Propanoic acid, 3-(4-pyridinylthio)-, methyl ester (9CI)

Base Information

• Chemical Name: Propanoic acid, 3-(4-pyridinylthio)-, methyl ester (9CI)
• CAS No.: 78526-49-5
• Molecular Formula: C9H11 N O2 S
• Molecular Weight: 197.25414
• Mol file: 78526-49-5.mol

Synonyms:Propionicacid, 3-(4-pyridylthio)-, methyl ester (7CI)

Chemical Property of Propanoic acid, 3-(4-pyridinylthio)-, methyl ester (9CI)

Chemical Property:

• PSA: 64.49000
• LogP: 1.73680

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Propanoic acid, 3-(4-pyridinylthio)-, methyl ester (9CI)

There total 5 articles about Propanoic acid, 3-(4-pyridinylthio)-, methyl ester (9CI) 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: 96.0%

3-(2',6'-Dimethyl-4'-oxo-4H,4'H-[1,1']bipyridinyl-4-ylsulfanyl)-propionic acid methyl ester (78526-30-4) → methyl 3-(pyridin-4-ylthio)propanoate (78526-49-5) + 2,6-dimethyl-1H-pyridin-4-one (7516-31-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In tetrachloromethane; dichloromethane; for 13h; Heating;

DOI:10.1039/P19810001585

Reference yield: 25.0%

pyridine-4-thiol (4556-23-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 3-(pyridin-4-ylthio)propanoate (78526-49-5)

Guidance literature:

With triethylamine; In acetonitrile; at 45 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.202109146

Reference yield:

2,6-Dimethyl-4'-p-tolylsulfanyl-4'H-[1,1']bipyridinyl-4-one (78526-32-6) → methyl 3-(pyridin-4-ylthio)propanoate (78526-49-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Ph₃CBF₄ / CH₂Cl₂

2: 87 percent / NaOEt / acetonitrile; ethanol / 0.25 h / 25 °C

3: 96 percent / azoisobutyronitrile / CCl₄; CH₂Cl₂ / 13 h / Heating

With 2,2'-azobis(isobutyronitrile); sodium ethanolate; trityl tetrafluoroborate; In tetrachloromethane; ethanol; dichloromethane; acetonitrile;

DOI:10.1039/P19810001585

upstream raw materials:

3-(2',6'-Dimethyl-4'-oxo-4H,4'H-[1,1']bipyridinyl-4-ylsulfanyl)-propionic acid methyl ester

2,6-Dimethyl-4'-p-tolylsulfanyl-4'H-[1,1']bipyridinyl-4-one

pyridine-4-thiol

acrylic acid methyl ester

Downstream raw materials:

4-(4-methoxylphenyl)pyridine

Refernces

• 1、 Sammes, Michael P.,Leung, Christopher W. F.,Mak, Chi Keung,Katritzky, Alan R.. "Synthetic Applications of N-N Linked Heterocycles. Part 12. The Preparation of 4-Alkylthio- and 4-Arylthio-pyridines by Regiospecific Attack of Thioalkoxide Ions on N-(4-Oxopyridin-1-yl)pyridinium Salts". . p. 1585 - 1590. Retrieved 2007/10/02.