2-Ethoxycarbonylvinylboronic acid pinacol ester

Base Information

• Chemical Name: 2-Ethoxycarbonylvinylboronic acid pinacol ester
• CAS No.: 1009307-13-4
• Molecular Formula: C11H21BO5
• Molecular Weight: 226.08
• Hs Code.: 2931900090
• Mol file: 1009307-13-4.mol

Synonyms:4-ethoxycarbonyloxy-3-methoxy-cinnamic acid;2-Propenoic acid,3-[4-[(ethoxycarbonyl)oxy]-3-methoxyphenyl]-,(E);3-Methoxy-4-carbaethoxyoxy-zimtsaeure;(E)-3-(4-(ethoxycarbonyloxy)-3-methoxyphenyl)acrylic acid;2-ethoxycarbonylvinylboronic acid pinacol ester;(2E)-3-{4-[(ethoxycarbonyl)oxy]-3-methoxyphenyl}acrylic acid;ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate;4-Aethoxycarbonyloxy-3-methoxy-zimtsaeure;(E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)acrylic acid ethyl ester;3-methoxy-4-ethoxycarbonyloxy-trans-cinnamic acid;3-Methoxy-4-aethoxycarbonyloxy-trans-zimtsaeure;(E)-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)acrylate;Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate;(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-acrylic acid ethyl ester;

Chemical Property of 2-Ethoxycarbonylvinylboronic acid pinacol ester

Chemical Property:

• Boiling Point: 236.8±42.0 °C(Predicted)
• Density: 1.01±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

2-EthoxycarbonylvinylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Use Description: 2-Ethoxycarbonylvinylboronic acid pinacol ester, a specific chemical compound, serves distinct roles in various fields. In organic synthesis, it is employed as a crucial reagent in Suzuki-Miyaura cross-coupling reactions, enabling the creation of complex carbon-carbon bonds and contributing to the synthesis of various organic molecules, including pharmaceuticals and materials. In medicinal chemistry, this compound can be utilized as an intermediate for the preparation of potential drug candidates, contributing to drug discovery efforts. Moreover, in the field of materials science, it plays a role in designing and producing functional materials with specific properties. Its applications in organic synthesis, medicinal chemistry, and materials science highlight its significance in driving innovation, scientific exploration, and practical applications across these diverse domains.

Technology Process of 2-Ethoxycarbonylvinylboronic acid pinacol ester

There total 2 articles about 2-Ethoxycarbonylvinylboronic 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: 100.0%

bis(pinacol)diborane (73183-34-3) + propynoic acid ethyl ester (623-47-2) → ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (1009307-13-4)

Guidance literature:

bis(pinacol)diborane; With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; at 20 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

propynoic acid ethyl ester; In tetrahydrofuran; methanol; Sealed tube; Schlenk technique; Inert atmosphere;

DOI:10.1021/jm3011838

Reference yield: 66.0%

ethyl (Z)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate → ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (1009307-13-4)

Guidance literature:

With thio-xanthene-9-one; In acetonitrile; at 20 ℃; for 1h; Irradiation;

DOI:10.1126/science.abb7235

Reference yield: 96.0%

ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (1009307-13-4) + 2-(5-chloro-2-ethoxy-4-fluoro-3-iodophenyl)-2-methyl-1,3-dioxolane → ethyl (2E)-3-[3-chloro-6-ethoxy-2-fluoro-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]acrylate

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate; In 1,4-dioxane; water; at 80 ℃; for 2h; Inert atmosphere;

upstream raw materials:

bis(pinacol)diborane

propynoic acid ethyl ester

Downstream raw materials:

4-(2-{[5-((E)-2-ethoxycarbonyl-vinyl)-2-phenyl-thiazole-4-carbonyl]-amino}-acetyl)-piperazine-1-carboxylic acid butyl ester

4-((S)-2-{[5-((E)-2-carboxy-vinyl)-2-phenyl-thiazole-4-carbonyl]-amino}-3-hydroxy-propionyl)-piperazine-1-carboxylic acid butyl ester

C₂₇H₃₄N₄O₇S

(E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate

Refernces

• 1、 Zeng, Xianghua,Gong, Chunhua,Guo, Haiyang,Xu, Hao,Zhang, Junyong,Xie, Jingli. "Efficient heterogeneous hydroboration of alkynes: enhancing the catalytic activity by Cu(0) incorporated CuFe2O4 nanoparticles". . p. 17346 - 17350. Retrieved 2018.
• 2、 Wienhold, Max,Molloy, John J.,Daniliuc, Constantin G.,Gilmour, Ryan. "Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons". supporting information. p. 685 - 689. Retrieved 2020/11/30.
• 3、 Molloy, John J.,Sch?fer, Michael,Wienhold, Max,Morack, Tobias,Daniliuc, Constantin G.,Gilmour, Ryan. "Boron-enabled geometric isomerization of alkenes via selective energy-transfer catalysis". . p. 302 - 306. Retrieved 2020/08/11.