505084-55-9 | 2-chloro-5-(trifluoromethyl)-4-iodopyridine

CAS:505084-55-9 | 2-chloro-5-(trifluoromethyl)-4-iodopyridine,Description

2-Chloro-4-iodo-5-(trifluoromethyl)pyridine is a chemical compound that is part of the pyridine family, characterized by the presence of chlorine, iodine, and a trifluoromethyl group attached to the pyridine ring. This compound is of interest due to its potential as an intermediate in organic synthesis, particularly in the creation of more complex molecules for various applications, including pharmaceuticals and agrochemicals.

Synthesis Analysis

The synthesis of 2-chloro-4-iodo-5-(trifluoromethyl)pyridine can be achieved through a process known as halogen shuffling. This involves starting with 2-chloro-6-(trifluoromethyl)pyridine, treating it with lithium diisopropylamide in tetrahydrofuran (THF) at -85°C, and subsequently with iodine to obtain the 3-iodo derivative. This intermediate can then be isomerized to yield the desired 2-chloro-4-iodo-5-(trifluoromethyl)pyridine. The iodo compound thus formed can be further manipulated through halogen/metal exchange and electrophilic trapping, demonstrating its versatility as a synthetic building block.

Molecular Structure Analysis

The molecular structure of related pyridine compounds has been extensively studied using various spectroscopic methods. For instance, 2-chloro-6-(trifluoromethyl)pyridine has been characterized by Fourier-transform infrared spectroscopy (FT-IR), proton and carbon-13 nuclear magnetic resonance (1H and 13C NMR), and density functional theory (DFT) calculations. These studies provide insights into the vibrational frequencies, chemical shifts, and electronic absorption spectra, which are crucial for understanding the reactivity and properties of the molecule.

Chemical Reactions Analysis

The reactivity of 2-chloro-4-iodo-5-(trifluoromethyl)pyridine allows for its use in various chemical reactions. For example, it can be used as a starting material for the synthesis of pyridine-4-yl-boronic acid, which is a valuable compound in Suzuki coupling reactions. The synthesis process involves reacting with n-butyl lithium reagent under controlled conditions, leading to high yields and purity of the boronic acid derivative.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2-chloro-4-iodo-5-(trifluoromethyl)pyridine and related compounds are influenced by their molecular structure. The presence of electronegative atoms such as chlorine, iodine, and fluorine affects the electron distribution within the molecule, as evidenced by computational studies on similar molecules. These studies include Mulliken's charges, molecular electrostatic potential (MEP), natural bond orbital (NBO) analysis, and thermodynamic properties. Such properties are essential for predicting the behavior of the compound in different environments and its interactions with other molecules.

Scientific Research Applications

Synthesis and Characterization

• Halogen Shuffling in Pyridines : 2-Chloro-4-iodo-5-(trifluoromethyl)pyridine can be derived from 2-chloro-6-(trifluoromethyl)pyridine using lithium diisopropylamide and iodine. This process demonstrates the versatility of halogen positions in pyridines for further chemical manipulations (Mongin, Tognini, Cottet, & Schlosser, 1998).
• Structural Characterization of Interaction Products : The interaction of 5-trifluoromethyl-pyridine-2-thione with iodine, leading to products similar to 2-chloro-4-iodo-5-(trifluoromethyl)pyridine, was investigated, providing insights into the molecular structure and bonding characteristics of such compounds (Chernov'yants, Burykin, Starikova, & Erofeev, 2011).
• Functionalizations of Chloro- and Iodo(trifluoromethyl)pyridines : This research explores the functionalization of various chloro- and iodo(trifluoromethyl)pyridines, including compounds akin to 2-chloro-4-iodo-5-(trifluoromethyl)pyridine, providing a framework for developing new chemical syntheses (Cottet, Marull, Mongin, Espinosa, & Schlosser, 2004).

Specific Applications and Synthesis Studies

• Synthesis of Boronic Acid Derivatives : The synthesis of 2-chloro-5-trifluoromethyl pyridine-4-yl-boronic acid using 2-chloro-4-iodo-5-trifluoromethyl pyridine as a raw material was studied, showcasing its potential application in creating boronic acid derivatives (Liu Guoqua, 2014).
• Summary of Synthetic Methods and Applications : This paper provides an overview of the synthesis methods for 2-chloro-5-trifluoromethyl pyridine, a related compound, and its applications in various fields like pharmaceuticals and agrochemicals, suggesting similar applications for 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (Li Zheng-xiong, 2004).

Safety And Hazards

2-Chloro-4-iodo-5-(trifluoromethyl)pyridine is considered hazardous. It causes skin irritation and serious eye irritation. It may also cause respiratory irritation. Safety measures include washing off immediately with soap and plenty of water while removing all contaminated clothes and shoes, and getting medical attention.

Future Directions

The major use of 2-Chloro-4-iodo-5-(trifluoromethyl)pyridine derivatives is in the protection of crops from pests. Several derivatives are also used in the pharmaceutical and veterinary industries. It is expected that many novel applications of 2-Chloro-4-iodo-5-(trifluoromethyl)pyridine will be discovered in the future.

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