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483877

Sigma-Aldrich

5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate

97%

Synonym(s):

S-(Trifluoromethyl)dibenzothiophenium triflate, S-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate

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About This Item

Empirical Formula (Hill Notation):
C14H8F6O3S2
CAS Number:
129946-88-9
Molecular Weight:
402.33
MDL number:
MFCD00236132
UNSPSC Code:
12352101
PubChem Substance ID:
24871923
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

150 °C (lit.)

SMILES string

[O-]S(=O)(=O)C(F)(F)F.FC(F)(F)[S+]1c2ccccc2-c3ccccc13

InChI

1S/C13H8F3S.CHF3O3S/c14-13(15,16)17-11-7-3-1-5-9(11)10-6-2-4-8-12(10)17;2-1(3,4)8(5,6)7/h1-8H;(H,5,6,7)/q+1;/p-1

InChI key

QXXHXTRTGZBOGD-UHFFFAOYSA-M

Application

  • Pd(II)-catalyzed trifluoromethylation
  • Electrophilic trifluoromethylation in ionic liquids
  • Used in the stereoselective preparation of trifluoromethylalkynes by trifluoromethylation of terminal alkynes using Umemoto′s reagent and a copper catalyst

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ionic liquids as new media for electrophilic trifluoromethylation reactions
Pegot, B.; et al.
Journal of Fluorine Chemistry, 134, 156-159 (2012)
Copper-catalyzed trifluoromethylation of terminal alkynes using Umemoto's reagent
Luo, D.-F.; et al.
Tetrahedron Letters, 53, 2769-2772 (2012)
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
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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