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483877

5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate

Name: 5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate
Brand: ALDRICH

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

Related Categories

Halogenation Reagents

Heterocyclic Building Blocks

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

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

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)

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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 alkenes through allylic C-H bond activation.

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

Copper-catalyzed trifluoromethylation of terminal alkynes using Umemoto's reagent

Luo, D.-F.; et al.

Tetrahedron Letters, 53, 2769-2772 (2012)

Pd(II)-catalyzed ortho trifluoromethylation of arenes and insights into the coordination mode of acidic amide directing groups.

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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