BENZENESULFONIC ANHYDRIDE Chemical Properties

Melting point:

60-85° (softens about 55°); mp 88-91° (softens about 75°)

Boiling point:

463.7±28.0 °C(Predicted)

Density 

1.439±0.06 g/cm3(Predicted)

form 

powder to crystal

color 

White to Light yellow to Light orange

Merck 

14,1071

Safety Information

RIDADR 

3261

HS Code 

2904.10.3700

HazardClass 

8

PackingGroup 

III

BENZENESULFONIC ANHYDRIDE Usage And Synthesis

Uses

In Friedel-Crafts sulfone synthesis; in other sulfonylation reactions.

Preparation

Benzenesulfonic anhydride is prepared on a large scale by heating benzenesulfonic acid with excess phosphorus pentoxide mixed with an inert support. An inert support of 1:1 Supercel kieselguhr and Gooch asbestos  was mixed with phosphorus pentoxide and slowly added to benzenesulfonic acid, first at rt then heating to 100 °C. The resultant mixture was heated at 100 °C for 5 h, 1,2-dichloroethane was added, and the solution  was refluxed for 10 min. After cooling and successive filtrations, benzenesulfonic anhydride was recovered in 70% yield.

storage

The reagent can be stored at rt for extended periods under anhydrous conditions. Liquefication occurs upon exposure to air for 2.5 h. Explosive when mixed with 90-95% H2O2.

Purification Methods

Crystallise the anhydride from Et2O (m 88.5-91.5o), CHCl3 or chlorobenzene (m 90-92o). Store it dry. [Field J Am Chem Soc 74 394 1952, Beilstein 11 H 3, 11 I 11, 11 II 23, 11 III 50, 11 IV 50.]

BENZENESULFONIC ANHYDRIDE(512-35-6)Related Product Information

• S-Methyl methanethiolsulfonate
• BENZENESULFINIC ACID
• P-Toluenesulfonic anhydride
• BENZENESULFONIC ANHYDRIDE
• Methanesulfonic anhydride