Sodium trifluoromethanesulfonate,It is an important chemical substance. The appearance is white powder, which is irritating, easily soluble in water, and hygroscopic. It should be stored in a dry and sealed manner to ensure its stability and avoid moisture absorption, as well as contact with oxides. It can serve as a source of fluorine substituents in organic synthesis, introducing them into organic molecules and altering their chemical properties. In the fields of pesticides and pharmaceuticals, it can play an important role as a key intermediate in the synthesis of certain drugs and pesticides. In fluorinated substituents, this compound has become an increasingly common structural motif in pharmaceuticals, as the introduction of this group into organic molecules has a profound impact on its stability, lipophilicity, and membrane permeability. It can also be used to prepare aryl fluorides (silver catalyzed fluorination of arylstananes) and ionic liquids, such as N, N-dialkylpyrrolidine trifluoromethanesulfonate, N, N-dialkylimidazolium trifluoromethanesulfonate, and N-alkylpyridine trifluoromethanesulfonate.
Additional information of chemical compound:
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Chemical Formula |
CF3NaO3S |
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Exact Mass |
171.94 |
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Molecular Weight |
172.05 |
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m/z |
171.94 (100.0%), 173.94 (4.5%), 172.95 (1.1%) |
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Elemental Analysis |
C,6.98; F, 33.13; Na, 13.36; O, 27.90; S, 18.63 |
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Melting point |
253-255℃(lit.) |
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Sodium trifluoromethanesulfonate is an important organic synthesis reagent and intermediate with a wide range of applications. The following is a detailed introduction to its use:
This compound can be used as an efficient fluorinating reagent to introduce trifluoromethanesulfonyl groups into organic molecules. This group has special chemical properties, such as strong electronegativity, stable C-F bonds, etc., which can significantly affect the acidity, dipole moment, and lipophilicity of the entire molecule. Therefore, by introducing trifluoromethanesulfonyl groups, the chemical properties of organic molecules can be altered, thereby endowing them with new biological activity or physical properties. By utilizing its fluorinating properties, organic compounds with specific fluorine substituents can be synthesized. These fluorine substituted compounds have a wide range of applications in fields such as medicine, pesticides, and materials science.
Fluorinating reagents in organic synthesis
For example, in the pharmaceutical field, fluorine substituted drug molecules typically exhibit better bioavailability, bioselectivity, and metabolic stability, resulting in better drug efficacy. It can also be used as a catalyst or reagent to participate in some complex organic reactions. For example, it can catalyze asymmetric Mannich type reactions, Mannich type reactions in water, and Diels Alder reactions. These reactions are of great significance in organic synthesis and can be used to synthesize organic molecules with complex structures. At the same time, the compound can also combine with other compounds to form ionic liquids. Ionic liquids are liquids with special properties, such as high temperature stability, low volatility, and high conductivity. Therefore, they have broad application prospects in fields such as electrochemistry, catalysis, and separation.
This compound can be used to synthesize drug molecules with specific biological activity. These drug molecules may have various pharmacological effects such as anti-tumor, antibacterial, antiviral, anti-inflammatory, etc. For example, it can be used to synthesize antipsychotic drugs such as fluphenazine, trifluoperazine, and triflumenidazole, as well as other types of drugs such as butyl fluoromethane and clomiphene citrate. By introducing this compound, the chemical properties of drug molecules can be altered, thereby improving their solubility, stability, bioavailability, and other properties. This helps to improve the absorption, distribution, metabolism, and excretion processes of drugs in the body, thereby enhancing their efficacy and safety. This compound can also be used to synthesize pesticide products with high efficiency, low toxicity, and environmental protection characteristics.
For example, it can be used to synthesize herbicides such as fluazinam and fluazinam, which have significant control effects on broad-leaved weeds and perennial weeds in wheat and cotton fields. Introducing it can significantly enhance the insecticidal, bactericidal, or herbicidal activity of pesticides. At the same time, it can also reduce the toxicity of pesticides and minimize their harm to the environment and human health.
Catalysts and surfactants
This compound can serve as an effective catalyst for asymmetric Mannich type reactions. This type of reaction is of great significance in organic synthesis and can be used to synthesize compounds with chiral structures. It can also catalyze Mannich type reactions in water, providing a new pathway for organic synthesis in aqueous phase. It can also catalyze Diels Alder reactions, which are important cycloaddition reactions that can be used to synthesize compounds with cyclic structures. In the plastic industry, this compound can serve as a catalyst for polymerization reactions, increasing reaction rates and polymerization degrees, thereby improving the quality and yield of plastics.
And in the production process of fuel, it can serve as a catalyst for esterification, dehydration and other reactions, improving production efficiency. Due to its unique chemical structure, this compound exhibits excellent surface activity in certain systems. It can be used as a surfactant to improve the dispersibility, stability, and flowability of the system. Although the specific application of surfactants may vary depending on the system, the introduction of this substance usually helps optimize the performance of the system.
