524-38-9 Usage
Chemical Properties
N-Hydroxyphthalimide is yellow moist powder
Uses
Different sources of media describe the Uses of 524-38-9 differently. You can refer to the following data:
1. N-Hydroxyphthalimide，additives in to DCC method of peptide synthesis used to improve yield of optically pure product.
2. Catalyst for oxidation reactions.
3. 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.
Application
N-Hydroxyphthalimide is used in the synthesis of a new class of antibacterials potent against macrolide resistant bacteria. Also used in the synthesis of pyrazolidines, isoxazolidines and tetrahydrooxazines.
Purification Methods
N -Hydroxyphthalimide [524-38-9] M 163.1, m 230o, ~235o(dec), 237-240o, 7.0. Dissolve the imide in H2O by adding Et3N to form the salt and while hot, acidify, cool and pour into a large volume of H2O. Filter off the solid, wash it with H2O and dry it over P2O5 in a vacuum. [Nefken & Teser J Am Chem Soc 83 1263 1961, Fieser 1 485 1976, Nefkens et al. Recl Trav Chim, Pays-Bas 81 683 1962] The O-acetyl derivative has m 178-180o (from EtOH). [Beilstein 21/11 V 100.]
Check Digit Verification of cas no
The CAS Registry Mumber 524-38-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 4 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 524-38:
(5*5)+(4*2)+(3*4)+(2*3)+(1*8)=59
59 % 10 = 9
So 524-38-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO3/c10-6-5-3-1-2-4-8(5,12)7(11)9-6/h1-5,12H,(H,9,10,11)
524-38-9Relevant articles and documents
Reactivity of phthalimide N-oxyl radical (PINO) toward the phenolic O-H bond. A kinetic study
Baciocchi, Enrico,Gerini, Maria Francesca,Lanzalunga, Osvaldo
, p. 8963 - 8966 (2004)
The reactivity of the phthalimide N-oxyl radical (PINO) toward the OH bond of a series of substituted phenols was kinetically investigated in CH 3CN. The reaction selectivity and the deuterium kinetic isotope effect were determined. Information on the kinetic solvent effect was also obtained with phenol as the substrate.
Synthesis method N -hydroxyphthalimide
-
Paragraph 0015-0022, (2021/09/15)
The invention discloses a synthesis method of N -hydroxyphthalimide. The reaction is carried out by reflux dehydration and dehydrochlorination in a high boiling point inert solvent by taking phthalic anhydride and hydroxylamine hydrochloride as raw materials, and N - hydroxyphthalimide is obtained in a high yield after the reaction is finished. The molar yield can reach above 98%, and the purity of the product reaches 99% or above. Compared with the prior art, the high-boiling-point inert solvent replaces a traditional water or dioxane aqueous solution as a solvent, so that a large amount of waste water generated is avoided. Pollution emission is reduced, production efficiency is improved, conversion rate is increased, and atom utilization rate is saved.
Ring opening of N-hydroxyphthalimide to construct phenylurea derivatives
Wu, Yinhui,Lv, Bin,Zhang, Yanan,Gao, Pan,Zhang, Min,Yuan, Yu
supporting information, p. 2025 - 2033 (2021/05/29)
Arylurea and their analogues have been one of the most ubiquitous backbone during the past century, and extensive studies have been conducted to establish practical synthetic methods for their derivatives. In particular, it is an effective pathway to synthesize arylureas by using commercially available phthalimide compounds. Reported herein is a triethoxyphosphine promoted ring-opening of the N-hydroxyphthalimide (NHPI) by the nucleophilic attack of amines. This transformation shows a wide range of functional-group tolerance under mild reaction conditions.
