Ethyl 5-cyanopicolinate

Base Information

• Chemical Name: Ethyl 5-cyanopicolinate
• CAS No.: 41051-03-0
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.175
• Hs Code.: 2933399090
• European Community (EC) Number: 893-804-3
• DSSTox Substance ID: DTXSID80496467
• Wikidata: Q82345345
• Mol file: 41051-03-0.mol

Synonyms:Ethyl 5-cyanopicolinate;41051-03-0;ethyl 5-cyano-2-pyridinecarboxylate;ethyl 5-cyanopyridine-2-carboxylate;5-Cyano-pyridine-2-carboxylic acid ethyl ester;SCHEMBL2333525;DTXSID80496467;ethyl5-cyano-2-pyridinecarboxylate;MFCD09152772;AKOS005071856;BB-0605;SB21174;CS-0317862;FT-0680838;A873162;J-521133

Chemical Property of Ethyl 5-cyanopicolinate

Chemical Property:

• Vapor Pressure: 0.000141mmHg at 25°C
• Melting Point: 74-76ºC
• Refractive Index: 1.528
• Boiling Point: 333°Cat760mmHg
• Flash Point: 155.2°C
• PSA: 62.98000
• Density: 1.21g/cm³
• LogP: 1.12998
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.6
• 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 5-cyano-2-pyridinecarboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=NC=C(C=C1)C#N
• Uses: Ethyl 5-Cyanopicolinate is used in preparation of substituted Pyrrolidine-2-carboxamides as antagonists of interaction between p53 and MDM2 protein and anticancer agents.

Technology Process of Ethyl 5-cyanopicolinate

There total 9 articles about Ethyl 5-cyanopicolinate 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: 22.0%

2-oxo-propionic acid ethyl ester (617-35-6) + pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) → ethyl 3-cyano-4-pyridinecarboxylate (91192-30-2) + ethyl 5-cyano-2-pyridinecarboxylate (41051-03-0) + ethyl 3-cyano-2-pyridinecarboxylate (97316-55-7)

Guidance literature:

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

Reference yield: 21.0%

2-oxo-propionic acid ethyl ester (617-35-6) + pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) → ethyl 3-cyano-4-pyridinecarboxylate (91192-30-2) + ethyl 5-cyano-2-pyridinecarboxylate (41051-03-0) + ethyl 3-cyano-2-pyridinecarboxylate (97316-55-7) + diethyl 3-cyano-2,4-pyridinedicarboxylate (110911-10-9)

Guidance literature:

With sulfuric acid; dihydrogen peroxide; iron(II) sulfate; In dichloromethane; water; for 0.25h; Further byproducts given;

DOI:10.3987/R-1987-03-0731

Reference yield:

5-carbamoyl-pyridine-2-carboxylic acid ethyl ester → ethyl 5-cyano-2-pyridinecarboxylate (41051-03-0)

Guidance literature:

With 1,1,1,4,4,4-hexafluoro-2,3-butanedione; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1055/s-2004-831200

upstream raw materials:

2-oxo-propionic acid ethyl ester

pyridine-3-carbonitrile

5-chlorocarbonyl-pyridine-2-carboxylic acid ethyl ester

Pyridine-2,5-dicarboxylic acid

Downstream raw materials:

5-cyano-2-pyridinecarboxamide

tert-bulyl N-[(6-cyanopyridin-3-yl)methyl]carbamate

((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester

((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester

Refernces

• 1、 Heinisch, Gottfried,Loetsch, Gerhard. "HOMOLYTIC ALKOXYCARBONYLATION REACTIONS IN TWO-PHASE SYSTEMS 3. INTRODUCTION OF A SINGLE CARBOXYLIC ACID ESTER FUNCTION INTO CYANO- OR ALKOXYCARBONYL SUBSTITUTED N-HETEROAROMATICS". . p. 731 - 744. Retrieved 2007/10/02.