2040-90-6 | 2-Chloro-6-fluorophenol

CAS:2040-90-6 | 2-Chloro-6-fluorophenol,Description

Synthesis Analysis

While specific synthesis methods for 2-Chloro-6-fluorophenol are not detailed in the available literature, the synthesis of related halogenated phenols often involves halogenation reactions, where halogen atoms are introduced into the phenol molecule. Techniques such as direct halogenation or via intermediates are common. For example, the synthesis of related compounds involves steps like substitution reactions where chlorine and fluorine atoms are introduced into the phenolic ring at specific positions under controlled conditions (Boiko et al., 2011).

Molecular Structure Analysis

The molecular structure of halogenated phenols, including 2-Chloro-6-fluorophenol, is crucial in determining their chemical behavior. Studies on similar molecules, such as 2-fluorophenol and 2,6-difluorophenol, have shown that the presence of halogen atoms affects the molecular geometry and can lead to the formation of weak intramolecular hydrogen bonds (Vajda & Hargittai, 1993). These structural characteristics are essential for understanding the reactivity and interactions of 2-Chloro-6-fluorophenol.

Scientific Research Applications

Hydrogen-Atom Tunneling and Isomerization

Studies have shown intriguing properties of 2-chloro-6-fluorophenol in low-temperature environments. For instance, infrared spectra of 2-chloro-6-fluorophenol in argon matrices at 20 K revealed a "Cl-type" isomer characterized by an OH···Cl hydrogen bond, but no "F-type" isomer with OH···F bonding. This contrasted with the existence of both isomers in the gas and liquid phases at room temperature. The absence of the F-type isomer at low temperatures suggests a hydrogen-atom tunneling phenomenon where the F-type isomer changes to the more stable Cl-type one in the matrix. This tunneling isomerization around the C-O bond was observed in the OH···X species but not in the OD···X species. UV-induced photoreactions were also studied, showing that different photoproducts are produced depending on the isomer type and the presence of deuterium (Nanbu, Sekine, & Nakata, 2011).

Photoreaction Mechanism in Halogenated Phenols

Further research on halogenated phenols, including 4-bromo-2-chloro-6-fluorophenol, under low-temperature conditions in argon matrices, revealed significant insights into the photoreaction mechanisms of these compounds. The study found that certain photoproducts, like 2-fluoro-4-bromocyclopentadienylidenemethanone, were produced from the Cl-type isomer by Wolff rearrangement after the dissociation of specific atoms. This work highlighted the influence of the bromine atom at the 4th position, which impacts the intramolecular migration of the Cl atom (Nanbu, Sekine, & Nakata, 2012).

Applications in Polymer Chemistry

2-Chloro-6-fluorophenol derivatives have been utilized in the field of polymer chemistry. For example, 2-fluoro-6-(3-methyl-2-butenyl)phenol (FMBP) was prepared and oxidatively polymerized with a copper-pyridine catalyst to yield a specific type of polyphenylene. The copolymerizability of FMBP with other compounds like 2,6-dimethylphenol was also explored, providing valuable insights into the polymerization processes of halogenated phenols (Hyun, Nishide, Tsuchida, & Yamada, 1988).

Molecular Docking and Antibacterial Applications

A study focusing on the molecular structure and antibacterial properties of 2-chloro-5-fluoro phenol demonstrated its potential in antibacterial applications. The compound showed significant activity against various bacterial strains, and molecular docking studies supported these findings. The study also delved into vibrational spectral determinations, non-linear optical properties, and hydrogen bond and thermodynamic parameters of the compound, indicating its stability and chemical reactivity (Vidhya, Austine, & Arivazhagan, 2020).

Safety And Hazards

2-Chloro-6-fluorophenol is classified as harmful if swallowed and causes severe skin burns and eye damage. It may cause respiratory irritation and is suspected of damaging fertility or the unborn child. It may cause genetic defects and is toxic to aquatic life with long-lasting effects. Appropriate safety measures should be taken while handling this compound, including wearing protective gloves, clothing, and eye/face protection.

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