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

Name: 1-(Fluorosulfonyl)-2,3-dimethyl-1<I>H</I>-imidazol-3-ium trifluoromethanesulfonate
Brand: ALDRICH

≥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

MDL number:

MFCD31693095

UNSPSC Code:

12352101

NACRES:

NA.22

Assay:

≥95%

Form:

solid

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Properties

assay

≥95%

form

solid

mp

64-65 °C

functional group

fluoro, triflate

storage temp.

2-8°C

SMILES string

F[S](=O)(=O)[n+]1c([n](cc1)C)C.FC(F)(F)[S](=O)(=O)[O-]

InChI

1S/C5H8FN2O2S.CHF3O3S/c1-5-7(2)3-4-8(5)11(6,9)10;2-1(3,4)8(5,6)7/h3-4H,1-2H3;(H,5,6,7)/q+1;/p-1

InChI key

YAZBWGHMIMMBFC-UHFFFAOYSA-M

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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