Substance
ID:716642
Names and Identifiers
IUPAC name
2-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione
IUPAC Traditional name
N-hydroxyphthalimide
Synonyms
N-HydroxyphthalimideN-羟基邻苯二甲酰亚胺NHPI
Registration numbers
CAS Number
Merck Index
EC Number
MDL Number
Beilstein Number
Properties
Safety Information
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
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
GHS Hazard statements
H315-H319-H335
TSCA Listed
是
Physical Property
Melting Point
ca 233°C dec.
Product Information
Purity
98+%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• 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).
• 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.