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

Name: 1-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 596819-10-2
Cat. No. CS-0176236
Molecule weight257.14
Purity≥98%
MDL No.None

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1-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-0176236

Structure of 596819-10-2

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General Information

CAS No. 596819-10-2
Cat. No. CS-0176236
Purity ≥98%
MDL No. None
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₀BNO₂
Molecular Weight 257.14
Synonym(s) N-methyl-2-(4,4,5,5-tetramethyldioxaborolan-2-yl)indole
SMILES O1B(OC(C)(C)C1(C)C)C2=CC=3C=CC=CC3N2C

Description

1-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole delivers a boronate-functionalized indole scaffold with enhanced stability and compatibility in cross-coupling reactions. The tetramethylboronate moiety enables efficient Suzuki-Miyaura coupling under mild conditions, while the methylated indole core ensures improved solubility and resistance to hydrolysis. This compound serves as a robust building block for constructing complex heterocyclic architectures in medicinal chemistry and materials science.

Application

1-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety enhances reactivity and functional group tolerance, enabling efficient C–C bond formation under mild conditions. Its indole core provides a versatile scaffold for medicinal chemistry applications, particularly in the synthesis of heterocyclic compounds and bioactive molecules.

Synthesis

Route1
- In-stock
  
  603-76-9
- 25015-63-8
- ~45%
- In-stock
  
  596819-10-2
References
- Mertins, Kristin; Zapf, Alexander; Beller, Matthias Journal of Molecular Catalysis A: Chemical, 2004 , vol. 207, # 1 p. 21 - 25
Route2
- In-stock
  
  603-76-9
- 25015-63-8
- ~%
- In-stock
  
  683229-61-0
- In-stock
  
  596819-10-2
References
- Obligacion, Jennifer V.; Semproni, Scott P.; Chirik, Paul J. Journal of the American Chemical Society, 2014 , vol. 136, # 11 p. 4133 - 4136
Route3
- In-stock
  
  603-76-9
- ~%
- In-stock
  
  596819-10-2
References
- Solomon; Del Grosso; Clark; Bagutski; McDouall; Ingleson Organometallics, 2012 , vol. 31, # 5 p. 1908 - 1916

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

Quality Control

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Computational Chemistry Data

TPSA 23.39
LogP 2.4775
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

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

CAS No. 596819-10-2

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