Methyl 2-methyl-6-(trifluoromethyl)nicotinate

Base Information

• Chemical Name: Methyl 2-methyl-6-(trifluoromethyl)nicotinate
• CAS No.: 205582-88-3
• Molecular Formula: C9H8F3NO2
• Molecular Weight: 219.163
• Hs Code.: 2933399990
• DSSTox Substance ID: DTXSID50381437
• Nikkaji Number: J929.136I
• Wikidata: Q82172250
• Mol file: 205582-88-3.mol

Synonyms:Methyl 2-methyl-6-(trifluoromethyl)nicotinate;205582-88-3;methyl 2-methyl-6-(trifluoromethyl)pyridine-3-carboxylate;3-(Ethoxycarbonyl)-2-methyl-6-(trifluoromethyl)pyridine;MFCD01311989;3-Pyridinecarboxylic acid, 2-methyl-6-(trifluoromethyl)-, methyl ester;SCHEMBL4195184;DTXSID50381437;2-METHYL-6-TRIFLUOROMETHYL-NICOTINIC ACID METHYL ESTER;AMY38670;TQ0033;AKOS016013040;AB08481;AT28792;PS-6500;methyl 2-methyl-6-trifluoromethyinicotinate;methyl 2-methyl-6-trifluoromethylnicotinate;CS-0315060;FT-0756169;A846834;W-206533;6-(Trifluoromethyl)-2-methylpyridine-3-carboxylic acid methyl ester

Chemical Property of Methyl 2-methyl-6-(trifluoromethyl)nicotinate

Chemical Property:

• Boiling Point: 209.0±40.0 °C(Predicted)
• PKA: -0.78±0.22(Predicted)
• PSA: 39.19000
• Density: 1.286±0.06 g/cm3(Predicted)
• LogP: 2.19540
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 219.05071298
• Heavy Atom Count: 15
• Complexity: 242

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 2-methyl-6-(trifluoromethyl)nicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=N1)C(F)(F)F)C(=O)OC

Technology Process of Methyl 2-methyl-6-(trifluoromethyl)nicotinate

There total 9 articles about Methyl 2-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: 88.0%

4-amino-1,1,1-trifluoro-3-buten-2-one (120417-45-0,184848-89-3) + acetoacetic acid methyl ester (105-45-3) → methyl 2-methyl-6-(trifluoromethyl)nicotinate (205582-88-3)

Guidance literature:

With trifluoroacetic acid; In benzene; for 24h; Heating;

DOI:10.3987/COM-97-S45

Reference yield: 82.0%

4-amino-1,1,1-trifluoro-3-buten-2-one (120417-45-0,184848-89-3) + acetoacetic acid methyl ester (105-45-3) → methyl 2-methyl-6-(trifluoromethyl)nicotinate (205582-88-3)

Guidance literature:

With trifluoroacetic acid; In toluene; at 80 ℃; for 16h;

Reference yield: 22.0%

bis(((trifluoromethyl)sulfinyl)oxy)zinc (39971-65-8) + methyl 2-methylnicotinate (65719-09-7) → methyl 2-methyl-4-(trifluoromethyl)nicotinate (198401-84-2) + methyl 2-methyl-6-(trifluoromethyl)nicotinate (205582-88-3)

Guidance literature:

With tert.-butylhydroperoxide; bis-(((isopropyl)sulfinyl)oxy)zinc; zinc sulfinate; In chloroform; water; at 20 - 50 ℃; for 12h; Overall yield = 48 %; regioselective reaction;

DOI:10.1021/ja406223k

upstream raw materials:

4-amino-1,1,1-trifluoro-3-buten-2-one

acetoacetic acid methyl ester

4-amino-1,1,1-trifluorobuten-2-one

bis(((trifluoromethyl)sulfinyl)oxy)zinc

Downstream raw materials:

6-chloro-5-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-4-(pyridin-4-yl)-pyridazin-3(2H)-one

8-bromo-7-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

4-(8-bromo-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)benzonitrile

3-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide

Refernces

• 1、 -. "Method for preparation of 6-trifluoromethylpyridine-3-carboxylic acid derivatives from 4,4,4-trifluoro-3-aminobutanoates". . . Retrieved 2015/01/18.
• 2、 O'Hara, Fionn,Blackmond, Donna G.,Baran, Phil S.. "Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: Scope, tunability, and predictability". supporting information. p. 12122 - 12134. Retrieved 2013/09/02.