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CS-W001157 4
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3-(Trifluoromethyl)-1H-indazole

  • CAS No. 57631-05-7

  • Cat. No. CS-0042765
  • Molecule weight186.13
  • Purity≥98%
  • MDL No.None

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

3-(Trifluoromethyl)-1H-indazole|CS-0042765

Structure of 57631-05-7

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General Information

  • CAS No. 57631-05-7
  • Cat. No. CS-0042765
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅F₃N₂
  • Molecular Weight 186.13
  • Synonym(s) 3-trifluoromethylindazole
  • SMILES FC(F)(F)C1=NNC2=CC=CC=C12

Description

3-(Trifluoromethyl)-1H-indazole is a bench-stable, electron-deficient heterocycle featuring a trifluoromethyl group at the 3-position, enhancing metabolic stability and lipophilicity. This configuration enables direct functionalization in cross-coupling reactions and facilitates incorporation into bioactive molecules for medicinal chemistry applications.

Application

3-(Trifluoromethyl)-1H-indazole serves as a valuable heterocyclic building block in medicinal chemistry, offering enhanced metabolic stability and modulated lipophilicity due to the electron-withdrawing trifluoromethyl group. It functions as a bioisostere for phenyl or pyridine moieties in drug discovery campaigns and participates reliably in standard coupling reactions, including Pd-catalyzed cross-couplings and electrophilic substitutions. The compound exhibits good bench stability and facilitates efficient synthesis of complex scaffolds under routine laboratory conditions.

Synthesis

  • Route1
    • 2,2,2-trifluoro-1-(2-iodophenyl)ethan-1-one|CS-1006232
      886370-80-5
    • ~%
    • In-stock
      3-(Trifluoromethyl)-1H-indazole|CS-0042765
      57631-05-7

    References

    • GLAXO GROUP LIMITED Patent: WO2008/148832 A1, 2008 ; Location in patent: Page/Page column 37-38 ; WO 2008/148832 A1
  • Route2
    • 2-(2,2,2-Trifluoroethyl)aniline|CS-0150079
      57631-04-6
    • ~%
    • In-stock
      3-(Trifluoromethyl)-1H-indazole|CS-0042765
      57631-05-7

    References

    • Zhu, Gui-Dong; Gong, Jianchun; Gandhi, Viraj B.; Woods, Keith; Luo, Yan; Liu, Xuesong; Guan, Ran; Klinghofer, Vered; Johnson, Eric F.; Stoll, Vincent S.; Mamo, Mulugeta; Li, Qun; Rosenberg, Saul H.; Giranda, Vincent L. Bioorganic and Medicinal Chemistry, 2007 , vol. 15, # 6 p. 2441 - 2452
  • Route3
    • null|null
      675106-80-6
    • ~%
    • In-stock
      3-(Trifluoromethyl)-1H-indazole|CS-0042765
      57631-05-7

    References

    • O'Dell, David K.; Nicholas, Kenneth M. Heterocycles, 2004 , vol. 63, # 2 p. 373 - 382

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   28.68
  • LogP   2.5817
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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