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N-Hydroxyphthalimide

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CAS:524-38-9
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N-Hydroxyphthalimide Basic information
Product Name:N-Hydroxyphthalimide
Synonyms:TIMTEC-BB SBB009098;N-HYDROXY-PHTALIMIDE;N-HYDROXYPHTHALIMIDE;2-hydroxy-1h-isoindole-3(2h)-dione;N-Hydroxyphthalimide, remainder 10-15% moisture;N-Hydroxyphehtalimide;N-HYDROXYMETHYL-3-METHYLOXETANE;N-Hydroxyphthalimide(Nop)
CAS:524-38-9
MF:C8H5NO3
MW:163.13
EINECS:208-358-1
Product Categories:Active Esters/Additives;Active Esters/AdditivesSynthetic Reagents;Coupling;Peptide Synthesis;Biochemistry;Carbon Radical Producing Catalysts (Environmentally-friendly Oxidation);Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Environmentally-friendly Oxidation;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Peptide Synthesis;Synthetic Organic Chemistry;API;intermediates;bc0001;524-38-9
Mol File:524-38-9.mol
N-Hydroxyphthalimide Structure
N-Hydroxyphthalimide Chemical Properties
Melting point 233 °C (dec.) (lit.)
Boiling point 290.19°C (rough estimate)
density 1.64 g/cm3
vapor pressure 0Pa at 25℃
refractive index 1.5510 (estimate)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
pka6.10±0.20(Predicted)
form Powder
color Yellow
Water Solubility Slightly soluble in water.
Merck 14,4838
BRN 131208
Major Applicationpeptide synthesis
InChI1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4,12H
InChIKeyCFMZSMGAMPBRBE-UHFFFAOYSA-N
SMILESON1C(=O)c2ccccc2C1=O
LogP0.14
CAS DataBase Reference524-38-9(CAS DataBase Reference)
EPA Substance Registry System1H-Isoindole-1,3(2H)-dione, 2-hydroxy- (524-38-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
WGK Germany 3
RTECS TI5200000
TSCA TSCA listed
HazardClass IRRITANT
HS Code 29251995
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
N-Hydroxyphthalimide English
ACROS English
SigmaAldrich English
ALFA English
N-Hydroxyphthalimide Usage And Synthesis
Chemical PropertiesN-Hydroxyphthalimide is yellow moist powder
UsesN-Hydroxyphthalimide,additives in to DCC method of peptide synthesis used to improve yield of optically pure product.
UsesCatalyst for oxidation reactions.
UsesAerobic 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.
ApplicationN-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.
Synthesis Reference(s)Tetrahedron Letters, 37, p. 2035, 1996 DOI: 10.1016/0040-4039(96)00211-0
reaction suitabilityreaction type: Addition Reactions
SynthesisOne method of synthesizing N-Hydroxyphthalimide from phthalic anhydride and hydroxylamine hydrochloride. Using hydrated organic solvent containing organic solvent C4H8O2 in 40-100 vol% as reaction medium system, and through reaction at 60-120 deg.c for 0.5-4 hr, reduced pressure distillation to recover solvent, and drying, the desired product is obtained with the yield of 90-95% and the purity of 97%.
Purification MethodsN -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.]
Tag:N-Hydroxyphthalimide(524-38-9) Related Product Information
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