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CS-W001157 4
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4,6-Difluoro-1H-indazole

  • CAS No. 885520-26-3

  • Cat. No. CS-0043959
  • Purity≥96%
  • MDL No.MFCD07781445

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

4,6-Difluoro-1H-indazole|CS-0043959

Structure of 885520-26-3

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General Information

  • CAS No. 885520-26-3
  • Cat. No. CS-0043959
  • Purity ≥96%
  • MDL No. MFCD07781445
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄F₂N₂
  • Molecular Weight 154.12
  • Synonym(s) 4-BROMO-6-(1H)INDAZOLE CARBOXYLIC ACID
  • SMILES FC1=CC2=C(C(F)=C1)C=NN2

Description

4,6-Difluoro-1H-indazole is a fluorinated heterocyclic scaffold featuring two strategically positioned fluorine atoms that enhance electron deficiency and metabolic stability. This configuration enables efficient coupling in cross-coupling reactions and improves membrane permeability. The molecule integrates readily into bioactive compounds for medicinal chemistry applications.

Application

4,6-Difluoro-1H-indazole serves as a versatile building block in medicinal chemistry, enabling direct functionalization at electron-deficient positions via palladium-catalyzed cross-coupling. Its enhanced reactivity profile facilitates efficient C–H arylation and heterocycle elaboration, while maintaining bench stability and compatibility with common protecting groups. This compound functions as a key scaffold for targeted synthesis of bioactive molecules, particularly in kinase inhibitor development.

Synthesis

  • Route1

    References

    • F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O'YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu Patent: WO2013/30138 A1, 2013 ; Location in patent: Page/Page column 237; 238 ;

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   1.8411
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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