4,4,5,5-Tetramethyl-2-(pent-4-en-1-yl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(pent-4-en-1-yl)-1,3,2-dioxaborolane
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CAS No. 157735-10-9
Cat. No. CS-0176208
Purity≥97%
MDL No.None

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4,4,5,5-Tetramethyl-2-(pent-4-en-1-yl)-1,3,2-dioxaborolane|CS-0176208

Structure of 157735-10-9

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General Information

CAS No. 157735-10-9
Cat. No. CS-0176208
Purity ≥97%
MDL No. None
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₂₁BO₂
Molecular Weight 196.09
Synonym(s) 4-Pentenylboronic acid pinacol ester
SMILES O1B(OC(C)(C)C1(C)C)CCCC=C

Description

This boronate ester features a pent-4-en-1-yl group that enables efficient coupling in palladium-catalyzed reactions. The tetramethyl substitution enhances stability and shelf life, while the vinyl handle facilitates further functionalization. Ideal for iterative synthesis workflows requiring robust, moisture-tolerant building blocks.

Application

4,4,5,5-Tetramethyl-2-(pent-4-en-1-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent that enables efficient Suzuki-Miyaura cross-coupling reactions. Its sterically protected boronate moiety offers enhanced air and moisture stability, facilitating straightforward handling and purification. The pendant pentenyl group provides a versatile handle for further functionalization, enabling the construction of complex molecular architectures in medicinal chemistry and materials synthesis workflows.

Safety Information

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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

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Computational Chemistry Data

TPSA 18.46
LogP 3.0448
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Olefins

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Key Words

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4,4,5,5-Tetramethyl-2-(pent-4-en-1-yl)-1,3,2-dioxaborolane

CAS No. 157735-10-9

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