Methyl 4-cyanonicotinate

Base Information

• Chemical Name: Methyl 4-cyanonicotinate
• CAS No.: 87544-83-0
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.148
• DSSTox Substance ID: DTXSID90515815
• Wikidata: Q82376904
• Mol file: 87544-83-0.mol

Synonyms:METHYL 4-CYANONICOTINATE;87544-83-0;Methyl 4-cyanopyridine-3-carboxylate;METHYL4-CYANONICOTINATE;SCHEMBL25085773;DTXSID90515815;SB54922;D87572

Chemical Property of Methyl 4-cyanonicotinate

Chemical Property:

• 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:

99%,98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 4-cyanonicotinate

There total 3 articles about Methyl 4-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:

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

Reference yield:

potassium cyanide (151-50-8) + C8H10NO3(1+)*CH3O4S(1-) → 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:

In acetonitrile; at 27 ℃; Yield given. Yields of byproduct given;

Reference yield:

potassium cyanide (151-50-8) + 3-carbomethoxy-1-dimethylaminocarbonyloxypyridinium chloride (91074-38-3) → 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:

In acetonitrile; at 27 ℃; Yield given. Yields of byproduct given;

upstream raw materials:

potassium cyanide

3-carbomethoxy-1-dimethylaminocarbonyloxypyridinium chloride

methyl 3-pyridinecarboxylate

trimethylsilyl cyanide

Downstream raw materials:

7-[(Z)-Benzylimino]-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one