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Merck
CN

259764

p-Toluenesulfonic anhydride

97%

Synonym(s):

(4-Methylphenyl)sulfonyl 4-methylbenzenesulfonate, 4-Methylbenzenesulfonic acid anhydride, 4-Methylbenzenesulfonic anhydride, 4-Methylphenylsulfonic anhydride, 4-Toluenesulfonic acid anhydride, Toluene-4-sulfonic acid ahnydride, p-Toluenesulfonic acid anhydride, p-Toluenesulfonyl anhydride, p-Tolylsulfonyl 4-methylbenzenesulfonate

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About This Item

Linear Formula:
(CH3C6H4SO2)2O
CAS Number:
4124-41-8
Molecular Weight:
326.39
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24855433
EC Number:
223-926-9
Beilstein/REAXYS Number:
2223702
MDL number:
MFCD00008548
Assay:
97%
Form:
solid

Key Documents

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InChI key

PDVFSPNIEOYOQL-UHFFFAOYSA-N

InChI

1S/C14H14O5S2/c1-11-3-7-13(8-4-11)20(15,16)19-21(17,18)14-9-5-12(2)6-10-14/h3-10H,1-2H3

SMILES string

Cc1ccc(cc1)S(=O)(=O)OS(=O)(=O)c2ccc(C)cc2

assay

97%

form

solid

mp

121-127 °C (lit.)

functional group

tosylate

Quality Level

200

Related Categories

General description

p-Toluenesulfonic anhydride acts as electrophilic species and activates 2-deoxy-sugar hemiacetals in situ, which reacts stereoselectively with nucleophilic acceptors to afford β-anomers.

Application

p-Toluenesulfonic anhydride has been employed as reagent in palladium-catalyzed allylic alkenylation of allylic alcohols with n-butyl acrylate.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN0545
BCCF9532
BCBT3335
BCBQ2378V
BCBK3858V

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John Paul Issa et al.
Journal of the American Chemical Society, 136(15), 5740-5744 (2014-03-29)
The efficient and stereoselective construction of glycosidic linkages remains one of the most formidable challenges in organic chemistry. This is especially true in cases such as β-linked deoxy-sugars, where the outcome of the reaction cannot be controlled using the stereochemical
Naofumi Tsukada et al.
Chemical communications (Cambridge, England), (19)(19), 2404-2405 (2003-11-01)
Various allylic alcohols reacted with n-butyl acrylate in the presence of p-toluenesulfonic anhydride and palladium catalysts to yield the corresponding n-butyl 2,5-dienoates with high regioselectivity.

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