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1,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

  • CAS No. 1220696-53-6

  • Cat. No. CS-0053846
  • Purity≥98%
  • MDL No.MFCD17214391

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

1,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole|CS-0053846

Structure of 1220696-53-6

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General Information

  • CAS No. 1220696-53-6
  • Cat. No. CS-0053846
  • Purity ≥98%
  • MDL No. MFCD17214391
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁BN₂O₂
  • Molecular Weight 272.15
  • Synonym(s) 1,3-DIMETHYLINDAZOLE-5-BORONIC ACID PINACOL ESTER
  • SMILES CC1(C)C(C)(C)OB(C2=CC3=C(N(C)N=C3C)C=C2)O1

Description

1,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole is a bench-stable boronate ester featuring a sterically protected dioxaborolane group. This indazole scaffold integrates readily into Suzuki-Miyaura coupling reactions under standard conditions, enabling efficient C–C bond formation with aryl and heteroaryl halides. The tetramethyl-substituted boronate moiety enhances stability and minimizes protodeboronation, facilitating reliable cross-coupling in complex molecular architectures.

Application

1,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling with aryl and heteroaryl halides under mild conditions, while the indazole core provides a stable, nitrogen-rich scaffold relevant to medicinal chemistry. Bench-stable and easily handled, it facilitates rapid diversification of indazole-based architectures in target-oriented synthesis.

Safety Information

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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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   36.28
  • LogP   2.18092
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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