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Sigma-Aldrich

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

≥95%

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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:
Molecular Weight:
328.26
UNSPSC Code:
12352101
NACRES:
NA.22

assay

≥95%

form

solid

mp

64-65 °C

storage temp.

2-8°C

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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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Corrosion

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Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Taijie Guo et al.
Angewandte Chemie (International ed. in English), 57(10), 2605-2610 (2017-12-26)
Sulfuryl fluoride, SO2 F2 , has been found to derivatize phenols in all kinds of environments, even those in highly functional molecules. We now report that a solid fluorosulfuryl imidazolium triflate salt delivers the same "F-SO2 +" fragment to Nu-H

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The Dong Lab focuses on the synthesis and application of main-group fluorides by studying the reactivity and transformation of those main-group fluorides into organic molecules, including new applications of sulfuryl fluoride chemistry; and new catalysts and process improvements for polysulfate and polysulfonate.

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