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  • 903132 - 1-(Fluorosulfonyl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate

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903132 Sigma-Aldrich

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

≥95%

Synonym: 1-(Fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate, Fluorosulfuryl imidazolium triflate salt, SuFEx-IT

  • CAS Number 2179072-33-2

  • Empirical Formula (Hill Notation) C6H8F4N2O5S2

  • Molecular Weight 328.26

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Properties

Related Categories C-X Bond Formation (Non-Halogen), Chemical Synthesis, Other Non-Halogen Reagents for C-X Bond Formation, Synthetic Reagents
assay   ≥95%
mp   64-65 °C
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.

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 & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Dong – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Dong – Professor Product Portal
Keywords: Click chemistry, Organic synthesis, transformation

Peer-Reviewed Papers
15

References

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