Methyl 4-pyridin-3-ylbenzoate

Base Information

• Chemical Name: Methyl 4-pyridin-3-ylbenzoate
• CAS No.: 90395-47-4
• Molecular Formula: C13H11 N O2
• Molecular Weight: 213.236
• DSSTox Substance ID: DTXSID60399705
• Nikkaji Number: J3.147.312H
• Mol file: 90395-47-4.mol

Synonyms:90395-47-4;Methyl 4-pyridin-3-ylbenzoate;methyl 4-(3-pyridinyl)benzoate;METHYL 4-(PYRIDIN-3-YL)BENZOATE;Methyl 4-(3-pyridyl)benzoate;Benzoic acid, 4-(3-pyridinyl)-, methyl ester;SCHEMBL2345607;DTXSID60399705;SMXKPSLCRALELV-UHFFFAOYSA-N;Methyl 4-[Pyridin-3-yl]-Benzoate;4-pyridin-3-yl-benzoic methyl ester;AKOS004114006;N,N'-DI(1-NAPHTHYL)BENZIDINE;4-(3-Pyridyl)benzoic acid methyl ester;METHYL4-(PYRIDIN-3-YL)BENZOATE;4-Pyridin-3-yl-benzoic acid methyl ester;BB 0222736;FT-0744558

Chemical Property of Methyl 4-pyridin-3-ylbenzoate

Chemical Property:

• PSA: 39.19000
• LogP: 2.53520
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 213.078978594
• Heavy Atom Count: 16
• Complexity: 234

Purity/Quality:

97% ^*data from raw suppliers

Methyl4-(pyridin-3-yl)benzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)C2=CN=CC=C2

Technology Process of Methyl 4-pyridin-3-ylbenzoate

There total 26 articles about Methyl 4-pyridin-3-ylbenzoate 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: 92.0%

3-Chloropyridine (626-60-8) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → methyl 4-(3-pyridinyl)benzoate (90395-47-4)

Guidance literature:

3-Chloropyridine; 4-methoxycarbonylphenylboronic acid; With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl; In dodecane; butan-1-ol; at 25 ℃; for 0.0833333h; Inert atmosphere; Glovebox;

With cesiumhydroxide monohydrate; In dodecane; water; butan-1-ol; at 80 ℃; for 4h; Glovebox; Inert atmosphere;

DOI:10.1002/ejoc.201200918

Reference yield: 90.0%

methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate (905966-40-7) + pyridin-3-yl methanesulfonate (52843-75-1) → methyl 4-(3-pyridinyl)benzoate (90395-47-4)

Guidance literature:

With potassium phosphate; trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine; In tetrahydrofuran; at 25 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo3001194

Reference yield: 90.0%

4-methoxycarbonylphenyl bromide (619-42-1) + sodium pyridine-3-sulfinate → methyl 4-(3-pyridinyl)benzoate (90395-47-4)

Guidance literature:

With palladium diacetate; potassium carbonate; tricyclohexylphosphine; In 1,4-dioxane; at 150 ℃;

DOI:10.1039/c7sc00675f

upstream raw materials:

3-iodopyridine

benzoic acid methyl ester

4-methoxycarbonylphenyl bromide

3-Diethylboranylpyridine

Downstream raw materials:

4-(pyridine-3-yl)benzoic acid

methyl 4-[pyridine-N-oxide-3-yl]-benzoate

(4-pyridin-3-yl-phenyl)-methanol

methyl 4-[1-(1-methylpiperidin-4-yl)-2-oxo-1,2-dihydropyridin-3-yl]benzoate

Refernces

• 1、 -. "PYRROLIDINE GLYCOSIDASE INHIBITORS". Page/Page column 144. . Retrieved 2020/03/15.
• 2、 Markovic, Tim,Rocke, Benjamin N.,Blakemore, David C.,Mascitti, Vincent,Willis, Michael C.. "Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides". . p. 4437 - 4442. Retrieved 2017/07/11.