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

Name: 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 885618-33-7
Cat. No. CS-W009185
Purity≥97%
MDL No.MFCD08059267

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4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole|CS-W009185

Structure of 885618-33-7

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General Information

CAS No. 885618-33-7
Cat. No. CS-W009185
Purity ≥97%
MDL No. MFCD08059267
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₇BN₂O₂
Molecular Weight 244.10
Synonym(s) 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indazole
SMILES CC1(C)OB(C2=CC=CC3=C2C=NN3)OC(C)1C

Description

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole delivers a boronate-functionalized indazole scaffold with enhanced stability and solubility. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura coupling protocols, enabling efficient C–C bond formation under mild conditions. The tetramethyl-dioxaborolane moiety ensures low toxicity and high functional group tolerance, while the electron-rich indazole core facilitates selective coupling in complex molecular architectures.

Application

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. Its stability under ambient conditions and tolerance to diverse functional groups enable reliable incorporation into complex molecular architectures. The indazole core provides a privileged scaffold for medicinal chemistry applications, while the pinacol boronate moiety facilitates efficient coupling with aryl, heteroaryl, and vinyl electrophiles. This reagent streamlines the synthesis of biologically active compounds and functionalized heterocycles in drug discovery workflows.

Synthesis

Route1
- In-stock
  
  73183-34-3
- In-stock
  
  186407-74-9
- ~60%
- In-stock
  
  885618-33-7
References
- Curis, Inc.; Bao, Rudi; Lai, Chengjung; Qian, Changgeng Patent: US2013/102595 A1, 2013 ; Location in patent: Paragraph 0173 ;
Route2
- In-stock
  
  73183-34-3
- In-stock
  
  186407-74-9
- ~60%
- In-stock
  
  271-44-3
- In-stock
  
  885618-33-7
References
- WO2007/127183 A1, ; Page/Page column 138 ; WO 2007/127183 A1
Route3
- In-stock
  
  41748-71-4
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  885618-33-7
References
- WO2009/146406 A1, ; Page/Page column 65 ; WO 2009/146406 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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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

CAS No. 885618-33-7

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