N-PROPARGYLPHTHALIMIDE Chemical Properties

Melting point:

148-152 °C

Boiling point:

304.1±25.0 °C(Predicted)

Density 

1.318±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

-2.54±0.20(Predicted)

color 

White to Light yellow to Light orange

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29251995

MSDS

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N-PROPARGYLPHTHALIMIDE Usage And Synthesis

Chemical Properties

Beige to orange powder

Synthesis

General procedure for the synthesis of N-propargyl phthalimide from phthalimide potassium salt and 3-bromopropargyl: 8.4 mmol of 3-bromopropargyl and 8.4 mmol of phthalimide potassium salt were dissolved in 10 mL of N,N-dimethylformamide. Subsequently, 0.2 g of manganese dioxide solid was added as a catalyst. The reaction mixture was stirred at 28°C for 2 hours. Upon completion of the reaction, the mixture was diluted by adding 100 mL of ethyl acetate to the mixture, followed by washing with water to collect the organic layer. The organic layer was further washed with saturated aqueous sodium chloride solution and dried with anhydrous sodium sulfate. The dried organic phase was separated and purified by column chromatography with the eluent being a solvent mixture of petroleum ether and ethyl acetate (5:1, v/v) to obtain pure N-propargyl phthalimide.

References

[1] Patent: CN105669525, 2016, A. Location in patent: Paragraph 0062; 0063; 0082
[2] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2002, vol. 377, p. 13 - 18
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 8, p. 1611 - 1614
[4] Patent: WO2005/82892, 2005, A2. Location in patent: Page/Page column 58-59
[5] European Journal of Organic Chemistry, 2017, vol. 2017, # 27, p. 3941 - 3946

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