628692-21-7

Basic information

• Product Name: 2-Fluoro-4-Methoxyphenylboronic acid pinacol ester
• Synonyms: 2-Fluoro-4-Methoxyphenylboronic acid pinacol ester;2-Fluoro-4-methoxybenzeneboronic acid pinacol ester
• CAS NO: 628692-21-7
• Molecular Formula: C₁₃H₁₈BFO₃
• Molecular Weight: 270.1049032
• Mol File: 628692-21-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 36-38℃
• Appearance: /
• CAS DataBase Reference: 2-Fluoro-4-Methoxyphenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-4-Methoxyphenylboronic acid pinacol ester(628692-21-7)
• EPA Substance Registry System: 2-Fluoro-4-Methoxyphenylboronic acid pinacol ester(628692-21-7)

Safety Data

• Hazardous Substances Data: 628692-21-7(Hazardous Substances Data)

Usage

General Description

2-Fluoro-4-Methoxyphenylboronic acid pinacol ester is a chemical compound with the molecular formula C13H17BF2O3. It is an organoboronic acid ester that is often used in organic synthesis and pharmaceutical research. The compound contains a boronic acid group, which is a versatile building block in the synthesis of complex organic molecules. The presence of the fluoro and methoxy substituents makes this compound suitable for use in cross-coupling reactions and other transformations to introduce these functional groups into organic molecules. Its pinacol ester moiety provides stability to the boronic acid group, making it easier to handle and store. 2-Fluoro-4-Methoxyphenylboronic acid pinacol ester is a valuable tool for chemical and pharmaceutical research due to its unique reactivity and selectivity in organic reactions.

Upstream product

• 458-50-4 1-bromo-2-fluoro-4-methoxybenzene 
• 73183-34-3 bis(pinacol)diborane 
• 456-49-5 1-fluoro-3-methoxybenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 1214344-33-8 2-fluoro-4-methoxy-1-(trifluoromethyl)benzene 

Relevant articles and documents

Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes

This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp2)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [18F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochemical yield and radiochemical purity. This entire process is performed on a benchtop without Schlenk or glovebox techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FXFN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative. The products, [18F]1-fluoro-3,5-dimethoxybenzene and an 18F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochemical yield and >99% radiochemical purity and 25% isolated radiochemical yield and 99% radiochemical purity, and 0.52 Ci/μmol (19.24 GBq/μmol) molar activity (Am), respectively.

METHODS FOR PRODUCING BORYLATED ARENES

Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectivel

Transition metal-free synthesis of pinacol arylboronate: Regioselective boronation of 1,3-disubstituted benzenes

The regioselective synthesis of pinacol arylboronate has been achieved from 1,3-disubstituted benzene through directed ortho-metallation (DoM)-borylation sequence. A wide range of substituents and borylating reagents were investigated. In situ lithiation and subsequent boronation predominantly occurred at the ortho-position to afford the desired products in moderate yields. CSIRO 2014.