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

Name: 1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
Brand: ChemScene
Availability: InStock
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CAS No. 683229-61-0
Cat. No. CS-0147286
Purity≥95%
MDL No.None

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1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-0147286

Structure of 683229-61-0

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General Information

CAS No. 683229-61-0
Cat. No. CS-0147286
Purity ≥95%
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-Methylindole-3-boronic acid pinacol ester
SMILES CC1(C)C(C)(C)OB(C2=CN(C)C3=C2C=CC=C3)O1

Description

1-Methyl-3-(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 tetramethyl-substituted dioxaborolane moiety enables reliable Suzuki-Miyaura coupling under mild conditions. This bench-stable reagent integrates readily into complex molecular architectures, offering efficient access to biologically relevant heterocycles.

Application

1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole serves as a versatile boronate building block for Suzuki–Miyaura cross-coupling reactions. The tetramethylboronate moiety offers excellent stability, mild handling requirements, and broad functional group tolerance, enabling efficient C–C bond formation under standard catalytic conditions. Its indole core provides a privileged scaffold for medicinal chemistry applications, facilitating the rapid assembly of biologically relevant heterocyclic architectures with predictable regiochemistry and high yields.

Synthesis

Route1
- In-stock
  
  603-76-9
- In-stock
  
  76-09-5
- In-stock
  
  55718-76-8
- ~84%
- In-stock
  
  683229-61-0
References
- THE UNIVERSITY OF MANCHESTER; INGLESON, Michael James Patent: WO2012/25760 A1, 2012 ; Location in patent: Page/Page column 54-55 ;
Route2
- In-stock
  
  603-76-9
- In-stock
  
  76-09-5
- 10294-34-5
- ~83%
- In-stock
  
  683229-61-0
References
- Del Grosso, Alessandro; Helm, Matthew D.; Solomon, Sophia A.; Caras-Quintero, Dolores; Ingleson, Michael J. Chemical Communications, 2011 , vol. 47, # 46 p. 12459 - 12461
Route3
- In-stock
  
  603-76-9
- 25015-63-8
- ~69%
- In-stock
  
  683229-61-0
References
- Stahl, Timo; Muether, Kristine; Ohki, Yasuhiro; Tatsumi, Kazuyuki; Oestreich, Martin Journal of the American Chemical Society, 2013 , vol. 135, # 30 p. 10978 - 10981

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

CAS No. 683229-61-0

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