Cas no 1428651-86-8 (4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one)

4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-one is a brominated tetrahydroisoquinoline derivative that serves as a versatile intermediate in organic synthesis and pharmaceutical research. Its structure features a reactive bromine substituent at the 4-position and a ketone functional group at the 8-position, enabling further functionalization through cross-coupling reactions, nucleophilic substitutions, or reductions. This compound is particularly valuable in the development of bioactive molecules, including potential CNS-targeting agents, due to the isoquinoline scaffold's prevalence in medicinal chemistry. Its well-defined reactivity profile and stability under standard conditions make it a reliable building block for constructing complex heterocyclic frameworks. The product is typically supplied with high purity, ensuring consistent performance in synthetic applications.
4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one structure
1428651-86-8 structure
Product Name:4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one
CAS No:1428651-86-8
MF:C9H8BrNO
MW:226.06992149353
MDL:MFCD25542135
CID:4599205
PubChem ID:71743380
Update Time:2025-05-20

4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one Chemical and Physical Properties

Names and Identifiers

    • 4-BROMO-6,7-DIHYDROISOQUINOLIN-8(5H)-ONE
    • 4-bromo-6,7-dihydro-5H-isoquinolin-8-one
    • 4-Bromo-5,6-dihydroisoquinoline-8(7H)-one
    • 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one
    • 8(5H)-Isoquinolinone, 4-bromo-6,7-dihydro-
    • MFCD25542135
    • DTXSID101275055
    • CS-0047443
    • 4-BROMO-6,7-DIHYDROISOQUINOLIN-8(5H)-ONE(WXC07920)
    • FACZUAXPWHUPAL-UHFFFAOYSA-N
    • 1428651-86-8
    • AKOS027252014
    • SY279522
    • EN300-254542
    • DB-205926
    • 4-Bromo-6,7-dihydro-8(5H)-isoquinolinone
    • SCHEMBL14799664
    • AS-64678
    • MDL: MFCD25542135
    • Inchi: 1S/C9H8BrNO/c10-8-5-11-4-7-6(8)2-1-3-9(7)12/h4-5H,1-3H2
    • InChI Key: FACZUAXPWHUPAL-UHFFFAOYSA-N
    • SMILES: BrC1=CN=CC2C(CCCC=21)=O

Computed Properties

  • Exact Mass: 224.97893 g/mol
  • Monoisotopic Mass: 224.97893 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 195
  • 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: 1.6
  • Topological Polar Surface Area: 30
  • Molecular Weight: 226.07

4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one Pricemore >>

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Additional information on 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one

Recent Advances in the Study of 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one (CAS: 1428651-86-8)

4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one (CAS: 1428651-86-8) is a key intermediate in the synthesis of various biologically active compounds, particularly in the field of medicinal chemistry. Recent studies have highlighted its significance in the development of novel therapeutic agents targeting neurological disorders, cancer, and infectious diseases. This research briefing provides an overview of the latest findings related to this compound, focusing on its synthesis, biological activities, and potential applications.

One of the most notable advancements in the study of 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one is its role as a precursor in the synthesis of isoquinoline derivatives. Isoquinolines are a class of heterocyclic compounds with diverse pharmacological properties, including antimicrobial, anticancer, and neuroprotective effects. Recent research has demonstrated that modifications to the isoquinoline scaffold, such as bromination at the 4-position, can significantly enhance the compound's bioactivity and selectivity.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers explored the use of 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one as a building block for the development of kinase inhibitors. The study reported that derivatives of this compound exhibited potent inhibitory activity against specific kinases involved in cancer cell proliferation. The findings suggest that 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one could serve as a valuable scaffold for designing next-generation anticancer drugs.

Another area of interest is the compound's potential application in neurodegenerative disease research. A recent study in ACS Chemical Neuroscience investigated the neuroprotective effects of isoquinoline derivatives synthesized from 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one. The results indicated that these derivatives could mitigate oxidative stress and inflammation in neuronal cells, offering a promising avenue for the treatment of conditions such as Alzheimer's and Parkinson's diseases.

From a synthetic chemistry perspective, advancements have been made in optimizing the production of 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one. A 2022 publication in Organic Process Research & Development detailed a scalable and cost-effective method for its synthesis, emphasizing the use of green chemistry principles. This development is particularly significant for industrial applications, where efficient and sustainable production methods are highly sought after.

In conclusion, 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-one (CAS: 1428651-86-8) continues to be a compound of great interest in the field of medicinal chemistry. Its versatility as a synthetic intermediate and its potential therapeutic applications make it a focal point for ongoing research. Future studies are expected to further elucidate its mechanisms of action and explore its utility in drug discovery and development.

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