Ethyl 6-cyanonicotinate

Base Information

• Chemical Name: Ethyl 6-cyanonicotinate
• CAS No.: 76196-79-7
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.175
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID40540096
• Wikidata: Q72458670
• Mol file: 76196-79-7.mol

Synonyms:Ethyl 6-cyanonicotinate;76196-79-7;2-cyano-5-ethoxycarbonylpyridine;ETHYL 6-CYANOPYRIDINE-3-CARBOXYLATE;MFCD06637534;Ethyl6-cyanonicotinate;ethyl-6-cyanonicotinate;3-Pyridinecarboxylicacid, 6-cyano-, ethyl ester;SCHEMBL3376117;OAUYNMCBOPUJCL-UHFFFAOYSA-;DTXSID40540096;OAUYNMCBOPUJCL-UHFFFAOYSA-N;ethyl 6-cyano-3-pyridinecarboxylate;AR3383;AKOS006292056;CS-W022716;DS-14308;SY107862;AM20061494;A865537;InChI=1/C9H8N2O2/c1-2-13-9(12)7-3-4-8(5-10)11-6-7/h3-4,6H,2H2,1H3

Chemical Property of Ethyl 6-cyanonicotinate

Chemical Property:

• Melting Point: 56-57℃
• Boiling Point: 125 °C(Press: 3 Torr)
• PKA: -2.25±0.10(Predicted)
• PSA: 62.98000
• Density: 1.21
• 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:

99.00% ^*data from raw suppliers

Ethyl6-Cyanonicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl 6-cyanonicotinate

There total 7 articles about Ethyl 6-cyanonicotinate 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: 36.0%

1-oxy-nicotinic acid ethyl ester (14906-63-9) + trimethylsilyl cyanide (7677-24-9) → 5-ethoxycarbonyl-2-pyridinecarbonitrile (76196-79-7) + ethyl 2-cyanopyridine-3-carboxylate (75358-90-6)

Guidance literature:

With triethylamine; In acetonitrile; for 3h; Heating;

Reference yield: 20.0%

3-pyridinecarboxylic acid ethyl ester (614-18-6) + potassium cyanide (151-50-8) → 5-ethoxycarbonyl-2-pyridinecarbonitrile (76196-79-7)

Guidance literature:

3-pyridinecarboxylic acid ethyl ester; With nitric acid; trifluoroacetic anhydride; at 20 ℃;

potassium cyanide; With sodium acetate; at 20 ℃; for 12h;

DOI:10.1055/s-2005-861849

Reference yield:

3-pyridinecarboxylic acid ethyl ester (614-18-6) → 5-ethoxycarbonyl-2-pyridinecarbonitrile (76196-79-7) + ethyl 2-cyanopyridine-3-carboxylate (75358-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C

2: potassium carbonate; N,N-Dimethylcarbamoyl chloride / dichloromethane / 48 h / 20 °C

With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; In dichloromethane;

upstream raw materials:

1-oxy-nicotinic acid ethyl ester

trimethylsilyl cyanide

potassium cyanide

ethanol

Downstream raw materials:

2-(imidazo[1,5-a]pyridin-6-ylmethoxy)-5-methoxybenzaldehyde

ethyl 6-(aminomethyl)-3-pyridinecarboxylate hydrochloride

ethyl imidazo[1,5-a]pyridine-6-carboxylate

Refernces

• 1、 -. "SUBSTITUTED BENZALDEHYDE COMPOUNDS AND METHODS FOR THEIR USE IN INCREASING TISSUE OXYGENATION". Paragraph 0141. . Retrieved 2013/07/19.
• 2、 Katritzky, Alan R.,Scriven, Eric F. V.,Majumder, Suman,Tu, Hongbin,Vakulenko, Anatoliy V.,Akhmedov, Novruz G.,Murugan, Ramiah. "Preparation of cyanopyridines by direct cyanation". . p. 993 - 997. Retrieved 2007/10/03.