373-53-5 | Fluoroiodomethane

CAS:373-53-5 | Fluoroiodomethane ,Description

Fluoroiodomethane (CH2FI) is a compound that has been the subject of various studies due to its unique properties and applications in organic synthesis. It is a valuable electrophilic source for transferring the CH2F unit to a range of nucleophiles, which is useful in the synthesis of organofluorine compounds. The compound is commercially available and offers excellent manipulability due to its liquid state at room temperature, with a boiling point of 53.4 °C .

Synthesis Analysis

The synthesis of fluoroiodomethane and related fluoroalkyl groups has been a topic of interest due to the unusual properties associated with fluorocarbons. Fluoroiodomethane is known to readily yield perfluoroalkyl radicals, which are useful for synthetic applications, such as addition polymerization with ethylene and acetylene . Additionally, fluoroiodomethane has been used as a platform for monofluoromethylation strategies, including nucleophilic substitutions, lithiation reactions, and transition-metal catalyzed transformations .

Molecular Structure Analysis

The molecular structure of fluoroiodomethane has been investigated through rotational spectroscopy and quantum-chemical calculations. Studies have recorded the rotational spectrum of fluoroiodomethane and its isotopic species, determining the ground-state rotational constants and the iodine quadrupole-coupling tensor. These investigations have enabled the derivation of a semi-experimental equilibrium structure for fluoroiodomethane .

Chemical Reactions Analysis

Fluoroiodomethane has been utilized in a variety of chemical reactions. It has been shown to be an effective electrophilic source for monofluoromethylation of heteroatoms under mild conditions, with applications to a variety of drugs currently on the market . Furthermore, fluoroiodomethyllithium, formed via deprotonation of fluoroiodomethane, has been used for the high-yielding synthesis of α-fluoroepoxides and α-fluoroaziridines, demonstrating excellent chemoselectivity .

Physical and Chemical Properties Analysis

The physical and chemical properties of fluoroiodomethane are influenced by the presence of the C-F bond, which is highly polar and the strongest in organic chemistry. The fluorine atom is nonpolarizable and a poor hydrogen-bonding acceptor, which makes fluoroiodomethane an interesting candidate for the design of nonviscous but polar organic compounds . The compound's properties have also been explored in the context of fluorinated polyurethanes, where it contributes to complex micro- and macrostructures, tensile properties, and surface characteristics .

Scientific Research Applications

Electrophilic Monofluoromethylation

Fluoroiodomethane is a valuable electrophilic source for transferring the CH2F unit to various heteroatom-centered nucleophiles. It's particularly effective due to its liquid state at room temperature, simplifying nucleophilic substitutions and retaining chiral information. This high-yielding methodology finds applications in modifying a range of drugs (Senatore et al., 2020).

Monofluoromethylation Platform

Fluoroiodomethane has become a prominent, environmentally friendly agent for monofluoromethylation strategies. It's used in a variety of chemical reactions like nucleophilic substitutions and lithiation reactions, demonstrating its versatility in preparing organofluorine compounds (Colella et al., 2022).

Radiopharmaceuticals Precursor

Fluoroiodomethane, when labeled as [18F]fluoroiodomethane, serves as an essential precursor for introducing [18F]fluoromethyl groups into radiopharmaceuticals. This process is crucial for developing new imaging agents in medical diagnostics (Zheng & Berridge, 2000).

Nucleophilic Fluoromethylation

Fluoroiodomethane has been used to generate lithium fluorocarbenoid, a critical intermediary in direct nucleophilic fluoromethylation of organic compounds. This technique is instrumental in synthesizing fluoroalcohols, fluoroamines, and fluoromethylated heterocycles (Parisi et al., 2017).

Halogen and Hydrogen Bonding Studies

Fluoroiodomethane plays a significant role in the study of halogen and hydrogen bonding. Its interactions with various Lewis bases have provided insights into these weak but crucial molecular interactions (Geboes et al., 2017).

Hydrofluoromethylation of Alkenes

A novel method employs fluoroiodomethane for hydrofluoromethylation of unactivated alkenes, leveraging photoredox catalysis and silane-mediated processes. This approach, using water as a solvent, enhances the reactivity of CH2F radicals (Hu et al., 2023).

Radical Fluoromethylation Activation

Fluoroiodomethane is pivotal in generating fluoromethyl radicals via halogen atom transfer. This method, facilitated by visible light, leads to the formation of C(sp3)–CH2F bonds, expanding the scope of synthesizing complex fluoromethylated compounds (Deneny et al., 2021)

Safety And Hazards

Fluoroiodomethane is toxic if inhaled and causes respiratory tract irritation. It may be harmful if absorbed through the skin and causes skin irritation. It also causes eye irritation and is toxic if swallowed .

Future Directions

Fluoroiodomethane has emerged as an easy-to-handle, non-ozone depleting agent and readily available platform for monofluoromethylation strategies . Its use in nucleophilic substitutions, lithiation reactions, transition-metal catalyzed transformations, radical processes, and 18F-radiolabelling chemistry showcase the potential of this reagent for the preparation of organofluorine compounds . This suggests that fluoroiodomethane has a promising future in various chemical applications.

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