912569-68-7

Basic information

• Product Name: 3-(Phenoxymethyl)benzeneboronic acid, pinacol ester
• Synonyms: 3-(Phenoxymethyl)benzeneboronic acid, pinacol ester;4,4,5,5-tetramethyl-2-[3-(phenoxymethyl)phenyl]-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-[3-(phenoxymethyl)phenyl]-1,3,2-dioxaborolane , 97+%;2-[3-(Phenoxymethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 912569-68-7
• Molecular Formula: C₁₉H₂₃BO₃
• Molecular Weight: 310.2
• Mol File: 912569-68-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 76.5-77.5
• Boiling Point: 433.9 °C at 760 mmHg
• Flash Point: 216.2 °C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 2.51E-07mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: 3-(Phenoxymethyl)benzeneboronic acid, pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Phenoxymethyl)benzeneboronic acid, pinacol ester(912569-68-7)
• EPA Substance Registry System: 3-(Phenoxymethyl)benzeneboronic acid, pinacol ester(912569-68-7)

Safety Data

• Hazardous Substances Data: 912569-68-7(Hazardous Substances Data)

Usage

General Description

3-(Phenoxymethyl)benzeneboronic acid, pinacol ester is a compound that belongs to the class of boronic acids and its derivatives. It is commonly used in organic synthesis and medicinal chemistry as a reagent for Suzuki-Miyaura cross-coupling reactions and other carbon-carbon bond forming reactions. 3-(Phenoxymethyl)benzeneboronic acid, pinacol ester is a pinacol ester derivative of 3-(phenoxymethyl)benzeneboronic acid, which makes it suitable for use in various organic reactions. Its distinct chemical structure and properties make it a valuable intermediate in the synthesis of pharmaceuticals and other organic compounds.

InChI:InChI=1/C19H23BO3/c1-18(2)19(3,4)23-20(22-18)16-10-8-9-15(13-16)14-21-17-11-6-5-7-12-17/h5-13H,14H2,1-4H3

Upstream product

• 214360-74-4 2-(3-(bromomethyl)phenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane 
• 108-95-2 phenol 
• 823-78-9 meta-bromobenzyl bromide 

Relevant articles and documents

Novel arylalkenylpropargylamines as neuroprotective, potent, and selective monoamine oxidase B inhibitors for the treatment of Parkinson's disease

To develop novel neuroprotective agents, a library of novel arylalkenylpropargylamines was synthesized and tested for inhibitory activities against monoamine oxidases. From this, a number of highly potent and selective monoamine oxidase B inhibitors were identified. Selected compounds were also tested for neuroprotection in in vitro studies with PC-12 cells treated with 6-OHDA and rotenone, respectively. It was observed that some of the compounds tested yielded a marked increase in survival in PC-12 cells treated with the neurotoxins. This indicates that these propargylamines are able to confer protection against the effects of the toxins and may also be considered as novel disease-modifying anti-Parkinsonian agents, which are much needed for the therapy of Parkinson's disease.

Microwave-mediated synthesis of an arylboronate library

A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3} respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.