1,3,5-Phenyltriboronic acid, pinacol ester

Base Information

• Chemical Name: 1,3,5-Phenyltriboronic acid, pinacol ester
• CAS No.: 365564-05-2
• Molecular Formula: C24H39B3O6
• Molecular Weight: 456.003
• Hs Code.: 2934999090
• Mol file: 365564-05-2.mol

Synonyms: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;

Chemical Property of 1,3,5-Phenyltriboronic acid, pinacol ester

Chemical Property:

• Melting Point: 286-287°C
• Boiling Point: 555.6±45.0 °C(Predicted)
• PSA: 55.38000
• Density: 1.05±0.1 g/cm3(Predicted)
• LogP: 2.58420
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

Benzene-1,3,5-triyltriboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1. Fabricated a 2D COF which when deposited onto a Gold electrode increases the hydrogen evolution reaction(HER) activity by up to three times compared with bare Gold. 2. Used as an aromatic linker to synthesise a twisted Perylenediimide (PDI) base multimer that has potential applications in organic photovoltaics.

Technology Process of 1,3,5-Phenyltriboronic acid, pinacol ester

There total 10 articles about 1,3,5-Phenyltriboronic acid, pinacol ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1,3,5-trisbromobenzene (626-39-1) + bis(pinacol)diborane (73183-34-3) → 1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (365564-05-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ja512311a

Reference yield: 95.0%

1,3,5-trichlorobenzene (108-70-3,63697-19-8) + bis(pinacol)diborane (73183-34-3) → 1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (365564-05-2)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium chloride; In toluene; at 100 ℃; for 15h;

DOI:10.1002/cctc.201600456

Reference yield: 87.0%

1,3,5-trifluorobenzene (372-38-3) + bis(pinacol)diborane (73183-34-3) → 1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (365564-05-2)

Guidance literature:

With chlorobis(tricyclohexylphosphine)copper(I); cesium fluoride; In toluene; at 80 ℃; for 24h;

DOI:10.1021/acscatal.7b01448

upstream raw materials:

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

benzene

2-ethynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

1,3,5-trisbromobenzene

Downstream raw materials:

1,3,5-tris(2',2''-bipyridin-6'-yl)benzene

1,3,5-tris(2',2'',6'',2'''-terpyridin-6'-yl)benzene

1,3,5-tris(2-thienyl)benzene

1,3,5-triphenylbenzene

Refernces

• 1、 Zhang, Na,Wang, Taisheng,Bu, Xiaohai,Wu, Qiong,Zhang, Zewu. "Preparation of few-layer two-dimensional polymers by self-assembly of bola-amphiphilic small molecules". . p. 1748 - 1755. Retrieved 2019.
• 2、 Mishra, Shantanu,Beyer, Doreen,Eimre, Kristjan,Liu, Junzhi,Berger, Reinhard,Gr?ning, Oliver,Pignedoli, Carlo A.,Müllen, Klaus,Fasel, Roman,Feng, Xinliang,Ruffieux, Pascal. "Synthesis and Characterization of π-Extended Triangulene". . p. 10621 - 10625. Retrieved 2019.
• 3、 Abufager, Paula,Alexa, Patrick,Busnengo, Heriberto Fabio,Grumelli, Doris,Gutzler, Rico,Haase, Frederik,Kern, Klaus,Lombardi, Juan Manuel,Lotsch, Bettina V.,Vyas, Vijay S.. "Enhancing Hydrogen Evolution Activity of Au(111) in Alkaline Media through Molecular Engineering of a 2D Polymer". . p. 8411 - 8415. Retrieved 2020.
• 4、 Fadaei-Tirani, Farzaneh,Giraldi, Erica,Scopelliti, Rosario,Severin, Kay. "Metal-Stabilized Boronate Ester Cages". supporting information. p. 10873 - 10879. Retrieved 2021/08/16.