4,4,5,5-Tetramethyl-2-(3-(trifluoromethoxy)phenyl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(3-(trifluoromethoxy)phenyl)-1,3,2-dioxaborolane
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CAS No. 262376-31-8
Cat. No. CS-0081147
Purity≥97%
MDL No.MFCD05863919

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4,4,5,5-Tetramethyl-2-(3-(trifluoromethoxy)phenyl)-1,3,2-dioxaborolane|CS-0081147

Structure of 262376-31-8

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General Information

CAS No. 262376-31-8
Cat. No. CS-0081147
Purity ≥97%
MDL No. MFCD05863919
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₆BF₃O₃
Molecular Weight 288.07
Synonym(s) 4,4,5,5-tetramethyl-2-[3-(trifluoromethoxy)phenyl]-1,3,2-dioxaborolane
SMILES FC(F)(F)OC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1

Description

This boronate ester features a trifluoromethoxy-substituted phenyl group and a tetramethylcyclopentadienone core, delivering enhanced stability and reactivity in Suzuki-Miyaura cross-coupling reactions. The electron-withdrawing trifluoromethoxy moiety promotes efficient coupling with aryl halides under standard conditions.

Application

This boronate ester serves as a stable, bench-ready building block for Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane enhances shelf stability and resistance to protodeboronation, while the 3-(trifluoromethoxy)phenyl group provides a sterically accessible aryl handle with favorable electronic properties. It facilitates efficient coupling with aryl halides and pseudohalides under standard catalytic conditions, enabling rapid construction of biaryl scaffolds relevant to medicinal chemistry and materials science.

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-H317
Precautionary Statements : P261-P264-P270-P272-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

TPSA 27.69
LogP 2.8844
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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4,4,5,5-Tetramethyl-2-(3-(trifluoromethoxy)phenyl)-1,3,2-dioxaborolane

CAS No. 262376-31-8

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