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3-Bromo-6-fluoro-1H-indazole

  • CAS No. 885522-04-3

  • Cat. No. CS-0042113
  • Purity≥95%
  • MDL No.MFCD07781603

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

3-Bromo-6-fluoro-1H-indazole|CS-0042113

Structure of 885522-04-3

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General Information

  • CAS No. 885522-04-3
  • Cat. No. CS-0042113
  • Purity ≥95%
  • MDL No. MFCD07781603
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrFN₂
  • Molecular Weight 215.02
  • Synonym(s) 3-BROMO-6-FLUORO (1H)INDAZOLE
  • SMILES FC1=CC2=C(C=C1)C(Br)=NN2

Description

3-Bromo-6-fluoro-1H-indazole is a halogenated heterocyclic scaffold featuring complementary electrophilic (bromo) and electron-withdrawing (fluoro) substituents. This configuration enables efficient cross-coupling reactions, particularly in palladium-catalyzed transformations. The molecule exhibits enhanced metabolic stability and favorable solubility profiles under standard reaction conditions, facilitating its integration into medicinal chemistry campaigns targeting kinase inhibitors and CNS-active compounds.

Application

3-Bromo-6-fluoro-1H-indazole serves as a versatile heterocyclic building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The bromine at C3 facilitates Suzuki, Stille, and Negishi couplings, while the fluorine at C6 offers enhanced metabolic stability and potential for directed ortho-metalation. Its bench-stable crystalline form simplifies handling and purification, making it well-suited for iterative synthesis of bioactive indazole derivatives.

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

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Computational Chemistry Data

  • TPSA   28.68
  • LogP   2.4645
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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