All Photos(1)
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
Linear Formula:
(CH3C6H4SO2)2O
CAS Number:
Molecular Weight:
326.39
Beilstein:
2223702
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
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)
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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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