Methyl 5-cyanonicotinate

Base Information

• Chemical Name: Methyl 5-cyanonicotinate
• CAS No.: 106726-82-3
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.148
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID50545259
• Nikkaji Number: J2.434.166F
• Wikidata: Q72459105
• Mol file: 106726-82-3.mol

Synonyms:Methyl 5-cyanonicotinate;106726-82-3;5-Cyano-3-pyridinecarboxylic acid methyl ester;methyl 5-cyanopyridine-3-carboxylate;MFCD07367902;3-Pyridinecarboxylic acid, 5-cyano-, methyl ester;methyl-5-cyano-nicotinate;5-carbomethoxy-3-cyanopyridine;SCHEMBL1413482;DTXSID50545259;RLUVYUFWNPLVPL-UHFFFAOYSA-N;AB9682;AKOS006286287;AB31365;DS-1765;AC-23038;SY029382;EN300-2490264;A801491;W-204610

Chemical Property of Methyl 5-cyanonicotinate

Chemical Property:

• Vapor Pressure: 0.00734mmHg at 25°C
• Refractive Index: 1.535
• Boiling Point: 269.235 °C at 760 mmHg
• PKA: -0.25±0.20(Predicted)
• Flash Point: 116.629 °C
• PSA: 62.98000
• Density: 1.256 g/cm³
• LogP: 0.73988
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.4
• 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

Methyl5-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=CC(=C1)C#N

Technology Process of Methyl 5-cyanonicotinate

There total 5 articles about Methyl 5-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: 94.0%

5-methanesulfonyloxy-nicotinic acid methyl ester + dicyanozinc (557-21-1) → 3-Cyano-5-methoxycarbonylpyridine (106726-82-3)

Guidance literature:

With palladium diacetate; PS-triphenylphosphine; In tetrahydrofuran; at 140 - 155 ℃; for 0.0416667h; microwave irradiation;

DOI:10.1080/00397910601039044

Reference yield: 60.0%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) + copper(l) cyanide → 3-Cyano-5-methoxycarbonylpyridine (106726-82-3)

Guidance literature:

In N,N-dimethyl-formamide; at 160 ℃; for 12h; Inert atmosphere;

Reference yield: 30.9%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) + copper(I) cyanide (544-92-3) → 3-Cyano-5-methoxycarbonylpyridine (106726-82-3)

Guidance literature:

In DMF (N,N-dimethyl-formamide); for 15h; Heating / reflux;

upstream raw materials:

dicyanozinc

5-bromo-3-pyridine carboxylic acid methyl ester

copper(I) cyanide

5-ethynylnicotinonitrile

Downstream raw materials:

N-(2-(2-(4-chlorophenyl)thiazol-4-yl)-2-methylpropyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide

N-(2-(2-(4-chlorophenyl)thiazol-4-yl)ethyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide

5-cyano-3-pyridinecarboxylic acid

N-((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide

Refernces

• 1、 -. "COMPOUNDS AND METHODS for the inhibition of HDAC". . . Retrieved 2015/11/24.
• 2、 -. "Pyridinecarboxyimidamide compounds and the use thereof". . . Retrieved 2008/06/13.