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

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

CAS No. 269410-24-4
Cat. No. CS-0041510
Purity≥97%
MDL No.MFCD03789263

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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-0041510

Structure of 269410-24-4

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General Information

CAS No. 269410-24-4
Cat. No. CS-0041510
Purity ≥97%
MDL No. MFCD03789263
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈BNO₂
Molecular Weight 243.11
Synonym(s) Indole-5-boronic acid pinacol ester
SMILES CC1(C)OB(OC1(C)C)C1=CC2=C(NC=C2)C=C1

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole integrates a stable boronate handle with an electron-rich indole core, enabling efficient Suzuki-Miyaura cross-coupling under standard conditions. This bench-stable reagent facilitates rapid access to biologically relevant heteroaryl architectures.

Application

5-(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 group enables efficient coupling with aryl and heteroaryl halides under mild conditions, offering excellent functional group tolerance and bench stability. Its indole core provides a privileged scaffold in medicinal chemistry, facilitating the synthesis of biologically relevant heterocycles and drug candidates through modular transformations.

Synthesis

Route1
- In-stock
  
  17422-32-1
- In-stock
  
  73183-34-3
- ~92%
- In-stock
  
  269410-24-4
References
- Billingsley, Kelvin L.; Barder, Timothy E.; Buchwald, Stephen L. Angewandte Chemie - International Edition, 2007 , vol. 46, # 28 p. 5359 - 5363
Route2
- In-stock
  
  10075-50-0
- In-stock
  
  73183-34-3
- ~83%
- In-stock
  
  269410-24-4
References
- Prieto, Monica; Zurita, Esther; Rosa, Esmeralda; Munoz, Lourdes; Lloyd-Williams, Paul; Giralt, Ernest Journal of Organic Chemistry, 2004 , vol. 69, # 20 p. 6812 - 6820
Route3
- In-stock
  
  10075-50-0
- 25015-63-8
- ~%
- In-stock
  
  269410-24-4
References
- Commonwealth Scientific and Industrial Research Organisation Patent: US6680401 B1, 2004 ; Location in patent: Page column 68 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 34.25
LogP 2.4671
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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

CAS No. 269410-24-4

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