929626-16-4

Basic information

• Product Name: 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-Chloro-5-methoxyphenylboronic acid, pinacol ester
• CAS NO: 929626-16-4
• Molecular Formula: C₁₃H₁₈BClO₃
• Molecular Weight: 268.54422
• Mol File: 929626-16-4.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(929626-16-4)
• EPA Substance Registry System: 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(929626-16-4)

Safety Data

• Hazardous Substances Data: 929626-16-4(Hazardous Substances Data)

Usage

General Description

2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a chemical compound consisting of a boron atom attached to a five-membered ring containing two oxygen atoms and a tetramethylphenyl group. It is often used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-oxygen bonds. 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has been studied for its potential application in medicinal chemistry, as it possesses unique chemical properties that make it a useful building block for the synthesis of complex molecules. Additionally, its boron-containing structure makes it suitable for use in various catalytic processes.

Upstream product

• 2845-89-8 1-chloro-3-methoxy-benzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 74-88-4 methyl iodide 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 

Downstream Products

• 65262-96-6 3-chloro-5-methoxyphenol 
• 915201-07-9 (3-chloro-5-methoxyphenyl)boronic acid 
• 33719-74-3 3,5-dichloroanisole 
• 174913-12-3 1-bromo-3-chloro-5-methoxybenzene 
• 1268263-04-2 C₁₉H₂₅ClN₄OS 
• 1258071-61-2 3-(3-chloro-5-methoxyphenyl)cyclohexanone 
• 1258071-60-1 4-(3-chloro-5-methoxyphenyl)butan-2-one 
• 1360804-21-2 1-chloro-3-methoxy-5-(perfluoropropyl)benzene 
• 886497-07-0 1-chloro-3-methoxy-5-(trifluoromethyl)benzene 
• 1442416-10-5 C₁₆H₁₇ClO 
• 1442416-18-3 C₁₇H₂₉ClO₂Si 
• 1442416-17-2 C₁₄H₁₈ClNO 
• 1442416-26-3 C₁₂H₁₅ClO 
• 1442416-22-9 C₁₁H₁₃ClO₂ 

Relevant articles and documents

Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics

A newly developed robust catalyst [Ir(COD)(Phen)Cl] (A) was used for the C-H borylation of three dozen aromatics and heteroaromatics with excellent yield and selectivity. Activation of the catalyst was identified by the use of catalytic amounts of water, alcohols, etc., when B2pin2 was used in noncoordinating solvents, while for THF catalytic use of HBpin was required. The results were on par with the in situ based expensive system [Ir(OMe)(COD)]2/dtbbpy or Me4Phen.

Highly active, separable and recyclable bipyridine iridium catalysts for C-H borylation reactions

Iridium complexes generated from Ir(i) precursors and PIB oligomer functionalized bpy ligands efficiently catalyzed the reactions of arenes with bis(pinacolato)diboron under mild conditions to produce a variety of arylboronate compounds. The activity of this PIB bound homogeneous catalyst is similar to that of an original non-recyclable catalyst which allows it to be used under milder conditions than other reported recyclable catalysts. This oligomer-supported Ir catalyst was successfully recovered through biphasic extraction and reused for eight cycles without a loss of activity. Biphasic separation after the initial use of the catalyst led to an insignificant amount of iridium leaching from the catalyst to the product, and no iridium leaching from the catalyst was observed in the subsequent recycling runs. Arylboronate products obtained after extraction are sufficiently pure as observed by 1H and 13C-NMR spectroscopy that they do not require further purification.

Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation

Boryl ligands hold promise in catalysis due to their very high electron-donating property. In this communication double N,B-type boryl anions were designed as bidentate ligands to promote an sp2 C-H borylation reaction. A symmetric pyridine-con