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

  • CAS No. 864771-17-5

  • Cat. No. CS-0051255
  • Purity≥97%
  • MDL No.None

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

3-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole|CS-0051255

Structure of 864771-17-5

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General Information

  • CAS No. 864771-17-5
  • Cat. No. CS-0051255
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₉BN₂O₂
  • Molecular Weight 258.12
  • Synonym(s) 3-METHYL-5-PINACOLATOBORYL-INDAZOLE
  • SMILES CC1=NNC2=C1C=C(C=C2)B1OC(C)(C)C(C)(C)O1

Description

3-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole features a boronate ester group enabling reliable Suzuki-Miyaura cross-coupling reactions. The tetramethylcycloborolane moiety ensures high stability and moisture tolerance, while the indazole scaffold provides a rigid, electron-deficient platform for diverse heterocyclic synthesis. This compound serves as a key building block in medicinal chemistry and materials science.

Application

3-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylborolane moiety enables efficient palladium-catalyzed coupling with aryl and heteroaryl halides under mild conditions. Its stability, ease of handling, and compatibility with diverse functional groups make it well-suited for the construction of complex indazole-based scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • US2007/173506 A1, ; Page/Page column 31; 32 ;
  • Route2

    References

    • WO2012/119046 A2, ;

Safety Information

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

Quality Control

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Computational Chemistry Data

  • TPSA   47.14
  • LogP   2.17052
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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