ChemicalBook--->CAS DataBase List--->2518-24-3

2518-24-3

2518-24-3 Structure

2518-24-3 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H317-H319-H335
[Precautionary statements ]

P261-P280-P305+P351+P338
[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
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

3-Aminophthalimide(2518-24-3).msds
Hazard InformationBack 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]

3-Nitrophthalimide

603-62-3

3-Aminophthalimide

2518-24-3

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
Spectrum DetailBack Directory
[Spectrum Detail]

3-Aminophthalimide(2518-24-3)1HNMR
3-Aminophthalimide(2518-24-3)IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

3-Aminophthalimide, 99%(2518-24-3)
[Sigma Aldrich]

2518-24-3(sigmaaldrich)
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