Phenyl trifluoromethanesulfonate

Name: Phenyl trifluoromethanesulfonate
Brand: ALDRICH

98%

Synonym(s):

Phenyl triflate

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About This Item

Linear Formula:

C₆H₅SO₃CF₃

CAS Number:

17763-67-6

Molecular Weight:

226.17

NACRES:

NA.22

PubChem Substance ID:

24866540

UNSPSC Code:

12352100

MDL number:

MFCD00192399

Assay:

98%

Form:

liquid

Key Documents

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InChI

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

SMILES string

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

InChI key

GRJHONXDTNBDTC-UHFFFAOYSA-N

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.)

functional group

fluoro, triflate

Quality Level

200

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This Item	164283	367907	ALD00422
Sigma-Aldrich 423939 Phenyl trifluoromethanesulfonate	Sigma-Aldrich 164283 Methyl trifluoromethanesulfonate	Sigma-Aldrich 367907 Sodium trifluoromethanesulfonate	Sigma-Aldrich ALD00422 2-Formylphenyl sulfofluoridate
assay 98%	assay ≥98%	assay 98%	assay -
bp 99-100 °C/60 mmHg (lit.)	bp 94-99 °C (lit.)	bp -	bp -
form liquid	form liquid	form solid	form liquid
refractive index n20/D 1.435 (lit.)	refractive index n20/D 1.326 (lit.)	refractive index -	refractive index n20/D 1.5086
density 1.396 g/mL at 25 °C (lit.)	density 1.45 g/mL at 25 °C (lit.)	density -	density 1.4545 g/mL at 25 °C
functional group fluoro	functional group fluoro, triflate	functional group fluoro, triflate	functional group -

General description

Phenyl trifluoromethanesulfonate (phenyl triflate) is an aryl fluorosulphonate. It has been synthesized by the reaction of phenol with fluorosulphonic anhydride.[1]

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.[2]
As a reactant in the one pot synthesis of carbazoles by palladium-catalyzed N-arylation of anilines with phenyl triflate followed by oxidative coupling.[3]
Synthesis of N-(2,6-diarylbenzoyl)anilines by diarylation of benzanilides with phenyl triflate in the presence of palladium-based catalyst.[4]
As an arylating agent in the synthesis of (R)-2-phenyl-2,3-dihydrofuran by the arylation of 2,3-dihydrofuran.[5]

pictograms

GHS06,GHS05

signalword

Danger

hcodes

H301 + H311,H314

pcodes

P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P361 + P364 - P405

Hazard Classifications

Acute Tox. 3 Oral - Skin Corr. 1B

Storage Class

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

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number

0000320539

0000257739

0000130132

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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)

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)

Regioselective arylation of benzanilides with aryl triflates or bromides under palladium catalysis.

Kametani Y, et al.

Tetrahedron Letters, 41(15), 2655-2658 (2000)

Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.

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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