N-(3-HYDROXYPROPYL)PHTHALIMIDE Chemical Properties

Melting point:

74-76 °C (lit.)

Boiling point:

376.5±25.0 °C(Predicted)

Density 

1.331±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

14.88±0.10(Predicted)

form 

Crystalline Powder

color 

White

BRN 

158489

CAS DataBase Reference

883-44-3(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29251900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-(3-HYDROXYPROPYL)PHTHALIMIDE Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

N-(3-Hydroxypropyl)phthalimide was used as standard in the synthesis of phthalimide derivatives at high-temperature, high-pressure and H₂O/EtOH mixtures as the solvent. It may be used in the synthesis of hydrophilic phosphorylcholine-containing polymer, poly-2-[3-(methacryloylamino)propylammonio] ethyl 3-aminopropyl phosphate.

Definition

ChEBI: N-(3-Hydroxypropyl)phthalimide is a member of phthalimides.

General Description

N-(3-Hydroxypropyl)phthalimide is ω-Hydroxyalkylphthalimide and is prepared by mixing phthalic anhydride and propanolamine and by heating at 160-180 °C for 4 hours.

Synthesis

3-Amino-1-propanol (10.0 g, 133.1 mmol) was dissolved in anhydrous toluene (100 mL). Phthalic anhydride (19.7 g, 133.1 mmol) was added to the solution under argon protection. The reaction mixture was heated with stirring at 125 °C for 6.5 hours. Upon completion of the reaction, it was cooled to room temperature and the solvent was removed by vacuum evaporation to afford the white powdery product 2-(3-hydroxypropyl)isodihydroindole-1,3-dione (31.7 g, quantitative yield), which could be used in subsequent steps without further purification.

References

[1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 644 - 647
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 32, p. 6094 - 6104
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 5903 - 5914
[4] Chemistry - A European Journal, 2014, vol. 20, # 44, p. 14256 - 14260
[5] Chemical Papers, 2017, vol. 71, # 11, p. 2293 - 2299

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