734039
4-tert-Butyl-2,6-dimethylphenylsulfur trifluoride
Synonym(s):
Fluolead™
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About This Item
Empirical Formula (Hill Notation):
C12H17F3S
CAS Number:
Molecular Weight:
250.32
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352002
MDL number:
InChI
1S/C12H17F3S/c1-8-6-10(12(3,4)5)7-9(2)11(8)16(13,14)15/h6-7H,1-5H3
SMILES string
Cc1cc(cc(C)c1S(F)(F)F)C(C)(C)C
InChI key
VRTQPEYVMHATOA-UHFFFAOYSA-N
form
solid
mp
62-68 °C
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:
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.
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
- 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.
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
Legal Information
Fluolead is a trademark of UBE America, Inc.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Skin Corr. 1B
supp_hazards
Storage Class
6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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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