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425583

Sigma-Aldrich

p-Tolyl trifluoromethanesulfonate

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
MDL number:
MFCD00192507
UNSPSC Code:
12352100
PubChem Substance ID:
24866645

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

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[1] and arylation of pyridine N-oxide.[2]

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_germany

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBF8388V
11114CB
10930EO
10826JG
02325AI

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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
Direct arylation of azine N-oxides with aryl triflates.
Schipper DJ, et al.
Tetrahedron, 65(26), 4977-4983 (2009)

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