Trifluoroacetic acid-d (TFA-d) is the deuterated form of trifluoroacetic acid (TFA), a strong organic acid. The “d” in TFA-d refers to deuterium, a stable isotope of hydrogen, where the hydrogen atoms are replaced with deuterium (denoted as ^2H). This substitution alters the physical properties of the compound, making it useful for various scientific applications, particularly in nuclear magnetic resonance (NMR) spectroscopy.

Chemical Structure and Properties:

• Chemical Formula: C2HF3O2-D (The deuterium atom replaces one of the hydrogen atoms in the trifluoromethyl group).
• Molecular Weight: Approximately 148.00 g/mol
• Appearance: Colorless liquid.
• Boiling Point: Around 72-75°C (at 760 mmHg).
• Melting Point: Approximately -14°C.
• Density: Around 1.49 g/cm³.

Trifluoroacetic acid-d contains three fluorine atoms, one oxygen atom, and a deuterium-substituted hydrogen atom. Its structure makes it highly acidic and highly soluble in water and organic solvents.

Uses and Applications:

1. NMR Spectroscopy:

   • Trifluoroacetic acid-d is widely used as a deuterated solvent in NMR spectroscopy.Specifically, the presence of deuterium helps eliminate proton (^1H) signals in the NMR spectrum, therefore allowing the observation of ^13C and other nuclei without interference from protons. As a result, this is particularly useful in the study of complex organic molecules, peptides, and proteins.

   • Moreover, the specific use of TFA-d in NMR is especially beneficial for quantitative analysis of molecules, including structural studies. Since the absence of hydrogen signals reduces background noise, it therefore significantly increases the clarity of the spectrum.

2. Isotope Labeling:

   • In certain research applications, deuterated compounds like TFA-d are used for isotope labeling.

3. Proteomics and Peptide Analysis:

   • Trifluoroacetic acid is a commonly used reagent for peptide synthesis and protein sequencing. The deuterated version (TFA-d) is helpful in high-resolution mass spectrometry (MS) and NMR spectroscopy for detailed peptide and protein structure determination.

4. Synthesis and Purification:

   • Trifluoroacetic acid-d is also highly valuable in organic synthesis, where it can serve both as a reagent and as a catalyst, depending on the specific reaction. For example, TFA-d may be used in deprotection reactions during the synthesis of peptides or other sensitive compounds. In particular, it plays a crucial role in facilitating the removal of protecting groups with high efficiency, thereby enabling the precise control of the reaction conditions. This makes TFA-d an essential tool for ensuring the successful synthesis of complex molecules, particularly in cases where minimizing side reactions and maximizing yields are critical

5. Labeling for Tracers:

   • TFA-d is used in tracer studies as a deuterium-labeled compound to study metabolic pathways and reaction mechanisms involving fluorinated species or acids.

Chemical Behavior:

• Acidity: Trifluoroacetic acid-d retains the strong acidic properties of the non-deuterated version. It has a pKa around 0.5, making it a strong acid that can protonate many organic and inorganic species.

• Solubility: Trifluoroacetic acid-d is highly soluble in water, alcohols, and many organic solvents. It can act as a proton donor in reactions, which makes it a versatile reagent in both aqueous and organic media.

Safety and Handling:

• Corrosive:
  TFA-d is corrosive and can cause severe burns to skin and eyes. Wear gloves, safety glasses, and a lab coat.

• Vapor Hazard:
  Avoid inhaling vapors, as they can irritate the respiratory system.

• Storage:
  Store TFA-d in tightly sealed containers in a cool, dry place, away from strong bases and metals.

Conclusion:

Trifluoroacetic acid-d (TFA-d) is a deuterated version of trifluoroacetic acid, commonly used in NMR spectroscopy and isotope labeling for scientific research. Its unique properties make it essential for applications requiring high precision and clarity in structural analysis, particularly for peptides, proteins, and complex organic molecules. The deuteration enhances its utility by reducing interference from hydrogen-based signals, improving the sensitivity and accuracy of analytical techniques.

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