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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.

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  • 365564-05-2 Structure
  • Basic information

    1. Product Name: 1,3,5-Phenyltriboronic acid, pinacol ester
    2. 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%
    3. CAS NO:365564-05-2
    4. Molecular Formula: C24H39B3O6
    5. Molecular Weight: 309.72394
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 365564-05-2.mol
  • Chemical Properties

    1. Melting Point: 286-287°C
    2. Boiling Point: 555.6±45.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.05±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: Inert atmosphere,Room Temperature
    8. Solubility: N/A
    9. CAS DataBase Reference: 1,3,5-Phenyltriboronic acid, pinacol ester(CAS DataBase Reference)
    10. NIST Chemistry Reference: 1,3,5-Phenyltriboronic acid, pinacol ester(365564-05-2)
    11. EPA Substance Registry System: 1,3,5-Phenyltriboronic acid, pinacol ester(365564-05-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 365564-05-2(Hazardous Substances Data)

365564-05-2 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 365564-05-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,6,5,5,6 and 4 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 365564-05:
(8*3)+(7*6)+(6*5)+(5*5)+(4*6)+(3*4)+(2*0)+(1*5)=162
162 % 10 = 2
So 365564-05-2 is a valid CAS Registry Number.

365564-05-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3,5-Tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

1.2 Other means of identification

Product number -
Other names 2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:365564-05-2 SDS

365564-05-2Relevant articles and documents

A Heteromeric Carboxylic Acid Based Single-Crystalline Crosslinked Organic Framework

Liang, Rongran,Samanta, Jayanta,Shao, Baihao,Zhang, Mingshi,Staples, Richard J.,Chen, Albert D.,Tang, Miao,Wu, Yuyang,Aprahamian, Ivan,Ke, Chenfeng

, p. 23176 - 23181 (2021)

The development of large pore single-crystalline covalently linked organic frameworks is critical in revealing the detailed structure-property relationship with substrates. One emergent approach is to photo-crosslink hydrogen-bonded molecular crystals. In

Preparation of few-layer two-dimensional polymers by self-assembly of bola-amphiphilic small molecules

Zhang, Na,Wang, Taisheng,Bu, Xiaohai,Wu, Qiong,Zhang, Zewu

, p. 1748 - 1755 (2019)

Two bola-amphiphilic small molecules, based on the diphenylanthracene skeleton structure, namely, BASM-1 and its functionalized small molecule BASM-2, were designed and synthesized. The self-assembly behavior and mechanism of these two molecules in aqueou

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

Bando, Masayoshi,Harada, Takunori,Naga, Naofumi,Nakano, Tamaki,Shimoda, Shuhei,Song, Zhiyi,Wang, Qingyu,Wang, Yuting,Yazawa, Koji

, p. 7681 - 7684 (2021)

Axial chirality was induced by circularly polarized light to covalent organic frameworks as well as hyperbranched polymers composed of bezene-1,3,5-triyl core units and oligo(benzene-1,4-diyl) as linker units where variation in induction efficiency was ra

Synthesis and Characterization of π-Extended Triangulene

Mishra, Shantanu,Beyer, Doreen,Eimre, Kristjan,Liu, Junzhi,Berger, Reinhard,Gr?ning, Oliver,Pignedoli, Carlo A.,Müllen, Klaus,Fasel, Roman,Feng, Xinliang,Ruffieux, Pascal

, p. 10621 - 10625 (2019)

The electronic and magnetic properties of nanographenes strongly depend on their size, shape and topology. While many nanographenes present a closed-shell electronic structure, certain molecular topologies may lead to an open-shell structure. Triangular-s

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

Biqing, Bao,Yuwen, Lihui,Zhan, Xiaowei,Wang, Lianhui

, p. 3431 - 3439 (2010)

New water-soluble hyperbranched polyfluorenes bearing carboxylate side chains have been synthesized by the simple "A2 + B2 + C3" protocol based on Suzuki coupling polymerization. The linear polyfluorene analogue LPFA was also synthesized for comparative i

Enhancing Hydrogen Evolution Activity of Au(111) in Alkaline Media through Molecular Engineering of a 2D Polymer

Abufager, Paula,Alexa, Patrick,Busnengo, Heriberto Fabio,Grumelli, Doris,Gutzler, Rico,Haase, Frederik,Kern, Klaus,Lombardi, Juan Manuel,Lotsch, Bettina V.,Vyas, Vijay S.

, p. 8411 - 8415 (2020)

The electrochemical splitting of water holds promise for the storage of energy produced intermittently by renewable energy sources. The evolution of hydrogen currently relies on the use of platinum as a catalyst—which is scarce and expensive—and ongoing r

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

K?nig, Burkhard,Wang, Hua,Wang, Shun

supporting information, p. 1653 - 1665 (2021/06/17)

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.

Novel compound and organic light emitting device comprising the same

-

Paragraph 0270-0274, (2021/07/27)

The present invention provides a novel compound and an organic light emitting device including the same.

Metal-Stabilized Boronate Ester Cages

Fadaei-Tirani, Farzaneh,Giraldi, Erica,Scopelliti, Rosario,Severin, Kay

supporting information, p. 10873 - 10879 (2021/08/16)

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.

Linkage Engineering by Harnessing Supramolecular Interactions to Fabricate 2D Hydrazone-Linked Covalent Organic Framework Platforms toward Advanced Catalysis

Qian, Cheng,Zhou, Weiqiang,Qiao, Jingsi,Wang, Dongdong,Li, Xing,Teo, Wei Liang,Shi, Xiangyan,Wu, Hongwei,Di, Jun,Wang, Hou,Liu, Guofeng,Gu, Long,Liu, Jiawei,Feng, Lili,Liu, Yuchuan,Quek, Su Ying,Loh, Kian Ping,Zhao, Yanli

supporting information, p. 18138 - 18149 (2020/11/02)

Covalent organic frameworks (COFs) are an emerging class of crystalline porous polymers with tailor-made structures and functionalities. To facilitate their utilization for advanced applications, it is crucial to develop a systematic approach to control the properties of COFs, including the crystallinity, stability, and functionalities. However, such an integrated design is challenging to achieve. Herein, we report supramolecular strategy-based linkage engineering to fabricate a versatile 2D hydrazone-linked COF platform for the coordination of different transition metal ions. Intra- and intermolecular hydrogen bonding as well as electrostatic interactions in the antiparallel stacking mode were first utilized to obtain two isoreticular COFs, namely COF-DB and COF-DT. On account of suitable nitrogen sites in COF-DB, the further metalation of COF-DB was accomplished upon the complexation with seven divalent transition metal ions M(II) (M = Mn, Co, Ni, Cu, Zn, Pd, and Cd) under mild conditions. The resultant M/COF-DB exhibited extended π-conjugation, improved crystallinity, enhanced stability, and additional functionalities as compared to the parent COF-DB. Furthermore, the dynamic nature of the coordination bonding in M/COF-DB allows for the easy replacement of metal ions through a postsynthetic exchange. In particular, the coordination mode in Pd/COF-DB endows it with excellent catalytic activity and cyclic stability as a heterogeneous catalyst for the Suzuki-Miyaura cross-coupling reaction, outperforming its amorphous counterparts and Pd/COF-DT. This strategy provides an opportunity for the construction of 2D COFs with designable functions and opens an avenue to create COFs as multifunctional systems.

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