Methyl 4-(2-phenylethenyl)benzoate

Base Information

• Chemical Name: Methyl 4-(2-phenylethenyl)benzoate
• CAS No.: 1149-18-4
• Molecular Formula: C16H14O2
• Molecular Weight: 238.286
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID40699058
• Mol file: 1149-18-4.mol

Synonyms:4-carbomethoxystilbene;DTXSID40699058;VWHFZNARASKJAS-UHFFFAOYSA-N;4-Styryl-benzoic acid methyl ester;methyl 4-(2-phenylethenyl)benzoate

Chemical Property of Methyl 4-(2-phenylethenyl)benzoate

Chemical Property:

• Melting Point: 159-160 °C(Solv: benzene (71-43-2))
• Boiling Point: 372.7±22.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.131±0.06 g/cm3(Predicted)
• LogP: 3.64360
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 238.099379685
• Heavy Atom Count: 18
• Complexity: 282

Purity/Quality:

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

4-((E)-STYRYL)-BENZOIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)C=CC2=CC=CC=C2

Technology Process of Methyl 4-(2-phenylethenyl)benzoate

There total 70 articles about Methyl 4-(2-phenylethenyl)benzoate 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%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + methyl 4-iodobenzoate (619-44-3) → (E)-methyl 4-styrylbenzoate (1149-18-4)

Guidance literature:

With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation;

DOI:10.1039/d0ra08749a

Reference yield: 99.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 4-methoxycarbonylphenyl bromide (619-42-1) → (E)-methyl 4-styrylbenzoate (1149-18-4)

Guidance literature:

With tetrabutylammomium bromide; sodium acetate; In N,N-dimethyl acetamide; water; at 120 ℃; for 16h; Reagent/catalyst; Inert atmosphere;

DOI:10.1002/aoc.5405

Reference yield: 98.0%

methyl 4-(phenylethynyl)benzoate (42497-80-3) → (E)-methyl 4-styrylbenzoate (1149-18-4)

Guidance literature:

With formic acid; (1,2-dimethoxyethane)dichloronickel(II); zinc; bis(2-diphenylphosphinoethyl)phenylphosphine; In 1,4-dioxane; at 120 ℃; for 16h; stereoselective reaction; Sealed tube;

DOI:10.1021/acs.joc.5b01047

upstream raw materials:

diazomethane

(E)-4-stilbenecarboxylic acid

Methyl 4-(bromomethyl)benzoate

benzaldehyde

Downstream raw materials:

trans-4-(3-phenyloxiran-2-yl)benzoic acid methyl ester

(E)-4-stilbenecarboxylic acid

(+/-)-erythro-α.α'-dibromo-bibenzyl-carboxylic acid-(4)-methyl ester

4-[1-Fluoro-2-phenyl-2-(2,2,2-trifluoro-acetoxy)-ethyl]-benzoic acid methyl ester

Refernces

• 1、 Cai, Ming-Zhong,Song, Cai-Sheng,Huang, Xian. "Silica-supported poly-γ-mercaptopropylsiloxane palladium(0) complex: A highly active and stereoselective catalyst for arylation of styrene and acrylic acid". . p. 521 - 523. Retrieved 1997.
• 2、 Kang, Suk-Ku,Yoon, Seok-Keun,Lim, Kwon-Ho,Son, Hoe-Joo,Baik, Tae-Gon. "Palladium-catalyzed carbon- carbon bond formation on a solid phase utilizing hypervalent iodonium salts". . p. 3645 - 3655. Retrieved 1998.
• 3、 Schroeter, Felix,Soellner, Johannes,Strassner, Thomas. "Cross-Coupling Catalysis by an Anionic Palladium Complex". . p. 3004 - 3009. Retrieved 2017.
• 4、 Alper,Arya,Bourque,Jefferson,Manzer. "Heck reaction using palladium complexed to dendrimers on silica". . p. 920 - 924. Retrieved 2000.
• 5、 Traficante, Carla I.,Fagundez, Catherine,Serra, Gloria L.,Mata, Ernesto G.,Delpiccolo, Carina M. L.. "Chemoselective and Sequential Palladium-Catalyzed Couplings for the Generation of Stilbene Libraries via Immobilized Substrates". . p. 225 - 229. Retrieved 2016.
• 6、 Dos Santos, Beatriz F.,Da Silva, Beatriz A. L.,De Oliveira, Aline R.,Sarragiotto, Maria H.,Rinaldi, Andrelson W.,Domingues, Nelson Luís C.. "Palladium Nanoparticles Anchored on Magnesium Organosilicate: An Effective and Selective Catalyst for the Heck Reaction". supporting information. p. 1301 - 1306. Retrieved 2020/11/04.
• 7、 Ning, Shulin,Zheng, Lianyou,Bai, Ya,Wang, Shutao,Wang, Siyu,Shi, Lingling,Gao, Qiansong,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao. "Highly selective electroreductive linear dimerization of electron-deficient vinylarenes". supporting information. . Retrieved 2021/11/16.