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3-Fluoroquinolin-6-ol

  • CAS No. 808755-53-5

  • Cat. No. CS-0155645
  • Molecule weight163.15
  • Purity≥98%
  • MDL No.MFCD18414584

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

3-Fluoroquinolin-6-ol|CS-0155645

Structure of 808755-53-5

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General Information

  • CAS No. 808755-53-5
  • Cat. No. CS-0155645
  • Purity ≥98%
  • MDL No. MFCD18414584
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆FNO
  • Molecular Weight 163.15
  • Synonym(s) 3-fluoro-6-hydroxyquinoline
  • SMILES C1=CC2=NC=C(C=C2C=C1O)F

Description

3-Fluoroquinolin-6-ol features a fluorinated quinoline core with a phenolic hydroxyl group, offering enhanced electron-withdrawing character and improved solubility. This scaffold integrates readily into bioactive molecules, enabling efficient access to kinase inhibitors and fluorescent probes under standard conditions.

Application

3-Fluoroquinolin-6-ol serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C6 position via nucleophilic substitution or transition-metal-catalyzed coupling. Its fluorinated quinoline core provides enhanced metabolic stability and favorable pharmacokinetic properties. The phenolic hydroxyl group facilitates derivatization for prodrug strategies or conjugation, while the molecule exhibits good bench stability and compatibility with common synthetic transformations.

Synthesis

  • Route1

    References

    • Lamberth, Clemens; Kessabi, Fiona Murphy; Beaudegnies, Renaud; Quaranta, Laura; Trah, Stephan; Berthon, Guillaume; Cederbaum, Fredrik; Vettiger, Thomas; Prasanna Synlett, 2014 , vol. 25, # 6 art. no. 98, p. 858 - 862
  • Route2

    References

    • SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED Patent: WO2006/58700 A1, 2006 ; Location in patent: Page/Page column 90 ;
  • Route3
    • 3-Bromo-6-nitroquinoline|CS-0155647
      7101-95-3
    • ~%
    • In-stock
      3-Fluoroquinolin-6-ol|CS-0155645
      808755-53-5

    References

    • Lamberth, Clemens; Kessabi, Fiona Murphy; Beaudegnies, Renaud; Quaranta, Laura; Trah, Stephan; Berthon, Guillaume; Cederbaum, Fredrik; Vettiger, Thomas; Prasanna Synlett, 2014 , vol. 25, # 6 art. no. 98, p. 858 - 862

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   33.12
  • LogP   2.0795
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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