(E)-methyl 3-(phenylamino)acrylate

Base Information

• Chemical Name: (E)-methyl 3-(phenylamino)acrylate
• CAS No.: 4916-28-3
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• NSC Number: 174208
• DSSTox Substance ID: DTXSID30420691
• Nikkaji Number: J2.731.856H
• Wikidata: Q82231997
• Mol file: 4916-28-3.mol

Synonyms:(E)-methyl 3-(phenylamino)acrylate;4916-28-3;methyl (E)-3-anilinoprop-2-enoate;NSC174208;SCHEMBL10565187;DTXSID30420691;(E)-methyl3-(phenylamino)acrylate;AKOS004906507;NSC-174208;3-(Phenylamino)propenoic acid methyl ester

Chemical Property of (E)-methyl 3-(phenylamino)acrylate

Chemical Property:

• Vapor Pressure: 0.00453mmHg at 25°C
• Boiling Point: 277.4°Cat760mmHg
• Flash Point: 121.6°C
• PSA: 38.33000
• Density: 1.139g/cm³
• LogP: 1.85820
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 183

Purity/Quality:

99% ^*data from raw suppliers

(E)-Methyl 3-(phenylamino)acrylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CNC1=CC=CC=C1
• Isomeric SMILES: COC(=O)/C=C/NC1=CC=CC=C1

Technology Process of (E)-methyl 3-(phenylamino)acrylate

There total 5 articles about (E)-methyl 3-(phenylamino)acrylate 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%

propynoic acid methyl ester (922-67-8) + aniline (62-53-3) → methyl (2Z)-3-(phenylamino)prop-2-enoate (4916-28-3)

Guidance literature:

In water; at 20 ℃; for 0.25h;

DOI:10.1080/00397911.2020.1757717

Reference yield: 91.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + aniline (62-53-3) → methyl (2Z)-3-(phenylamino)prop-2-enoate (4916-28-3)

Guidance literature:

With oxygen; palladium diacetate; lithium bromide; In tetrahydrofuran; at 50 ℃; for 8h; Reagent/catalyst; Solvent; stereoselective reaction; Schlenk technique;

DOI:10.1021/jo402117r

Reference yield: 87.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + aniline (62-53-3) → methyl (2Z)-3-(phenylamino)prop-2-enoate (4916-28-3) + (E)-methyl 3-(phenylamino)acrylate (7542-84-9)

Guidance literature:

With tetrabutylammomium bromide; oxygen; palladium dichloride; In acetonitrile; at 75 ℃; for 12h; under 750.075 Torr; optical yield given as %de;

DOI:10.1039/c1ob05440f

upstream raw materials:

propynoic acid methyl ester

aniline

acrylic acid methyl ester

Downstream raw materials:

methyl 1,4-diphenyl-1,4-dihydropyridine-3-carboxylate

dimethyl 2-phenylaminoethylene-1,1-dicarboxylate

(Z)-methyl 3-[(4-bromophenyl)amino]acrylate

(Z)-methyl 2-bromo-3-(phenylamino)acrylate

Refernces

• 1、 Le, Truong-Giang,Pham, Hoai-Thu,Martin, James P.,Chataigner, Isabelle,Renaud, Jean-Luc. "Organocatalyzed regioselective and enantioselective synthesis of 1,4- and 1,2-dihydropyridines". supporting information. p. 2673 - 2684. Retrieved 2020/08/07.
• 2、 Jiang, Huanfeng,Huang, Wei,Yu, Yue,Yi, Songjian,Li, Jiawei,Wu, Wanqing. "Transition-metal-free synthesis of β-trifluoromethylated enamines with trifluoromethanesulfinate". supporting information. p. 7473 - 7476. Retrieved 2017/07/12.