259764

Sigma-Aldrich

p-Toluenesulfonic anhydride

97%

Linear Formula:
(CH3C6H4SO2)2O
CAS Number:
Molecular Weight:
326.39
Beilstein/REAXYS Number:
2223702
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

97%

mp

121-127 °C (lit.)

SMILES string

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

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

InChI key

PDVFSPNIEOYOQL-UHFFFAOYSA-N

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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.

Packaging

5, 25 g in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2585PSN2 8 / PGIII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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.
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...

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