131600-43-6 | Diisopropylethylamine trihydrofluoride

CAS:131600-43-6 | Diisopropylethylamine trihydrofluoride ,Description

Diisopropylethylamine trihydrofluoride (DIPE-THF) is a novel fluorinating reagent that has been used in a variety of chemical and biochemical applications. It is a strong fluorinating agent that is more selective and less hazardous than other commonly used fluorinating reagents. It is also a versatile reagent that can be used in a variety of chemical and biochemical applications.
 

Scientific Research Applications

Nucleophilic Fluorination

Diisopropylethylamine mono(hydrogen fluoride), a derivative of diisopropylethylamine trihydrofluoride, is an effective and selective nucleophilic fluorinating reagent. It's particularly useful in halogen-exchange reactions of chloromethyl ethers, crucial in synthesizing volatile anesthetics like sevoflurane. This specificity is due to its amine component not reacting with the starting material to form quaternary ammonium salts, a common issue with similar reagents (Kudzma et al., 2001).

Stereoselective Aldol-Type Cyclization

The combination of dibutylboron triflate with diisopropylethylamine facilitates stereoselective aldol-type cyclization, providing a straightforward route to synthesize cyclic ethers like 4-cis-tetrahydropyranones. The process likely involves an S(N)1-type mechanism through a chair-like transition state, underscoring its efficiency and specificity in stereochemical arrangements (Das, Li, & Sinha, 2004).

Selective Acylation of Carbohydrates and Diols

Diisopropylethylamine enables a self-catalyzed, regioselective acylation process for carbohydrates and diols. The method is comparatively green and mild, utilizing less organic base compared to other selective acylation methods. Mechanistic studies indicate an interaction involving the formation of a carboxylate ion by diisopropylethylamine, which then catalyzes the selective acylation via dual H-bonding interaction (Ren et al., 2018).

Ionic Liquid Studies

Diisopropylethylamine, when mixed with formic acid, leads to phase separation resulting in an ionic liquid. NMR and DFT studies have shed light on the composition and structural dynamics of this phase, crucial in applications like dye-sensitized solar cells. The understanding of the proton transfer in the system, which is about 65-80%, is particularly significant for its application in various chemical processes (Hansen et al., 2016).

Fluorodehydroxylation Processes

Diisopropylethylamine trihydrofluoride plays a role in the fluorodehydroxylation processes, converting aliphatic primary or secondary hydroxy groups into their corresponding fluoro compounds. The scope, mechanisms, and side reactions of these processes are pivotal in organic synthesis, especially in the formation of complex organic fluorinated compounds (Vorbrueggen, 2008).

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