Ethyl 3-(6-chloropyridin-3-yl)-3-oxopropanoate

Base Information

• Chemical Name: Ethyl 3-(6-chloropyridin-3-yl)-3-oxopropanoate
• CAS No.: 216317-64-5
• Molecular Formula: C10H10ClNO3
• Molecular Weight: 227.647
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID60439630
• Wikidata: Q82255633
• Mol file: 216317-64-5.mol

Synonyms:Ethyl 3-(6-chloropyridin-3-yl)-3-oxopropanoate;216317-64-5;Ethyl 3-(6-Chloro-3-pyridyl)-3-oxopropanoate;Ethyl3-(6-chloropyridin-3-yl)-3-oxopropanoate;SCHEMBL3173315;DTXSID60439630;GDJNNARPYCGJSG-UHFFFAOYSA-N;CS-0433514;FT-0727378;ethyl 3-(6-chloro-3-pyridyl)-3-oxopropionate;F79417;A1-04775;3-(6-chloropyridin-3-yl)-3-oxopropionic acid ethyl ester;3-(6-Chloro-pyridin-3-yl)-3-oxo-propionic acid ethyl ester

Chemical Property of Ethyl 3-(6-chloropyridin-3-yl)-3-oxopropanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.525
• Boiling Point: 346.313 °C at 760 mmHg
• PKA: 9.18±0.48(Predicted)
• Flash Point: 163.244 °C
• PSA: 56.26000
• Density: 1.271 g/cm³
• LogP: 1.87090
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 227.0349209
• Heavy Atom Count: 15
• Complexity: 245

Purity/Quality:

99%min ^*data from raw suppliers

Ethyl3-(6-chloropyridin-3-yl)-3-oxopropanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C1=CN=C(C=C1)Cl

Technology Process of Ethyl 3-(6-chloropyridin-3-yl)-3-oxopropanoate

There total 6 articles about Ethyl 3-(6-chloropyridin-3-yl)-3-oxopropanoate 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: 79.0%

6-chloronicotinonitrile (33252-28-7) + ethyl bromoacetate (105-36-2) → ethyl 3-(6-chloropyridin-3-yl)-3-oxopropanoate (216317-64-5)

Guidance literature:

6-chloronicotinonitrile; ethyl bromoacetate; In tetrahydrofuran; at 60 - 120 ℃; for 0.166667h; Flow reactor; Green chemistry;

With hydrogenchloride; In tetrahydrofuran; for 1h; Green chemistry;

DOI:10.1039/c6gc02619b

Reference yield: 52.0%

ethyl 3-[3-(6-chloropyridyl)]-3-hydroxypropanoate (350229-56-0) → ethyl 3-(6-chloropyridin-3-yl)-3-oxopropanoate (216317-64-5)

Guidance literature:

With 3 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.3987/com-00-9080

Reference yield:

6-Chloronicotinoyl chloride (58757-38-3) + hydrogen ethyl malonate (1071-46-1) → ethyl 3-(6-chloropyridin-3-yl)-3-oxopropanoate (216317-64-5)

Guidance literature:

hydrogen ethyl malonate; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.166667h;

6-Chloronicotinoyl chloride; In tetrahydrofuran; at -78 ℃; for 1.08333h;

upstream raw materials:

ethyl 3-[3-(6-chloropyridyl)]-3-hydroxypropanoate

6-chloronicotinylaldehyde

6-Chloronicotinoyl chloride

ethyl potassium malonate

Downstream raw materials:

3-acetyl-6-chloropyridine

ethyl (+/-)-2-[3-(6-chloropyridyl)]-4-oxo-2-cyclohexene-1-carboxylate

Refernces

• 1、 Huck,Berton,De La Hoz,Díaz-Ortiz,Alcázar. "Reformatsky and Blaise reactions in flow as a tool for drug discovery. One pot diversity oriented synthesis of valuable intermediates and heterocycles". supporting information. p. 1420 - 1424. Retrieved 2017/05/12.
• 2、 -. "PRODUCTION PROCESS OF 2,3'-BIPYRIDYL-6'-ONE". Page/Page column 9. . Retrieved 2010/02/17.