7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine

Name: 7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 908268-52-0
Cat. No. CS-0050125
Purity≥97%
MDL No.None

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FedEx Limited Quantities Ground	$0.00
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7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine|CS-0050125

Structure of 908268-52-0

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General Information

CAS No. 908268-52-0
Cat. No. CS-0050125
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₇BN₂O₂
Molecular Weight 244.10
Synonym(s) Please input a keyword. Imidazo[1,2-a]pyridine-7-boronic acid pinacol ester
SMILES CC1(C)OB(OC1(C)C)C1=CC2=NC=CN2C=C1

Description

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine features a boronate ester group conjugated to an imidazo[1,2-a]pyridine core, enabling efficient Suzuki-Miyaura cross-coupling reactions. This bench-stable reagent integrates readily into complex heterocyclic scaffolds under standard conditions, offering high functional group tolerance and predictable regioselectivity for advanced medicinal chemistry applications.

Application

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The stable, bench-ready boronate ester facilitates efficient C–C bond formation with aryl and heteroaryl halides under mild conditions. Its compatibility with diverse functional groups and high chemoselectivity make it a practical choice for constructing complex imidazo[1,2-a]pyridine-based scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  4532-25-6
- In-stock
  
  73183-34-3
- ~91%
- In-stock
  
  908268-52-0
References
- Aicher, Thomas Daniel; Anzeveno, Peter Biagio; Li, Renhua; Krasutsky, Alexei Pavlovych; Mabry, Thomas Edward; Saeed, Ashraf; Snyder, Nancy June; Stephenson, Gregory Alan; Tian, Hongqi; Wallace, Owen Brendan; Winneroski, JR., Leonard Larry; Xu, Yanping Patent: US2009/111800 A1, 2009 ; Location in patent: Page/Page column 45 ; US 20090111800 A1
Route2
- In-stock
  
  808744-34-5
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  908268-52-0
References
- GLAXOSMITHKLINE LLC; ADAMS, Nicholas, David; CHAUDHARI, Amita, M.; KIESOW, Terence, John; McSHERRY, Allison, K.; MOORE, Michael, Lee; PARRISH, Cynthia, Ann; REIF, Alexander, Joseph; RIDGERS, Lance, Howard Patent: WO2014/8223 A2, 2014 ; Location in patent: Page/Page column 58-59 ;

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 35.76
LogP 1.6335
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine

CAS No. 908268-52-0

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