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483869

Sigma-Aldrich

5-(Trifluoromethyl)dibenzothiophenium tetrafluoroborate

97%

Synonyme(s) :

S-(Trifluoromethyl)dibenzothiophenium tetrafluoroborate, Umemoto reagent

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About This Item

Formule empirique (notation de Hill):
C13H8BF7S
Numéro CAS:
131880-16-5
Poids moléculaire :
340.07
Numéro MDL:
MFCD01073545
Code UNSPSC :
12352101
ID de substance PubChem :
24871922
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

97%

Pf

162-164 °C (lit.)

Chaîne SMILES 

F[B-](F)(F)F.FC(F)(F)[S+]1c2ccccc2-c3ccccc13

InChI

1S/C13H8F3S.BF4/c14-13(15,16)17-11-7-3-1-5-9(11)10-6-2-4-8-12(10)17;2-1(3,4)5/h1-8H;/q+1;-1

Clé InChI

VTVISWLINKWMQZ-UHFFFAOYSA-N

Application

  • Pd(II)-catalyzed trifluoromethylation
  • Copper-catalyzed trifluoromethylation of aryl boronic acids using a Collidine as a trifluoromethylating reagent
  • Pd-catalyzed electrophilic ortho-trifluoromethylation of arenes

Used in the stereoselective preparation of
  • Trifluoromethyl-substituted alkenes via copper-catalyzed trifluoromethylation of terminal alkenes
  • Trifluoromethyl-bearing quaternary carbon centers by Pd-catalyzed intramolecular decarboxylative allylation of α-trifluoromethyl β-keto esters

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Difluoromethyl triflate 95%

Sigma-Aldrich

792764

Difluoromethyl triflate

Jun Xu et al.
Chemical communications (Cambridge, England), 47(14), 4300-4302 (2011-03-08)
A copper-catalyzed process for trifluoromethylation of aryl, heteroaryl, and vinyl boronic acids has been developed. The reaction is conducted under mild conditions and shows tolerance to moisture and a variety of functional groups.
Construction of Trifluoromethyl-Bearing Quaternary Carbon Centers by Intramolecular Decarboxylative Allylation of α-Trifluoromethyl β-Keto Esters
Shibata, N.; et al.
Advanced Synthesis & Catalysis, 353, 2037-2041 (2011)
Jun Xu et al.
Journal of the American Chemical Society, 133(39), 15300-15303 (2011-09-15)
An unprecedented type of reaction for Cu-catalyzed trifluoromethylation of terminal alkenes is reported. This reaction represents a rare instance of catalytic trifluoromethylation through C(sp(3))-H activation. It also provides a mechanistically unique example of Cu-catalyzed allylic C-H activation/functionalization. Both experimental and
Xisheng Wang et al.
Journal of the American Chemical Society, 132(11), 3648-3649 (2010-02-27)
A Pd(II)-catalyzed C-H activation/trifluoromethylation of arenes with an electrophilic trifluoromethylation reagent using diverse heterocycle directing groups is reported. The presence of trifluoroacetic acid is crucial for this catalytic reaction.
Xing-Guo Zhang et al.
Journal of the American Chemical Society, 134(29), 11948-11951 (2012-07-12)
A Pd(II)-catalyzed trifluoromethylation of ortho C-H bonds with an array of N-arylbenzamides derived from benzoic acids is reported. N-Methylformamide has been identified as a crucial promoter of C-CF(3) bond formation from the Pd center. X-ray characterization of the C-H insertion

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