Overview

3-Chloro-4-Iodo-1H-Pyrrolo[2,3-b]Pyridine, also known as CAS No. 1190313-54-2, is a highly specialized organic compound that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound belongs to the class of pyrrolopyridines, which are heterocyclic structures combining pyrrole and pyridine rings. The presence of chlorine and iodine substituents at the 3 and 4 positions, respectively, imparts unique electronic and structural properties to this molecule.

The synthesis of 3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine typically involves multi-step organic reactions, often utilizing palladium-catalyzed cross-coupling techniques. Recent advancements in catalytic methods have enabled the efficient construction of such complex heterocycles with high yields and purity. Researchers have explored various precursor molecules, including substituted pyrroles and pyridines, to optimize the synthesis pathway for this compound.

One of the most promising applications of 3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine lies in its potential as a building block for drug discovery. Its rigid structure and ability to form hydrogen bonds make it an ideal candidate for targeting specific protein-protein interactions (PPIs). Recent studies have demonstrated its effectiveness in inhibiting certain oncogenic pathways, suggesting its potential as an anti-cancer agent. Additionally, the compound's electronic properties make it a strong candidate for use in optoelectronic materials, such as organic light-emitting diodes (OLEDs) and photovoltaic devices.

The structural uniqueness of 3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine has also led to its investigation in the field of supramolecular chemistry. Researchers have explored its ability to form self-assembled structures through non-covalent interactions, which could have applications in nanotechnology and molecular recognition systems. Furthermore, its iodine substituent allows for potential radiotherapeutic applications, as iodine can be isotopically labeled for imaging and treatment purposes.

In terms of pharmacokinetics, studies have shown that 3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine exhibits favorable absorption profiles in preclinical models. Its lipophilic nature enhances its ability to cross biological membranes, while its metabolic stability ensures sustained activity within the body. These properties make it a compelling candidate for further preclinical development.

The development of CAS No. 1190313-54-2 has been supported by cutting-edge analytical techniques such as X-ray crystallography and nuclear magnetic resonance (NMR) spectroscopy. These methods have provided detailed insights into the compound's three-dimensional structure and dynamic behavior in solution. Computational modeling has also played a crucial role in predicting the compound's interactions with biological targets and optimizing its pharmacological properties.

In conclusion, 3-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine, or CAS No. 1190313-54-2, represents a significant advancement in heterocyclic chemistry with diverse applications across multiple scientific domains. Its unique structure and functional groups continue to inspire innovative research directions, positioning it as a key molecule in the development of novel therapeutic agents and advanced materials.

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