CHLOROMETHYL PHENYL SULFONE

CHLOROMETHYL PHENYL SULFONE Property

Melting point:

51-53 °C (lit.)

Boiling point:

130 °C / 1mmHg

Density 

1.336±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

BRN 

2046644

InChIKey

NXAIQSVCXQZNRY-UHFFFAOYSA-N

CAS DataBase Reference

7205-98-3(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

21

HS Code 

29049095

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

CHLOROMETHYL PHENYL SULFONE Chemical Properties,Usage,Production

Uses

Chloromethyl Phenyl Sulfone is used to synthesis of α,β-epoxy sulfones and aziridines; reacts with electrophilic arenes, heterocyclic arenes, and alkenes; source of the α-phenylsulfonylmethyl radical.

Preparation

Preparative Methods of Chloromethyl Phenyl Sulfone: several methods are available. The most convenient is the reaction of Sodium Benzenesulfinate dihydrate with bromochloromethane in dimethyl sulfoxide.

Synthesis

The general procedure for the synthesis of phenylmethyl sulfone and chloromethyl phenyl sulfone from methyl phenyl sulfide was as follows: 0.25 g (2 mmol) of methyl phenyl sulfide was used as a substrate and added to a 50 mL three-necked flask along with 10 mL of acetonitrile and 2 mL of water. The internal temperature of the flask was maintained at 23 °C. Subsequently, 0.09 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals were added in portions with continuous stirring. During the reaction, the internal temperature of the flask was increased to 28°C and then gradually decreased. GC analysis was performed 3 h after the start of the reaction and showed that 22% of the methyl phenyl sulfide was converted to methyl phenyl sulfoxide and 65% to methyl phenyl sulfone. By-products included 6% chloromethyl phenyl sulfoxide and 7% chloromethyl phenyl sulfone, and a total of 0.8% advanced chlorides. Addition of 0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was continued and stirring was continued for 1 hour. At this point, the methyl phenyl sulfide and methyl phenyl sulfoxide completely disappeared and the yield of methyl phenyl sulfone increased to 87%. Impurities included 11% chloromethyl phenyl sulfone, 0.5% dichloromethyl phenyl sulfone and 1.3% trichloromethyl phenyl sulfone.

Solubility in organics

Chloromethyl Phenyl Sulfone is soluble in THF, CHCl3, CH2Cl2, and most organic solvents.

References

[1] Patent: JP2017/52730, 2017, A. Location in patent: Paragraph 0046