1073354-86-5

Basic information

• Product Name: E-2-(3,5-DIMETHOXYPHENYL)VINYLBORONIC ACID PINACOL ESTER
• Synonyms: TRANS-2-(3,5-DIMETHOXYPHENYL)VINYLBORONIC ACID PINACOL ESTER;E-2-(3,5-DIMETHOXYPHENYL)VINYLBORONIC ACID PINACOL ESTER;(E)-2-(3,5-DiMethoxystyryl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;2-[(1E)-2-(3,5-Dimethoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;trans-2-(3,5-Dimethoxyphenyl)vinylboronic acid pinacol ester 97%
• CAS NO: 1073354-86-5
• Molecular Formula: C₁₆H₂₃BO₄
• Molecular Weight: 290.16
• Mol File: 1073354-86-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 56-62 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: E-2-(3,5-DIMETHOXYPHENYL)VINYLBORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: E-2-(3,5-DIMETHOXYPHENYL)VINYLBORONIC ACID PINACOL ESTER(1073354-86-5)
• EPA Substance Registry System: E-2-(3,5-DIMETHOXYPHENYL)VINYLBORONIC ACID PINACOL ESTER(1073354-86-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1073354-86-5(Hazardous Substances Data)

Usage

General Description

E-2-(3,5-DIMETHOXYPHENYL)VINYLBORONIC ACID PINACOL ESTER is a chemical compound with the molecular formula C15H19BO4. It is an ester of boronic acid and is commonly used in organic synthesis as a reagent for the Suzuki-Miyaura cross-coupling reaction. This reaction is widely used in the formation of carbon-carbon bonds, making E-2-(3,5-DIMETHOXYPHENYL)VINYLBORONIC ACID PINACOL ESTER an important tool for the construction of complex organic molecules in the field of medicinal chemistry and pharmaceutical drug development. Additionally, the presence of both boronic acid and vinyl functional groups in this compound makes it a valuable building block for the synthesis of various other organic molecules.

Upstream product

• 171290-52-1 1-Ethynyl-3,5-dimethoxy-benzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 75927-49-0 pinacol vinylboronate 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1321601-41-5 C₄₀H₄₀O₈S₂ 
• 20578-92-1 (E)-3,5,2',4'-tetramethoxystilbene 
• 10083-24-6 trans-piceatannol 
• 83088-26-0 (E)-tetramethylpiceatannol 

Relevant articles and documents

AgSbF6-Catalyzed: Anti -Markovnikov hydroboration of terminal alkynes

AgSbF6-Catalyzed anti-Markovnikov addition of pinacolborane (HBpin) to terminal alkynes to produce the E-vinylboronates is reported. This efficient methodology is scalable, compatible with sterically and electronically diverse alkynes, and works at room temperature under solvent-free condition. The utility of this method is demonstrated in the facile synthesis of the clinically important (E)-2,4,3′,5′-tetramethoxystilbene.

Nickel(II)-Catalyzed Borylation of Alkenyl Methyl Ethers via C-O Bond Cleavage

A new protocol has been developed for the borylation of conjugated alkenyl methyl ethers using B2Pin2 via C-O bond cleavage catalyzed by Ni(II). In this cross-coupling reaction, both E/Z isomers of alkenyl ethers are converted into (E)-alkenyl boronic esters with good reactivity. This transformation exhibits high chemoselectivity in the presence of competitive C-O bonds such as aryl ether, ester, amide, and thioether groups, thus providing a new method for the construction of various alkenyl boronates.