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6-Bromoisoquinolin-1-one

  • CAS No. 82827-09-6

  • Cat. No. CS-B0782
  • Purity≥95%
  • MDL No.MFCD07374394

*For research and further manufacturing use only, not for direct human use.

6-Bromoisoquinolin-1-one|CS-B0782

Structure of 82827-09-6

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General Information

  • CAS No. 82827-09-6
  • Cat. No. CS-B0782
  • Purity ≥95%
  • MDL No. MFCD07374394
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆BrNO
  • Molecular Weight 224.05
  • Synonym(s) 6-Bromo-2H-isoquinolin-1-one; 6-bromoisoquinolin-1(2H)-one
  • SMILES O=C1NC=CC2=C1C=CC(Br)=C2

Description

6-Bromoisoquinolin-1-one features a bromine substituent at the 6-position of an isoquinolin-1-one core, delivering enhanced reactivity for cross-coupling applications. The electron-deficient carbonyl and halogen handle enable efficient functionalization in palladium-catalyzed transformations. This bench-stable compound integrates readily into complex molecular architectures.

Application

6-Bromoisoquinolin-1-one serves as a versatile building block in medicinal chemistry and synthetic organic chemistry, enabling direct functionalization at the C6 position via palladium-catalyzed cross-coupling reactions. The isoquinolin-1-one core provides a rigid, planar scaffold with inherent hydrogen-bonding capacity and moderate lipophilicity, facilitating its use in drug discovery campaigns. Bench-stable and readily purified by flash chromatography or recrystallization, it exhibits broad compatibility with nucleophiles, organometallic reagents, and transition-metal catalysis under standard conditions.

Synthesis

  • Route1

    References

    • WO2008/77552 A1, ; Page/Page column 54 ; WO 2008/077552 A1
  • Route2

    References

    • US2004/44258 A1, ; Page 159-160 ;
  • Route3

    References

    • US6034093 A1, ; US 6034093 A

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   32.86
  • LogP   2.2906
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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