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3-Chloroquinolin-8-ol

  • CAS No. 102878-83-1

  • Cat. No. CS-0186812
  • Molecule weight179.61
  • Purity≥98%
  • MDL No.MFCD16877648

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

3-Chloroquinolin-8-ol|CS-0186812

Structure of 102878-83-1

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General Information

  • CAS No. 102878-83-1
  • Cat. No. CS-0186812
  • Purity ≥98%
  • MDL No. MFCD16877648
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆ClNO
  • Molecular Weight 179.61
  • Synonym(s) 3-Chloro-8-quinolinol
  • SMILES C1=CC2=CC(=CN=C2C(=C1)O)Cl

Description

3-Chloroquinolin-8-ol delivers a rigid, electron-deficient quinoline scaffold bearing a strategically positioned hydroxyl group. This configuration enables direct functionalization at the 8-position and enhances solubility in polar solvents. The chloro substituent at C3 supports downstream cross-coupling reactions, while the phenolic OH facilitates hydrogen bonding and metal coordination. Bench-stable under standard conditions, this compound serves as a key intermediate in the synthesis of bioactive heterocycles and ligands for transition metal catalysis.

Application

3-Chloroquinolin-8-ol serves as a versatile building block in medicinal chemistry, enabling efficient construction of quinoline-based scaffolds. Its chlorine and phenolic hydroxyl groups provide orthogonal reactivity for palladium-catalyzed cross-coupling and directed functionalization. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis campaigns in API development and target-oriented discovery.

Synthesis

  • Route1

    References

    • Gershon, Herman; Clarke, Donald D. Monatshefte fuer Chemie, 1991 , vol. 122, # 11 p. 935 - 942
  • Route2

    References

    • Gershon, Herman; Clarke, Donald D. Monatshefte fuer Chemie, 1991 , vol. 122, # 11 p. 935 - 942
  • Route3
    • 3-Chloro-8-nitroquinoline|CS-0326488
      73868-16-3
    • ~%
    • In-stock
      3-Chloroquinolin-8-ol|CS-0186812
      102878-83-1

    References

    • Gershon, Herman; Clarke, Donald D. Monatshefte fuer Chemie, 1991 , vol. 122, # 11 p. 935 - 942

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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