7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

Name: 7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole
Brand: ChemScene
Availability: InStock
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CAS No. 915411-02-8
Cat. No. CS-0050126
Purity≥97%
MDL No.None

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7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole|CS-0050126

Structure of 915411-02-8

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General Information

CAS No. 915411-02-8
Cat. No. CS-0050126
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₇BN₂O₂
Molecular Weight 244.10
Synonym(s) 1H-Indazole, 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
SMILES CC1(C)OB(OC1(C)C)C1=C2NN=CC2=CC=C1

Description

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole features a boronate ester group enabling reliable Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane enhances stability and solubility in organic media. This bench-stable reagent integrates readily into diverse synthetic sequences for constructing biaryl architectures in medicinal chemistry and materials science.

Application

7-(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. Its stability under ambient conditions and compatibility with diverse functional groups enable efficient construction of biaryl architectures. The indazole core provides a pharmacophoric scaffold relevant to medicinal chemistry, while the pinacol boronate moiety facilitates mild, palladium-catalyzed coupling with aryl halides and triflates, offering reliable access to complex heterocyclic frameworks in drug discovery and materials science.

Synthesis

Route1
- In-stock
  
  73183-34-3
- In-stock
  
  53857-58-2
- ~75%
- In-stock
  
  915411-02-8
References
- LOCUS PHARMACEUTICALS, INC. Patent: WO2008/8059 A1, 2008 ; Location in patent: Page/Page column 66 ;
Route2
- In-stock
  
  73183-34-3
- In-stock
  
  186407-74-9
- ~%
- In-stock
  
  915411-02-8
References
- WO2006/46031 A1, ; Page/Page column 33-35 ; WO 2006/046031 A1

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 47.14
LogP 1.8621
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indazole compounds

Key Words

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7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

CAS No. 915411-02-8

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