Methyl 6-cyanopyridine-3-carboxylate

Base Information

• Chemical Name: Methyl 6-cyanopyridine-3-carboxylate
• CAS No.: 89809-65-4
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.148
• European Community (EC) Number: 872-608-1
• DSSTox Substance ID: DTXSID80521703
• Wikidata: Q82386329
• Mol file: 89809-65-4.mol

Synonyms:METHYL 6-CYANOPYRIDINE-3-CARBOXYLATE;89809-65-4;Methyl 6-cyanonicotinate;MFCD09927471;3-Pyridinecarboxylic acid, 6-cyano-, methyl ester;SCHEMBL880697;DTXSID80521703;FZVAWHJPGGLCPC-UHFFFAOYSA-N;6-cyanonicotinic acid methyl ester;AMY35372;AKOS006312878;SB40758;BEHENICACIDPALMITYLESTERCRYSTALLINE;AS-42933;SY008637;METHYL6-CYANOPYRIDINE-3-CARBOXYLATE;CS-0044469;EN300-188419;A861053;Z1198265899

Chemical Property of Methyl 6-cyanopyridine-3-carboxylate

Chemical Property:

• Vapor Pressure: 0.000684mmHg at 25°C
• Boiling Point: 308.4oC at 760 mmHg
• PKA: -2.36±0.10(Predicted)
• Flash Point: 140.3oC
• PSA: 62.98000
• Density: 1.25g/cm3
• LogP: 0.73988
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 218

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl6-Cyanopyridine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 6-cyanopyridine-3-carboxylate

There total 9 articles about Methyl 6-cyanopyridine-3-carboxylate 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: 100.0%

methyl 6-aminonicotinoate (36052-24-1) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 6-cyanopyridine-3-carboxylate (89809-65-4)

Guidance literature:

In methanol; diethyl ether; at 0 - 20 ℃; for 2h;

Reference yield: 64.0%

zinc(II) cyanide (557-21-1) + methyl 6-bromonicotinate (26218-78-0) → methyl 6-cyanopyridine-3-carboxylate (89809-65-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 100 ℃; for 16h;

DOI:10.1021/acs.jmedchem.8b01381

Reference yield:

methyl 3-pyridinecarboxylate (93-60-7) + trimethylsilyl cyanide (7677-24-9) → 3-carbomethoxy-2-pyridinecarbonitrile (75358-89-3) + 4-cyanonicotinic acid methyl ester (87544-83-0) + methyl 6-cyanopyridine-3-carboxylate (89809-65-4)

Guidance literature:

methyl 3-pyridinecarboxylate; With trifluoromethylsulfonic anhydride; In chloroform; at 20 ℃; for 1h; Inert atmosphere; Sealed tube;

trimethylsilyl cyanide; In chloroform; at 60 ℃; for 3h; Inert atmosphere; Sealed tube;

With 4-methyl-morpholine; In chloroform; at 60 ℃; for 17h; Overall yield = 96 %; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201703931

upstream raw materials:

1-oxy-nicotinic acid methyl ester

trimethylsilyl cyanide

potassium cyanide

3-carbomethoxy-1-dimethylaminocarbonyloxypyridinium chloride

Downstream raw materials:

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

5-(aminomethyl)pyridine-2-carboximidamide

5-(aminomethyl)pyridine-2-carbonitrile

5-(hydroxymethyl)pyridine-2-carbonitrile

Refernces

• 1、 Elbert, Bryony L.,Farley, Alistair J. M.,Gorman, Timothy W.,Johnson, Tarn C.,Genicot, Christophe,Lallemand, Bénédicte,Pasau, Patrick,Flasz, Jakub,Castro, José L.,MacCoss, Malcolm,Paton, Robert S.,Schofield, Christopher J.,Smith, Martin D.,Willis, Michael C.,Dixon, Darren J.. "C?H Cyanation of 6-Ring N-Containing Heteroaromatics". supporting information. p. 14733 - 14737. Retrieved 2017/10/07.
• 2、 -. "Novel thiophene derivatives, their process of preparation and the pharmaceutical compositions which comprise them". Page/Page column 23. . Retrieved 2010/11/30.