106877-18-3

Basic information

• Product Name: 2-Methyl-3-(trifluoromethyl)pyridine
• Synonyms: 2-Methyl-3-(trifluoromethyl)pyridine
• CAS NO: 106877-18-3
• Molecular Formula: C₇H₆F₃N
• Molecular Weight: 161.13
• Mol File: 106877-18-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2-Methyl-3-(trifluoromethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-3-(trifluoromethyl)pyridine(106877-18-3)
• EPA Substance Registry System: 2-Methyl-3-(trifluoromethyl)pyridine(106877-18-3)

Safety Data

• Statements: 36
• Safety Statements: 26
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 106877-18-3(Hazardous Substances Data)

Usage

General Description

2-Methyl-3-(trifluoromethyl)pyridine is a chemical compound with the molecular formula C8H6F3N. It is a pyridine derivative with a trifluoromethyl group attached to the third position and a methyl group attached to the second position of the pyridine ring. 2-Methyl-3-(trifluoromethyl)pyridine is often used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is a colorless liquid with a strong odor and is flammable. It is also known for its use as a building block in the preparation of various functional materials and organic compounds. 2-Methyl-3-(trifluoromethyl)pyridine is considered to be of low toxicity, but proper safety measures should be taken when handling and storing this chemical.

Upstream product

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Relevant articles and documents

Trifluoromethylation of aryl and heteroaryl halides with fluoroform-derived CuCF3: Scope, limitations, and mechanistic features

Fluoroform-derived CuCF3 recently discovered in our group exhibits remarkably high reactivity toward aryl and heteroaryl halides, performing best in the absence of extra ligands. A broad variety of iodoarenes undergo smooth trifluoromethylation with the ligandless CuCF3 at 23-50 C to give the corresponding benzotrifluorides in nearly quantitative yield. A number of much less reactive aromatic bromides also have been trifluoromethylated, including pyridine, pyrimidine, pyrazine, and thiazole derivatives as well as aryl bromides bearing electron-withdrawing groups and/or ortho substituents. Only the most electrophilic chloroarenes can be trifluoromethylated, e.g., 2-chloronicotinic acid. Exceptionally high chemoselectivity of the reactions (no side-formation of arenes, biaryls, and C2F5 derivatives) has allowed for the isolation of a large number of trifluoromethylated products in high yield on a gram scale (up to 20 mmol). The CuCF3 reagent is destabilized by CuX coproduced in the reaction, the magnitude of the effect paralleling the Lewis acidity of CuX: CuCl > CuBr > CuI. While SNAr and SRN1 mechanisms are not operational, there is a well-pronounced ortho effect, i.e., the enhanced reactivity of ortho-substituted aryl halides 2-RC6H4X toward CuCF3. Intriguingly, this ortho-effect is observed for R = NO2, COOH, CHO, COOEt, COCH3, OCH3, and even CH3, but not for R = CN. The fluoroform-derived CuCF3 reagent and its reactions with haloarenes provide an unmatched combination of reactivity, selectivity, and low cost.

Process for perfluoroalkylation of aromatic derivatives

A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.