Cas no 127827-54-7 (6-Bromo-7-chloroquinoline)

6-Bromo-7-chloroquinoline is a halogenated quinoline derivative with significant utility in organic synthesis and pharmaceutical research. Its bromo and chloro substituents at the 6- and 7-positions, respectively, enhance its reactivity, making it a versatile intermediate for cross-coupling reactions, nucleophilic substitutions, and metal-catalyzed transformations. The compound's rigid quinoline scaffold provides a stable framework for constructing complex heterocyclic systems, often employed in drug discovery and material science. High purity and well-defined structural properties ensure consistent performance in synthetic applications. Its stability under standard conditions and compatibility with diverse reaction conditions further underscore its value as a building block in medicinal chemistry and advanced material development.
6-Bromo-7-chloroquinoline structure
6-Bromo-7-chloroquinoline structure
Product Name:6-Bromo-7-chloroquinoline
CAS No:127827-54-7
MF:C9H5BrClN
MW:242.499700307846
CID:1024075
PubChem ID:14548344
Update Time:2025-06-09

6-Bromo-7-chloroquinoline Chemical and Physical Properties

Names and Identifiers

    • 6-Bromo-7-chloroquinoline
    • ACT10702
    • AGN-PC-001RSR
    • AK101776
    • ANW-62685
    • CTK8B9539
    • KB-247985
    • SB69816
    • CS-0444146
    • DB-369190
    • AKOS016004129
    • MFCD22376736
    • DTXSID30561533
    • 127827-54-7
    • MDL: MFCD22376736
    • Inchi: 1S/C9H5BrClN/c10-7-4-6-2-1-3-12-9(6)5-8(7)11/h1-5H
    • InChI Key: LTMBJODLNOMUAB-UHFFFAOYSA-N
    • SMILES: BrC1C(=CC2C(=CC=CN=2)C=1)Cl

Computed Properties

  • Exact Mass: 240.92945
  • Monoisotopic Mass: 240.92939g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 165
  • 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: 3.5
  • Topological Polar Surface Area: 12.9?2

Experimental Properties

  • Density: 1.673
  • Melting Point: 128-130 oC
  • PSA: 12.89

6-Bromo-7-chloroquinoline Pricemore >>

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Additional information on 6-Bromo-7-chloroquinoline

Research Briefing on 6-Bromo-7-chloroquinoline (CAS: 127827-54-7) in Chemical Biology and Pharmaceutical Applications

6-Bromo-7-chloroquinoline (CAS: 127827-54-7) is a halogenated quinoline derivative that has garnered significant attention in recent years due to its versatile applications in medicinal chemistry and drug discovery. Quinoline scaffolds are known for their broad pharmacological activities, including antimicrobial, anticancer, and anti-inflammatory properties. This briefing synthesizes the latest research on 6-Bromo-7-chloroquinoline, focusing on its synthesis, biological activities, and potential therapeutic applications.

Recent studies have highlighted the role of 6-Bromo-7-chloroquinoline as a key intermediate in the synthesis of more complex quinoline-based compounds. Its halogenated structure provides reactive sites for further functionalization, making it a valuable building block in medicinal chemistry. For instance, researchers have utilized this compound to develop novel kinase inhibitors targeting cancer pathways, leveraging its ability to interact with ATP-binding sites in kinases.

In a 2023 study published in the Journal of Medicinal Chemistry, 6-Bromo-7-chloroquinoline was employed as a precursor for the synthesis of selective JAK2 inhibitors. The study demonstrated that derivatives of this compound exhibited potent inhibitory activity against JAK2, a kinase implicated in myeloproliferative disorders. The researchers attributed this activity to the compound's ability to form critical hydrogen bonds and hydrophobic interactions within the kinase domain.

Another area of interest is the antimicrobial potential of 6-Bromo-7-chloroquinoline. A recent publication in Bioorganic & Medicinal Chemistry Letters reported that this compound and its derivatives showed promising activity against drug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA). The mechanism of action appears to involve disruption of bacterial cell membrane integrity and inhibition of efflux pumps, which are often overexpressed in resistant strains.

From a synthetic chemistry perspective, advances in the preparation of 6-Bromo-7-chloroquinoline have been reported. A 2022 paper in Organic Process Research & Development described an optimized, scalable synthesis route with improved yield and purity. This development is particularly significant for industrial-scale production, as it addresses previous challenges related to byproduct formation and purification.

Looking forward, the unique properties of 6-Bromo-7-chloroquinoline position it as a promising scaffold for the development of new therapeutic agents. Current research directions include exploring its potential in neurodegenerative diseases, given the quinoline core's ability to cross the blood-brain barrier. Additionally, its application in photodynamic therapy is being investigated, taking advantage of the halogen substituents' influence on the compound's photophysical properties.

In conclusion, 6-Bromo-7-chloroquinoline (CAS: 127827-54-7) represents a valuable chemical entity with diverse applications in drug discovery and development. The latest research underscores its importance as both a synthetic intermediate and a biologically active compound. Future studies will likely expand its therapeutic potential and optimize its properties for specific medical applications.

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