Trifluoromethanesulphonamide
[CAS# 421-85-2]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: Trifluoromethanesulphonamide
• Synonyms: triflimidic acid
• Molecular Formula: CH₂F₃NO₂S
• Molecular Weight: 149.09
• CAS Registry Number: 421-85-2
• EC Number: 627-705-1
• SMILES: C(F)(F)(F)S(=O)(=O)N

Properties

• Melting point: 120-124 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Trifluoromethanesulphonamide, with the chemical formula CF3SO2NH2, is an organofluorine compound characterized by the presence of a trifluoromethyl group attached to a sulphonamide moiety. This compound is recognized for its unique chemical properties and diverse applications in organic synthesis and material science.

The discovery of trifluoromethanesulphonamide emerged from the broader study of sulphonamide derivatives and their potential applications. The trifluoromethyl group, known for its electron-withdrawing properties, enhances the reactivity of the sulphonamide functionality. The synthesis of trifluoromethanesulphonamide involves the reaction of trifluoromethylsulphonyl chloride with ammonia or primary amines. This process provides a straightforward route to obtain the trifluoromethanesulphonamide with high purity.

In organic synthesis, trifluoromethanesulphonamide is widely used as a reagent and catalyst. Its strong electron-withdrawing trifluoromethyl group makes it an effective electrophile in various chemical reactions. For instance, it can participate in nucleophilic substitution reactions where it acts as a sulphonamide donor, facilitating the formation of new carbon-nitrogen bonds. Additionally, it is employed in the synthesis of complex molecules and pharmaceuticals due to its ability to modify functional groups and enhance reaction selectivity.

The compound also finds applications in materials science, particularly in the development of fluorinated polymers and advanced materials. Trifluoromethanesulphonamide can be used to introduce trifluoromethyl groups into polymers, imparting unique properties such as increased hydrophobicity and chemical resistance. These modified polymers are valuable in various industrial applications, including coatings, adhesives, and membranes.

Moreover, trifluoromethanesulphonamide is utilized in the pharmaceutical industry for the synthesis of active pharmaceutical ingredients (APIs). Its reactivity allows for the introduction of trifluoromethyl groups into drug molecules, which can enhance their biological activity and stability. Research continues to explore its potential in the development of new therapeutic agents and advanced drug delivery systems.

In summary, trifluoromethanesulphonamide is a versatile chemical compound with significant applications in organic synthesis, materials science, and pharmaceuticals. Its unique chemical properties make it a valuable reagent and catalyst in various chemical transformations and material modifications.

References

1993. Sulfonylmethanesulfonamide inhibitors of carbonic anhydrase. Journal of Medicinal Chemistry, 36(15).
DOI: 10.1021/jm00067a012

2024. Triflamidation of Camphene in Nitrile Medium. Russian Journal of Organic Chemistry, 60(6).
DOI: 10.1134/s1070428024060101

2021. Development of a proton exchange membrane based on trifluoromethanesulfonylimide-grafted polybenzimidazole. Polymer Journal, 53(12).
DOI: 10.1038/s41428-021-00551-6