4-Ethylphenylboronic acid pinacol ester

Base Information

• Chemical Name: 4-Ethylphenylboronic acid pinacol ester
• CAS No.: 1075719-87-7
• Molecular Formula: C₁₄H₂₁BO₂
• Molecular Weight: 232.131
• Hs Code.: 2931900090
• Mol file: 1075719-87-7.mol

Synonyms:2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 4-Ethylphenylboronic acid pinacol ester

Chemical Property:

• Boiling Point: 313.0±21.0 °C(Predicted)
• Density: 0.97±0.1 g/cm3(Predicted)

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Ethylphenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: suzuki reaction

Technology Process of 4-Ethylphenylboronic acid pinacol ester

There total 16 articles about 4-Ethylphenylboronic 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: 96.0%

4-ethyl-1-iodobenzene (25309-64-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1075719-87-7)

Guidance literature:

With magnesium; triethylamine; In tetrahydrofuran; for 15h; Inert atmosphere; Reflux;

DOI:10.1021/ja1052973

Reference yield: 94.8%

1-bromo-4-ethylbenzene (1585-07-5) + bis(pinacol)diborane (73183-34-3) → 2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1075719-87-7)

Guidance literature:

With palladium diacetate; triphenylphosphine; cesium pivalate; In 1,4-dioxane; at 95 ℃; for 2h; Reagent/catalyst; Inert atmosphere;

Reference yield: 90.0%

1-bromo-4-ethylbenzene (1585-07-5) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1075719-87-7)

Guidance literature:

With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; at -60 ℃;

DOI:10.1021/ol2010006

upstream raw materials:

4-ethyl-1-iodobenzene

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

1-bromo-4-ethylbenzene

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

tert-butyl (S)-1-((1R,2R)-1-cyano-2-(4'-ethylbiphenyl-4-yl)cyclopropylamino)-1-oxobutan-2-ylcarbamate

(S)-2-amino-N-(1R,2R)-1-cyano-2-(4'-ethylbiphenyl-4-ylcyclopropyl)butanamide

4-Ethylphenol

1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone

Refernces

• 1、 Murphy, Chris L.,Hall, Aaron,Roberts, Emily J.,Ryan, Matthew D.,Clary, Jacob W.,Singaram, Bakthan. "Preparation and reactions of 4-iodobutyl pinacolborate. Synthesis of substituted alkyl and aryl pinacolboronates via 4-iodobutyl pinacolborate utilizing tetrahydrofuran as the leaving group". . p. 3032 - 3033. Retrieved 2015.
• 2、 Pintaric, Christine,Olivero, Sandra,Gimbert, Yves,Chavant, Pierre Y.,Dunach, Elisabet. "An opportunity for Mg-catalyzed grignard-type reactions: Direct coupling of benzylic halides with pinacolborane with 10 mol % of magnesium". . p. 11825 - 11827. Retrieved 2010.
• 3、 Asako, Sobi,Ilies, Laurean,Jin, Yushu,Ramadoss, Boobalan. "Remote steric control for undirected meta-selective C-H activation of arenes". . p. 658 - 663. Retrieved 2022/02/21.
• 4、 -. "Preparation method of aryl borate catalyzed by cesium neovalerate". Paragraph 0034-0037; 0068-0069. . Retrieved 2021/09/22.