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259764

Sigma-Aldrich

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
Beilstein:
2223702
EC Number:
223-926-9
MDL number:
MFCD00008548
UNSPSC Code:
12352100
PubChem Substance ID:
24855433
NACRES:
NA.22

Quality Level

200

Assay

97%

form

solid

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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