76-05-1 | Trifluoroacetic acid

CAS:76-05-1 | Trifluoroacetic acid ,Description

Trifluoroacetic acid (TFA) is a colorless, volatile, and highly acidic compound that is widely used in the lab for a variety of purposes. It is a powerful acid, with a pKa of 0.25, which is much lower than the pKa of other organic acids. TFA is a versatile compound that can be used in a variety of applications, from organic synthesis to protein structure analysis. It is also used for the synthesis of pharmaceuticals and other compounds.
 

Scientific Research Applications

• Organic Synthesis: TFA is highly efficient in synthesizing 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones and 3-arylmethyl-2-amino-quinolines from Baylis-Hillman derivatives via Claisen rearrangement (Pathak, Madapa, & Batra, 2007). It also promotes intramolecular hydroamination of unfunctionalized olefins bearing electron-rich amino groups, yielding N-heterocycles in good isolated yields (Liu, Cui, Sun, & Li, 2014), and efficiently catalyzes Prins cyclizations of enol ethers to produce tetrahydropyrans (Hart & Bennett, 2003).
• Neuropharmacology: As a selective allosteric modulator at the glycine receptor, TFA potentially impacts the secondary effects of volatile anesthetics and the presence of trifluoroacetate in HPLC-purified peptides (Tipps, Iyer, & Mihic, 2012).
• Environmental Studies: The formation of TFA from the degradation of HCFC and HFCs, despite being a small contributor to global TFA levels, warrants attention due to its long environmental lifetime and uncertain sources (Solomon et al., 2016).
• Bioanalysis: In the bioanalysis of basic compounds using hydrophilic interaction chromatography-electrospray tandem mass spectrometry (HILIC-ESI/MS/MS), adding acetic acid or propionic acid to TFA-containing mobile phases enhances analyte signals while maintaining chromatography integrity (Shou & Naidong, 2005).
• Imaging and Spectroscopy: F and H nuclear magnetic resonance imaging and spectroscopy can monitor the uptake of TFA in plants, providing noninvasive insight into xenobiotic movement and location (Rollins, Barber, Elliott, & Wood, 1989).
• Liquid Chromatography: TFA is used as an ion-pair reagent in reversed-phase liquid chromatography for the separation of small ionizable compounds (Cai & Li, 1999).
• Medical Toxicology: Exposure to TFA can cause chemical burns, similar to hydrofluoric acid, but with less systemic toxicity (Sun & Corbett, 2017).

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