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CS-W001157 4
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5-Bromo-3-iodoindazole

  • CAS No. 459133-66-5

  • Cat. No. CS-M1446
  • Purity≥98%
  • MDL No.MFCD07781637

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

5-Bromo-3-iodoindazole|CS-M1446

Structure of 459133-66-5

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General Information

  • CAS No. 459133-66-5
  • Cat. No. CS-M1446
  • Purity ≥98%
  • MDL No. MFCD07781637
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrIN₂
  • Molecular Weight 322.93
  • Synonym(s) 5-Bromo-3-iodo-1H-indazole
  • SMILES BrC1=CC2=C(NN=C2I)C=C1

Description

5-Bromo-3-iodoindazole is a halogenated indazole scaffold featuring complementary reactive sites at the 5-bromo and 3-iodo positions. This dual-halogenation enables efficient cross-coupling transformations, particularly in palladium-catalyzed reactions, facilitating rapid access to complex heterocyclic architectures. The molecule exhibits high stability under standard conditions and serves as a key intermediate in medicinal chemistry and materials science applications.

Application

5-Bromo-3-iodoindazole serves as a versatile biaryl building block for transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of complex indazole-based scaffolds. The orthogonal halogen reactivity facilitates sequential functionalization, while the compound exhibits excellent bench stability and compatibility with standard Pd(0)-catalyzed coupling protocols. Its defined substitution pattern supports precise molecular design in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Crestey, Francois; Collot, Valerie; Stiebing, Silvia; Rault, Sylvain Synthesis, 2006 , # 20 p. 3506 - 3514

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   28.68
  • LogP   2.93
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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