Methyl 3-(3-cyanophenyl)propanoate

Base Information

• Chemical Name: Methyl 3-(3-cyanophenyl)propanoate
• CAS No.: 193151-11-0
• Molecular Formula: C11H11 N O2
• Molecular Weight: 189.214
• DSSTox Substance ID: DTXSID50604214
• Wikidata: Q72457893
• Mol file: 193151-11-0.mol

Synonyms:METHYL 3-(3-CYANOPHENYL)PROPANOATE;193151-11-0;3-Cyanobenzenepropanoic acid methyl ester;SCHEMBL3926844;DTXSID50604214;YPAZQTSKIDBDAQ-UHFFFAOYSA-N;3-(3-Cyano-phenyl)-propionic acid methyl ester

Chemical Property of Methyl 3-(3-cyanophenyl)propanoate

Chemical Property:

• Boiling Point: 298℃
• Flash Point: 137℃
• PSA: 50.09000
• Density: 1.11
• LogP: 1.66388
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 241

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC1=CC(=CC=C1)C#N

Technology Process of Methyl 3-(3-cyanophenyl)propanoate

There total 12 articles about Methyl 3-(3-cyanophenyl)propanoate 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%

bis(pinacol)diborane (73183-34-3) + 3-(3-cyano-phenyl)-acrylic acid methyl ester (193151-10-9) → 3-(3-cyano-phenyl)-propionic acid methyl ester (193151-11-0)

Guidance literature:

With methanol; copper(l) iodide; caesium carbonate; In tetrahydrofuran; at 20 ℃; for 30h; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.04.094

Reference yield: 96.0%

methanol (67-56-1) + 3-(3-cyanophenyl)propanoic acid (42287-97-8) → 3-(3-cyano-phenyl)-propionic acid methyl ester (193151-11-0)

Guidance literature:

for 18h; Heating / reflux;

Reference yield: 75.0%

methyl 3-(3-cyanophenyl) acrylate (52116-81-1) → 3-(3-cyano-phenyl)-propionic acid methyl ester (193151-11-0)

Guidance literature:

With 2-(Aminomethyl)pyridine; bromopentacarbonylmanganese(I); potassium tert-butylate; hydrogen; In 1,4-dioxane; at 120 ℃; for 24h; under 37503.8 Torr; chemoselective reaction; Autoclave;

DOI:10.1016/j.apcata.2021.118280

upstream raw materials:

methyl 3-(3-cyanophenyl) acrylate

3-(3-cyanophenyl)propanoic acid

diazomethyl-trimethyl-silane

dicyanozinc

Downstream raw materials:

3-(3-{[(1-Methyl-1 H-imidazole-4-sulfonyl)-(4-pyrazin-2-yl-benzyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

3-(3-cyano-phenyl)-2-methyl-propionic acid methyl ester

2-Methyl-3-{3-[(4-pyrazol-1-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

3-(3-{[benzenesulfonyl-(4-pyrazol-1-yl-benzyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid methyl ester

Refernces

• 1、 Chen, Hao,Mondal, Arup,Wedi, Philipp,Van Gemmeren, Manuel. "Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes". . p. 1979 - 1984. Retrieved 2019/02/19.
• 2、 -. "Novel Compounds". Page/Page column 68. . Retrieved 2008/06/13.