365564-05-2

Basic information

• Product Name: 1,3,5-Phenyltriboronic acid, pinacol ester
• Synonyms: 1,3,5-Phenyltriboronic acid, pinacol ester;1,3,5-Phenyltriboronic acid, tris(pinacol) ester;1,3,5-Tris(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzene;1,3,5-Benzenetriboronic Acid Tris(pinacol) Ester;2-[3,5-Bis(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;benzene-1,3,5-triyltriboronic acid pinacol ester;1,3,5-Phenyltriboronicacid,Tris(Pinacol)Esteraldrichcpr;1,3,5-Phenyltriboronic acid, tris(pinacol) ester >=97%
• CAS NO: 365564-05-2
• Molecular Formula: C₂₄H₃₉B₃O₆
• Molecular Weight: 309.72394
• Mol File: 365564-05-2.mol
• Article Data: 33

Chemical Properties

• Melting Point: 286-287°C
• Boiling Point: 555.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.05±0.1 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 1,3,5-Phenyltriboronic acid, pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Phenyltriboronic acid, pinacol ester(365564-05-2)
• EPA Substance Registry System: 1,3,5-Phenyltriboronic acid, pinacol ester(365564-05-2)

Safety Data

• Hazardous Substances Data: 365564-05-2(Hazardous Substances Data)

Usage

Description

1,3,5-Phenyltriboronic acid, pinacol ester is an organic compound that features a phenyl ring with three boronic ester functional groups attached to it. This molecule is known for its unique properties and potential applications in various fields due to its structural characteristics.

Uses

Used in Electrochemistry:
1,3,5-Phenyltriboronic acid, pinacol ester is used as a component in the fabrication of 2D covalent organic frameworks (COFs) for enhancing the hydrogen evolution reaction (HER) activity. When deposited onto a gold electrode, it increases the HER activity by up to three times compared to a bare gold electrode, making it a promising material for improving the efficiency of electrochemical processes.
Used in Organic Photovoltaics:
In the field of organic photovoltaics, 1,3,5-Phenyltriboronic acid, pinacol ester serves as an aromatic linker for synthesizing twisted Perylenediimide (PDI) base multimers. These multimers have potential applications in organic photovoltaic devices, where they can contribute to improved performance and efficiency by facilitating charge transport and light absorption.

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 71-43-2 benzene 
• 347389-74-6 2-ethynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 626-39-1 1,3,5-trisbromobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 99770-93-1 benzene-1,4-diboronic acid bispinacol ester 
• 123-91-1 1,4-dioxane 
• 408492-28-4 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane 
• 108-70-3 1,3,5-trichlorobenzene 
• 372-38-3 1,3,5-trifluorobenzene 

Downstream Products

• 1138337-69-5 1,3,5-tris[2,3,5,6-tetramethyl-4-(pyridin-4-yl)phenyl]benzene 
• 1026024-63-4 1,3,5-tris(2',2''-bipyridin-6'-yl)benzene 
• 1185738-82-2 1,3,5-tris(2',2'',6'',2'''-terpyridin-6'-yl)benzene 
• 15509-95-2 1,3,5-tris(2-thienyl)benzene 
• 612-71-5 1,3,5-triphenylbenzene 
• 1397264-18-4 C₂₇H₁₈O₉ 
• 1397264-16-2 dimethyl 3,3’’-dimethoxy-5’-(3-methoxy-4-(methoxycarbonyl)phenyl)-[1,1’:3’,1’’-terphenyl]-4,4’’-dicarboxylate 
• 161299-90-7 1,3,5-tris(5-bromothiophen-2-yl)benzene 
• 1482413-54-6 1,3,5-tris(6’,6’’,6’’’-formylpyridin-3-yl)benzene 
• 89641-21-4 benzene-1,3,5-triyltriboronic acid 
• 1660960-30-4 1,3,5-tris(3-amino-4-carboxyphenyl)benzene 
• 1660960-35-9 1,3,5-tris(3-fluoro-4-carboxyphenyl)benzene 
• 1219604-00-8 C₅₄H₃₆N₆ 

Relevant articles and documents

A Heteromeric Carboxylic Acid Based Single-Crystalline Crosslinked Organic Framework

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Optically active covalent organic frameworks and hyperbranched polymers with chirality induced by circularly polarized light

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Water-Soluble hyperbranched polyelectrolytes with high fluorescence quantum yield: Facile synthesis and selective chemosensor for Hg2+and Cu2+ ions

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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.

Metal-Stabilized Boronate Ester Cages

Molecular cages with arylboronate ester caps at the vertices are described. The cages were obtained by metal-templated polycondensation reactions of a tris(2-formylpyridine oxime) ligand with arylboronic acids. Suited templates are triflate or triflimide salts of ZnII, FeII, CoII, or MnII. In the products, the metal ions are coordinated internally to the pyridyl and oximato N atoms adjacent to the boronate ester, resulting in an improved hydrolytic stability of the latter. It is possible to decorate the cages with cyano or aldehyde groups using functionalized arylboronic acids. The aldehyde groups allow for a postsynthetic modification of the cages via an imine bond formation.