39890-95-4 | 2-Chloro-6-(trifluoromethyl)pyridine

CAS:39890-95-4 | 2-Chloro-6-(trifluoromethyl)pyridine,Description

2-Chloro-6-(trifluoromethyl)pyridine is a colorless to off-white liquid. It is a key structural motif in active agrochemical and pharmaceutical ingredients.

Synthesis Analysis

The synthesis of 2-Chloro-6-(trifluoromethyl)pyridine involves a condensation step that includes the reaction between a trifluoromethyl pyridine building block and a larger chlorinated counterpart. The chloride was transformed into 4H-pyran-4-one 3c intermediate by the synthesis of (E)-4-methoxybut-3-en-2-one 3b with LiHMDS at −78 °C, followed by TFA-mediated cyclization.

Molecular Structure Analysis

The molecular structure of 2-Chloro-6-(trifluoromethyl)pyridine is characterized by the presence of a fluorine atom and a pyridine in its structure.

Chemical Reactions Analysis

The major use of 2-Chloro-6-(trifluoromethyl)pyridine derivatives is in the protection of crops from pests. The biological activities of these derivatives are thought to be due to the combination of the unique physicochemical properties of the fluorine atom and the unique characteristics of the pyridine moiety.

Physical And Chemical Properties Analysis

2-Chloro-6-(trifluoromethyl)pyridine is a colorless to off-white liquid. The presence of a fluorine atom and a pyridine in its structure bestows many of the distinctive physical–chemical properties observed with this class of compounds.

Scientific Research Applications

Halogen Shuffling and Electrophilic Substitutions

2-Chloro-6-(trifluoromethyl)pyridine demonstrates significant potential in halogen shuffling and electrophilic substitutions. For instance, when treated with lithium diisopropylamide and iodine, it converts into 3-iodo derivatives and 2-chloro-4-iodo-6-(trifluoromethyl)pyridine, which are valuable for further chemical manipulation in sequences involving halogen/metal exchange and electrophilic trapping (Mongin et al., 1998).

Spectroscopic and Structural Properties

The spectroscopic and structural properties of 2-Chloro-6-(trifluoromethyl)pyridine have been extensively studied. It has been characterized using FT-IR and NMR spectroscopy, and its molecular structure and vibrational frequencies have been computed using various computational methods. These studies provide insights into its molecular electrostatic potential, natural bond orbital analysis, and thermodynamic properties (Evecen et al., 2017).

Applications in Pharmaceuticals and Agrochemicals

2-Chloro-6-(trifluoromethyl)pyridine serves as an intermediate in the production of pharmaceuticals, agrochemicals, biochemicals, and particularly herbicides. Its versatility and reactivity make it a valuable component in the synthesis of various complex compounds (Zheng-xiong, 2004).

Functionalization and Metalation

This compound has been studied for its functionalization capabilities. It can be converted into various carboxylic acids, demonstrating its adaptability in organic synthesis. These transformations employ organometallic methods, highlighting the compound's utility in more complex chemical syntheses (Cottet et al., 2004).

Synthesis of Derivatives and Intermediates

2-Chloro-6-(trifluoromethyl)pyridine has been utilized in synthesizing various derivatives and intermediates, essential for developing trifluoromethylated N-heterocycles and other complex molecules. These syntheses are pivotal in creating compounds with potential applications in different chemical and pharmaceutical domains (Channapur et al., 2019).

Safety And Hazards

2-Chloro-6-(trifluoromethyl)pyridine is considered hazardous. It is combustible and can cause skin irritation, serious eye irritation, and respiratory irritation. It is harmful if swallowed, in contact with skin, or if inhaled.

Future Directions

The demand for 2-Chloro-6-(trifluoromethyl)pyridine derivatives has been increasing steadily in the last 30 years. It is expected that many novel applications of 2-Chloro-6-(trifluoromethyl)pyridine will be discovered in the future.

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