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
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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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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.

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

Computational Chemistry Data

TPSA 47.14
LogP 1.8621
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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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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