Cas no 900514-08-1 (5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine)

5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine is a halogenated heterocyclic compound featuring both chloro and iodo substituents on a pyrrolopyridine scaffold. This structure serves as a versatile intermediate in pharmaceutical and agrochemical synthesis, particularly in the development of kinase inhibitors and other biologically active molecules. The presence of halogen atoms at the 3- and 5-positions enhances its reactivity in cross-coupling reactions, such as Suzuki or Sonogashira couplings, facilitating further functionalization. Its rigid fused-ring system contributes to stability while offering precise spatial orientation for target interactions. The compound is typically handled under inert conditions due to its sensitivity to light and moisture.
5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine structure
900514-08-1 structure
Product Name:5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine
CAS No:900514-08-1
MF:C7H4ClIN2
MW:278.47753238678
MDL:MFCD08457790
CID:797531
PubChem ID:329771952
Update Time:2025-05-20

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

Names and Identifiers

    • 5-Chloro-3-iodo-7-azaindole
    • 1H-Pyrrolo[2,3-b]pyridine,5-chloro-3-iodo-
    • 5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine
    • LZTOGEVTAZHIFX-UHFFFAOYSA-N
    • PB25056
    • FCH1324242
    • SY096652
    • ST2418734
    • AX8026255
    • X6194
    • 5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine, AldrichCPR
    • 5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (ACI)
    • DTXSID20640109
    • P10596
    • 900514-08-1
    • AKOS015850511
    • MFCD08457790
    • DS-11096
    • J-517347
    • CS-0002358
    • SCHEMBL1053943
    • MDL: MFCD08457790
    • Inchi: 1S/C7H4ClIN2/c8-4-1-5-6(9)3-11-7(5)10-2-4/h1-3H,(H,10,11)
    • InChI Key: LZTOGEVTAZHIFX-UHFFFAOYSA-N
    • SMILES: ClC1C=C2C(NC=C2I)=NC=1

Computed Properties

  • Exact Mass: 277.91100
  • Monoisotopic Mass: 277.911
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 155
  • 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: 2.6

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 2.156
  • Melting Point: 228-229°C
  • Boiling Point: No data available
  • Flash Point: No data available
  • Refractive Index: 1.784
  • PSA: 28.68000
  • LogP: 2.82090
  • Vapor Pressure: No data available

5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine Security Information

  • Signal Word:Warning
  • Hazard Statement: H302
  • Warning Statement: P280-P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • Safety Instruction: H303+H313+H333
  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT
  • Storage Condition:Keep in dark place,Inert atmosphere,2-8°C

5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Additional information on 5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

Introduction to 5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (CAS No. 900514-08-1) and Its Applications in Modern Chemical Biology

5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine, identified by the chemical identifier CAS No. 900514-08-1, is a heterocyclic compound that has garnered significant attention in the field of chemical biology due to its unique structural properties and versatile reactivity. This bicyclic molecule consists of a pyrrole ring fused with a pyridine ring, featuring both chloro and iodo substituents at strategic positions. These functional groups make it a valuable intermediate in the synthesis of various biologically active compounds, particularly in the development of pharmaceuticals and agrochemicals.

The structural motif of 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine is highly conducive to further functionalization through cross-coupling reactions, such as Suzuki-Miyaura, Stille, and Buchwald-Hartwig couplings. These reactions are pivotal in constructing complex molecular architectures, enabling the synthesis of novel compounds with potential therapeutic applications. The presence of both electron-withdrawing (chloro) and electron-donating (iodo) groups on the same scaffold enhances its utility as a versatile building block in medicinal chemistry.

In recent years, there has been a surge in research focused on developing small-molecule inhibitors targeting various biological pathways. 5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine has emerged as a key precursor in the synthesis of inhibitors for enzymes involved in cancer metabolism and signal transduction. For instance, studies have demonstrated its role in generating derivatives that exhibit inhibitory activity against kinases and other enzymes implicated in tumor growth and progression. The halogenated pyrrolopyridine core is particularly adept at interacting with metal centers in enzymes, facilitating the design of potent and selective inhibitors.

One notable application of 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine is in the development of antiviral agents. The compound’s ability to undergo facile functionalization allows for the creation of derivatives with enhanced binding affinity to viral proteases and polymerases. Recent advancements in computational chemistry have further accelerated the design process by predicting optimal substitution patterns on the pyrrolopyridine scaffold. This synergy between experimental synthesis and computational modeling has led to the discovery of several lead compounds with promising antiviral activity.

The pharmaceutical industry has also leveraged 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine as a scaffold for designing novel antibiotics. The compound’s structural features are conducive to mimicking natural product scaffolds, which are often responsible for antibiotic activity. By incorporating different substituents at the chloro and iodo positions, researchers have generated libraries of compounds that exhibit broad-spectrum antimicrobial properties. These efforts are particularly crucial in addressing the growing challenge of antibiotic resistance.

Beyond pharmaceuticals, 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine finds applications in materials science, where its ability to form coordination complexes with transition metals makes it useful in catalysis and luminescent materials. The halogen atoms facilitate strong interactions with metal centers, enabling the design of efficient catalysts for organic transformations. Additionally, derivatives of this compound have been explored as components in organic light-emitting diodes (OLEDs) due to their fluorescence properties.

The synthesis of 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine typically involves multi-step processes starting from readily available precursors such as pyrrole and pyridine derivatives. Advanced synthetic methodologies, including transition-metal-catalyzed reactions and flow chemistry techniques, have been employed to improve yield and scalability. These innovations have not only streamlined the production process but also opened new avenues for derivative synthesis.

As research continues to uncover new biological targets and therapeutic strategies, the demand for specialized intermediates like 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine is expected to grow. The compound’s versatility and adaptability make it an indispensable tool in drug discovery pipelines across academia and industry. Collaborative efforts between chemists, biologists, and pharmacologists are essential to fully harness its potential in addressing global health challenges.

In conclusion,5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (CAS No. 900514-08-1) represents a cornerstone molecule in modern chemical biology. Its unique structural features and reactivity profile have positioned it as a key intermediate in the synthesis of biologically active compounds with applications ranging from pharmaceuticals to materials science. As research progresses,this compound will continue to play a pivotal role in advancing our understanding of molecular interactions and developing innovative solutions for complex biological problems.

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