Ethyl 2-cyanoisonicotinate

Base Information

• Chemical Name: Ethyl 2-cyanoisonicotinate
• CAS No.: 58481-14-4
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.175
• Hs Code.: 29333990
• DSSTox Substance ID: DTXSID60540098
• Nikkaji Number: J3.611.836I
• Wikidata: Q72473932
• Mol file: 58481-14-4.mol

Synonyms:Ethyl 2-cyanoisonicotinate;58481-14-4;Ethyl 2-cyanopyridine-4-carboxylate;2-Cyano-4-pyridinecarboxylic Acid Ethyl Ester;MFCD10574965;Ethyl2-cyanoisonicotinate;SCHEMBL508971;DTXSID60540098;HZIKYLAZZZSYKF-UHFFFAOYSA-N;BCP18491;2-cyano-isonicotinic acid ethyl ester;AKOS006302690;DS-1480;SY067112;AM20061346;CS-0030408;A869437;J-520749;Ethyl 2-Cyanopyridine-4-carboxylate

Chemical Property of Ethyl 2-cyanoisonicotinate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 42-44℃
• Refractive Index: 1.529
• Boiling Point: 308.616 °C at 760 mmHg
• Flash Point: 140.446 °C
• PSA: 62.98000
• Density: 1.21 g/cm³
• LogP: 1.12998
• Storage Temp.: Sealed in dry,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:

97% ^*data from raw suppliers

2-Cyano-4-pyridinecarboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=NC=C1)C#N
• Uses: 2-Cyano-4-pyridinecarboxylic Acid Ethyl Ester, can be used in the synthesis of various pharmaceutical compounds, such as tuberculostatic drugs of the isonicotinic acid hydrazide type.

Technology Process of Ethyl 2-cyanoisonicotinate

There total 4 articles about Ethyl 2-cyanoisonicotinate 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: 85.0%

zinc(II) cyanide (557-21-1) + ethyl isonicotinate N-oxide (14906-37-7) → 2-cyano-isonicotinic acid ethyl ester (58481-14-4)

Guidance literature:

With N,N-Dimethylcarbamoyl chloride; In toluene; for 2h; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2016.11.026

Reference yield: 30.0%

2-oxo-propionic acid ethyl ester (617-35-6) + 2-Cyanopyridine (100-70-9,1232006-36-8) → 2-cyano-isonicotinic acid ethyl ester (58481-14-4) + ethyl-6-cyano-2-pyridinecarboxylate (97483-79-9)

Guidance literature:

With sulfuric acid; dihydrogen peroxide; iron(II) sulfate; In water; for 0.25h; Product distribution; other cyanopyridines, alkyl pyridinecarboxylates and eyhyl 4-pyridazinecarboxylate; other alkyl pyruvate; var. ratios reagents and solvents;

DOI:10.3987/R-1987-03-0731

Reference yield:

sodium cyanide (773837-37-9) + C11H15N2O5S(1+)*CF3O3S(1-) → 2-cyano-isonicotinic acid ethyl ester (58481-14-4)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 1h; Sealed tube;

DOI:10.1021/jacs.7b05414

upstream raw materials:

2-oxo-propionic acid ethyl ester

2-Cyanopyridine

ethyl isonicotinate N-oxide

trimethylsilyl cyanide

Downstream raw materials:

2-cyanoisonicotinic acid hydrazide

Ethyl 2-{[(tert-butoxycarbonyl)amino]methyl}isonicotinate

ethyl 2-(5-{(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazol-3-yl)isonicotinate

(3R)-6-cyclohexyl-3-{3-[4-(ethoxycarbonyl)-2-pyridinyl]-1,2,4-oxadiazol-5-yl}hexanoic acid