Ethyl alpha-cyano-beta-phenylcinnamate

Base Information

• Chemical Name: Ethyl alpha-cyano-beta-phenylcinnamate
• CAS No.: 2025-40-3
• Molecular Formula: C12H11 N O2
• Molecular Weight: 201.225
• Hs Code.: 2926909090
• European Community (EC) Number: 217-972-9
• NSC Number: 8904
• DSSTox Substance ID: DTXSID701275289
• Nikkaji Number: J1.245.708A
• Mol file: 2025-40-3.mol

Synonyms:14533-87-0;2-Propenoic acid, 2-cyano-3-phenyl-, ethyl ester, (2Z)-;Ethyl 2-cyanocinnamate;ethyl z-cyano-cinnamate;Ethyl2-cyano-3-phenylacrylate;SCHEMBL988236;NSC8904;DTXSID701275289;(z)-ethyl2-cyano-3-phenylacrylate;NSC-8904;(z)-ethyl 2-cyano-3-phenylacrylate;CAK122472;MFCD00550088;AKOS000499611;alpha-Cyanoallocinnamic acid ethyl ester;2-Cyano-3-phenyl-acrylic acid ethyl ester;ethyl (2Z)-2-cyano-3-phenylprop-2-enoate;ethyl (Z)-2-cyano-3-phenyl-prop-2-enoate;Ethyl .alpha.-cyano-.beta.-phenylcinnamate;Ethyl (2Z)-2-cyano-3-phenyl-2-propenoate;A814361

Chemical Property of Ethyl alpha-cyano-beta-phenylcinnamate

Chemical Property:

• Vapor Pressure: 0.000251mmHg at 25°C
• Melting Point: 51-53 °C(lit.)
• Refractive Index: 1.5033 (estimate)
• Boiling Point: 188 °C15 mm Hg(lit.)
• Flash Point: 156.4°C
• PSA: 50.09000
• Density: 1.139g/cm³
• LogP: 2.15668
• Solubility.: soluble in Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 292

Purity/Quality:

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

(E)-2-Cyano-3-phenyl-acrylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl alpha-cyano-beta-phenylcinnamate

There total 39 articles about Ethyl alpha-cyano-beta-phenylcinnamate 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%

benzaldehyde dimethyl acetal (1125-88-8) + ethyl 2-cyanoacetate (105-56-6) → ethyl benzylidenecyanoacetate (2025-40-3)

Guidance literature:

With DMAN-SO₃H-SiO₂-5-5; In water; for 10h; Reagent/catalyst; Catalytic behavior;

DOI:10.1039/c3cy00269a

Reference yield: 99.0%

ethyl 2-cyanoacetate (105-56-6) + benzyl alcohol (100-51-6,185532-71-2) → ethyl benzylidenecyanoacetate (2025-40-3)

Guidance literature:

With dihydrogen peroxide; In water; acetonitrile; at 80 ℃; for 6h; Reagent/catalyst; Solvent; Catalytic behavior; Kinetics;

DOI:10.1002/cctc.201501365

Reference yield: 98.0%

dimethyl 2-benzylidenepropanedioate (6626-84-2) + ethyl 2-cyanoacetate (105-56-6) → ethyl benzylidenecyanoacetate (2025-40-3)

Guidance literature:

With recovered palladium catalyst; In ethanol; at 20 ℃; for 18h; Green chemistry;

DOI:10.1039/c3gc40991k

upstream raw materials:

acetic anhydride

benzylidene phenylamine

ethyl 2-cyanoacetate

ethanol

Downstream raw materials:

ethyl 2-amino-4-phenyl-4H-pyrano<3,2-h>quinoline-3-carboxylate

7-Amino-4-oxo-5-phenyl-2-thioxo-3,4,4a,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

7-Amino-4-oxo-5-phenyl-2-thioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

3-Amino-6-oxo-1,4-diphenyl-1,4,5,6-tetrahydro-pyrano[2,3-c]pyrazole-5-carbonitrile

Refernces

• 1、 Sun, Zunming,Yang, Xinyue,Huang, Xianpei,Zhang, Mengmeng,Bian, Guomin,Qi, Yonglin,Yang, Xinlin,Zhang, Wangqing. "Mesoporous polymeric catalysts with both sulfonic acid and basic amine groups for the one-pot deacetalization-Knoevenagel reaction". . p. 16676 - 16684. Retrieved 2019.
• 2、 Fujita, Shin-Ichiro,Katagiri, Ayaka,Watanabe, Hiroyuki,Asano, Sayaka,Yoshida, Hiroshi,Arai, Masahiko. "Preparation of Nitrogen-Doped Carbon from Polyacrylonitrile and its Application as a Solid-Base Catalyst". . p. 2965 - 2970. Retrieved 2015.
• 3、 Saito,Goto,Honda,Fujii. "Acid-base catalysts derived from weakly acidic ion exchange resin: Efficiency in the Knoevenagel condensation". . p. 7535 - 7538. Retrieved 1992.
• 4、 Prieto-Ramírez, Mary Cruz,Fernández, Israel,da Silva, Ivan,González-Platas, Javier,de Armas, Pedro,García-Tellado, Fernando. "Stereodiversified Modular Synthesis of Non-planar Five-Membered Cyclic N-Hydroxylamidines: Reactivity Study and Application to the Synthesis of Cyclic Amidines". . p. 4362 - 4371. Retrieved 2018.
• 5、 Schneider, Elia M.,Raso, Renzo A.,Hofer, Corinne J.,Zeltner, Martin,Stettler, Robert D.,Hess, Samuel C.,Grass, Robert N.,Stark, Wendelin J.. "Magnetic superbasic proton sponges are readily removed and permit direct product isolation". . p. 10908 - 10915. Retrieved 2014.
• 6、 Huang, Hui-Lin,Huang, Wen-Yen,Wang, Sue-Lein. "From Bola-Surfactant Templated Bimetal Phosphites to the Design of Crystalline Inorganic Mesoporous Frameworks". . p. 4962 - 4966. Retrieved 2017.
• 7、 Zhang, Ying-Ying,Liu, Qing,Zhang, Lin-Yan,Bao, Yu-Mei,Tan, Jing-Yi,Zhang, Na,Zhang, Jian-Yong,Liu, Zhen-Jiang. "MOFs assembled from C 3symmetric ligands: Structure, iodine capture and role as bifunctional catalysts towards the oxidation-Knoevenagel cascade reaction". . p. 647 - 659. Retrieved 2021/01/28.
• 8、 Bazi, Fathallaah,Elkouali, M. Hammed,Ennesyry, Elmustapha,Hamza, Mohammed,Hannache, Hassan,Mounir, Bahija,Talbi, Mohammed. "Knoevenagel Condensations Catalyzed by New Oil Shale Recyclable Catalyst at Room Temperature and Assisted by Ultrasounds Irradiations". . p. 1295 - 1301. Retrieved 2022/01/24.