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425583

p-Tolyl trifluoromethanesulfonate

Name: <I>p</I>-Tolyl trifluoromethanesulfonate
Brand: ALDRICH

97%

Synonym(s):

p-Tolyl triflate

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About This Item

Linear Formula:

CF₃SO₃C₆H₄CH₃

CAS Number:

29540-83-8

Molecular Weight:

240.20

UNSPSC Code:

12352100

PubChem Substance ID:

24866645

MDL number:

MFCD00192507

Assay:

97%

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Properties

assay

97%

refractive index

n20/D 1.441 (lit.)

bp

115 °C/50 mmHg (lit.)

density

1.342 g/mL at 25 °C (lit.)

SMILES string

Cc1ccc(OS(=O)(=O)C(F)(F)F)cc1

InChI

1S/C8H7F3O3S/c1-6-2-4-7(5-3-6)14-15(12,13)8(9,10)11/h2-5H,1H3

InChI key

XXSBXVHIYGQWDV-UHFFFAOYSA-N

Description

General description

p-Tolyl trifluoromethanesulfonate (p-tolyl triflate) is an aryl triflate.

Application

p-Tolyl trifluoromethanesulfonate (p-tolyl triflate) may be used in the asymmetric α-arylation of ketones and arylation of pyridine N-oxide.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2 - Skin Corr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

192.2 °F - closed cup

flash_point_c

89 °C - closed cup

ppe

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

Regulatory Information

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Direct arylation of azine N-oxides with aryl triflates.

Schipper DJ, et al.

Tetrahedron, 65(26), 4977-4983 (2009)

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