Ethyl 4-Cyanocinnamate

Base Information

• Chemical Name: Ethyl 4-Cyanocinnamate
• CAS No.: 62174-99-6
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.225
• European Community (EC) Number: 680-035-1
• NSC Number: 636708
• Nikkaji Number: J581.921K,J672.950I
• ChEMBL ID: CHEMBL4851252
• Mol file: 62174-99-6.mol

Synonyms:Ethyl 3-(4-cyanophenyl)acrylate;Ethyl 4-Cyanocinnamate;62174-99-6;20655-58-7;(E)-ethyl 3-(4-cyanophenyl)acrylate;ethyl (E)-3-(4-cyanophenyl)prop-2-enoate;NSC636708;4-Cyanocinnamic Acid Ethyl Ester;2-Propenoic acid, 3-(4-cyanophenyl)-, ethyl ester;SCHEMBL2244754;SCHEMBL4512561;CHEMBL4851252;AMY4601;Ethyl(E)-3-(4-cyanophenyl)acrylate;4-Cyanobenzeneacrylic acid ethyl ester;AKOS015836386;Ethyl (E)-3-(4-cyanophenyl)acrylate;NSC-636708;AS-68124;BS-23553;CS-0061538;Ethyl (2E)-3-(4-cyanophenyl)-2-propenoate;D73192;W11633;Ethyl (2E)-3-(4-cyanophenyl)-2-propenoate #;A868538

Chemical Property of Ethyl 4-Cyanocinnamate

Chemical Property:

• Vapor Pressure: 3.96E-05mmHg at 25°C
• Melting Point: 70 °C
• Refractive Index: 1.541
• Boiling Point: 352 °C at 760 mmHg
• Flash Point: 168 °C
• PSA: 50.09000
• Density: 1.12 g/cm³
• LogP: 2.13458
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 279

Purity/Quality:

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

Ethyl(E)-3-(4-Cyanophenyl)prop-2-enoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC=C(C=C1)C#N
• Isomeric SMILES: CCOC(=O)/C=C/C1=CC=C(C=C1)C#N

Technology Process of Ethyl 4-Cyanocinnamate

There total 29 articles about Ethyl 4-Cyanocinnamate 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: 99.5%

4-bromobenzenecarbonitrile (623-00-7) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (E)-4-cyanocinnamate (20655-58-7,92636-30-1,62174-99-6)

Guidance literature:

With [PdCl{[(η⁵-C5H5)]Fe[(η⁵-C5H3)CH=NCy]}(PCy3)]; triethylamine; In N,N-dimethyl-formamide; at 140 ℃; for 24h;

DOI:10.1039/b608825b

Reference yield: 99.0%

diazoacetic acid ethyl ester (623-73-4) + 4-cyanobenzaldehyde (105-07-7) → ethyl (E)-4-cyanocinnamate (20655-58-7,92636-30-1,62174-99-6)

Guidance literature:

With Fe(TCP)Cl; polyethylene supported arsine; polymethylhydrosiloxane; In toluene; at 110 ℃; for 12h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c1cc16747b

Reference yield: 97.0%

ethyl acrylate (140-88-5,9003-32-1) + 4-cyanobenzenediazonium benzo[d][1,3,2]dithiazol-2-ide 1,1,3,3-tetraoxide → ethyl (E)-4-cyanocinnamate (20655-58-7,92636-30-1,62174-99-6)

Guidance literature:

palladium diacetate; In ethanol; at 20 - 25 ℃; for 17h;

DOI:10.1016/j.tet.2006.01.027

upstream raw materials:

4-cyanobenzaldehyde

ethyl (triphenylphosphoranylidene)acetate

4-Cyanochlorobenzene

ethyl acrylate

Downstream raw materials:

3-(4-cyano-phenyl)-propionic acid ethyl ester

benzylamine

(2S,3R)-ethyl 3-(4-cyanophenyl)-2,3-dihydroxypropanoate

p-cyanocinnamaldehyde

Refernces

• 1、 Ramavath, Vijayalakshmi,Rupanawar, Bapurao D.,More, Satish G.,Bansode, Ajay H.,Suryavanshi, Gurunath. "Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents". . p. 8806 - 8813. Retrieved 2021/05/26.
• 2、 Buonomo, Joseph A.,Cole, Malcolm S.,Eiden, Carter G.,Aldrich, Courtney C.. "1,3-Diphenyldisiloxane Enables Additive-Free Redox Recycling Reactions and Catalysis with Triphenylphosphine". . p. 3583 - 3594. Retrieved 2020/09/15.