269410-26-6

Basic information

• Product Name: Phenoxyphenyl-4-boronic acid pinacol ester
• Synonyms: phenoxyphenyl-4-boronic acid pinacol ester;4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane;(4-Phenoxy)phenylboronic acid pinacol
• CAS NO: 269410-26-6
• Molecular Formula: C₁₈H₂₁BO₃
• Molecular Weight: 296.17
• Mol File: 269410-26-6.mol
• Article Data: 23

Chemical Properties

• Melting Point: 54 °C
• Boiling Point: 393.2±25.0 °C(Predicted)
• Appearance: /
• Density: 1.09
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: Phenoxyphenyl-4-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phenoxyphenyl-4-boronic acid pinacol ester(269410-26-6)
• EPA Substance Registry System: Phenoxyphenyl-4-boronic acid pinacol ester(269410-26-6)

Safety Data

• Hazardous Substances Data: 269410-26-6(Hazardous Substances Data)

Usage

General Description

Phenoxyphenyl-4-boronic acid pinacol ester is a chemical compound primarily used in organic synthesis and pharmaceutical research. It is a boronic acid derivative, specifically an ester of pinacol boronic acid, and contains a phenoxyphenyl group. Phenoxyphenyl-4-boronic acid pinacol ester is commonly employed in Suzuki-Miyaura cross-coupling reactions, where it serves as a valuable reagent for the construction of carbon-carbon bonds. Its unique properties and reactivity make it a versatile building block for the synthesis of various organic molecules and pharmaceuticals with potential applications in medicinal chemistry and drug discovery. Additionally, its boronic acid functionality allows for further derivatization and modification, making it an important tool in the field of chemical biology and materials science.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 51067-38-0 4-phenoxyphenylboronic acid 
• 101-55-3 4-Bromodiphenyl ether 
• 73183-34-3 bis(pinacol)diborane 
• 1374791-08-8 2-(4-phenoxyphenoxy)pyridine 
• 831-82-3 4-Phenoxyphenol 
• 101-84-8 diphenylether 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 330-84-7 4-fluorophenoxybenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 13517-10-7 boron triiodide 
• 370-12-7 4-phenoxybenzoyl fluoride 
• 67-36-7 4-phenoxy benzaldehyde 

Downstream Products

• 1187951-67-2 C₂₉H₂₃N₃O₃S 
• 1187951-71-8 C₃₀H₂₅N₃O₃S 
• 1415309-83-9 C₁₆H₁₃N₃O₂ 
• 2519-16-6 4,4'-diphenoxy-1,1'-biphenyl 
• 99770-93-1 benzene-1,4-diboronic acid bispinacol ester 
• 1022150-11-3 (3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine 
• 330786-24-8 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1187951-62-7 potassium trifluoro(4-phenoxyphenyl)borate 

Relevant articles and documents

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis

Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.

Multiple Electrophilic C-H Borylation of Arenes Using Boron Triiodide

Electrophilic C-H borylation of arenes using boron triiodide has been developed. This reaction proceeded smoothly in the absence of additives, and the diiodoboryl group was installed at the most sterically accessible carbon, where the HOMO is localized to a certain extent. Moreover, regioselective multiple borylation of polycyclic aromatic compounds was achieved by using excess boron triiodide. The borylated intermediates were transformed into a variety of arylboron compounds such as arylboronates, boronic acids, and trifluoroborates.