(Z)-Ethyl cinnamate

Base Information

• Chemical Name: (Z)-Ethyl cinnamate
• CAS No.: 4192-77-2
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• Hs Code.: 2916 39 90
• Nikkaji Number: J461.035K
• Wikidata: Q67866089
• Mol file: 4192-77-2.mol

Synonyms:(Z)-Ethyl cinnamate;4610-69-9;CIS-ETHYL CINNAMATE;ethyl (Z)-3-phenylprop-2-enoate;Ethyl cis-cinnamate;(Z)-Ethyl 3-phenylacrylate;(2Z)-3-Phenyl-2-propenoic Acid Ethyl Ester;cis-Ethyl Cinnamate (contains up to 10per cent Ethyl dihydrocinnamate);trans-Ethyl cinnamate;Ethyl cinnamate, trans;Ethyl (Z)-cinnamate;ethyl (2E)-3-phenylacrylate;Ethyl (2E)-3-phenyl-2-propenoate;(Z)-Cinnamic Acid Ethyl Ester;Ethyl allocinnamate;ethyl cinnamate (cis);Ethyl cinnamate, (Z);Ethyl (Z)-cinnamic acid;(2Z)-3-Phenylprop-2-enoic Acid Ethyl Ester;SCHEMBL12001792;FEMA 2430;Ethyl (Z)-3-phenyl-2-propenoate;Cinnamic acid, ethyl ester, (Z)-;cis-Ethyl Cinnamate (contains up to 10% Ethyl dihydrocinnamate);cis-3-phenyl-acrylic acid ethyl ester;3-Phenyl-ethyl ester(E)-2-Propenoic acid;CS-0526896;2-Propenoic acid, 3-phenyl-, ethyl ester, (Z)-;2-Propenoic acid, 3-phenyl-, ethyl ester, (2Z)-;Q67866089

Chemical Property of (Z)-Ethyl cinnamate

Chemical Property:

• Melting Point: 125℃
• Refractive Index: 1.5597 (589.3 nm 20℃)
• Boiling Point: 269.35 °C at 760 mmHg
• Flash Point: 148.572 °C
• PSA: 26.30000
• Density: 1.056 g/cm³
• LogP: 2.26290
• Storage Temp.: Store below +30°C.
• Water Solubility.: Insoluble in water
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 176.083729621
• Heavy Atom Count: 13
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

Ethyl (E)-Cinnamate >99.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (Z)-Ethyl cinnamate

There total 393 articles about (Z)-Ethyl cinnamate 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: 88.0%

benzaldehyde (100-52-7) + ethyl bromoacetate (105-36-2) + triphenylphosphine (603-35-0) → Triphenylphosphine oxide (791-28-6) + ethyl cinnamate (4192-77-2)

Guidance literature:

With Mg/La mixed oxide; In N,N-dimethyl-formamide; at 20 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1016/j.molcata.2010.01.012

Reference yield: 87.0%

ethyl 3-phenylglycidate (121-39-1) → Ethyl 3-hydroxy-3-phenylpropanoate (5764-85-2) + ethyl cinnamate (4192-77-2)

Guidance literature:

With bis(acetylacetonate)nickel(II); diethylzinc; tricyclohexylphosphine; In tetrahydrofuran; hexane; at 50 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.151518

Reference yield: 83.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + benzaldehyde (100-52-7) → benzoic acid (65-85-0,8013-63-6) + ethyl cinnamate (4192-77-2)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; benzaldehyde; With potassium carbonate; for 6h; Neat (no solvent); high-speed ball milling;

With Oxone; for 12h; optical yield given as %de; diastereoselective reaction; Neat (no solvent); high-speed ball milling;

DOI:10.1039/c0gc00671h

upstream raw materials:

cinnamonitrile

ethanol

ethyl 3-phenylglycidate

triphenylphosphine

Downstream raw materials:

ethyl 3-(ethoxycarbonylmethylmercapto)-3-phenylpropanoate

ethyl 3-phenyl-3-piperidinopropanoate

(E)-3-phenyl-1-(piperidin-1-yl)-prop-2-en-1-one

3-morpholin-4-yl-3-phenyl-propionic acid ethyl ester

Refernces

• 1、 Ahuja, Ritu,Samuelson, Ashoka G.. "Catalytic cyclopropanation of olefins using copper(I) diphosphinoamines". . p. 1153 - 1160. Retrieved 2009.
• 2、 Beletskaya, Irina P.,Kashin, Alexander N.,Karlstedt, Natalia B.,Mitin, Anton V.,Cheprakov, Andrei V.,Kazankov, Grigoriy M.. "NC-palladacycles as highly effective cheap precursors for the phosphine-free Heck reactions". . p. 89 - 96. Retrieved 2001.
• 3、 Taskin, Meltem,Cognigni, Alice,Zirbs, Ronald,Reimhult, Erik,Bica, Katharina. "Surface-active ionic liquids for palladium-catalysed cross coupling in water: Effect of ionic liquid concentration on the catalytically active species". . p. 41144 - 41151. Retrieved 2017.
• 4、 Zawisza, Anna Maria,Muzart, Jacques. "Intermolecular phosphine-free Heck reactions: Amino alcohols as effective ligands". . p. 1015 - 1017. Retrieved 2011.
• 5、 Crisostomo, Fernando R. Pinacho,Carrillo, Romen,Martin, Tomas,Garcia-Tellado, Fernando,Martin, Victor S.. "A convenient and chemoselective one-pot oxidation/Wittig reaction for the C2-homologation of carbohydrate-derived glycols". . p. 10099 - 10101. Retrieved 2005.
• 6、 Petrovic, Zorica D.,Markovic, Svetlana,Simijonovic, Dusica,Petrovic, Vladimir. "Mechanistic insight into the preactivation of a modern palladium catalyst precursor in phosphine-free Heck reactions". . p. 371 - 374. Retrieved 2009.
• 7、 Zhang, Xiangyang,Chen, Peter. "[ReO3(bipy)]+[X]--catalyzed aldehyde olefination: Carbene and phosphorane intermediates". . p. 1852 - 1859. Retrieved 2003.
• 8、 Yasui, Eiko,Ishimine, Kanako,Nitanai, Sohta,Hatakeyama, Nanami,Nagumo, Shinji. "Synthesis of α-diazoesters from α-hydrazonoesters: Utilization of α-hydrazonoesters and α-diazoesters for convenient interconversion". . . Retrieved 2022/04/07.
• 9、 Karimi, Sabah,Masteri-Farahani, Majid,Niakan, Mahsa,Shekaari, Hemayat. "Pd supported on clicked cellulose-modified magnetite-graphene oxide nanocomposite for C-C coupling reactions in deep eutectic solvent". . . Retrieved 2020/10/02.