In lithium-ion batteries, this compound can be used as an alternative electrolyte salt. Due to its excellent ion conductivity and chemical stability, it helps to improve the performance of lithium-ion batteries. Specifically, the electrolyte can provide higher ion migration rate and lower internal resistance, thereby increasing the charging and discharging rate and cycling stability of the battery. In addition, it can also suppress the self discharge phenomenon of the battery to a certain extent, extending the service life of the battery. In addition to lithium-ion batteries, it can also be used as an electrolyte in other electrochemical devices. Meanwhile, due to its high chemical stability and wide electrochemical window, it can also improve the safety and reliability of these electrochemical devices to a certain extent.
In addition, it can also be combined with other electrolyte materials to improve their performance through modification. For example, it can be combined with materials such as polymers and inorganic salts to form composite electrolytes, thereby improving the mechanical strength, thermal stability, and ion conductivity of the electrolyte. This modified electrolyte material has broader application prospects in electrochemical devices such as lithium-ion batteries and supercapacitors.
Environmental Impact
Sodium trifluoromethanesulfonate (NaOTf) is a strongly acidic sulfonic acid salt with the molecular formula CF ∝ SO ∝ Na and a molecular weight of 172.05. Its core functional group trifluoromethanesulfonate (CF ∝ SO ∝⁻) has strong electron withdrawing and dissociation abilities, and is widely used in organic synthesis, electrochemical energy storage, pesticide and pharmaceutical intermediates, and other fields. However, its chemical stability and high reactivity have also raised concerns about environmental risks.
Water pollution: from acute toxicity to chronic ecological damage
Acute toxic effects
The toxicity of NaOTf to aquatic organisms mainly stems from its strong acidity and fluoride ion (F ⁻) release characteristics. Experimental data shows that zebrafish embryos: In the 96 hour exposure experiment, the median lethal concentration (LC ₅₀) of NaOTf was 12.5 mg/L, manifested as delayed hatching, decreased heart rate, and axial abnormalities. Daphnia: In the 48 hour exposure experiment, the half effect concentration (EC ₅₀) was 8.3 mg/L, mainly inhibiting motor ability and leading to an increase in mortality rate.
Direct damage: CF ∝ SO ∝⁻ destroys the gill cell membrane of aquatic organisms, leading to suffocation; F ⁻ combines with calcium ions to form calcium fluoride (CaF ₂), which interferes with nerve conduction and muscle contraction.
Indirect effects: Acidic environment (pH<3) disrupts the water buffering system, inhibits algal photosynthesis, and triggers food chain disruption.
Chronic cumulative effects
Long term low concentration exposure (0.1-1 mg/L) can cause chronic toxicity in aquatic organisms:
Fish: Accumulation of F ⁻ in the bones leads to fluorosis, manifested as skeletal fragility and delayed growth.
Benthic organisms: NaOTf adsorbs onto sediments and is transmitted through the food chain to invertebrates (such as mosquito larvae), resulting in a decrease of over 60% in reproductive rates.
Soil Ecology: From Microbial Inhibition to Plant Toxicity
Imbalance of Microbial Communities
The toxicity threshold of NaOTf to soil microorganisms is 50 mg/kg, mainly affecting nitrifying bacteria and nitrogen fixing bacteria:
Nitrification inhibition: At a concentration of 50 mg/kg, the activity of ammonia oxidizing bacteria decreased by 60%, leading to the obstruction of soil nitrogen cycling.
Azogenase inactivation: F ⁻ binds to magnesium ions in the enzyme active center, resulting in a 40% decrease in nitrogen fixation efficiency of rhizobia.
Repair strategy:
Adding lime (CaO) can neutralize acidity and fix F ⁻. Experiments have shown that applying 5% CaO to soil contaminated with 100 mg/kg NaOTf can restore microbial activity to 80% of the control level after 60 days.
Plant growth disorders
The toxicity of NaOTf to plants is manifested as:
Root development obstruction: F ⁻ inhibits cytokinin synthesis, resulting in a 30% reduction in Arabidopsis root length.
Decreased photosynthetic efficiency: At a concentration of 10 mg/kg, the chlorophyll content in wheat leaves decreased by 25%, and the net photosynthetic rate decreased by 18%.
Atmospheric diffusion: synergistic risk of volatility and particulate matter
Release of volatile organic compounds (VOCs)
NaOTf can decompose under high temperature (>100 ℃) or acidic conditions to produce trifluoromethanesulfonic acid (CF ∝ SO ∝ H), with a vapor pressure of 0.1 mmHg (25 ℃), which can easily enter the atmosphere through volatilization. Model predictions show that in an unprotected storage tank leakage scenario, 1 kg of NaOTf can form a pollution cloud with a radius of 50 meters within 24 hours.
Particle Adsorption and Long Distance Transport
NaOTf can adsorb onto PM2.5 particles and achieve cross regional transport through atmospheric circulation:
Dry settling efficiency: Under a wind speed of 3 m/s, the settling rate of NaOTf particles is 0.5 cm/s, with a half-life of 15 days.
