524-38-9 Usage
Description
N-Hydroxyphthalimide is a yellow moist powder that serves as a versatile compound in various chemical and pharmaceutical applications due to its unique properties.
Uses
Used in Peptide Synthesis:
N-Hydroxyphthalimide is used as an additive in the DCC method of peptide synthesis for improving the yield of optically pure products.
Used as a Catalyst:
N-Hydroxyphthalimide is used as a catalyst for oxidation reactions, facilitating the conversion of various substrates into desired products.
Used in Aerobic Oxidation:
N-Hydroxyphthalimide, in combination with Co(acac), is used as a catalyst for the aerobic oxidation of various alcohols, providing a practical method to convert alkylbenzenes into carboxylic acids under mild conditions.
Used in Organic Substrate Oxidation:
N-Hydroxyphthalimide catalyzes the oxidation of organic substrates by molecular oxygen, enabling free radical functionalization of organic compounds.
Used in Hydrocarbon Oxygenation:
N-Hydroxyphthalimide, combined with transition metal salts, is used to catalyze the hydroxylation of polycyclic alkanes with molecular oxygen under mild conditions.
Used in Synthesis of Antibacterials:
N-Hydroxyphthalimide is used in the synthesis of a new class of antibacterials that are potent against macrolide-resistant bacteria.
Used in Synthesis of Heterocyclic Compounds:
N-Hydroxyphthalimide is also utilized in the synthesis of pyrazolidines, isoxazolidines, and tetrahydrooxazines, which have potential applications in various industries.
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, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid
Yu, Chen-Sheng,Wang, Qiao,Bajsa-Hirschel, Joanna,Cantrell, Charles L.,Duke, Stephen O.,Liu, Xing-Hai
, p. 6423 - 6430 (2021/06/28)
Nicotinic acid, also known as niacin, is a natural product, which is widely found in plants and animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibited excellent herbicidal activity against Agrostis stolonifera (bentgrass) at 100 μM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)oxy)nicotinamide) possessed excellent herbicidal activity against Lemna paucicostata (duckweed), with an IC50 value of 7.8 μM, whereas the commercial herbicides clomazone and propanil had values of 125 and 2 μM, respectively. The structure-activity relationships reported in this paper could be used for the development of new herbicides against monocotyledonous weeds.
Me3SI-promoted chemoselective deacetylation: a general and mild protocol
Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj
, p. 19310 - 19315 (2021/06/03)
A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.