Methyl 2-chloro-4-(trifluoromethyl)nicotinate

Base Information

• Chemical Name: Methyl 2-chloro-4-(trifluoromethyl)nicotinate
• CAS No.: 196708-48-2
• Molecular Formula: C₈H₅ClF₃NO₂
• Molecular Weight: 239.581
• Hs Code.: 2933399990
• DSSTox Substance ID: DTXSID50593230
• Wikidata: Q82487672
• Mol file: 196708-48-2.mol

Synonyms:methyl 2-chloro-4-(trifluoromethyl)nicotinate;196708-48-2;methyl 2-chloro-4-(trifluoromethyl)pyridine-3-carboxylate;Methyl2-chloro-4-(trifluoromethyl)nicotinate;SCHEMBL6381481;DTXSID50593230;FDASGHWJBUNFFL-UHFFFAOYSA-N;WHA70848;MFCD12827815;AKOS005072946;GD-0754;CS-0449329;J-521980

Chemical Property of Methyl 2-chloro-4-(trifluoromethyl)nicotinate

Chemical Property:

• PSA: 39.19000
• LogP: 2.54040
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 238.9960906
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 2-chloro-4-(trifluoromethyl)nicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CN=C1Cl)C(F)(F)F

Technology Process of Methyl 2-chloro-4-(trifluoromethyl)nicotinate

There total 3 articles about Methyl 2-chloro-4-(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: 71.0%

(trifluoromethyl)trimethylsilane (81290-20-2) + 2-chloro-4-iodonicotinic acid methyl ester (185041-05-8) → methyl 2-chloro-4-(trifluoromethyl)nicotinate (196708-48-2)

Guidance literature:

With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline; Trimethyl borate; In dimethyl sulfoxide; at 60 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol501967c

Reference yield: 14.0%

→ methyl 2-chloro-4-(trifluoromethyl)nicotinate (196708-48-2)

Guidance literature:

Reference yield:

methyl 4-bromo-2-chloronicotinate (1064678-14-3) + (1,10-phenanthroline)(trifluoromethyl)copper (I) → methyl 2-chloro-4-(trifluoromethyl)nicotinate (196708-48-2)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃; for 8h; regioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1021/ol500422t

upstream raw materials:

methyl 4-bromo-2-chloronicotinate

(trifluoromethyl)trimethylsilane

2-chloro-4-iodonicotinic acid methyl ester

Refernces

• 1、 Gonda, Zsombor,Kovacs, Szabolcs,Weber, Csaba,Gati, Tamas,Meszaros, Attila,Kotschy, Andras,Novak, Zoltan. "Efficient copper-catalyzed trifluoromethylation of aromatic and heteroaromatic iodides: The beneficial anchoring effect of borates". supporting information. p. 4268 - 4271. Retrieved 2014/09/30.