(Z)-2-(2-Ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: (Z)-2-(2-Ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
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CAS No. 219489-07-3
Cat. No. CS-0099988
Purity≥90%
MDL No.MFCD09702441

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(Z)-2-(2-Ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0099988

Structure of 219489-07-3

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General Information

CAS No. 219489-07-3
Cat. No. CS-0099988
Purity ≥90%
MDL No. MFCD09702441
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₉BO₃
Molecular Weight 198.07
Synonym(s) [(Z)-2-Ethoxyvinyl]boronic acid, pinacol ester
SMILES CC1(C)C(C)(C)OB(/C=C\OCC)O1

Description

(Z)-2-(2-Ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a bench-stable boronate ester featuring a stereodefined (Z)-ethenylic vinylboronate moiety. This configuration enhances coupling efficiency in palladium-catalyzed cross-coupling reactions. The tetramethyl-substituted dioxaborolane ring provides excellent stability and moisture tolerance. It integrates readily into complex molecule synthesis under standard conditions.

Application

(Z)-2-(2-Ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its (Z)-configured vinylborane moiety enables stereoselective introduction of functionalized alkenyl groups into complex molecular architectures. The tetramethyl-substituted dioxaborolane ring enhances air and moisture stability, facilitating handling and purification. This reagent functions effectively in late-stage diversification and heterocycle synthesis, offering predictable regiochemistry and high compatibility with diverse coupling partners.

Synthesis

Route1
- 109-92-2
- 25015-63-8
- ~%
- In-stock
  
  1201905-61-4
- In-stock
  
  219489-07-3
References
- WO2012/10538 A2, ; Page/Page column 30-31 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : 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

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Computational Chemistry Data

TPSA 27.69
LogP 2.168
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Key Words

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(Z)-2-(2-Ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 219489-07-3

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