N-Hydroxyphthalimide

• Catalog No.: A13862
• CAS Number: 524-38-9
• M. F.: C8H5NO3
• M. W.: 163.1302
• Purity: 98+%

SYNONYMS

• Title: N-羟基邻苯二甲酰亚胺
• IUPAC name: 2-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: N-hydroxyphthalimide
• Synonyms: NHPI

DATABASE IDS

• Merck Index: 144838
• MDL Number: MFCD00005891
• EC Number: 208-358-1
• CAS Number: 524-38-9
• Beilstein Number: 131208

PROPERTIES

• Purity: 98+%
• Melting Point: ca 233°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
• RTECS: TI5200000
• Safety Statements: 26-37
• TSCA Listed: 是

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).