2-Methyl-beta-styrylboronic acid pinacoal ester

Base Information

• Chemical Name: 2-Methyl-beta-styrylboronic acid pinacoal ester
• CAS No.: 1294009-26-9
• Molecular Formula: C15H21BO2
• Molecular Weight: 244.142
• Hs Code.: 2934999090
• Mol file: 1294009-26-9.mol

Synonyms:(E)-4,4,5,5-Tetramethyl-2-(2-methylstyryl)-1,3,2-dioxaborolane;(E)-2-(2-tolyl)ethenylboronic acid pinacol ester;

Chemical Property of 2-Methyl-beta-styrylboronic acid pinacoal ester

Chemical Property:

• PSA: 18.46000
• LogP: 3.63960
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

(E)-4,4,5,5-Tetramethyl-2-(2-methylstyryl)-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 2-Methyl-beta-styrylboronic acid pinacoal ester

There total 14 articles about 2-Methyl-beta-styrylboronic acid pinacoal 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) → 4,4,5,5-tetramethyl-2-[(E)-2-(o-tolyl)vinyl]-1,3,2-dioxaborolane (1294009-26-9)

Guidance literature:

With bis(cyclopentadienyl)dihydrozirconium; In toluene; at 25 ℃; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201908931

Reference yield: 90.0%

1-ethynyl-2-methylbenzene (766-47-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-[(E)-2-(o-tolyl)vinyl]-1,3,2-dioxaborolane (1294009-26-9)

Guidance literature:

With lithium diisobutyl-tert-butoxyaluminum hydride; In neat (no solvent); at 50 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c9nj03931g

Reference yield: 89.0%

1-ethynyl-2-methylbenzene (766-47-2) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[(E)-2-(o-tolyl)vinyl]-1,3,2-dioxaborolane (1294009-26-9)

Guidance literature:

With [Cu(phen)(xantphosTEPD)]PF₆; potassium carbonate; In water; acetonitrile; at 20 ℃; for 7h; diastereoselective reaction; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1002/anie.202101874

upstream raw materials:

1-ethynyl-2-methylbenzene

bis(pinacol)diborane

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

3-(2-methylphenyl)prop-2-ynoic acid

Downstream raw materials:

(E)-1-methyl-2-(3,3,3-trifluoroprop-1-en-1-yl)benzene

Refernces

• 1、 Aelterman, Maude,Jubault, Philippe,Poisson, Thomas,Sayes, Morgane. "Electrochemical Hydroboration of Alkynes". supporting information. p. 8277 - 8282. Retrieved 2021/05/27.
• 2、 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.