734039

Sigma-Aldrich

4-tert-Butyl-2,6-dimethylphenylsulfur trifluoride

Synonym(s):
Fluolead
Empirical Formula (Hill Notation):
C12H17F3S
CAS Number:
Molecular Weight:
250.32
MDL number:
PubChem Substance ID:
NACRES:
NA.22

mp

62-68 °C

Quality Level

SMILES string

Cc1cc(cc(C)c1S(F)(F)F)C(C)(C)C

InChI

1S/C12H17F3S/c1-8-6-10(12(3,4)5)7-9(2)11(8)16(13,14)15/h6-7H,1-5H3

InChI key

VRTQPEYVMHATOA-UHFFFAOYSA-N

General description

4-tert-Butyl-2,6-dimethylphenylsulfur trifluoride is a thermally stable, easy-to-handle, versatile deoxofluorinating agent that also shows high stability on contact with water. It is a superior alternative to diethylaminosulfur trifluoride (DAST).

Application

Features:
  • Tolerance of many functional groups
  • Highly selective functionalization
  • Highly efficient and broad reaction scope
  • Mild reaction conditions

Generally superior reactivity and selectivity to SF4 and easier and safer to handle.

Shown to promote nucleophilic deoxofluorination reactions and exhibits excellent thermal stability, up to 150 °C, therefore rendering it safely applicable in a variety of processes, including industrial scale production.

Fluolead Scheme 1
Novel fluorinating reagent applicable to a variety of chemical processes (Scheme 1).

Refer to the Datasheet for more information on Fluolead: A Novel New Versatile Fluorinating Agent

Packaging

25 g in PFA/FEP bottle
1 g in PFA/FEP bottle
5 g in poly bottle

Legal Information

Fluolead is a trademark of UBE America, Inc.

Certificate of Analysis

Certificate of Origin

Kirk, K. L
Organic Process Research & Development, 12, 305-321 (2008)
Discovery of 4-tert-butyl-2, 6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity.
Umemoto T, et al.
Journal of the American Chemical Society, 132(51), 18199-18205 (2010)
Teruo Umemoto et al.
Journal of the American Chemical Society, 132(51), 18199-18205 (2010-12-04)
Versatile, safe, shelf-stable, and easy-to-handle fluorinating agents are strongly desired in both academic and industrial arenas, since fluorinated compounds have attracted considerable interest in many areas, such as drug discovery, due to the unique effects of fluorine atoms when incorporated...

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