Methyl 6-(trifluoromethyl)nicotinate

Base Information

• Chemical Name: Methyl 6-(trifluoromethyl)nicotinate
• CAS No.: 221313-10-6
• Molecular Formula: C₈H₆F₃NO₂
• Molecular Weight: 205.136
• Hs Code.: 2933399990
• European Community (EC) Number: 671-247-5
• DSSTox Substance ID: DTXSID50379632
• Wikidata: Q72492041
• Mol file: 221313-10-6.mol

Synonyms:methyl 6-(trifluoromethyl)nicotinate;221313-10-6;methyl 6-(trifluoromethyl)pyridine-3-carboxylate;METHYL6-(TRIFLUOROMETHYL)NICOTINATE;MFCD03001346;3-pyridinecarboxylic acid, 6-(trifluoromethyl)-, methyl ester;Methyl 6-trifluoromethylnicotinate;6-Trifluoromethyl-nicotinic acid methyl ester;Methyl 6-(trifluoromethyl) nicotinate;SCHEMBL1317978;AMY3058;DTXSID50379632;BCP05949;AKOS005063505;AB12803;CS-W015385;EA-0870;AC-29136;SY007338;FT-0645553;O11962;methyl-2-(trifluoromethyl)pyridine-5-carboxylate;A815955;J-522521;6-(TRIFLUOROMETHYL)NICOTINIC ACID METHYL ESTER;METHYL 2-(TRIFLUOROMETHYL)-5-PYRIDINECARBOXYLATE

Chemical Property of Methyl 6-(trifluoromethyl)nicotinate

Chemical Property:

• Vapor Pressure: 0.203mmHg at 25°C
• Melting Point: 61-62°C
• Refractive Index: 1.446
• Boiling Point: 209.4 °C at 760 mmHg
• Flash Point: 80.4 °C
• PSA: 39.19000
• Density: 1.331 g/cm³
• LogP: 1.88700
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Soluble in acetone. Insoluble in water.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 205.03506292
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

98% ^*data from raw suppliers

Methyl6-(Trifluoromethyl)nicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CN=C(C=C1)C(F)(F)F
• Uses: Methyl 6-(trifluoromethyl)nicotinate is used as a pharmaceutical intermediate.

Technology Process of Methyl 6-(trifluoromethyl)nicotinate

There total 9 articles about Methyl 6-(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: 100.0%

methanol (67-56-1) + 6-trifluoromethylnicotinic acid (231291-22-8) → methyl 6-(trifluoromethyl)pyridine-3-carboxylate (221313-10-6)

Guidance literature:

With sulfuric acid; for 5h; Reflux;

Reference yield: 79.0%

1-(p-methoxybenzyl)-2-trifluoromethyl-5-methoxycarbonyl-1,2-dihydropyridine (946137-02-6) → methyl 6-(trifluoromethyl)pyridine-3-carboxylate (221313-10-6)

Guidance literature:

With ammonium cerium(IV) nitrate; In methanol; at 20 ℃;

DOI:10.1021/jo0703552

Reference yield: 71.9%

trimethylsilyl 2-chloro-2,2-difluoroacetate + methyl 6-iodo-3-pyridinecarboxylate (173157-33-0) → methyl 6-(trifluoromethyl)pyridine-3-carboxylate (221313-10-6)

Guidance literature:

With potassium fluoride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 90 ℃; for 8h; Reagent/catalyst; Catalytic behavior; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.oprd.6b00079

upstream raw materials:

diazomethane

carbon dioxide

2-(trifluoromethyl)pyridine

1-(p-methoxybenzyl)-2-trifluoromethyl-5-methoxycarbonyl-1,2-dihydropyridine

Downstream raw materials:

6-(trifluoromethyl)pyridin-3-ylmethanol

3-chloromethyl-6-(trifluoromethyl)pyridine

2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile

Refernces

• 1、 Wang, Jian,Zhang, Xiaomin,Wan, Zehong,Ren, Feng. "TCDA: Practical Synthesis and Application in the Trifluoromethylation of Arenes and Heteroarenes". . p. 836 - 839. Retrieved 2016/05/19.
• 2、 -. "NOVEL TRPV3 MODULATORS". Paragraph 1570; 1571. . Retrieved 2013/06/04.