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734039

Sigma-Aldrich

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

Sinónimos:

Fluolead™

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About This Item

Fórmula empírica (notación de Hill):
C12H17F3S
Número de CAS:
947725-04-4
Peso molecular:
250.32
MDL number:
MFCD11858620
UNSPSC Code:
12352002
PubChem Substance ID:
329764866
NACRES:
NA.22

form

solid

mp

62-68 °C

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

Legal Information

Fluolead is a trademark of UBE America, Inc.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

hcodes

H301,H314

Hazard Classifications

Acute Tox. 3 Oral - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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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