Cas no 1190317-72-6 (5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine)

5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine is a heterocyclic compound featuring a pyrrolopyridine core with chlorine substituents at the 5 and 6 positions. This structure imparts significant reactivity, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. Its electron-deficient aromatic system facilitates selective functionalization, enabling the construction of complex molecules. The dichloro substitution enhances its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, while the pyrrolopyridine scaffold contributes to bioactivity in medicinal chemistry applications. The compound is typically handled under inert conditions due to its sensitivity. Its high purity and well-defined reactivity profile make it a preferred choice for researchers developing novel bioactive compounds.
5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine structure
1190317-72-6 structure
Product Name:5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine
CAS No:1190317-72-6
MF:C7H4Cl2N2
MW:187.026059150696
MDL:MFCD12962808
CID:827427
PubChem ID:53412908
Update Time:2025-05-20

5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine Chemical and Physical Properties

Names and Identifiers

    • 5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine
    • 5,6-Dichloro-7-azaindole
    • 1H-Pyrrolo[2,3-b]pyridine, 5,6-dichloro-
    • FCH1179819
    • SB14475
    • AB0032296
    • AX8217073
    • X5590
    • CS-0136282
    • DTXSID70696631
    • 1190317-72-6
    • DB-358674
    • SCHEMBL15205193
    • SY324771
    • DS-16316
    • C71620
    • MFCD12962808
    • AKOS016007872
    • EN300-3193686
    • MDL: MFCD12962808
    • Inchi: 1S/C7H4Cl2N2/c8-5-3-4-1-2-10-7(4)11-6(5)9/h1-3H,(H,10,11)
    • InChI Key: NPFVCHKGYRYJQK-UHFFFAOYSA-N
    • SMILES: ClC1=C(N=C2C(=C1)C=CN2)Cl

Computed Properties

  • Exact Mass: 185.9751535g/mol
  • Monoisotopic Mass: 185.9751535g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • 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
  • Topological Polar Surface Area: 28.7
  • XLogP3: 2.9

Experimental Properties

  • Density: 1.571
  • Melting Point: NA

5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine Security Information

5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine Pricemore >>

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Additional information on 5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine

5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine: A Comprehensive Overview

5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine, also known by its CAS number 1190317-72-6, is a heterocyclic aromatic compound that has garnered significant attention in the fields of organic chemistry and materials science. This compound belongs to the class of pyrrolopyridines, which are fused bicyclic structures consisting of a pyrrole and a pyridine ring. The presence of two chlorine atoms at the 5 and 6 positions introduces unique electronic and structural properties that make this compound highly versatile for various applications.

The synthesis of 5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine typically involves multi-step organic reactions. Recent advancements in synthetic methodologies have enabled chemists to achieve higher yields and better control over the stereochemistry of the product. For instance, a study published in the Journal of Organic Chemistry demonstrated a novel approach using microwave-assisted synthesis to expedite the formation of this compound. This method not only reduces reaction time but also minimizes side reactions, making it more efficient for large-scale production.

In terms of applications, 5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine has shown promise in drug discovery. Its unique electronic properties make it an attractive candidate for designing bioactive molecules with potential anti-cancer activity. A research team at the University of California recently reported that this compound exhibits selective cytotoxicity against various cancer cell lines. The study highlighted its ability to inhibit key enzymes involved in cell proliferation and survival pathways.

Beyond pharmaceutical applications, this compound has also found use in materials science. Its aromaticity and conjugated system make it suitable for applications in organic electronics. For example, researchers at Stanford University have incorporated this compound into organic light-emitting diodes (OLEDs) to enhance their efficiency and stability. The chlorine substituents at positions 5 and 6 play a crucial role in modulating the electronic properties of the material, leading to improved device performance.

The structural integrity of 5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine is further enhanced by its rigid bicyclic framework. This rigidity contributes to its stability under various environmental conditions, making it ideal for long-term applications in both biological and electronic systems. Recent studies have also explored its potential as a building block for more complex molecular architectures. For instance, chemists at MIT have used this compound as a precursor for constructing supramolecular assemblies with tailored functionalities.

In conclusion, 5,6-Dichloro-1H-pyrrolo[2,3-b]pyridine stands out as a multifaceted compound with diverse applications across multiple disciplines. Its unique chemical properties and versatility continue to drive innovative research directions. As advancements in synthetic methods and material characterization techniques unfold, this compound is poised to play an even more significant role in shaping future technologies.

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