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4-Chloro-6-hydroxyquinoline

  • CAS No. 148018-29-5

  • Cat. No. CS-0042911
  • Purity≥97%
  • MDL No.MFCD00456102

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

4-Chloro-6-hydroxyquinoline|CS-0042911

Structure of 148018-29-5

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General Information

  • CAS No. 148018-29-5
  • Cat. No. CS-0042911
  • Purity ≥97%
  • MDL No. MFCD00456102
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆ClNO
  • Molecular Weight 179.60
  • Synonym(s) 6-quinolinol, 4-chloro-
  • SMILES OC1=CC=C2N=CC=C(Cl)C2=C1

Description

4-Chloro-6-hydroxyquinoline is a heterocyclic compound featuring a chlorine substituent at the 4-position and a hydroxyl group at the 6-position of the quinoline core. This arrangement imparts enhanced polarity and hydrogen-bonding capacity, facilitating solubility in polar solvents and enabling participation in directed synthesis pathways. The electron-withdrawing chlorine modulates the electronic profile of the aromatic system, while the adjacent hydroxyl group supports metal coordination and further functionalization. This scaffold serves as a key intermediate in medicinal chemistry and materials science applications.

Application

4-Chloro-6-hydroxyquinoline serves as a versatile building block for the synthesis of functionalized quinoline derivatives. The hydroxyl group enables direct derivatization via etherification or acylation, while the chloro substituent supports palladium-catalyzed cross-coupling reactions. Its bench-stable nature and compatibility with standard protecting group strategies facilitate efficient access to complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Journal of the American Chemical Society, , vol. 69, p. 1659,1660
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 69, p. 1659,1660
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 69, p. 1659,1660

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

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