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903132

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C6H8F4N2O5S2
CAS Number:
2179072-33-2
Molecular Weight:
328.26
UNSPSC Code:
12352101
NACRES:
NA.22

Assay

≥95%

form

solid

mp

64-65 °C

storage temp.

2-8°C

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

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Product No.
Description
Pricing

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

306975

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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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