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

Name: 2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole
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CAS No. 885698-95-3
Cat. No. CS-0041372
Purity≥96%
MDL No.MFCD11109437

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2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole|CS-0041372

Structure of 885698-95-3

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General Information

CAS No. 885698-95-3
Cat. No. CS-0041372
Purity ≥96%
MDL No. MFCD11109437
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₉BN₂O₂
Molecular Weight 258.12
Synonym(s) 2-Methyl-2H-indazole-4-boronic acid pinacol ester
SMILES CC1(C)C(C)(C)OB(C2=CC=CC3=NN(C)C=C23)O1

Description

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole features a boronate ester group enabling reliable Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety enhances stability and solubility in organic media. This indazole scaffold offers a rigid, electron-deficient platform for constructing complex heterocyclic architectures under standard conditions.

Application

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient palladium-catalyzed coupling under mild conditions, while the indazole core provides a rigid, nitrogen-rich scaffold relevant to medicinal chemistry. Bench-stable and readily purified by flash chromatography, it functions effectively in late-stage functionalization and heterocycle diversification workflows.

Synthesis

Route1
- 74-88-4
- ~%
- In-stock
  
  885698-94-2
- In-stock
  
  885698-95-3
References
- WO2006/46031 A1, ; Page/Page column 84 ; WO 2006/046031 A1

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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Computational Chemistry Data

TPSA 36.28
LogP 1.8725
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indazole compounds

Key Words

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

CAS No. 885698-95-3

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