2-Ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Name: 2-Ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 957346-47-3
Cat. No. CS-0092144
Purity≥98%
MDL No.MFCD11617874

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2-Ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0092144

Structure of 957346-47-3

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General Information

CAS No. 957346-47-3
Cat. No. CS-0092144
Purity ≥98%
MDL No. MFCD11617874
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₃
Molecular Weight 249.11
Synonym(s) 2-Ethoxypyridine-4-boronic acid, pinacol ester
SMILES CC1(C)C(C)(C)OB(C2=CC(OCC)=NC=C2)O1

Description

2-Ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group that enables efficient Suzuki-Miyaura coupling under mild conditions. The ethoxy substituent enhances solubility in organic solvents, while the tetramethyl-substituted dioxaborolane ring ensures high stability and low hydrolytic reactivity. This compound serves as a robust building block for constructing complex heterocyclic architectures in medicinal chemistry and materials science.

Application

2-Ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile boronate ester building block for Suzuki-Miyaura cross-coupling reactions. The pyridyl core enables efficient functionalization in medicinal chemistry and materials synthesis, while the tetramethyl-dioxaborolane moiety offers excellent stability, ease of handling, and compatibility with diverse reaction conditions. This reagent facilitates direct coupling with aryl halides and pseudohalides under mild catalytic conditions, enabling rapid assembly of biaryl and heteroaryl scaffolds with predictable regiochemistry.

Synthesis

Route1
- In-stock
  
  57883-26-8
- In-stock
  
  73183-34-3
- ~80%
- In-stock
  
  957346-47-3
References
- US2009/286798 A1, ; Page/Page column 31 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H317-H319
Precautionary Statements : P261-P264-P272-P280-P302+P352-P362+P364-P501

Quality Control

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Computational Chemistry Data

TPSA 40.58
LogP 1.7795
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

CAS No. 957346-47-3

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