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

• ChemBase ID: 53490
• Molecular Formular: C8H5NO3
• Molecular Mass: 163.1302
• Monoisotopic Mass: 163.02694303
• SMILES: N1(C(=O)c2c(C1=O)cccc2)O
• Canonical SMILES: ON1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4,12H
• InChIKey: CFMZSMGAMPBRBE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: N-hydroxyphthalimide
• Synonyms: 2-Hydroxy-1H-isoindole-1,3(2H)-dione; 2-hydroxyisoindoline-1,3-dione; N-Hydroxyphthalimide; NHPI; 2-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione; 2-Hydroxy-1H-isoindole-1,3(2H)-dione; 2-Hydroxyisoindolin-1,3-dione; N-Hydroxyphthalimide; N-羟基邻苯二甲酰亚胺

Database IDs

• CAS Number: 524-38-9
• EC Number: 208-358-1
• MDL Number: MFCD00005891
• Beilstein Number: 131208
• Merck Index: 144838
• PubChem SID: 162058253; 24879985; 24895686
• PubChem CID: 10665

CALCULATED PROPERTIES

• Acid pKa: 7.4305606
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.68519646
• LogD (pH = 7.4): 0.40592098
• Log P: 0.69024134
• Molar Refractivity: 41.0794 cm^3
• Polarizability: 14.836741 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~235 °C (dec.); 233 °C (dec.)(lit.); 233(dec.)°C; ca 233°C dec.
• Hydrophobicity(logP): 0.678

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: IRRITANT; Irritant
• RTECS: TI5200000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (T); 95%; 97%; 98%; 98+%
• Grade: purum
• Empirical Formula (Hill Notation): C8H5NO3

DETAILS

MP Biomedicals - 05203357

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02151307

Crystalline
Used as additive in DCC method of peptide synthesis to increase yield of product.

Sigma Aldrich - H53704

Packaging
100, 500 g in poly bottle
5 g in glass bottle
Application
For preparation of amine nucleosides for coupling into non-anionic, anti-sense oligonucleosides.1

REFERENCES

• Additive in the carbodiimide method of peptide coupling, leading to decreased racemization: J. Am. Chem. Soc., 89, 7151 (1967). For alternative reagents, see N,N'-Dicyclohexylcarbodiimide, A10973, and Appendix 6.
• O-Alkylation followed by hydrazinolysis gives O-alkylhydroxylamines: Bull. Soc. Chim. Fr., 833 (1976). Copper-promoted coupling with arylboronic acids, followed by hydrazinolysis, affords O-arylhydroxylamines: Org. Lett., 3, 139 (2001).
• Efficient electron carrier for electrochemical oxidation of alcohols: J. Chem. Soc., Chem. Commun., 479 (1983). Has also been found to be an efficient catalyst for non-electrochemical oxidation of benzylic groups in benzonitrile solution with atmospheric pressure oxygen: J. Org. Chem., 60, 3934 (1995). The method can be extended to alkanes by the use of a catalyst such as 0.5-1 mol% Co(acac)₂. Thus cyclohexane is oxidized to cyclohexanone and adipic acid; adamantane gives mainly 1-adamantanol with minor amounts of 2-adamantanone and 1,3-adamantanediol: J. Org. Chem., 61, 4520 (1996). Under similar conditions alkynes can be oxygenated to ɑ?-acetylenic ketones in good yields: Chem. Commun., 2037 (1998).