1-(chloromethyl)-4-(phenylthio)benzene Chemical Properties

Boiling point:

372℃

Density 

1.22

Flash point:

167℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Yellow to brown Liquid

1-(chloromethyl)-4-(phenylthio)benzene Usage And Synthesis

Uses

(4-(Chloromethyl)phenyl)(phenyl)sulfane can be used as reactant/reagent in preparation of fenticonazole nitrate by phase transfer-catalyzed benzylation of (dichlorophenyl)imidazoleethanol with (phenylthio)benzyl chloride.

Synthesis

The general procedure for the synthesis of 4-phenylthiobenzyl chloride from 4-phenylthiobenzyl alcohol was as follows: 518.0 g of 4-phenylthiobenzyl alcohol, 147 mL of pyridine, and 2444 mL of dichloromethane were added to a 5000 mL reaction flask at room temperature (25 °C), mixed well, and then cooled in an ice-water bath to control the temperature. Thionyl chloride was slowly added dropwise at 20-24 °C, and after completion of the dropwise addition, the reaction mixture was stirred at room temperature (25 °C) for 2 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent was hexane: ethyl acetate = 10:1) until the reaction was completed. After completion of the reaction, the reaction mixture was washed with water and subsequently neutralized with water and dried with anhydrous magnesium sulfate. The dried mixture was filtered and the filtrate was concentrated to dryness under reduced pressure (pressure 1720 Pa, temperature 25 °C). After recovery of dichloromethane, 548.0 g of brownish red oily product was obtained in 97.7% yield and 99.66% HPLC purity. The product can be cured by freezing to about -10°C.

References

[1] Patent: CN107573288, 2018, A. Location in patent: Paragraph 0016; 0024
[2] Patent: CN107652238, 2018, A. Location in patent: Paragraph 0026; 0027
[3] Arzneimittel-Forschung/Drug Research, 1982, vol. 31, # 12, p. 2123 - 2126
[4] Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 12, p. 2127 - 2133
[5] Patent: US5420128, 1995, A

1-(chloromethyl)-4-(phenylthio)benzene (1208-87-3)Related Product Information

• TIMTEC-BB SBB003011
• 4-(METHYLTHIO)BENZYL CHLORIDE
• 1-(chloromethyl)-4-(phenylthio)benzene