Ammonium trifluoromethanesulfonate
[CAS# 38542-94-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonate / sulfinate
• Name: Ammonium trifluoromethanesulfonate
• Synonyms: azanium trifluoromethanesulfonate
• Molecular Formula: CH₄F₃NO₃S
• Molecular Weight: 167.11
• CAS Registry Number: 38542-94-8
• EC Number: 629-264-0
• SMILES: C(F)(F)(F)S(=O)(=O)[O-].[NH4+]

Properties

• Melting point: 224-226 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Ammonium trifluoromethanesulfonate, also known as ammonium triflate, is a chemical compound with the formula CF₃SO₃NH₄. It is a white crystalline salt and belongs to the class of triflate compounds, characterized by the presence of the trifluoromethanesulfonate group (CF₃SO₃-). The compound has gained attention in both organic synthesis and industrial applications due to its stability, solubility, and unique chemical properties.

Ammonium trifluoromethanesulfonate was discovered during the development of triflate salts for use as non-nucleophilic bases and catalysts in organic reactions. Its synthesis typically involves the reaction of trifluoromethanesulfonic acid with ammonia or an ammonium source, resulting in the formation of the ammonium salt. The triflate group is highly electronegative and stable, providing the compound with its distinctive characteristics.

One of the main applications of ammonium trifluoromethanesulfonate is as a catalyst in various organic reactions, particularly in processes that require a strong, non-coordinating anion. The compound is often used in esterifications, alkylations, and other transformations where traditional acids may be too reactive or cause unwanted side reactions. Its ability to act as a proton donor without nucleophilic interference makes it ideal for these applications.

In addition to its catalytic role, ammonium triflate is also employed as a supporting electrolyte in electrochemical systems, including batteries and fuel cells. Its high solubility in organic solvents and stability under various conditions make it a useful component in the development of efficient and durable electrochemical devices. The compound enhances the conductivity of electrolytes without significantly affecting the stability of the system.

Ammonium trifluoromethanesulfonate is also used in material science, particularly in the synthesis of polymers and coatings. Its inclusion in polymerization reactions can improve the thermal and chemical resistance of the resulting materials, making them suitable for use in harsh environments. The compound’s stability and low reactivity also make it an attractive additive in high-performance coatings and adhesives.

Overall, ammonium trifluoromethanesulfonate has proven to be a versatile compound in both organic synthesis and industrial applications. Its discovery and development have expanded the range of available triflate salts, enabling advancements in catalysis, electrochemistry, and material science.

References

2019. Quaternary Ammonium Compounds: Simple in Structure, Complex in Application. Topics in current chemistry (Cham), 377(3).
DOI: 10.1007/s41061-019-0239-2

2019. Highly efficient and facile synthesis of β-enaminones catalyzed by diphenylammonium triflate. Chemical Papers, 73(12).
DOI: 10.1007/s11696-019-00838-2

1997. Synthesis and properties of ambient temperature molten salts based on the quaternary ammonium ion. Ionics, 3(5-6).
DOI: 10.1007/bf02375710