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

Name: 1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole
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CAS No. 885698-94-2
Cat. No. CS-0052444
Purity≥97%
MDL No.None

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1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole|CS-0052444

Structure of 885698-94-2

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General Information

CAS No. 885698-94-2
Cat. No. CS-0052444
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₉BN₂O₂
Molecular Weight 258.12
Synonym(s) 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole
SMILES CN1N=CC2=C(C=CC=C12)B1OC(C)(C)C(C)(C)O1

Description

1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole features a boronate ester group enabling efficient Suzuki-Miyaura cross-coupling reactions. The tetramethylcycloborane moiety enhances stability and solubility in organic solvents, while the indazole core provides a rigid, electron-deficient scaffold ideal for bioactive molecule synthesis. This compound integrates readily into complex heterocyclic architectures under mild conditions.

Application

1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole serves as a versatile boron building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylborolane moiety enables reliable C–C bond formation under mild conditions, with excellent stability and ease of handling. It functions effectively in the construction of biaryl scaffolds and heterocyclic frameworks commonly found in pharmaceutical research, offering high functional group tolerance and straightforward purification.

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

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302
Precautionary Statements : P264-P270-P330-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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1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

CAS No. 885698-94-2

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