BENZENESULFINYL CHLORIDE

Uses

Benzenesulfinyl Chloride is used in preparation of sulfoxides and sulfones; synthesis of chiral sulfinyl-transfer reagents.

Preparation

Benzenesulfinyl Chloride is prepared by reacting sodium benzenesulfinyl or sodium p-toluenesulfinyl with thionyl chloride^[1].

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 3973, 1992 DOI: 10.1016/0040-4039(92)88076-H

Safety Profile

May explode if stored in a sealedcontainer. When heated to decomposition it emits toxicfumes of SOx and Cl^-.

Synthesis

A mixture of 30.4 g (0.2 mol) of phenyl thioacetate and 20.4 g (0.2 mol) of acetic anhydride is chlorinated at -10 to 0℃. The color changes to yellow, then red, and then back to yellow. The reaction mixture is heated to 80℃ under reduced pressure (3.5 kPa), until the residue begins to boil, after which it is cooled; yield: 31.5–31.8 g (98.1– 99.1%).

storage

Benzenesulfinyl Chloride has been reported that arenesulfinyl chlorides should not be distilled above 2 mmHg pressure because of the danger of explosion. Care also should be taken to avoid exposure of these sulfinyl chlorides to moisture (i.e. air, skin) owing to decomposition and formation of corrosive HCl.

References

[1]. Kurzer, F. OSC 1963, 4, 937.

Raw materials

Preparation Products