(Z)-Methyl cinnamate

Base Information

• Chemical Name: (Z)-Methyl cinnamate
• CAS No.: 19713-73-6
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• UNII: C8O8SZU001
• DSSTox Substance ID: DTXSID401031262
• Nikkaji Number: J192.733G
• Wikidata: Q27275326
• Mol file: 19713-73-6.mol

Synonyms:(Z)-Methyl cinnamate;Methyl cis-cinnamate;Methyl cis-3-phenylacrylate;cis-Methyl 3-phenyl-2-propenoate;Methyl (Z)-cinnamate;Methyl cinnamate, (Z)-;19713-73-6;UNII-C8O8SZU001;(Z)-Methyl 3-phenylacrylate;C8O8SZU001;2-Propenoic acid, 3-phenyl-, methyl ester, (2Z)-;(Z)-3-phenyl-2-propenoic acid methyl ester;cis-methyl cinnamate;Methyl cinnamate, (E);Methyl (2E)-3-phenyl-2-propenoate;Methyl cinnamate, (Z);methyl (Z)-3-phenylacrylate;cis-cinnamic acid methyl ester;Methyl ester(e)-Cinnamic acid;(z)-cinnamic acid methyl ester;SCHEMBL2425288;FEMA 2698;CHEBI:194139;DTXSID401031262;Cinnamic acid, methyl ester, (Z);Cinnamic acid, methyl ester, cis-;(Z)-3-phenyl-acrylic acid methyl ester;(z)-3-phenylpropenoic acid, methyl ester;CINNAMIC ACID,METHYL ESTER (TRANS);3-Phenyl-methyl ester(E)-2-Propenoic acid;METHYL (2Z)-3-PHENYLPROP-2-ENOATE;3-Phenyl-methyl ester(2E)-2-propenoic acid;cis-3-phenyl-prop-2-enoic acid methyl ester;A800700;methyl (Z)-3-phenylprop-2-enoate;Methyl cinnamate;Q27275326

Chemical Property of (Z)-Methyl cinnamate

Chemical Property:

• PSA: 26.30000
• LogP: 1.87280
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

(Z)-3-PHENYL-2-PROPENOIC 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)C=CC1=CC=CC=C1
• Isomeric SMILES: COC(=O)/C=C\C1=CC=CC=C1

Technology Process of (Z)-Methyl cinnamate

There total 128 articles about (Z)-Methyl 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: 99.0%

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) + benzyl alcohol (100-51-6,185532-71-2) → methyl (2Z)-3-phenylprop-2-enoate (19713-73-6,1754-62-7) + Methyl cinnamate (103-26-4,1754-62-7)

Guidance literature:

benzyl alcohol; With Celite; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 3h;

methyl (triphenylphosphoranylidene)acetate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1055/s-2004-817762

Reference yield: 92.0%

benzaldehyde (100-52-7) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl (2Z)-3-phenylprop-2-enoate (19713-73-6,1754-62-7) + Methyl cinnamate (103-26-4,1754-62-7)

Guidance literature:

for 3h; Heating;

DOI:10.1055/s-2004-817762

Reference yield: 71.0%

phenylpropynoic acid methyl ester (4891-38-7) → methyl (2Z)-3-phenylprop-2-enoate (19713-73-6,1754-62-7) + Methyl cinnamate (103-26-4,1754-62-7)

Guidance literature:

With formic acid; dihydridotetrakis(triphenylphosphine)ruthenium; In N,N-dimethyl-formamide; at 20 ℃; for 48h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.201001143

upstream raw materials:

methanol

cis-cinnamic acid

methyl iodide

diazomethane

Downstream raw materials:

3-phenylpropanoic acid methyl ester

(Z)-cinnamyl acetate

Refernces

• 1、 Valiente, Alejandro,Martínez-Pardo, Pablo,Kaur, Gurpreet,Johansson, Magnus J.,Martín-Matute, Belén. "Electrochemical Proton Reduction over Nickel Foam for Z-Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes". . . Retrieved 2021/12/22.
• 2、 Makhubela, Banothile C. E.,Matsheku, Asanda C.,Maumela, Munaka C.. "Synthesis of new adamantyl-imine palladium(II) complexes and their application in Mizoroki-Heck and Suzuki-Miyaura C[sbnd]C cross-coupling reactions". . . Retrieved 2021/06/18.