2-(4-METHOXYPHENYL)-VINYLBORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 2-(4-METHOXYPHENYL)-VINYLBORONIC ACID PINACOL ESTER
• CAS No.: 149777-83-3
• Molecular Formula: C15H21BO3
• Molecular Weight: 260.141
• Hs Code.: 2934999090
• Mol file: 149777-83-3.mol

Synonyms:PINACOL 2-(4-METHOXYPHENYL)-VINYLBORONATE;2-[2-(4-METHOXY-PHENYL)-VINYL]-4,4,5,5-TETRAMETHYL-[1,3,2] DIOXABOROLANE;4-Methoxy-trans-beta-styrylbo;4-Methoxy-trans-beta-styrylbor;4-Methoxy-trans-beta-styrylboronic acid pinacol ester, 98%;

Chemical Property of 2-(4-METHOXYPHENYL)-VINYLBORONIC ACID PINACOL ESTER

Chemical Property:

• Boiling Point: 320.9±44.0 °C(Predicted)
• PSA: 27.69000
• Density: 1.02±0.1 g/cm3(Predicted)
• LogP: 3.33980
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxy-Trans-β-StyrylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(4-METHOXYPHENYL)-VINYLBORONIC ACID PINACOL ESTER

There total 49 articles about 2-(4-METHOXYPHENYL)-VINYLBORONIC 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%

4-methoxyphenylacetylen (768-60-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-[(E)-2-(4-methoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (149777-83-3)

Guidance literature:

With C₂₈H₄₀CuNO; In acetonitrile; at 20 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.jorganchem.2016.09.025

Reference yield: 95.0%

4-Methoxystyrene (637-69-4,24936-44-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-[(E)-2-(4-methoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (149777-83-3) + 1-(4-methoxyphenyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethane + 2-[2-(4-methoxy-phenyl)-ethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Guidance literature:

chloro(1,5-cyclooctadiene)rhodium(I) dimer; In toluene; byproducts: CH3OC6H4CH2CH3; pinacolborane and vinylarene were added to a mixt. of Rh-complex in toluene under Ar, the mixt. was stirred at room temp. for 4 h; diluted with toluene, washed with water, dried over MgSO4, evapd., distilled with Kugelrohr or chromy. on silica gel;

DOI:10.1246/bcsj.75.825

Reference yield: 94.0%

4-methoxyphenylacetylen (768-60-5) + bis(pinacol)diborane (73183-34-3) → 2-[(E)-2-(4-methoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (149777-83-3)

Guidance literature:

With triphenylphosphine; In ethanol; at 50 ℃; for 2h;

DOI:10.1002/asia.201700856

upstream raw materials:

1-bromo-4-methoxy-benzene

pinacol vinylboronate

4-Methoxystyrene

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

Downstream raw materials:

(E)-2-(4-methoxyphenyl)vinylboronic acid

7-hexyl-5-(4-methoxyphenyl)-1-tosyl-2,3,4,5-tetrahydro-1H-indole

N,N-diethyl-2-(4-methoxyphenyl)ethanamine

2-((E)-3-(4-methoxyphenyl)-1-morpholinoallyl)phenol

Refernces

• 1、 Arnaud, Alexandre,Doléans-Jordheim, Anne,Gioia, Bruna,Radix, Sylvie,Rocheblave, Luc,Walchshofer, Nadia. "Solvent- and metal-free hydroboration of alkynes under microwave irradiation". . . Retrieved 2020.
• 2、 Hunt,Stewart,Whiting. "Heck versus Suzuki palladium catalysed cross-coupling of a vinylboronate ester with aryl halides". . p. 3599 - 3602. Retrieved 1993.
• 3、 Eddarir, Said,Cotelle, Nicole,Bakkour, Youssef,Rolando, Christian. "An efficient synthesis of chalcones based on the Suzuki reaction". . p. 5359 - 5363. Retrieved 2003.
• 4、 Kumar, Gobbilla Sai,Moorthy, Shruti,Karmakar, Himadri,Singh, Saurabh Kumar,Panda, Tarun K.. "Neosilyllithium-Catalyzed Hydroboration of Alkynes and Alkenes in the Presence of Pinacolborane (HBpin)". supporting information. . Retrieved 2021/11/13.
• 5、 Zhong, Mingbing,Gagné, Yohann,Hope, Taylor O.,Pannecoucke, Xavier,Frenette, Mathieu,Jubault, Philippe,Poisson, Thomas. "Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes". supporting information. p. 14498 - 14503. Retrieved 2021/05/21.