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CS-W001157 4
Total: USD 88.00

1-Chloro-6-methoxy-isoquinoline

  • CAS No. 132997-77-4

  • Cat. No. CS-D0758
  • Molecule weight193.63
  • Purity≥97%
  • MDL No.MFCD06738659

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

1-Chloro-6-methoxy-isoquinoline|CS-D0758

Structure of 132997-77-4

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General Information

  • CAS No. 132997-77-4
  • Cat. No. CS-D0758
  • Purity ≥97%
  • MDL No. MFCD06738659
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈ClNO
  • Molecular Weight 193.63
  • Synonym(s) 1-Chloro-6-methoxyisoquinoline
  • SMILES ClC1=NC=CC2=C1C=CC(OC)=C2

Description

1-Chloro-6-methoxy-isoquinoline features a chlorine atom at the C1 position and a methoxy group at C6, creating a strategically positioned electrophilic site flanked by an electron-donating substituent. This electronic asymmetry enhances reactivity in palladium-catalyzed cross-coupling reactions while maintaining bench-stable handling properties. The molecule integrates readily into complex heterocyclic architectures under mild conditions.

Application

1-Chloro-6-methoxy-isoquinoline serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its well-established reactivity at the C1 position. The methoxy group at C6 provides electronic modulation and enhances solubility, while the chloro substituent offers excellent functional group tolerance and bench stability. It functions reliably in Suzuki-Miyaura, Negishi, and Buchwald-Hartwig coupling protocols, facilitating efficient construction of complex isoquinoline-based scaffolds for drug discovery applications.

Synthesis

  • Route1

    References

    • Bristol-Myers Squibb Company Patent: US2009/285773 A1, 2009 ; Location in patent: Page/Page column 12 ; US 20090285773 A1
  • Route2
    • null|null
      266690-46-4
    • ~88%
    • In-stock
      1-Chloro-6-methoxy-isoquinoline|CS-D0758
      132997-77-4

    References

    • Akzo Nobel N.V. Patent: US6903107 B1, 2005 ; Location in patent: Page/Page column 9-10 ;
  • Route3

    References

    • EP2332917 A1, ; EP 2332917 A1

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

Quality Control

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Computational Chemistry Data

  • TPSA   22.12
  • LogP   2.8968
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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