Methyl 2-(4-cyanophenyl)propanoate

Base Information

• Chemical Name: Methyl 2-(4-cyanophenyl)propanoate
• CAS No.: 125670-62-4
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.214
• DSSTox Substance ID: DTXSID301288282
• Nikkaji Number: J2.415.996E
• Mol file: 125670-62-4.mol

Synonyms:methyl 2-(4-cyanophenyl)propanoate;125670-62-4;SCHEMBL8224397;methyl2-(4-cyanophenyl)propanoate;DTXSID301288282;2-(4-cyano-phenyl)-propionic acid methyl ester

Chemical Property of Methyl 2-(4-cyanophenyl)propanoate

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 245

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Methyl 2-(4-cyanophenyl)propanoate

There total 11 articles about Methyl 2-(4-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: 80.0%

propanoic acid methyl ester (554-12-1) + 4-bromobenzenecarbonitrile (623-00-7) → α-methyl-4-cyanobenzeneacetic acid methyl ester (125670-62-4)

Guidance literature:

propanoic acid methyl ester; With sodium hexamethyldisilazane; In toluene; at -60 ℃; for 1.5h; Inert atmosphere; Sealed tube;

With zinc(II) chloride; In tetrahydrofuran; toluene; at -35 ℃; for 1h; Inert atmosphere; Sealed tube;

4-bromobenzenecarbonitrile; With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; toluene; at -15 - 20 ℃; for 4h; Inert atmosphere; Sealed tube;

DOI:10.1021/jo401476f

Reference yield: 75.0%

2-chloro-propionic acid methyl ester (17639-93-9) + 4-bromobenzenecarbonitrile (623-00-7) → α-methyl-4-cyanobenzeneacetic acid methyl ester (125670-62-4)

Guidance literature:

With manganese; (2,2'-bipyridine)nickel(II) dibromide; trifluoroacetic acid; In N,N-dimethyl-formamide; at 50 ℃; for 1h;

DOI:10.1016/j.tet.2006.11.055

Reference yield: 68.0%

methanol (67-56-1) + 4-ethenylbenzonitrile (3435-51-6) + carbon monoxide (201230-82-2) → α-methyl-4-cyanobenzeneacetic acid methyl ester (125670-62-4)

Guidance literature:

4-ethenylbenzonitrile; carbon monoxide; With hydrogenchloride; In water; for 20h; under 30003 Torr; Schlenk technique; Inert atmosphere;

methanol; With diazomethyl-trimethyl-silane; In water; for 2h; Schlenk technique; Inert atmosphere; Reflux;

DOI:10.3390/molecules25153421

upstream raw materials:

2-chloro-propionic acid methyl ester

4-bromobenzenecarbonitrile

methyl 2-(p-chlorophenyl)propionate

dicyanozinc

Downstream raw materials:

2-(4-cyano-phenyl)-propionic acid

Refernces

• 1、 Guan, Zheng-Hui,Ren, Zhi-Hui,Wang, Yuan,Yang, Hui-Yi,Yao, Ya-Hong,Zou, Xian-Jin. "Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids". supporting information. p. 23117 - 23122. Retrieved 2021/09/18.
• 2、 Gao, Mengyu,Sun, Deli,Gong, Hegui. "Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides". supporting information. p. 1645 - 1648. Retrieved 2019/03/11.