2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 103477
• Molecular Formular: C8H5NO2
• Molecular Mass: 147.1308
• Monoisotopic Mass: 147.03202841
• SMILES: O=C1NC(=O)c2c1cccc2
• Canonical SMILES: O=C1NC(=O)c2c1cccc2
• InChI: InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)8(11)9-7/h1-4H,(H,9,10,11)
• InChIKey: XKJCHHZQLQNZHY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: phthalimide
• Synonyms: Phthalimide; Phthalimidoyl (deprotonated); Phthalimide; Benzene-1,2-dicarboxylic acid imide; Isoindole-1,3-dione; 1,3-Dihydro-1,3-dioxoisoindole; PHTHALIMIDE; 邻苯二甲酰亚胺; 酞酰亚胺; 苯邻二甲酰亚胺

Database IDs

• CAS Number: 85-41-6
• EC Number: 201-603-3
• MDL Number: MFCD00005881
• Beilstein Number: 118522
• Merck Index: 147373
• PubChem SID: 24862742; 162103298; 24854410
• PubChem CID: 6809
• CHEBI ID: 38817
• CHEMBL: 277294
• Chemspider ID: 6550
• Wikipedia Title: Phthalimide

CALCULATED PROPERTIES

• Acid pKa: 8.402129
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.69284976
• LogD (pH = 7.4): 0.6526804
• Log P: 0.69342303
• Molar Refractivity: 39.3148 cm^3
• Polarizability: 14.162762 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: <0.1 g/100 ml (19.5 °C) in water; Slightly soluble in water. Soluble in aqueous alkali hydroxides
• Apperance: White solid
• Melting Point: 232-235 °C(lit.); 232-236 °C; 232-236°C; 238°C
• Boiling Point: 336°C (sublimes); 366°C
• Flash Point: 150 °C; 165°C(329°F); 302 °F
• Density: 1.21
• pKa: 8.3
• pKb: 5.7

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: TI3920000
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98%; ≥99%; ≥99.0% (T); 98%; 99%
• Grade: PESTANAL®, analytical standard; puriss.
• Impurities: ≤0.05% ash
• Empirical Formula (Hill Notation): C8H5NO2

DETAILS

MP Biomedicals - 02151878

Free Base
Purity: 98+%

Sigma Aldrich - 240230

Packaging
1 kg in poly bottle
50, 250 g in poly bottle

Sigma Aldrich - 36734

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

REFERENCES

• For use in the Gabriel synthesis of primary amines, see: Potassium phthalimide, A11134. For an example of N-alkylation in the presence of K₂CO₃, see: Org. Synth. Coll., 2, 83 (1943). The N-alkylation by alkyl halides can be effected using KF, RbF or CsF as base; NaF and LiF are ineffective: J. Am. Chem. Soc., 99, 498 (1977).
• The direct conversion of alcohols to N-alkylphthalimides and hence to amines can be effected in the presence of the Mitsunobu reagent: Org. Synth. Coll., 7, 501 (1990):