2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy) ethan-1-amine

Name: 2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethan-1-amine 

Molecular Formula: C14H22BNO3 

CAS#: 2684271-71-2 

SMILES: CC(C(C)(C)O1)(C)OB1C2=CC=CC(OCCN)=C2 

MDL#:  

Catalog#: AMTB1432-TD24 

Molecular weight: 263.14 g/mol 

Other names: 

• 2-(3-(Pinacol boronate)phenoxy)ethylamine  
• Aryl boronic ester amine linker 

Fields of Interest: cross-coupling, medicinal chemistry, materials science, conjugation chemistry 

Background & Applications:  

Background 

2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethan-1-amine (CAS# 2684271-71-2) is a heterobifunctional boronic ester-functionalized linker featuring an aryl boronic acid pinacol ester and a terminal primary amine connected through an ether spacer. The boronic ester moiety provides a stable and reactive handle for Suzuki–Miyaura cross-coupling reactions, while the primary amine enables straightforward coupling to activated carboxylic acids, NHS esters, and isocyanates. The ether linkage contributes flexibility and compatibility with both aqueous and organic systems. This dual-functional architecture makes the compound a versatile intermediate within a broader portfolio of functionalized linkers designed for modular molecular assembly and carbon–carbon bond formation. 

Applications 

This aryl boronic ester–amine linker is commonly used in cross-coupling chemistry, medicinal chemistry, and materials science applications where orthogonal reactivity is required. It is especially strong as a dual-reactivity building block bridging cross-coupling and conjugation chemistry. Typical uses include palladium-catalyzed coupling with aryl or vinyl halides to construct substituted aromatic systems, followed by amine-based conjugation to peptides, polymers, or small molecules. The combination of Suzuki-compatible boronate chemistry and amine coupling functionality enables stepwise synthesis of multifunctional intermediates, PEGylated analogs, and advanced materials. As part of a comprehensive functionalized linker product line, this compound supports modular design strategies in pharmaceutical research, diagnostics, and specialty chemical synthesis. 

Appearance: White Powder 

Purity: 98%  

Storage: Room Temp 

Solubility: Dichloromethane, Chloroform, Acetonitrile 

Literature:  

• WO2021/155004, 2021, A1Citation 2