Methyl 3-(2-cyanophenyl)propanoate

Base Information

• Chemical Name: Methyl 3-(2-cyanophenyl)propanoate
• CAS No.: 39220-74-1
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.214
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID10549177
• Wikidata: Q82428130
• Mol file: 39220-74-1.mol

Synonyms:39220-74-1;METHYL 3-(2-CYANOPHENYL)PROPANOATE;SCHEMBL12255638;DTXSID10549177

Chemical Property of Methyl 3-(2-cyanophenyl)propanoate

Chemical Property:

• PSA: 50.09000
• 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=C1C#N

Technology Process of Methyl 3-(2-cyanophenyl)propanoate

There total 5 articles about Methyl 3-(2-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: 12.0%

methyl 3-(2-bromophenyl)-2-cyanopropanoate → 3-(2-cyano-phenyl)-propionic acid methyl ester (39220-74-1) + methyl 2-cyano-4-phenylpropanoate (57519-78-5)

Guidance literature:

With tri-n-butyl-tin hydride; In benzene; for 3h; Heating;

DOI:10.1039/c39870000666

Reference yield:

3-phenylpropanoic acid methyl ester (103-25-3) + copper(l) cyanide → 3-(2-cyano-phenyl)-propionic acid methyl ester (39220-74-1) + 3-(p-Cyanophenyl)-propansaeuremethylester (75567-85-0) + 3-(3-cyano-phenyl)-propionic acid methyl ester (193151-11-0)

Guidance literature:

With 3-(trifluoromethyl)quinoline; palladium diacetate; silver fluoride; N-acetylglycine; at 90 ℃; for 18h; Overall yield = 31 %Chromat.;

DOI:10.1021/acscatal.8b04639

Reference yield:

zinc(II) cyanide (557-21-1) + 3-phenylpropanoic acid methyl ester (103-25-3) → 3-(2-cyano-phenyl)-propionic acid methyl ester (39220-74-1) + 3-(p-Cyanophenyl)-propansaeuremethylester (75567-85-0) + 3-(3-cyano-phenyl)-propionic acid methyl ester (193151-11-0)

Guidance literature:

With 3-(trifluoromethyl)quinoline; palladium diacetate; silver fluoride; N-acetylglycine; at 80 ℃; for 18h; Overall yield = 71 %;

DOI:10.1021/acscatal.8b04639

upstream raw materials:

diazomethane

3-(2-cyanophenyl)propionic acid

trans-3-(2-cyanophenyl)propenoic acid

3-phenylpropanoic acid methyl ester

Refernces

• 1、 Beckwith, Athelstan L. J.,O'Shea, Dennis M.,Gerba, Sendaba,Westwood, Steven W.. "Cyano or Acyl Group Migration by Consecutive Homolytic Addition and β-Fission". . p. 666 - 667. Retrieved 2007/10/02.