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2-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole

  • CAS No. 1189746-27-7

  • Cat. No. CS-0051854
  • Purity≥97%
  • MDL No.None

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

2-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole|CS-0051854

Structure of 1189746-27-7

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General Information

  • CAS No. 1189746-27-7
  • Cat. No. CS-0051854
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₉BN₂O₂
  • Molecular Weight 258.12
  • Synonym(s) 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole
  • SMILES CN1C=C2C=C(C=CC2=N1)B1OC(C)(C)C(C)(C)O1

Description

This boronate-functionalized indazole integrates seamlessly into cross-coupling reactions under standard conditions. The tetramethyl-1,3,2-dioxaborolan-2-yl group delivers enhanced stability and reactivity, enabling efficient C–C bond formation. Its bench-stable nature simplifies handling in synthetic workflows.

Application

2-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient palladium-catalyzed coupling with aryl and vinyl halides under mild conditions. Its stability, ease of handling, and compatibility with diverse functional groups make it ideal for constructing complex heterocyclic architectures in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • US2009/253750 A1, ; Page/Page column 6 ;

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   36.28
  • LogP   1.8725
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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