N-Aminophthalimide

• Catalog No.: A19914
• CAS Number: 1875-48-5
• M. F.: C8H6N2O2
• M. W.: 162.14544
• Purity: 94%

SYNONYMS

• Title: N-氨基邻苯二甲酰亚胺
• IUPAC name: 2-amino-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-aminoisoindole-1,3-dione

DATABASE IDS

• EC Number: 217-505-9
• Beilstein Number: 383756
• CAS Number: 1875-48-5
• MDL Number: MFCD00005895

PROPERTIES

• Purity: 94%
• Melting Point: ca 195°C dec.
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: 否

REFERENCES

• May be oxidized with lead(IV) acetate to "phthalimidonitrene", which adds to alkenes to give aziridines. The phthalimido group can be cleaved with hydrazine hydrate: J. Chem. Soc. (C), 576 (1970); J. Am. Chem. Soc., 92, 1784 (1970); Helv. Chim. Acta,55, 1276 (1972); Org. Synth. Coll., 6, 56 (1988). Addition to cyclopentadienes leads to substituted pyridines after ring-opening with base: Heterocycles, 22, 1369 (1984). Addition to the (racemic) acrylic ester below shows an extremely high facial selectivity, adding to the less hindered side (290:1): Helv. Chim. Acta, 72, 1095 (1989).
  
• Aziridination has also been achieved in high yield by electrochemical oxidation: J. Am. Chem. Soc., 124, 530 (2002).