4,4,5,5-Tetramethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborolane
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CAS No. 219488-97-8
Cat. No. CS-0468706
Purity≥98%
MDL No.None

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4,4,5,5-Tetramethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborolane|CS-0468706

Structure of 219488-97-8

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Description

This boronate moiety integrates a sterically hindered tetramethyl-1,3,2-dioxaborolane ring with a triphenylvinyl substituent, enhancing stability and enabling efficient cross-coupling under standard conditions. The electron-rich framework facilitates rapid palladium-catalyzed reactions, while the bulky aryl groups suppress protodeboronation and promote chemoselective transformations in complex synthesis workflows.

Application

4,4,5,5-Tetramethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its sterically protected boronate moiety exhibits high functional group tolerance and resistance to protodeboronation, enabling reliable coupling with aryl and heteroaryl halides. The triphenylvinyl substituent imparts enhanced solubility and facilitates purification by chromatography, making it a practical choice for constructing complex molecular architectures in medicinal chemistry and materials science workflows.

General Information

CAS No. 219488-97-8
Cat. No. CS-0468706
Purity ≥98%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₇BO₂
Molecular Weight 382.30
Synonym(s) 2-(alpha,beta-Diphenylstyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
SMILES CC1(C)C(C)(C)OB(C(C2=CC=CC=C2)=C(C3=CC=CC=C3)C4=CC=CC=C4)O1

Computational Chemistry Data

TPSA 18.46
LogP 6.2771
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 4

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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Other Classifications

Building Blocks Functional Group Olefins

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4,4,5,5-Tetramethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborolane

CAS No. 219488-97-8

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