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Potassium phthalimide

Catalog No. A11134 Name Alfa Aesar
CAS Number 1074-82-4 Website
M. F. C8H4KNO2 Telephone
M. W. 185.22116 Fax
Purity 98+% Email
Storage Chembase ID: 129076

SYNONYMS

Title
苯邻二甲酰亚胺钾
IUPAC name
potassium 1,3-dioxo-2,3-dihydro-1H-isoindol-2-ide
IUPAC Traditional name
potassium 1,3-dioxo-2H-isoindol-2-ide
Synonyms
Phthalimide potassium salt

DATABASE IDS

EC Number 214-046-6
Beilstein Number 3598719
CAS Number 1074-82-4
MDL Number MFCD00005887

PROPERTIES

Purity 98+%
Density 1.63
Melting Point >300°C
GHS Pictograms GHS07
GHS Hazard statements H315-H319-H335
European Hazard Symbols Irritant Irritant (Xi)
GHS Precautionary statements P261-P305+P351+P338-P302+P352-P321-P405-P501A
Risk Statements 36/37/38
Safety Statements 26-37
Storage Warning Moisture Sensitive
TSCA Listed

DETAILS

REFERENCES

  • For an example of the classical Gabriel synthesis of primary amines from an alkyl halide by alkylation of potassium phthalimide followed by hydrolysis, see: Org. Synth. Coll., 2, 25 (1943). For use of the Gabriel reaction on Merrifield resin as the first step of a synthesis of a polymer-supported carbodiimide, see: Org. Synth. Coll., 6, 951 (1988). The phthalimide alkylation is often carried out in DMF. A liquid-liquid phase-transfer method using (n-Hexadecyl)tri-n-butylphosphonium bromide, L01335, as catalyst also gives excellent results: Synthesis, 389 (1976).
  • The standard method for cleavage of the N-substituted phthalimide is with hydrazine hydrate, effective under milder conditions than acid or base hydrolysis. Other hydrazines and primary amines have also been successful, e.g. methylhydrazine or N,N-dimethylpropanediamine: Org. Synth. Coll., 9, 13, 16 (1998). Another technique involves borohydride reduction to the hydroxy amide, and liberation of the amine with acetic acid, with cyclization to phthalide: Tetrahedron Lett., 25, 2093 (1984). For suggested improvements to the cleavage conditions in the Gabriel synthesis, see: J. Org. Chem., 61, 8063 (1996). Review of the Gabriel reaction: Angew. Chem. Int. Ed., 7, 919 (1968).
  • For an alternative approach to the formation of primary amines, see Dibenzylamine, A11554.