potassium 1,3-dioxo-2,3-dihydro-1H-isoindol-2-ide

• ChemBase ID: 129076
• Molecular Formular: C8H4KNO2
• Molecular Mass: 185.22116
• Monoisotopic Mass: 184.98791005
• SMILES: c1ccc2c(c1)C(=O)[N-]C2=O.[K+]
• Canonical SMILES: O=C1[N-]C(=O)c2c1cccc2.[K+]
• InChI: InChI=1S/C8H5NO2.K/c10-7-5-3-1-2-4-6(5)8(11)9-7;/h1-4H,(H,9,10,11);/q;+1/p-1
• InChIKey: FYRHIOVKTDQVFC-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• 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: Potassium phthalimide; Phthalimide potassium salt; Potassium phthalimide; Potassium 1,3-dioxoisoindolin-2-ide; potassium 1,3-dioxo-2,3-dihydro-1H-isoindol-2-ide; 苯邻二甲酰亚胺钾

Database IDs

• CAS Number: 1074-82-4
• EC Number: 214-046-6
• MDL Number: MFCD00005887
• Beilstein Number: 3598719
• PubChem SID: 162223375
• PubChem CID: 3356745
• Chemspider ID: 10627162
• Wikipedia Title: Potassium_phthalimide

CALCULATED PROPERTIES

• Acid pKa: 8.402129
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.69284976
• LogD (pH = 7.4): 0.6526804
• Log P: 0.69342303
• Molar Refractivity: 38.5148 cm^3
• Polarizability: 13.896068 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble in water
• Apperance: Light yellow solid
• Melting Point: > 300 °C; >300°C
• Density: 1.63
• Hydrophobicity(logP): -0.09

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37; R
• TSCA Listed: 是
• GHS Pictograms: GHS07
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 95%; 95+%; 98+%

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.