1,4-Benzenediboronic acid bis(pinacol) ester

Base Information

• Chemical Name: 1,4-Benzenediboronic acid bis(pinacol) ester
• CAS No.: 99770-93-1
• Molecular Formula: C18H28 B2 O4
• Molecular Weight: 330.04
• Hs Code.: 29349990
• European Community (EC) Number: 691-283-5
• DSSTox Substance ID: DTXSID30442257
• Nikkaji Number: J1.053.215I
• Wikidata: Q82259438
• Mol file: 99770-93-1.mol

Synonyms:p-Benzenediboronicacid, cyclic bis(tetramethylethylene) ester (7CI); 1,4-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene;1,4-Phenylenebis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Chemical Property of 1,4-Benzenediboronic acid bis(pinacol) ester

Chemical Property:

• Melting Point: 241-245 °C
• Boiling Point: 416.3°Cat760mmHg
• Flash Point: 205.6°C
• PSA: 36.92000
• Density: 1.03g/cm³
• LogP: 2.28500
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Toluene
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 330.2173697
• Heavy Atom Count: 24
• Complexity: 405

Purity/Quality:

98% ^*data from raw suppliers

1,4-BenzenediboronicAcidBis(pinacol)Ester1,4-BenzenediboronicAcidBis(Pinacol)Ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)B3OC(C(O3)(C)C)(C)C
• Uses: Reagent used forSuzuki-Miyaura cross-coupling reactions and polymerizations Reagent used in Prepration ofEfficient solar cell photoelectric polymers Field-effect transistors and photovoltaic cells Fluorescent compounds and materials such as Blue OLED devices, Blue Polymeric Light Emitting Diodes, and White LEDs

Technology Process of 1,4-Benzenediboronic acid bis(pinacol) ester

There total 84 articles about 1,4-Benzenediboronic acid bis(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: 97.0%

para-diiodobenzene (624-38-4,1032416-46-8) + bis(pinacol)diborane (73183-34-3) → benzene-1,4-diboronic acid bispinacol ester (99770-93-1)

Guidance literature:

With 10H-phenothiazine; caesium carbonate; In acetonitrile; for 48h; Irradiation; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.9b12519

Reference yield: 97.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1,4-Phenyldiboronic acid (4612-26-4) → benzene-1,4-diboronic acid bispinacol ester (99770-93-1)

Guidance literature:

With magnesium sulfate; In methanol; at 30 ℃;

DOI:10.1055/s-2002-25773

Reference yield: 95.0%

bis(pinacol)diborane (73183-34-3) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → benzene-1,4-diboronic acid bispinacol ester (99770-93-1) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6)

Guidance literature:

With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)diiridium(I) dichloride; In neat (no solvent); at 80°C for 16 h;

DOI:10.1021/ja0173019

upstream raw materials:

para-diiodobenzene

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

1.4-dibromobenzene

benzene

Downstream raw materials:

1-(2,5-dimethoxyphenyl)-8-[4-(4',4',5',5'-tetramethyl[1',3',2']dioxaborolan-2'-yl)-1-phenyl]naphthalene

1,4-bis(pyrid-3-yl)benzene

1-iodo-8-[4'-(8''-[2''',5'''-dimethoxyphenyl]-1''-naphthyl)-1'-phenyl]naphthalene

(S)-tert-butyl 2-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1Hbenzo[d]imidazol-2-yl)pyrrolidine-1-carboxylate

Refernces

• 1、 Cui, Suqian,Hao, Zhaoran,Lei, Gangtie,Liu, Yajun,Liu, Yu,Zhang, Kai,Zhu, Weiguo. "A feasible approach to obtain near-infrared (NIR) emission from binuclear platinum(II) complexes containing centrosymmetric isoquinoline ligand in PLEDs". . . Retrieved 2020.
• 2、 Chen, Zicong,Ng, Shan Shan,So, Chau Ming,Yuen, On Ying. "Palladium-Catalyzed Chemoselective Borylation of (Poly)halogenated Aryl Triflates and Their Application in Consecutive Reactions". . . Retrieved 2022/03/15.
• 3、 -. "Novel compound and organic light emitting device comprising the same". Paragraph 0249; 0255-0258. . Retrieved 2021/07/27.