Ethyl 2-(Trifluoromethyl)nicotinate

Base Information

• Chemical Name: Ethyl 2-(Trifluoromethyl)nicotinate
• CAS No.: 208517-35-5
• Molecular Formula: C₉H₈F₃NO₂
• Molecular Weight: 219.163
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID70437041
• Nikkaji Number: J2.601.061F
• Wikidata: Q72477551
• Mol file: 208517-35-5.mol

Synonyms:Ethyl 2-(Trifluoromethyl)nicotinate;208517-35-5;2-Trifluoromethyl-nicotinic acid ethyl ester;Ethyl 2-(trifluoromethyl)pyridine-3-carboxylate;Ethyl2-(trifluoromethyl)nicotinate;2-(Trifluoromethyl)nicotinic acid ethyl ester;3-PYRIDINECARBOXYLIC ACID, 2-(TRIFLUOROMETHYL)-, ETHYL ESTER;2-(TRIFLUOROMETHYL)-3-PYRIDINECARBOXYLIC ACID ETHYL ESTER;SCHEMBL3662007;DTXSID70437041;MFCD08741365;AKOS015891523;AB48764;AS-5604;AC-24315;A4534;AM20050935;CS-0102861;FT-0645204;I10113;J-510356;2-(Trifluoromethyl)pyridine-3-carboxylic acid ethyl ester

Chemical Property of Ethyl 2-(Trifluoromethyl)nicotinate

Chemical Property:

• Boiling Point: 235.757 °C at 760 mmHg
• PKA: -1.38±0.22(Predicted)
• Flash Point: 96.383 °C
• PSA: 39.19000
• Density: 1.285 g/cm³
• LogP: 2.27710
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 219.05071298
• Heavy Atom Count: 15
• Complexity: 230

Purity/Quality:

99% ^*data from raw suppliers

Ethyl2-(Trifluoromethyl)nicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Ethyl 2-(Trifluoromethyl)nicotinate

There total 7 articles about Ethyl 2-(Trifluoromethyl)nicotinate 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: 90.0%

ethyl 5-(dimethylamino)-2-(2,2,2-trifluoroacetyl)-penta-2,4-dienoate (1146961-22-9) → ethyl 2-(trifluoromethyl)pyridine-3-carboxylate (208517-35-5)

Guidance literature:

With ammonia; In methanol; water; at 70 ℃; for 0.333333h;

Reference yield: 90.0%

ethyl (4E)-5-(dimethylamino)-2-(2,2,2-trifluoroacetyl)penta-2,4-dienoate (1022901-65-0) → ethyl 2-(trifluoromethyl)pyridine-3-carboxylate (208517-35-5)

Guidance literature:

With ammonia; In ethanol; water; at 70 ℃; for 0.333333h;

DOI:10.1021/ol800458k

Reference yield: 26.0%

ethyl 3-amino-4,4,4-trifluorocrotonate (141860-78-8) + acrolein (107-02-8,25068-14-8) → ethyl 2-(trifluoromethyl)pyridine-3-carboxylate (208517-35-5)

Guidance literature:

ethyl 3-amino-4,4,4-trifluorocrotonate; acrolein;

With sulfur; Heating;

DOI:10.1055/s-2005-872165

upstream raw materials:

ethyl iodide

3-trifluoroacetyl-2-trifluoromethylpyridine

ethyl 3-amino-4,4,4-trifluorocrotonate

acrolein

Downstream raw materials:

2-(trifluoromethyl)nicotinic acid

6-chloro-2-(trifluoromethyl)pyridin-3-amine

6-chloro-2-(trifluoromethyl)pyridine-3-carboxylic acid

ethyl 6-chloro-2-(trifluoromethyl)pyridine-3-carboxylate

Refernces

• 1、 Lishchynskyi, Anton,Novikov, Maxim A.,Martin, Eddy,Escudero-Adan, Eduardo C.,Novak, Petr,Grushin, Vladimir V.. "Trifluoromethylation of aryl and heteroaryl halides with fluoroform-derived CuCF3: Scope, limitations, and mechanistic features". . p. 11126 - 11146. Retrieved 2013/12/04.
• 2、 Roy, Patrick J.,Dufresne, Claude,Lachance, Nicolas,Leclerc, Jean-Philippe,Boisvert, Michel,Wang, Zhaoyin,Leblanc, Yves. "The Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles". . p. 2751 - 2757. Retrieved 2007/10/03.