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| | P-Toluenesulfonic anhydride Basic information |
| | P-Toluenesulfonic anhydride Chemical Properties |
| Melting point | 121-127 °C(lit.) | | Boiling point | 478.0±48.0 °C(Predicted) | | density | 1.361±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,2-8°C | | form | Powder, Crystals and/or Chunks | | color | Off-white to gray | | Sensitive | Moisture Sensitive | | BRN | 2223702 | | 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 | | InChIKey | PDVFSPNIEOYOQL-UHFFFAOYSA-N | | SMILES | Cc1ccc(cc1)S(=O)(=O)OS(=O)(=O)c2ccc(C)cc2 | | CAS DataBase Reference | 4124-41-8(CAS DataBase Reference) |
| Hazard Codes | C | | Risk Statements | 34 | | Safety Statements | 26-36/37/39-45 | | RIDADR | UN 2585 8/PG 3 | | WGK Germany | 3 | | F | 10-21 | | Hazard Note | Irritant | | HazardClass | 8 | | PackingGroup | II | | HS Code | 29041000 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Eye Dam. 1
Skin Corr. 1B |
| | P-Toluenesulfonic anhydride Usage And Synthesis |
| Chemical Properties | Off-white to cream powder | | Uses | p-Toluenesulfonic anhydride has been employed as reagent in palladium-catalyzed allylic alkenylation of allylic alcohols with n-butyl acrylate. | | Reactions | Used as Reagent for tosylation.
p-Toluenesulfonic anhydride is a reliable way for the tosylation of many nucleophiles, primarily, for alcohols. The regent is a shelf-stable, well-soluble solid and “softer” electrophile than p-toluenesulfonyl chloride. Lipophilic alcohols can be easily tosylated in a very economical and eco-friendly way simply by using Ts2O in water without any catalyst. The tosylation can be realized in a few minutes under microwave assistance, giving p-toluenesulfonic acid as the only byproduct[1]. Besides, it can be applied as an additive in palladium-catalyzed allylic alkenylation of allylic alcohols.
 | | 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. | | Chemical Reactivity | 4-Toluenesulfonic anhydride has a high chemical reactivity towards common nucleophilic reagents. It can undergo sulfonylation reaction with alcohol hydroxyl groups or amine compounds under alkaline conditions.
| | Synthesis | Add p-toluenesulfonic acid and an m-phosphorous compound used as raw materials into a reaction kettle, dropwise adding thionyl chloride while stirring. Controlling the temperature in the reaction kettle at 68-76 ℃ and heating to perform condensation after dropwise addition; inputting water and hydrochloric acid into the reaction kettle, cooling to 0 ℃. The reaction solution generated in the previous step was drawn into the water, vacuum filtration was performed, and centrifuging was used to obtain a crude product, p-toluenesulfonic anhydride. Furthermore, it was inputting ethyl acetate, performing heating reflux, and freezing to perform crystallization, thus obtaining the qualified finished product. | | References | [1] OLIVERIO M, COSTANZO P, PAONESSA R, et al. Catalyst-free tosylation of lipophilic alcohols in water†[J]. RSC Advances, 2012, 8: 2548-2552. DOI:10.1039/C2RA23067D. |
| | P-Toluenesulfonic anhydride Preparation Products And Raw materials |
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