Ethyl 6-fluoronicotinate

Base Information

• Chemical Name: Ethyl 6-fluoronicotinate
• CAS No.: 116241-59-9
• Molecular Formula: C8H8FNO2
• Molecular Weight: 169.155
• DSSTox Substance ID: DTXSID80558615
• Wikidata: Q82440982
• Mol file: 116241-59-9.mol

Synonyms:Ethyl 6-fluoronicotinate;116241-59-9;Ethyl 6-fluoropyridine-3-carboxylate;Ethyl6-fluoronicotinate;3-Pyridinecarboxylic acid, 6-fluoro-, ethyl ester;SCHEMBL6087503;DTXSID80558615;MFCD12756554;CS-0452032

Chemical Property of Ethyl 6-fluoronicotinate

Chemical Property:

• Boiling Point: 228.5±20.0 °C(Predicted)
• PKA: -2.36±0.10(Predicted)
• PSA: 39.19000
• Density: 1 +-.0.06 g/cm3(Predicted)
• LogP: 1.39740
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 169.05390666
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl6-Fluoronicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Ethyl 6-fluoronicotinate

There total 6 articles about Ethyl 6-fluoronicotinate 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: 91.0%

3-ethyloxycarbonylpyridin-6-(4-aza-1-azoniabicyclo[2.2.2]octane) trifluoromethanesulfonate → (6-fluoropyridin-3-yl)carboxylic acid ethyl ester (116241-59-9)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1039/c9cc09434b

Reference yield:

C8H9FNO2(1+)*BF4(1-) (116241-52-2) → 3-(ethoxycarbonyl)-2-fluoropyridine (113898-56-9) + (6-fluoropyridin-3-yl)carboxylic acid ethyl ester (116241-59-9)

Guidance literature:

With triethylamine; for 0.0833333h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00268a041

Reference yield:

3-pyridinecarboxylic acid ethyl ester (614-18-6) → (6-fluoropyridin-3-yl)carboxylic acid ethyl ester (116241-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBF₄, 20 percentF₂/N₂ / acetonitrile / -40 °C

2: Et₃N / 0.08 h / Ambient temperature

With sodium tetrafluoroborate; fluorine; triethylamine; In acetonitrile;

DOI:10.1021/jo00268a041

upstream raw materials:

C₈H₉FNO₂⁽¹⁺⁾*BF₄^(1-)

3-pyridinecarboxylic acid ethyl ester

ethyl 6-hydroxypyridine-3-carboxylate

6-hydroxy-3-pyridinecarboxylic acid

Refernces

• 1、 Umemoto, Teruo,Tomizawa, Ginjiro. "Preparation of 2-Fluoropyridines via Base-Induced Decomposition of N-Fluoropyridinium Salts". . p. 1726 - 1731. Retrieved 2007/10/02.