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

Properties

• Quality Level: 200
• assay: 97%
• form: solid
• mp: 121-127 °C (lit.)
• functional group: tosylate
• 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

Description

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.

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H314
• pcodes: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Storage Class: 8A - Combustible corrosive hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges