Methyl 4-methoxycinnamate

Base Information

• Chemical Name: Methyl 4-methoxycinnamate
• CAS No.: 3901-07-3
• Molecular Formula: C11H12 O3
• Molecular Weight: 192.214
• Hs Code.: 2918990090
• European Community (EC) Number: 223-455-9
• NSC Number: 26461
• UNII: 1F58T0S3Q7
• Nikkaji Number: J217.745E,J109.142E
• Wikidata: Q27159285
• Metabolomics Workbench ID: 44539
• Mol file: 3901-07-3.mol

Synonyms:4-methoxycinnamate methyl ester;4-methoxycinnamate methyl ester, (E)-isomer;4-methoxycinnamate methyl ester, (Z)-isomer;4-methoxymethyl cinnamate

Chemical Property of Methyl 4-methoxycinnamate

Chemical Property:

• Vapor Pressure: 0.000594mmHg at 25°C
• Melting Point: 88-89℃
• Boiling Point: 310.6°Cat760mmHg
• Flash Point: 126.9°C
• PSA: 35.53000
• Density: 1.102g/cm³
• LogP: 1.88140
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-(4-methoxyphenyl)acrylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=CC(=O)OC
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/C(=O)OC

Technology Process of Methyl 4-methoxycinnamate

There total 184 articles about Methyl 4-methoxycinnamate 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: 98.0%

methanol (67-56-1) + (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) → 3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3)

Guidance literature:

With thionyl chloride; at 0 ℃; for 6h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201410039

Reference yield: 98.0%

methanol (67-56-1) + 3-(4'-methoxyphenyl)propenoic acid (830-09-1) → 3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3)

Guidance literature:

With sulfuric acid; Inert atmosphere; Reflux;

DOI:10.1021/ol402780k

Reference yield: 96.0%

4-methoxybenzenediazonium 4-methylbenzenesulfonate (123155-78-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3)

Guidance literature:

With palladium diacetate; In water; at 75 ℃; for 0.0333333h; Microwave irradiation; Green chemistry;

DOI:10.3762/bjoc.11.41

upstream raw materials:

methanol

p-methoxycinnamoyl chloride

p-Coumaric Acid

methyl iodide

Downstream raw materials:

2,3-dibromo-3-(4-methoxyphenyl)propionic acid methyl ester

3-amino-3-(4-methoxyphenyl)propionic acid

methyl trans-2-(p-methoxyphenyl)cyclopropanecarboxylate

(R,R)-methyl 2-bromo-3-methoxy-3-(p-methoxyphenyl)propanoate

Refernces

• 1、 Sobolev, Victor S.,Horn, Bruce W.,Potter, Thomas L.,Deyrup, Stephen T.,Gloer, James B.. "Production of stilbenoids and phenolic acids by the peanut plant at early stages of growth". . p. 3505 - 3511. Retrieved 2006.
• 2、 Handy, Scott T.. "One-pot halogenation-Heck coupling reactions in ionic liquids". . p. 3176 - 3178. Retrieved 2006.
• 3、 Moineau, Johanne,Pozzi, Gianluca,Quici, Silvio,Sinou, Denis. "Palladium-catalyzed Heck reaction in perfluorinated solvents". . p. 7683 - 7686. Retrieved 1999.
• 4、 Roesecke, Joachim,Koenig, Wilfried A. "Constituents of the fungi Daedalea quercina and Daedaleopsis confragosa var. tricolor". . p. 757 - 762. Retrieved 2000.
• 5、 Cao, Jiafu,Li, Qiji,Liao, Xiu,Wang, Enhua,Wang, Li,Yang, Juan,Yang, Lishou,Yang, Qian,Yang, Xiaosheng,Yang, Yan. "Synthesis of novel 1-phenyl-benzopyrrolizidin-3-one derivatives and evaluation of their cytoneuroprotective effects against NMDA-induced injury in PC12 cells". supporting information. . Retrieved 2022/02/23.
• 6、 Hawkins, Paige M. E.,Liu, Dennis Y.,Linington, Roger G.,Payne, Richard J.. "Solid-phase synthesis of coralmycin A/epi-coralmycin A and desmethoxycoralmycin A". supporting information. p. 6291 - 6300. Retrieved 2021/07/28.