2-methylstyrene boronic acid pinacol ester

Base Information

• Chemical Name: 2-methylstyrene boronic acid pinacol ester
• CAS No.: 1377152-50-5
• Molecular Formula: C₁₅H₂₁BO₂
• Molecular Weight: 244.142
• Mol file: 1377152-50-5.mol

Synonyms:2-methylstyrene boronic acid pinacol ester

Chemical Property of 2-methylstyrene boronic acid pinacol ester

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methylstyrene boronic acid pinacol ester

There total 8 articles about 2-methylstyrene boronic 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: 99.0%

1-methyl-2-vinyl-benzene (611-15-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-methylstyrene boronic acid pinacol ester (1377152-50-5)

Guidance literature:

With bis(cyclopentadienyl)dihydrozirconium; In toluene; at 25 ℃; under 760.051 Torr; Inert atmosphere;

Reference yield: 91.0%

1-ethynyl-2-methylbenzene (766-47-2) + bis(pinacol)diborane (73183-34-3) → 2-methylstyrene boronic acid pinacol ester (1377152-50-5) + 4,4,5,5-tetramethyl-2-(1-(o-tolyl)vinyl)-1,3-dioxa-2-borolane

Guidance literature:

bis(pinacol)diborane; With C₂₉H₃₉ClCuN; sodium t-butanolate; In tetrahydrofuran; at 22 ℃; for 0.0833333h; Inert atmosphere;

1-ethynyl-2-methylbenzene; In tetrahydrofuran; methanol; at 22 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.202106107

Reference yield: 75.0%

1-ethynyl-2-methylbenzene (766-47-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-methylstyrene boronic acid pinacol ester (1377152-50-5) + 2,2'-(2-(o-tolyl)ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (1172611-47-0)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,4-di(diphenylphosphino)-butane; In 1,2-dichloro-ethane; at 20 ℃; for 24h; regioselective reaction;

DOI:10.1055/s-0028-1088131

upstream raw materials:

1-ethynyl-2-methylbenzene

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

bis(pinacol)diborane

1-methyl-2-vinyl-benzene

Downstream raw materials:

(E)-2-(2-(2-methylstyryl)phenyl)pyridine

Refernces

• 1、 Bertrand, Guy,Engle, Keary M.,Gao, Yang,Grotjahn, Douglas B.,Jazzar, Rodolphe,Junor, Glen P.,Kang, Taeho,Kendrick, Aaron,Yazdani, Sima. "Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**". supporting information. p. 19871 - 19878. Retrieved 2021/08/13.
• 2、 Liu, Shiwen,Meng, Lingling,Zeng, Xiaojun,Hammond, Gerald B.,Xu, Bo. "Synthesis of Acrylonitriles via Mild Base Promoted Tandem Nucleophilic Substitution-Isomerization of α-Cyanohydrin Methanesulfonates". supporting information. p. 913 - 917. Retrieved 2021/04/05.