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423939

Sigma-Aldrich

Phenyl trifluoromethanesulfonate

98%

Synonym(s):

Phenyl triflate

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About This Item

Linear Formula:
C6H5SO3CF3
CAS Number:
17763-67-6
Molecular Weight:
226.17
MDL number:
MFCD00192399
UNSPSC Code:
12352100
PubChem Substance ID:
24866540
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.435 (lit.)

bp

99-100 °C/60 mmHg (lit.)

density

1.396 g/mL at 25 °C (lit.)

SMILES string

FC(F)(F)S(=O)(=O)Oc1ccccc1

InChI

1S/C7H5F3O3S/c8-7(9,10)14(11,12)13-6-4-2-1-3-5-6/h1-5H

InChI key

GRJHONXDTNBDTC-UHFFFAOYSA-N

Related Categories

General description

Phenyl trifluoromethanesulfonate (phenyl triflate) is an aryl fluorosulphonate. It has been synthesized by the reaction of phenol with fluorosulphonic anhydride.

Application

Phenyl trifluoromethanesulfonate (phenyl triflate) may be used in the following studies:
  • As an arylating agent for the asymmetric α-arylation of ketones catalyzed by Pd(dba)2 and difluorphos.
  • As a reactant in the one pot synthesis of carbazoles by palladium-catalyzed N-arylation of anilines with phenyl triflate followed by oxidative coupling.
  • Synthesis of N-(2,6-diarylbenzoyl)anilines by diarylation of benzanilides with phenyl triflate in the presence of palladium-based catalyst.
  • As an arylating agent in the synthesis of (R)-2-phenyl-2,3-dihydrofuran by the arylation of 2,3-dihydrofuran.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301 + H311,H314

Hazard Classifications

Acute Tox. 3 Oral - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

159.8 °F - closed cup

Flash Point(C)

71 °C - closed cup

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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Palladium cross-coupling reactions of aryl fluorosulfonates: an alternative to triflate chemistry.
Roth GP and Fuller CE.
The Journal of Organic Chemistry, 56(11), 3493-3496 (1991)
One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling.
Watanabe T, et al.
Chemical Communications (Cambridge, England), 43, 4516-4518 (2007)
Regioselective arylation of benzanilides with aryl triflates or bromides under palladium catalysis.
Kametani Y, et al.
Tetrahedron Letters, 41(15), 2655-2658 (2000)
Palladium-catalyzed asymmetric arylation of 2, 3-dihydrofuran with phenyl triflate. A novel asymmetric catalysis involving a kinetic resolution process.
Ozawa F, et al.
Organometallics, 12(10), 4188-4196 (1993)
Xuebin Liao et al.
Journal of the American Chemical Society, 130(1), 195-200 (2007-12-14)
The asymmetric alpha-arylation of ketones with aryl triflates is described, and the use of this electrophile with nickel and palladium catalysts containing a segphos derivative increases substantially the scope of highly enantioselective arylations of ketone enolates. The combination of aryl

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