4-broMo-trans-beta-styrylboronic acid pinacol ester

Base Information

• Chemical Name: 4-broMo-trans-beta-styrylboronic acid pinacol ester
• CAS No.: 1242770-51-9
• Molecular Formula: C14 H18 B Br O2
• Molecular Weight: 309.011
• Hs Code.: 2934999090
• Mol file: 1242770-51-9.mol

Synonyms:TRANS-4-BROMO-BETA-STYRYLBORONIC ACID PINACOL ESTER;

Chemical Property of 4-broMo-trans-beta-styrylboronic acid pinacol ester

Chemical Property:

• PSA: 18.46000
• LogP: 4.09370

Purity/Quality:

99%min ^*data from raw suppliers

(E)-2-(4-Bromostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-broMo-trans-beta-styrylboronic acid pinacol ester

There total 12 articles about 4-broMo-trans-beta-styrylboronic 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: 97.0%

4-bromo-1-ethynylbenzene (766-96-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (E)-1-(4’,4’,5’,5’-tetramethyl)-1’,3’,2’-dioxaboronalyl-2-(4’’-bromophenyl)ethene (1242770-51-9)

Guidance literature:

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With C₃₂H₄₁CuN₂O₂S; In toluene; at 20 ℃; for 0.25h; Schlenk technique; Inert atmosphere;

4-bromo-1-ethynylbenzene; In toluene; at 20 ℃; for 2h; stereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1039/c9ob00839j

Reference yield: 93.0%

4-bromo-1-ethynylbenzene (766-96-1) + bis(pinacol)diborane (73183-34-3) → (E)-1-(4’,4’,5’,5’-tetramethyl)-1’,3’,2’-dioxaboronalyl-2-(4’’-bromophenyl)ethene (1242770-51-9)

Guidance literature:

bis(pinacol)diborane; With bis[2-(diphenylphosphino)phenyl] ether; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; at 25 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

4-bromo-1-ethynylbenzene; In tetrahydrofuran; methanol; at 25 ℃; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1039/c5ob00917k

Reference yield: 92.0%

1-bromo-4-ethenyl-benzene (2039-82-9) + pinacol vinylboronate (75927-49-0) → (E)-1-(4’,4’,5’,5’-tetramethyl)-1’,3’,2’-dioxaboronalyl-2-(4’’-bromophenyl)ethene (1242770-51-9)

Guidance literature:

With carbonylchlorohydridobis(tricyclohexylphosphine)ruthenium(II); In toluene; at 80 ℃; for 5h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c7ob00054e

upstream raw materials:

4-bromo-1-ethynylbenzene

bis(pinacol)diborane

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

3-(4-bromophenyl)-2-propynoic acid

Downstream raw materials:

(E)-1-bromo-4-(2-bromovinyl)benzene

(Z)-1-[2-bromovinyl]-4-bromobenzene

Refernces

• 1、 Szyling, Jakub,Franczyk, Adrian,Stefanowska, Kinga,Klarek, Mateusz,Maciejewski, Hieronim,Walkowiak, J?drzej. "An Effective Catalytic Hydroboration of Alkynes in Supercritical CO2 under Repetitive Batch Mode". . p. 531 - 539. Retrieved 2018.
• 2、 Mai, Binh Khanh,Nguyen, Thanh Vinh,Ton, Nhan N. H.. "Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies". . p. 9117 - 9133. Retrieved 2021/07/19.
• 3、 Altarejos, Julia,Carreras, Javier,Sucunza, David,Vaquero, Juan J.. "Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates". supporting information. p. 6174 - 6178. Retrieved 2021/08/18.