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483869

Sigma-Aldrich

5-(Trifluoromethyl)dibenzothiophenium tetrafluoroborate

97%

Synonym(s):

S-(Trifluoromethyl)dibenzothiophenium tetrafluoroborate, Umemoto reagent

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About This Item

Empirical Formula (Hill Notation):
C13H8BF7S
CAS Number:
131880-16-5
Molecular Weight:
340.07
MDL number:
MFCD01073545
UNSPSC Code:
12352101
PubChem Substance ID:
24871922
NACRES:
NA.22

Assay

97%

mp

162-164 °C (lit.)

SMILES string

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

InChI key

VTVISWLINKWMQZ-UHFFFAOYSA-N

Related Categories

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

PRTR

Class I Designated Chemical Substances

JAN Code

483869-1G:4548173159713
483869-BULK:
483869-VAR:

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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Sigma-Aldrich

342017

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Difluoromethyl triflate 95%

Sigma-Aldrich

792764

Difluoromethyl triflate

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.
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.
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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