| Identification | More | [Name]
4-Methylbenzenesulfonic anhydride | [CAS]
4124-41-8 | [Synonyms]
1,3-BIS(4-METHYLPHENYL)-1,1,3,3-TETRAOXO-1LAMBDA6,3LAMBDA6-DITHIOXANE
4-TOLUENESULPHONIC ANHYDRIDE
P-TOLUENESULFONIC ANHYDRIDE
P-TOLUENESULPHONIC ANHYDRIDE
TOLUENE-4-SULFONIC ANHYDRIDE
Tosic anhydride
toluene-p-sulphonic anhydride
4-Toluenesulphonic acid anhydride
4-TOLUENESULFONIC ANHYDRIDE
3-Toluenesulfonicanhydride
4-Methylbenzenesulfonic anhydride
(4-Methylphenyl)sulfonyl 4-methylbenzenesulfonate
Toluene-4-sulfonic acid anhydride
Toluene-p-anhydride
Bis(4-methylbenzenesulfonic)anhydride
Bis(p-toluenesulfonic)anhydride
Di-p-toluenesulfonic anhydride | [EINECS(EC#)]
223-926-9 | [Molecular Formula]
C14H14O5S2 | [MDL Number]
MFCD00008548 | [Molecular Weight]
326.39 | [MOL File]
4124-41-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white to cream powder | [Melting point ]
121-127 °C(lit.)
| [Boiling point ]
478.0±48.0 °C(Predicted) | [density ]
1.361±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [form ]
Powder, Crystals and/or Chunks | [color ]
Off-white to gray | [Sensitive ]
Moisture Sensitive | [BRN ]
2223702 | [InChIKey]
PDVFSPNIEOYOQL-UHFFFAOYSA-N | [CAS DataBase Reference]
4124-41-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Danger | [Hazard statements ]
H314 | [Precautionary statements ]
P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363 | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2585 8/PG 3
| [WGK Germany ]
3
| [F ]
10-21 | [Hazard Note ]
Irritant | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29041000 |
| Hazard Information | Back Directory | [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. |
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