Wet deposition risk: Acidic precipitation (pH<4.5) can accelerate the dissolution of NaOTf, leading to secondary water pollution. For example, in a haze event in a certain city, the concentration of NaOTf in PM2.5 reached 0.8 μ g/m ³, causing the F ⁻ concentration in the river 50 kilometers downstream to exceed the standard by twice.
Comparison between Sodium Trifluoromethanesulfonate and Traditional Electrolytes (such as NaCl)
Comparison of Physical and Chemical Properties
Solubility: NaCl: It has extremely high solubility in water, about 360g/L at 20 ° C, and its solubility does not change significantly with temperature. This makes NaCl an ideal electrolyte in many aqueous solution systems, making it easy to prepare solutions of different concentrations.
NaOTf: Although NaOTf has a relatively high solubility in water, the specific value may vary depending on temperature and solvent. Generally speaking, due to the presence of its organic anions, NaOTf has better solubility in certain organic solvents than NaCl, which provides the possibility for its application in non-aqueous systems.
Conductivity: NaCl: In aqueous solutions, NaCl has a high conductivity, especially at high concentrations, which can form effective ion conduction pathways. However, as the concentration further increases, due to the enhanced interaction between ions, the conductivity may reach a maximum value and then slightly decrease.
The conductivity of NaOTf: NaOTf solution also exhibits concentration dependence, but due to the larger volume and lower charge density of OTf ⁻ anions, their conductivity at the same concentration may be slightly lower than that of NaCl. However, under certain specific conditions, such as using mixed solvents or optimizing solution composition, the conductivity of NaOTf can be significantly improved.
Viscosity and fluidity: The viscosity of NaCl: NaCl aqueous solution is close to that of pure water, and the viscosity changes little with increasing concentration, maintaining good fluidity.
NaOTf: Due to the larger volume of OTf ⁻ anions, the viscosity of NaOTf solution may be slightly higher than that of NaCl solution of the same concentration, especially at high concentrations. This may affect its performance in certain applications that require high liquidity.
Thermal stability and chemical stability: NaCl: NaCl has extremely high thermal and chemical stability, can maintain stability over a wide range of temperatures and pH, and is not easily decomposed or undergoes chemical reactions.
NaOTf also exhibits good thermal stability, but its decomposition temperature may be slightly lower than NaCl. In terms of chemical stability, NaOTf may be more sensitive to certain strong oxidants or reducing agents, and the selection should be based on specific application conditions.
Comparison of application fields
Battery technology
NaCl: Although NaCl itself is not directly used in modern high-performance batteries, its fundamental research as an electrolyte is crucial for understanding ion conduction mechanisms. In addition, NaCl solution is sometimes used as an electrolyte for low-cost, low performance battery systems, such as certain types of zinc air batteries.
NaOTf: Due to its excellent solubility, conductivity, and stability in organic solvents, NaOTf has shown great potential in high-performance energy storage devices such as lithium-ion batteries, sodium ion batteries, and supercapacitors. Especially in non-aqueous batteries, NaOTf as a supporting electrolyte can significantly improve the energy density and cycling stability of the battery.
Biomedical research
NaCl: NaCl is the main component of physiological saline and is widely used in cell culture, drug delivery, and buffer preparation in biological experiments. Its biocompatibility and stability make it a standard electrolyte in the biomedical field.
NaOTf: Although its applications in the biomedical field are relatively limited, its unique chemical properties make it potentially valuable in certain specific studies. For example, as a probe molecule or marker, it is used to study the charge distribution on ion channels or cell membranes. However, due to the incomplete understanding of the biological activity of OTf ⁻ anions, their biomedical applications require careful evaluation.
Electrochemical synthesis and catalysis
NaCl plays an important role as an electrolyte in electrochemical synthesis, such as the production of chlorine and hydrogen in the chlor alkali industry. Its low cost and easy availability make it an ideal choice for large-scale industrial applications.
NaOTf: Due to its excellent electrochemical properties, NaOTf has attracted attention in the fields of organic electrosynthesis and catalysis. It can promote the electrochemical conversion of complex organic molecules, improve the selectivity and efficiency of the reaction. In addition, NaOTf can also be used as a component of ionic liquids or deep eutectic solvents for green chemistry and sustainable development technologies.
Sodium trifluoromethanesulfonate is a versatile chemical compound with a wide range of applications in organic synthesis, electrochemistry, and analytical chemistry. Its unique physical and chemical properties, such as high solubility, strong acidity of its conjugate acid, and excellent stability, make it a valuable reagent and electrolyte in various industrial and research processes. However, it is important to be aware of its potential hazards and take appropriate safety measures when handling and storing the compound. By understanding its properties and applications, we can make the most of sodium trifluoromethanesulfonate while minimizing its negative impacts on human health and the environment.
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