164298-23-1 | Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate

CAS:164298-23-1 | Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate ,Description

Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate (FTHFP) is an organic compound that has several applications in the scientific research field. It is a quaternary ammonium salt with the molecular formula C4H10FN3P and a molecular weight of 209.15 g/mol. FTHFP is a colorless, odorless, and hygroscopic solid that is soluble in water and organic solvents. It is a highly reactive compound that is used as a reagent in several chemical reactions.
 

Scientific Research Applications

Reactivity in Self-Assembled Monolayers

Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate (TFFH) demonstrates unique reactivity towards self-assembled monolayers (SAMs) of 16-mercaptohexadecanoic acid on gold, forming interchain carboxylic anhydrides (ICAs) instead of acid fluorides under most conditions. This highlights its role in SAM-based reactions and approaches to ICA formation from carboxylic acid-terminated SAMs (Chi & Choi, 2006).

Synthesis and Application in Organic Synthesis

TFFH is used in organic synthesis for acyl fluoride formation, coupling reagent for amide preparation, and both solution and solid-phase peptide synthesis. It also aids in the preparation of isothiocyanates and acylhydrazides (El‐Faham & Huang, 2008) .

Source of Nonhydrated Fluoride Ion

N,N,N',N'-tetramethylformamidinium bifluoride, a derivative of TFFH, serves as a new source of nonhydrated fluoride ion. It's instrumental in generating perfluoroalkyl carbanions and studied through 19F NMR spectroscopy, showing its utility in fluorine chemistry (Delyagina et al., 1981) .

Catalysis in Ortho-Fluorination

TFFH has a crucial role in Pd(OTf)2 x 2 H2O-catalyzed ortho-fluorination processes, particularly in medicinal chemistry and synthesis, showing its importance in developing synthetically useful functional groups (Wang et al., 2009).

Historical Perspective on N-F Fluorinating Agents

The historical development and utility of N-F fluorinating agents, including TFFH, have been significant. They are important due to their easy handling and diverse applications in various research areas, highlighting TFFH's role in the evolution of fluorinating agents (Umemoto et al., 2021).

Mechanochemical Nucleophilic Substitution

TFFH is used in mechanochemical methods for nucleophilic substitution of alcohols, presenting a new approach in solvent-free synthetic chemistry. This method showcases TFFH's versatility in creating various chemical products (Dalidovich et al., 2021).

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