BENZENESULFINYL CHLORIDE Property

Melting point:

38°C

Boiling point:

117.5°C (estimate)

Density 

1.347

refractive index 

1.3470

solubility 

sol Et2O, CHCl3

form 

solid

color 

Plates

Stability:

decomposes in H2O and alcohol

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H290May be corrosive to metals

H314Causes severe skin burns and eye damage

Precautionary statements

P234Keep only in original container.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P363Wash contaminated clothing before reuse.

P390Absorb spillage to prevent material damage.

P405Store locked up.

P406Store in corrosive resistant/… container with a resistant inner liner.

P501Dispose of contents/container to..…

BENZENESULFINYL CHLORIDE Chemical Properties,Usage,Production

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.