Cas no 1260760-06-2 (8-Bromoisoquinolin-3-amine)

8-Bromoisoquinolin-3-amine is a brominated isoquinoline derivative featuring an amine functional group at the 3-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. The bromine substituent enhances its reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling efficient derivatization. The amine group further allows for modifications via acylation, alkylation, or condensation reactions. Its well-defined structure and high purity make it suitable for research and industrial applications requiring precise molecular scaffolds. The compound’s stability and compatibility with diverse reaction conditions contribute to its utility in synthetic chemistry.
8-Bromoisoquinolin-3-amine structure
8-Bromoisoquinolin-3-amine structure
Product Name:8-Bromoisoquinolin-3-amine
CAS No:1260760-06-2
MF:C9H7BrN2
MW:223.069280862808
MDL:MFCD15526547
CID:1091254
PubChem ID:53419047
Update Time:2025-05-23

8-Bromoisoquinolin-3-amine Chemical and Physical Properties

Names and Identifiers

    • 8-Bromoisoquinolin-3-amine
    • 8-bromo-isoquinolin-3-yl-amine
    • MFCD15526547
    • DB-342094
    • 3-Amino-8-bromoisoquinoline
    • 3-Isoquinolinamine, 8-bromo-
    • 1260760-06-2
    • DTXSID10697485
    • SCHEMBL2553675
    • A926406
    • SY258361
    • AKOS022176664
    • AS-38811
    • EN300-2996740
    • CS-0210681
    • MDL: MFCD15526547
    • Inchi: 1S/C9H7BrN2/c10-8-3-1-2-6-4-9(11)12-5-7(6)8/h1-5H,(H2,11,12)
    • InChI Key: MELBFTIXTXTDDR-UHFFFAOYSA-N
    • SMILES: BrC1=CC=CC2C=C(N)N=CC=21

Computed Properties

  • Exact Mass: 221.97926g/mol
  • Monoisotopic Mass: 221.97926g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 163
  • 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: 2.4
  • Topological Polar Surface Area: 38.9?2

8-Bromoisoquinolin-3-amine Security Information

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Additional information on 8-Bromoisoquinolin-3-amine

Introduction to 8-Bromoisoquinolin-3-amine (CAS No. 1260760-06-2)

8-Bromoisoquinolin-3-amine, identified by the Chemical Abstracts Service Number (CAS No.) 1260760-06-2, is a significant heterocyclic compound that has garnered considerable attention in the field of pharmaceutical chemistry and medicinal biology. This compound belongs to the isoquinoline class, a structurally diverse family of nitrogen-containing aromatic organic compounds known for their broad spectrum of biological activities. The presence of both bromine and amine functional groups in its molecular structure imparts unique reactivity and makes it a valuable intermediate in synthetic chemistry, particularly in the development of novel therapeutic agents.

The isoquinoline scaffold, characterized by a fused benzene and pyridine ring system, has been extensively studied for its pharmacological properties. Derivatives of isoquinoline have shown promise in various therapeutic applications, including anticancer, antimicrobial, and anti-inflammatory treatments. Among these derivatives, 8-Bromoisoquinolin-3-amine stands out due to its structural versatility and potential to serve as a precursor for more complex molecules. The bromine atom at the 8-position provides a handle for further functionalization via cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, while the amine group at the 3-position allows for modifications like acylation or alkylation, enabling the construction of diverse pharmacophores.

In recent years, there has been a surge in research focused on developing small-molecule inhibitors targeting specific enzymes and pathways involved in diseases such as cancer and neurodegenerative disorders. 8-Bromoisoquinolin-3-amine has been explored as a key building block in the synthesis of inhibitors that interact with proteins like kinases and transcription factors. For instance, studies have demonstrated its utility in generating compounds that modulate the activity of tyrosine kinases, which are often overexpressed in cancer cells. The ability to fine-tune the electronic and steric properties of isoquinoline derivatives allows researchers to optimize binding affinity and selectivity, making them promising candidates for drug development.

The pharmaceutical industry has increasingly leveraged computational chemistry and high-throughput screening techniques to identify novel scaffolds with therapeutic potential. 8-Bromoisoquinolin-3-amine has been incorporated into virtual screening campaigns aimed at discovering new drugs against challenging targets. Its structural features make it an attractive candidate for designing molecules that can penetrate biological membranes and exhibit favorable pharmacokinetic profiles. Additionally, its role in generating libraries of diverse compounds for experimental validation underscores its importance in drug discovery pipelines.

Advances in synthetic methodologies have further enhanced the accessibility of 8-Bromoisoquinolin-3-amine, enabling researchers to produce it with high purity and yield. Modern techniques such as flow chemistry and microwave-assisted synthesis have streamlined its preparation, reducing reaction times and improving scalability. These advancements are crucial for supporting large-scale drug development programs where cost-effective and efficient synthesis is paramount.

The biological activity of 8-Bromoisoquinolin-3-amine has been investigated across multiple disease models. Preclinical studies have highlighted its potential as an antimicrobial agent, with some derivatives exhibiting efficacy against resistant bacterial strains. Furthermore, its interaction with biological targets suggests possible applications in treating inflammatory diseases by modulating immune responses. The compound’s ability to cross cell membranes makes it an appealing candidate for delivering bioactive molecules directly to target sites within cells.

In conclusion,8-Bromoisoquinolin-3-amine (CAS No. 1260760-06-2) is a versatile intermediate with significant implications in pharmaceutical research and drug development. Its unique structural features enable diverse functionalization strategies, making it a valuable tool for synthesizing novel therapeutic agents targeting various diseases. As research continues to uncover new biological activities and synthetic applications, this compound is poised to remain at the forefront of medicinal chemistry innovation.

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