N-(PHENYLTHIO)PHTHALIMIDE Chemical Properties

Melting point:

160-163 °C(lit.)

Boiling point:

432.2±28.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO: soluble25mg/mL, clear, yellow

pka

-3.05±0.20(Predicted)

form 

powder to crystal

color 

White to Light yellow

CAS DataBase Reference

14204-27-4

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich

N-(PHENYLTHIO)PHTHALIMIDE Usage And Synthesis

Preparation

(a) Preparation of benzenesulfenyl chloride. To a stirred solution of 55 gm (0.5 mole) of benzene thiol in 300 ml of η -pentane at 0°C is added chlorine gas until an assay (GC) of the resulting red-orange solution shows quantitative conversion to the sulfenyl chloride. The reaction usually re­quires about 39 gm (0.6 mole) of chlorine.
(b) Reaction of benzenesulfenyl chloride with phthalimide. To a stirred solution of 73.5 gm (0.5 mole) of phthalimide in 200 ml of dimethylforma-mide is first added 60 gm (0.6 mole) of triethylamine. Then the sulfenyl chloride solution from (a) is slowly added dropwise. The reaction mixture is stirred for \ hr, poured into 2 liters of cold water, filtered, and dried to afford 121 gm (95%), m.p. 160-161°C (recrystallized from ethanol).
Complex imides such as camphorimide and 9,10-dihydroanthracene-9,10-endo-a,/3-succinimide have been alkylated in methylene dichloride with alkyl halides, using tetrabutylammonium bromide as a phase-transfer catalyst and aqueous potassium hydroxide as a base.

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