903132

1-(Fluorosulfonyl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate

≥95%

• Synonym(s): 1-(Fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate, Fluorosulfuryl imidazolium triflate salt, SuFEx-IT
• Empirical Formula (Hill Notation): C₆H₈F₄N₂O₅S₂
• CAS Number: 2179072-33-2
• Molecular Weight: 328.26
• UNSPSC Code: 12352101
• NACRES: NA.22

Properties

• assay: ≥95%
• form: solid
• mp: 64-65 °C
• functional group: fluoro; triflate
• storage temp.: 2-8°C

Description

Application

This solid fluorosulfuryl imidazolium triflate salt, SuFEx-IT, is a convenient alternative to sulfuryl fluoride (SO₂F₂), which is a harmful fumigant gas with difficult handling procedures that make SO₂F₂ -- and the products it is capable of making -- difficult to access. However, this reagent possesses novel reactivity, selectivity, and scope and was demonstrated by the labs of K. Barry Sharpless and Jiajia Dong to convert phenols, primary amines, and secondary amines to fluorosulfates and sulfamoyl fluorides. Fluorosulfates are used widely in biological studies, medicinal chemistry, and work as a pseudohalide in Pd-catalysed cross-coupling reactions.
Store in dry environment (desiccator advised) at 4 °C.

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Other Notes

A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an “F^-SO²⁺” Donor of Unprecedented Reactivity, Selectivity, and Scope

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H314
• pcodes: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Storage Class: 8A - Combustible corrosive hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable