Sodium trifluoroacetate
[CAS# 2923-18-4]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic sodium
• Name: Sodium trifluoroacetate
• Synonyms: Trifluoroacetic acid sodium salt
• Molecular Formula: C₂F₃NaO₂
• Molecular Weight: 136.00
• CAS Registry Number: 2923-18-4
• EC Number: 220-879-6
• SMILES: C(=O)(C(F)(F)F)[O-].[Na+]

Properties

• Density: 1.49 g/mL (Expl.)
• Melting point: 205 - 207 ºC (Decomposes) (Expl.)
• Solubility: 625 g/L (25 ºC) (Expl.)

Safety Data

• Hazard Symbols: GHS06;GHS09 Danger
• Hazard Statements: H300-H400-H410
• Precautionary Statements: P264-P270-P273-P301+P316-P321-P330-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H300
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

Sodium trifluoroacetate is an organofluorine salt with the molecular formula CF₃COONa. It is derived from trifluoroacetic acid through neutralization with sodium hydroxide or other sodium bases, producing a white crystalline solid that is soluble in water and polar organic solvents. The compound is stable under normal laboratory conditions and is widely used in chemical synthesis, particularly in fluorine chemistry, because of the strong electron-withdrawing effect of the trifluoromethyl group.

The discovery and development of sodium trifluoroacetate are linked to the broader exploration of trifluoroacetic acid and its derivatives in the early and mid-20th century, when organofluorine chemistry expanded due to increasing industrial and pharmaceutical interest in fluorinated molecules. The trifluoromethyl group, with its high electronegativity and metabolic stability, was recognized as an important structural motif in drug discovery, agrochemicals, and materials science. Sodium trifluoroacetate provided chemists with a convenient and stable source of the trifluoroacetate anion for diverse transformations.

In synthetic chemistry, sodium trifluoroacetate has been employed as a trifluoroacetylating reagent and as a precursor in reactions that introduce the CF₃ group into organic molecules. It serves as an intermediate in the preparation of trifluoroacetic anhydride and other related compounds. Its use extends to transition metal-catalyzed reactions, where it can function as a ligand or additive that influences the reactivity of catalysts by modifying the electronic environment. In oxidative reactions, sodium trifluoroacetate has also been utilized as a mild oxidant or as a promoter to facilitate radical pathways.

The compound has found application in the pharmaceutical field, especially in processes that require selective fluorination or trifluoroacetylation steps. Since fluorinated drugs often display enhanced lipophilicity, metabolic stability, and bioavailability, the role of sodium trifluoroacetate in providing access to such modifications is notable. Beyond pharmaceuticals, it has been used in agrochemical synthesis, particularly in the development of herbicides and fungicides, where fluorinated motifs contribute to environmental persistence and biological activity. Its applications also extend to the polymer industry, where fluorinated intermediates are used to design high-performance materials with chemical resistance and thermal stability.

In biochemical research, sodium trifluoroacetate is sometimes employed as a component in peptide synthesis and purification processes. It can serve as a counterion in peptide salts, offering enhanced solubility and stability compared to non-fluorinated analogues. In addition, trifluoroacetate salts, including sodium trifluoroacetate, are occasionally used in protein crystallography and structural biology, where they affect protein solubility and crystallization behavior.

The stability of sodium trifluoroacetate and its ability to generate volatile by-products upon decomposition, such as carbonyl fluoride under certain conditions, has also made it useful in specific analytical and industrial contexts. Its volatility and decomposition profile can be harnessed in specialized reactions, although handling requires standard laboratory safety precautions due to the potential release of corrosive or toxic fluorinated gases under extreme conditions.

Today, sodium trifluoroacetate remains an important reagent in both academic and industrial research. Its discovery and application illustrate the broader significance of trifluoroacetic acid derivatives in modern chemistry, providing versatile tools that have contributed to the advancement of organic synthesis, drug design, agrochemicals, and materials science.

References

2025. Hydrothermal Liquefaction of Coffee Silverskin and Spent Coffee Grounds: Bioenergy and Biochemical Potential. BioEnergy Research, 18.
DOI: 10.1007/s12155-025-10867-3

2025. A machine learning approach to designing and understanding tough, degradable polyamides. npj Computational Materials, 11(1).
DOI: 10.1038/s41524-025-01696-1

2025. High-molecular-weight disinfection byproducts in simulated drinking water: characterization and identification via matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Frontiers of Environmental Science & Engineering, 19(5).
DOI: 10.1007/s11783-025-2024-5