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A13862 N-Hydroxyphthalimide, 98+%

CAS Number
524-38-9
Synonyms
NHPI

Stock No. Size Price ($) Quantity Availability
A13862-22 100g 34.60
A13862-36 500g 123.00
A13862-0E 2500g 488.00
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N-Hydroxyphthalimide, 98+%

MDL
MFCD00005891
EINECS
208-358-1

Chemical Properties

Formula
C8H5NO3
Formula Weight
163.13
Melting point
ca 233° dec.
Storage & Sensitivity
Ambient temperatures.
Solubility
Slightly soluble in water.

Applications

Aerobic oxidation of various alcohols has been accomplished by using a new catalytic system, N-hydroxyphthalimide (NHPI) combined with Co (acac). A practical catalytic method to convert alkylbenzenes into the corresponding carboxylic acids under atmospheric dioxygen at ambient temperature using a combined catalytic system consisting of N-hydroxyphthalimide (NHPI) and Co (OAc) 2 was developed. Novel catalysis by N-hydroxyphthalimide in the oxidation of organic substrates by molecular oxygen was described. Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide. Purely organic and catalytic systems of anthraquinones and N-hydroxyphthalimide efficiently promote oxygenation of hydrocarbons with dioxygen under mild conditions. Hydroxylation of polycyclic alkanes with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) combined with was transition metal salts.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.

Literature References

Yasutaka Ishii,; Takahiro Iwahama,; Satoshi Sakaguchi,; Kouichi Nakayama,; Yutaka Nishiyama. Alkane Oxidation with Molecular Oxygen Using a New Efficient Catalytic System:? N-Hydroxyphthalimide (NHPI) Combined with Co(acac)n (n = 2 or 3). J. Org. Chem., 1996, 61 (14), 4520-4526.

Yasushi Yoshino,; Yoshiaki Hayashi,; Takahiro Iwahama,; Satoshi Sakaguchi,; Yasutaka Ishii. Catalytic Oxidation of Alkylbenzenes with Molecular Oxygen under Normal Pressure and Temperature by N-Hydroxyphthalimide Combined with Co(OAc)2. J. Org. Chem. 1997, 62 (20), 6810-6813.

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 ɑß-acetylenic ketones in good yields: Chem. Commun., 2037 (1998).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,4838
Beilstein
131208
Harmonized Tariff Code
2928.00
TSCA
Yes
RTECS
TI5200000

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