Ethyl 4-cyano-2-pyridinecarboxylate

Base Information

• Chemical Name: Ethyl 4-cyano-2-pyridinecarboxylate
• CAS No.: 97316-50-2
• Molecular Formula: C9H8 N2 O2
• Molecular Weight: 176.17
• Hs Code.: 2933399990
• DSSTox Substance ID: DTXSID00541862
• Nikkaji Number: J466.153B
• Wikidata: Q82418320
• Mol file: 97316-50-2.mol

Synonyms:ethyl 4-cyanopicolinate;97316-50-2;ethyl 4-cyano-2-pyridinecarboxylate;ethyl 4-cyanopyridine-2-carboxylate;2-Pyridinecarboxylic acid, 4-cyano-, ethyl ester;SCHEMBL3077434;2-ethoxycarbonyl-4-cyanopyridine;4-cyano-2-ethoxycarbonylpyridine;DTXSID00541862;YJZQRRZEDGIEFC-UHFFFAOYSA-N;XDA31650;MFCD09152770;AKOS005071845;BB-0602;SB52609;CS-0085180;C77339;J-521006

Chemical Property of Ethyl 4-cyano-2-pyridinecarboxylate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 91-93ºC
• Refractive Index: 1.529
• Boiling Point: 307.8°Cat760mmHg
• PKA: -2.34±0.10(Predicted)
• Flash Point: 140°C
• Density: 1.21g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 176.058577502
• Heavy Atom Count: 13
• Complexity: 231

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 4-cyano-2-pyridinecarboxylate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl 4-cyano-2-pyridinecarboxylate

There total 2 articles about Ethyl 4-cyano-2-pyridinecarboxylate 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: 81.0%

2-oxo-propionic acid ethyl ester (617-35-6) + pyridine-4-carbonitrile (100-48-1) → ethyl 4-cyanopyridine-2-carboxylate (97316-50-2) + diethyl 4-cyano-2,6-pyridinedicarboxylate (97316-54-6) + diethyl 4-cyano-2,3-pyridinedicarboxylate (97316-52-4) + diethyl 4-cyano-2,5-pyridinedicarboxylate (97316-53-5)

Guidance literature:

With sulfuric acid; water; dihydrogen peroxide; In dichloromethane; at -5 - 0 ℃; for 0.25h; Yields of byproduct given;

Reference yield:

→ ethyl 4-cyanopyridine-2-carboxylate (97316-50-2)

Guidance literature:

4-Cyano-pyridin, wss. KMnO4, wss. Lsg. v. Ethylpyruvat, H2O2, FeSO4 (neben anderen Verb.);

DOI:10.1016/S0040-4039(00)72422-1

Reference yield: 43.0%

ethyl 4-cyanopyridine-2-carboxylate (97316-50-2) + laudanosine (1699-51-0,20412-65-1) → ethyl 4-(3,4-dimethoxybenzyl)picolinate

Guidance literature:

With trimethylsilyl cyanide; phenanthrene; In acetonitrile; at 20 ℃; for 28h; UV-irradiation; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00652

upstream raw materials:

2-oxo-propionic acid ethyl ester

pyridine-4-carbonitrile

Downstream raw materials:

2-(4-cyano-2-pyridyl)-4,4-bis(4-fluorophenyl)-2-imidazoline

Refernces

• 1、 Heinisch, Gottfried,Loetsch, Gerhard. "Entscheidende Steigerung der Regioselektivitaet bei radikalischen Substitutionen: Minisci-Reaktion im Zweiphasensystem". . p. 694 - 695. Retrieved 2007/10/02.