3-Aminophthalimide Chemical Properties

Melting point:

268.5-273.5 °C (lit.)

Boiling point:

288.82°C (rough estimate)

Density 

1.3264 (rough estimate)

refractive index 

1.5770 (estimate)

storage temp. 

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

pka

9.76±0.20(Predicted)

Appearance

Yellow to orange Solid

CAS DataBase Reference

2518-24-3(CAS DataBase Reference)

NIST Chemistry Reference

3-Aminophthalimide(2518-24-3)

EPA Substance Registry System

1H-Isoindole-1,3(2H)-dione, 4-amino- (2518-24-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-42/43

Safety Statements 

22-26-36/37-45

WGK Germany 

3

HS Code 

29251995

MSDS

• Language:English Provider:3-Aminophthalimide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-Aminophthalimide Usage And Synthesis

Chemical Properties

yellow fine powder

Uses

3-Aminophthalimide may be used in direct chemiluminescent cellular bioassays. It may also be used in the preparation of 3-bromopthalimide.

General Description

3-Aminophthalimide (API) is a stable precursor of luminol. API can be prepared by the hydrogenation of 3-nitrophthalimide and methanol in the presence of 10% Pd-C.

Synthesis

The general procedure for the synthesis of 3-amino phthalimide from 3-nitrophthalimide was as follows: 3-nitrophthalimide (LOOGR) was placed in a hydrogenation reactor and dissolved by adding 500 mL of dimethylformamide (DMF). Subsequently, 20 g of wet Ruanne nickel catalyst was added to the solution. The hydrogenation reaction was started by applying a hydrogen pressure of 20-40 psi at 20-30 °C. After the initial exothermic phase of the reaction, the hydrogen pressure was increased to 40-60 psi and the reaction temperature was raised to 40-50 °C to continue the reaction. After the hydrogen is completely absorbed, a sample is taken and analyzed by thin layer chromatography (TLC) to confirm that the 3-nitrophthalimide has been completely converted. Upon completion of the reaction, the reaction mixture was filtered while hot to remove the catalyst. The filtrate was concentrated under reduced pressure at 60-80 °C to remove the solvent. To the residue was added 500 mL of water and stirred for 20-30 minutes. The product was separated by filtration and dried at 60-70 °C to give a yellow crystalline solid 3-aminophthalimide (80 g, 95% yield). The melting point of the product was 262-264 °C.

References

[1] MedChemComm, 2016, vol. 7, # 2, p. 292 - 296
[2] Patent: WO2004/43919, 2004, A1. Location in patent: Page 6
[3] Patent: WO2004/43919, 2004, A1. Location in patent: Page 7
[4] Patent: WO2004/43919, 2004, A1. Location in patent: Page 7
[5] Journal of Chemical Research, 2011, vol. 35, # 6, p. 326 - 328

3-Aminophthalimide(2518-24-3)Related Product Information

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• ALTRENOGEST
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