Cas no 552331-06-3 (6-Bromo-3-chloroisoquinoline)

6-Bromo-3-chloroisoquinoline is a halogenated isoquinoline derivative commonly utilized as a versatile intermediate in organic synthesis and pharmaceutical research. Its distinct bromo and chloro substituents at the 6- and 3-positions, respectively, make it a valuable building block for constructing complex heterocyclic compounds. The compound exhibits high reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling efficient derivatization. Its stability under standard storage conditions and well-defined crystalline structure further enhance its utility in medicinal chemistry and material science applications. Researchers favor this compound for its predictable reactivity and compatibility with diverse synthetic methodologies.
6-Bromo-3-chloroisoquinoline structure
6-Bromo-3-chloroisoquinoline structure
Product Name:6-Bromo-3-chloroisoquinoline
CAS No:552331-06-3
MF:C9H5BrClN
MW:242.499700307846
MDL:MFCD08703290
CID:838845
PubChem ID:22607530
Update Time:2025-11-01

6-Bromo-3-chloroisoquinoline Chemical and Physical Properties

Names and Identifiers

    • 6-Bromo-3-chloroisoquinoline
    • 6-bromo-3-chloro-isoquinoline
    • Isoquinoline, 6-bromo-3-chloro-
    • HYCCUWZOOADPGN-UHFFFAOYSA-N
    • RP05912
    • SB12367
    • 6-Bromo-3-chloroisoquinoline, AldrichCPR
    • SY019645
    • AB0025458
    • W6926
    • ST24029660
    • AM20061858
    • J-518363
    • CS-W006052
    • EN300-172015
    • 552331-06-3
    • MFCD08703290
    • AKOS015851185
    • DB-071961
    • KH-0723
    • SCHEMBL6833006
    • DTXSID00626860
    • MDL: MFCD08703290
    • Inchi: 1S/C9H5BrClN/c10-8-2-1-6-5-12-9(11)4-7(6)3-8/h1-5H
    • InChI Key: HYCCUWZOOADPGN-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2C=NC(=CC=2C=1)Cl

Computed Properties

  • Exact Mass: 240.92900
  • 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
  • Topological Polar Surface Area: 12.9
  • XLogP3: 3.8

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.7±0.1 g/cm3
  • Melting Point: No data available
  • Boiling Point: 349.5°C at 760 mmHg
  • Flash Point: 165.2±22.3 °C
  • Refractive Index: 1.68
  • PSA: 12.89000
  • LogP: 3.65070
  • Vapor Pressure: 0.0±0.7 mmHg at 25°C

6-Bromo-3-chloroisoquinoline Customs Data

  • HS CODE:2933499090
  • Customs Data:

    China Customs Code:

    2933499090

    Overview:

    2933499090. Other compounds containing quinoline or isoquinoline ring system [but not further fused]. 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:

    2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

6-Bromo-3-chloroisoquinoline Pricemore >>

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6-Bromo-3-chloroisoquinoline Production Method

Additional information on 6-Bromo-3-chloroisoquinoline

Introduction to 6-Bromo-3-chloroisoquinoline (CAS No. 552331-06-3)

6-Bromo-3-chloroisoquinoline, identified by its Chemical Abstracts Service (CAS) number 552331-06-3, is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the isoquinoline family, a class of nitrogen-containing aromatic organic compounds known for their diverse biological activities and applications in drug development. The presence of both bromine and chlorine substituents in its molecular structure enhances its reactivity, making it a valuable intermediate in synthetic chemistry and a potential candidate for further functionalization.

The isoquinoline scaffold is structurally reminiscent of benzene but incorporates a nitrogen atom into the aromatic ring system, which imparts unique electronic and steric properties. These properties make isoquinoline derivatives attractive for designing molecules with specific interactions with biological targets. In particular, 6-Bromo-3-chloroisoquinoline has been explored in various synthetic pathways due to its ability to undergo selective reactions at the bromo and chloro substituents, facilitating the construction of more complex molecular architectures.

Recent advancements in pharmaceutical research have highlighted the utility of 6-Bromo-3-chloroisoquinoline in the development of novel therapeutic agents. Its structural features suggest potential applications in targeting enzymes and receptors involved in diseases such as cancer, inflammation, and neurodegeneration. For instance, studies have demonstrated that isoquinoline derivatives can modulate kinase activity, which is crucial for regulating cell proliferation and survival. The bromo and chloro groups provide handles for further chemical modification, allowing researchers to fine-tune the pharmacological properties of these compounds.

One notable area of research involves the use of 6-Bromo-3-chloroisoquinoline as a precursor in the synthesis of small-molecule inhibitors. These inhibitors are designed to disrupt aberrant signaling pathways that contribute to disease progression. The compound’s reactivity at the halogenated positions enables the introduction of additional functional groups, such as amides or ureas, which can enhance binding affinity to biological targets. This flexibility has been exploited in the development of molecules with improved selectivity and reduced toxicity.

The synthesis of 6-Bromo-3-chloroisoquinoline typically involves multi-step organic reactions starting from readily available precursors. Common synthetic routes include cyclization reactions followed by halogenation steps to introduce the bromine and chlorine substituents at specific positions on the isoquinoline ring. The choice of reaction conditions is critical to achieving high yields and purity, which are essential for subsequent applications in drug discovery.

In addition to its pharmaceutical applications, 6-Bromo-3-chloroisoquinoline has shown promise in materials science and chemical biology. Its ability to participate in various chemical transformations makes it a versatile building block for creating complex organic molecules. Researchers have also explored its use in developing sensors and probes for detecting biological molecules, leveraging its interaction with target analytes.

The growing interest in 6-Bromo-3-chloroisoquinoline underscores its significance as a key intermediate in modern chemical synthesis. As our understanding of its reactivity and biological potential continues to expand, this compound is likely to play an increasingly important role in the discovery and development of new drugs and functional materials. The integration of computational methods and high-throughput screening techniques will further enhance our ability to harness its full potential.

Future research directions may focus on optimizing synthetic methodologies to improve scalability and sustainability while reducing environmental impact. Additionally, exploring novel derivatives of 6-Bromo-3-chloroisoquinoline could uncover additional therapeutic applications or functionalities that are not yet fully appreciated. The combination of experimental chemistry with advanced computational modeling will be essential in unlocking the full potential of this versatile compound.

In conclusion, 6-Bromo-3-chloroisoquinoline (CAS No. 552331-06-3) represents a promising candidate for further exploration in pharmaceuticals, materials science, and chemical biology. Its unique structural features and reactivity make it a valuable tool for synthetic chemists and medicinal researchers alike. As our understanding of its properties continues to grow, so too will its applications across multiple scientific disciplines.

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