Methyl 4-Aminocinnamate

Base Information

• Chemical Name: Methyl 4-Aminocinnamate
• CAS No.: 66417-26-3
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Mol file: 66417-26-3.mol

Synonyms:2-Propenoic acid, 3-(4-aminophenyl)-, methyl ester, (2E)-;

Chemical Property of Methyl 4-Aminocinnamate

Chemical Property:

• Melting Point: 127-129℃
• Boiling Point: 335.3 °C at 760 mmHg
• PKA: 2.89±0.10(Predicted)
• Flash Point: 183.7 °C
• PSA: 52.32000
• Density: 1.16 g/cm³
• LogP: 2.03620
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 4-Aminocinnamate

There total 9 articles about Methyl 4-Aminocinnamate 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%

p-nitrocinnamic acid methyl ester (637-57-0) → methyl (2E)-3-(4-aminophenyl)acrylate (66417-26-3)

Guidance literature:

With borohydride exchange resin; nickel diacetate; In methanol; at 20 ℃; for 0.5h;

DOI:10.3987/COM-05-10425

Reference yield: 99.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + p-aminoiodobenzene (540-37-4) → methyl (2E)-3-(4-aminophenyl)acrylate (66417-26-3)

Guidance literature:

With caesium carbonate; In water; at 100 ℃; for 2h; Catalytic behavior; Green chemistry;

DOI:10.1002/aoc.5158

Reference yield: 85.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + 4-bromo-aniline (106-40-1) → methyl (2E)-3-(4-aminophenyl)acrylate (66417-26-3)

Guidance literature:

With potassium phosphate; tetrabutylammomium bromide; palladium diacetate; 2-benzothiazolecarboxaldehyde N,N-diphenylhydrazone; In N,N-dimethyl acetamide; for 1h; Catalytic behavior; Irradiation;

DOI:10.1002/cjoc.201700390

upstream raw materials:

p-nitrocinnamic acid methyl ester

acrylic acid methyl ester

4-bromo-aniline

methanol

Downstream raw materials:

4-(4-phenyl-benzylidenamino)-trans-cinnamic acid methyl ester

(R,E)-dimethyl 2-(3-(((4-(3-methoxy-3-oxoprop-1-en-1-yl)phenyl)amino)methyl)benzamido)pentanedioate

(R,E)-2-(3-(((4-(2-carboxyvinyl)phenyl)amino)methyl)benzamido)pentanedioic acid

Refernces

• 1、 Bokosi, Fostino R. B.,Beteck, Richard M.,Laming, Dustin,Hoppe, Heinrich C.,Tshiwawa, Tendamudzimu,Khanye, Setshaba D.. "Synthesis of 2-(N-cyclicamino)quinoline combined with methyl (E)-3-(2/3/4-aminophenyl)acrylates as potential antiparasitic agents". . . Retrieved 2021/03/16.
• 2、 Lei, Lei. "Pd–Schiff base complex supported on Fe3O4 magnetic nanoparticles: A new and highly efficient reusable catalyst for C–C bond formation in water". . . Retrieved 2019/09/06.