2-Phenyl-nicotinic acid ethyl ester

Base Information

• Chemical Name: 2-Phenyl-nicotinic acid ethyl ester
• CAS No.: 144501-28-0
• Molecular Formula: C14H13NO2
• Molecular Weight: 227.263
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID20445752
• Nikkaji Number: J553.554I
• Wikidata: Q72497971
• Mol file: 144501-28-0.mol

Synonyms:144501-28-0;Ethyl 2-phenylnicotinate;2-Phenyl-nicotinic acid ethyl ester;Ethyl 2-phenylpyridine-3-carboxylate;MFCD12828078;2-Phenylnicotinic acid ethyl ester;SCHEMBL2564440;DTXSID20445752;RQHOSUIKZMCYGD-UHFFFAOYSA-N;Ethyl2-phenylpyridine-3-carboxylate;AKOS015891519;CS-W004428;SB55473;AC-29788;DS-11303;SY056853;FT-0645200;2-Phenyl-3-pyridinecarboxylic acid ethyl ester;A26190;O11760;3-Pyridinecarboxylic acid, 2-phenyl-, ethyl ester;Ethyl 2-Phenylpyridine-3-carboxylate

Chemical Property of 2-Phenyl-nicotinic acid ethyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.559
• Boiling Point: 359.54 °C at 760 mmHg
• Flash Point: 171.244 °C
• PSA: 39.19000
• Density: 1.123 g/cm³
• LogP: 2.92530
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 227.094628657
• Heavy Atom Count: 17
• Complexity: 249

Purity/Quality:

99% ^*data from raw suppliers

Ethyl2-Phenylnicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N=CC=C1)C2=CC=CC=C2

Technology Process of 2-Phenyl-nicotinic acid ethyl ester

There total 34 articles about 2-Phenyl-nicotinic acid ethyl ester 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: 95.0%

ethyl 2-chloronicotinate (1452-94-4) + phenylboronic acid (98-80-6) → 2-phenylpyridine-3-carboxylic acid ethyl ester (144501-28-0)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 140 ℃; for 0.25h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/acs.jmedchem.7b01255

Reference yield: 91.0%

iodobenzene (591-50-4) + C8H8ClMgNO2 → 2-phenylpyridine-3-carboxylic acid ethyl ester (144501-28-0)

Guidance literature:

iodobenzene; With TurboGrignard; In tetrahydrofuran; at -40 ℃; for 1h; Inert atmosphere;

With tbepc; In tetrahydrofuran; at -40 - 0 ℃; for 2h; Inert atmosphere;

C₈H₈ClMgNO₂; Further stages;

DOI:10.1039/c4cc08494b

Reference yield: 90.0%

Ethyl 2-phenyl-5-(phenylseleno)-1,4,5,6-tetrahydro-3-pyridinecarboxylate (151476-90-3) → 2-phenylpyridine-3-carboxylic acid ethyl ester (144501-28-0)

Guidance literature:

With dihydrogen peroxide; In methanol; 1.) 0 deg C, 15 min, 2.) 40 deg C, 0.5 h;

DOI:10.1021/jo00074a042

upstream raw materials:

iodobenzene

2-iodonicotinic acid ethyl ester

Ethyl 2-bromo-3-pyridinecarboxylate

Ethyl 2-phenyl-5-(phenylseleno)-1,4,5,6-tetrahydro-3-pyridinecarboxylate

Downstream raw materials:

3-(chloromethyl)-2-phenylpyridine

ethyl 2-phenylpiperidine-3-carboxylate

Refernces

• 1、 Miao, Wenjun,Ni, Chuanfa,Xiao, Pan,Jia, Rulong,Zhang, Wei,Hu, Jinbo. "Nickel-Catalyzed Reductive 2-Pyridination of Aryl Iodides with Difluoromethyl 2-Pyridyl Sulfone". supporting information. p. 711 - 715. Retrieved 2021/01/26.
• 2、 Gao, Peng,Chen, Huai-Juan,Bai, Zi-Jing,Zhao, Mi-Na,Yang, Desuo,Wang, Juan,Wang, Ning,Du, Lele,Guan, Zheng-Hui. "IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines". . p. 7939 - 7951. Retrieved 2020/07/16.