Methyl 2-acetylisonicotinate

Base Information

• Chemical Name: Methyl 2-acetylisonicotinate
• CAS No.: 138715-82-9
• Molecular Formula: C9H9NO3
• Molecular Weight: 179.17300
• Hs Code.: 2933399990
• European Community (EC) Number: 896-588-9
• DSSTox Substance ID: DTXSID20468860
• Nikkaji Number: J2.312.906J
• Wikidata: Q72486524
• Mol file: 138715-82-9.mol

Synonyms:METHYL 2-ACETYLISONICOTINATE;138715-82-9;Methyl 2-acetylpyridine-4-carboxylate;2-ACETYL-ISONICOTINIC ACID METHYL ESTER;4-Pyridinecarboxylic acid, 2-acetyl-, methyl ester;MFCD09032412;Methyl2-acetylisonicotinate;methyl-2-acetylisonicotinate;SCHEMBL1759313;DTXSID20468860;VKPFTQQVEGRJCF-UHFFFAOYSA-N;AKOS006288623;DS-4633;SB52344;SY017474;CS-0043679;FT-0736085;EN300-7359827;J-400984

Chemical Property of Methyl 2-acetylisonicotinate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Boiling Point: 296.59oC at 760 mmHg
• PKA: 0.35±0.10(Predicted)
• Flash Point: 133.173oC
• PSA: 56.26000
• Density: 1.178g/cm3
• LogP: 1.07080
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 179.058243149
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

98% ^*data from raw suppliers

2-Acetyl-isonicotinicacidmethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=NC=CC(=C1)C(=O)OC

Technology Process of Methyl 2-acetylisonicotinate

There total 6 articles about Methyl 2-acetylisonicotinate 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: 66.0%

4-pyridinecarboxylic acid, methyl ester (2459-09-8) + acetaldehyde (75-07-0,9002-91-9) → methyl 2-acetylpyridine-4-carboxylate (138715-82-9)

Guidance literature:

4-pyridinecarboxylic acid, methyl ester; acetaldehyde; With tert.-butylhydroperoxide; ferrous(II) sulfate heptahydrate; trifluoroacetic acid; In acetonitrile; for 3h; Reflux;

With sodium hydroxide; In water;

DOI:10.1021/om900481g

Reference yield: 65.0%

4-pyridinecarboxylic acid, methyl ester (2459-09-8) + paracetaldehyde (123-63-7) → methyl 2-acetylpyridine-4-carboxylate (138715-82-9)

Guidance literature:

With tert.-butylhydroperoxide; ferrous(II) sulfate heptahydrate; trifluoroacetic acid; In acetonitrile; at 60 ℃; for 18h;

DOI:10.1021/acs.inorgchem.7b01632

Reference yield:

2-bromoisonicotinic acid (66572-56-3) → methyl 2-acetylpyridine-4-carboxylate (138715-82-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Cooling with ice

2.1: diisopropylamine / bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 0.5 h / Inert atmosphere

2.2: 10 - 20 °C / Inert atmosphere

3.1: mercury(II) diacetate; sulfuric acid / tetrahydrofuran / 3 h / 50 °C

With sulfuric acid; mercury(II) diacetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; acetonitrile;

upstream raw materials:

4-pyridinecarboxylic acid, methyl ester

acetaldehyde

2-Bromo-4-picoline

2-bromoisonicotinic acid

Downstream raw materials:

2-acetyl-isonicotinic acid

C₁₄H₁₁NO₄