| Identification | More | [Name]
3-Aminophthalimide | [CAS]
2518-24-3 | [Synonyms]
3-AMINOPHTHALIMIDE
4-AMINO-1H-ISOINDOLE-1,3(2H)-DIONE
1H-Isoindole-1,3(2H)-dione, 4-amino-
1H-Isoindole-1,3(2H)-dione,4-amino-
3-Amino-phthalamide
4-amino-1h-isoindole-3(2h)-dione
4-Amino-isoindole-1,3-dione
4-Amino-1H-isoindole
3-AMINOPHTHALIMIDE[4-AMINO-1H-ISOINDOLE-1,3(2H)-DIONE]
3-AMINOPHTHALIMIDE 99%
4-Aminoisoindoline-1,3-dione | [Molecular Formula]
C8H6N2O2 | [MDL Number]
MFCD00041853 | [Molecular Weight]
162.15 | [MOL File]
2518-24-3.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow fine powder | [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) | [InChI]
1S/C8H6N2O2/c9-5-3-1-2-4-6(5)8(12)10-7(4)11/h1-3H,9H2,(H,10,11,12) | [InChIKey]
GQBONCZDJQXPLV-UHFFFAOYSA-N | [SMILES]
Nc1cccc2C(=O)NC(=O)c12 | [CAS DataBase Reference]
2518-24-3(CAS DataBase Reference) | [NIST Chemistry Reference]
3-Aminophthalimide(2518-24-3) | [EPA Substance Registry System]
2518-24-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [WGK Germany ]
3
| [TSCA ]
TSCA listed | [HS Code ]
29251995 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 |
| Hazard Information | Back Directory | [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 |
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