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CS-W001157 4
Total: USD 88.00

2-Hydroxy-4-(trifluoromethyl)quinoline

  • CAS No. 25199-84-2

  • Cat. No. CS-W010483
  • Purity≥98%
  • MDL No.MFCD11707181

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

2-Hydroxy-4-(trifluoromethyl)quinoline|CS-W010483

Structure of 25199-84-2

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General Information

  • CAS No. 25199-84-2
  • Cat. No. CS-W010483
  • Purity ≥98%
  • MDL No. MFCD11707181
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆F₃NO
  • Molecular Weight 213.16
  • Synonym(s) 4-trifluoromethyl-2(1H)-quinolinone
  • SMILES OC2=NC1=CC=CC=C1C(=C2)C(F)(F)F

Description

2-Hydroxy-4-(trifluoromethyl)quinoline features a strategically positioned trifluoromethyl group that enhances electron-withdrawing character and metabolic stability. The phenolic hydroxyl enables hydrogen bonding and facilitates conjugation in synthetic scaffolds. This compound serves as a key building block in medicinal chemistry, particularly for developing kinase inhibitors and fluorescent probes.

Application

2-Hydroxy-4-(trifluoromethyl)quinoline serves as a versatile scaffold in medicinal chemistry, enabling efficient access to bioactive heterocycles. Its trifluoromethyl group enhances metabolic stability and membrane permeability, while the phenolic hydroxyl facilitates downstream functionalization via etherification or metal-catalyzed coupling. The compound exhibits bench stability and compatibility with standard purification methods, making it a practical building block for lead optimization campaigns targeting kinase inhibitors and other pharmaceutical candidates.

Synthesis

  • Route1
    • null|null
      74497-02-2
    • null|null
      372-31-6
    • ~70%
    • In-stock
      2-Hydroxy-4-(trifluoromethyl)quinoline|CS-W010483
      25199-84-2

    References

    • Berbasov, Dmitrii O.; Soloshonok, Vadim A. Synthesis, 2003 , # 13 p. 2005 - 2010
  • Route2
    • 4,4,4-Trifluoro-3-oxo-n-phenylbutanamide|CS-0672700
      836-31-7
    • ~89%
    • In-stock
      2-Hydroxy-4-(trifluoromethyl)quinoline|CS-W010483
      25199-84-2

    References

    • Marull, Marc; Lefebvre, Olivier; Schlosser, Manfred European Journal of Organic Chemistry, 2004 , # 1 p. 54 - 63
  • Route3
    • null|null
      74497-02-2
    • ~%
    • In-stock
      2-Hydroxy-4-(trifluoromethyl)quinoline|CS-W010483
      25199-84-2

    References

    • Journal of Medicinal Chemistry, , vol. 49, # 21 p. 6143 - 6146

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   2.9592
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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