159269-48-4 | 1-Fluoro-4-methyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate

CAS:159269-48-4 | 1-Fluoro-4-methyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate ,Description

1-Fluoro-4-methyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate, also known as FMDB, is an organofluorine compound that has been studied for its potential applications in scientific research. FMDB is a fluorinated derivative of the cyclic diamide 1,4-diazabicyclo[2.2.2]octane (DABCO) and is an important compound for the synthesis of various organic molecules. FMDB has been studied for its ability to act as a catalyst in organic reactions and for its potential applications in medicinal chemistry.
 

Scientific Research Applications

Electrophilic Fluorination of Aromatics

This compound, known under the trade name Selectfluor™, facilitates the direct electrophilic fluorination of a variety of aromatic compounds under mild conditions, producing fluoroaromatics with good to excellent yields. This is significant for synthesizing fluoroaromatics, as fluorine's introduction into organic molecules can profoundly affect their physical, chemical, and biological properties (Shamma et al., 1999) .

Fluorinating Agent for Diverse Organic Substrates

The compound's efficiency extends beyond aromatics to the fluorination of steroidal enol acetates, silyl enol ethers, phenyl-substituted olefins, and certain carbanions. Its application shows good yields and regioselectivity, underlining the reagent's versatility and effectiveness in introducing fluorine into various organic substrates (Lal, 1993).

Site-Selective Fluorination

The compound has been highlighted for its role in the site-selective fluorination of polycyclic aromatic hydrocarbons, demonstrating its capability to target specific sites within molecules. This selective fluorination is crucial for the development of compounds with desired properties and for the study of molecular structure-activity relationships (Stavber & Zupan, 1996).

Water as Reaction Medium

Research has also explored its use in aqueous conditions, showcasing the compound's adaptability to environmentally benign solvents. This approach aligns with green chemistry principles, aiming to reduce the environmental impact of chemical syntheses (Borodkin et al., 2015).

Advancements in Organic Synthesis

Beyond fluorination, the compound serves as a "fluorine-free" functional reagent in various organic reactions, exemplifying its utility as a versatile tool in organic synthesis. This includes its role as a transition metal oxidant and radical initiator, further broadening its application scope in modern synthetic methodologies (Yang et al., 2020).

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