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CS-W001157 4
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5-Chloroquinolin-4-ol

  • CAS No. 23443-05-2

  • Cat. No. CS-0160672
  • Purity≥98%
  • MDL No.MFCD16659125

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

5-Chloroquinolin-4-ol|CS-0160672

Structure of 23443-05-2

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General Information

  • CAS No. 23443-05-2
  • Cat. No. CS-0160672
  • Purity ≥98%
  • MDL No. MFCD16659125
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆ClNO
  • Molecular Weight 179.60
  • Synonym(s) 4-hydroxy-5-chloroquinoline
  • SMILES OC1=CC=NC2=CC=CC(Cl)=C12

Description

5-Chloroquinolin-4-ol delivers a rigid, electron-deficient quinoline scaffold bearing a strategically positioned hydroxyl group. This combination enables direct functionalization at the 4-position and enhances solubility in polar solvents. The chloro substituent at the 5-position supports further derivatization via cross-coupling reactions. This compound serves as a key intermediate in medicinal chemistry campaigns targeting kinase inhibitors and antimalarial agents.

Application

5-Chloroquinolin-4-ol serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C4 position via nucleophilic substitution or transition-metal-catalyzed coupling. The chloro group exhibits high reactivity under palladium-catalyzed conditions, while the phenolic hydroxyl offers orthogonal handling for derivatization. Bench-stable and readily purified by recrystallization, it functions effectively in the synthesis of quinoline-based pharmaceutical scaffolds and agrochemical intermediates.

Synthesis

  • Route1
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      35973-28-5
    • ~%
    • In-stock
      5-Chloroquinolin-4-ol|CS-0160672
      23443-05-2

    References

    • Surrey; Hammer Journal of the American Chemical Society, 1946 , vol. 68, p. 113,115
  • Route2
    • null|null
      108-42-9
    • ~%
    • In-stock
      5-Chloroquinolin-4-ol|CS-0160672
      23443-05-2

    References

    • Surrey; Hammer Journal of the American Chemical Society, 1946 , vol. 68, p. 113,115
  • Route3
    • null|null
      21640-98-2
    • ~%
    • In-stock
      5-Chloroquinolin-4-ol|CS-0160672
      23443-05-2

    References

    • Andersag Chemische Berichte, 1948 , vol. 81, p. 499,505

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   33.12
  • LogP   2.5938
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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