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| | N-Hydroxyphthalimide Basic information |
| | 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) | | pka | 6.10±0.20(Predicted) | | form | Powder | | color | Yellow | | Water Solubility | Slightly soluble in water. | | Merck | 14,4838 | | BRN | 131208 | | InChIKey | CFMZSMGAMPBRBE-UHFFFAOYSA-N | | LogP | 0.14 | | CAS DataBase Reference | 524-38-9(CAS DataBase Reference) | | EPA Substance Registry System | 1H-Isoindole-1,3(2H)-dione, 2-hydroxy- (524-38-9) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | RTECS | TI5200000 | | TSCA | Yes | | HazardClass | IRRITANT | | HS Code | 29251995 |
| | N-Hydroxyphthalimide Usage And Synthesis |
| Chemical Properties | N-Hydroxyphthalimide is yellow moist powder
| | Uses | N-Hydroxyphthalimide，additives in to DCC method of peptide synthesis used to improve yield of optically pure product.
| | Uses | Catalyst for oxidation reactions. | | Uses | 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. | | Synthesis Reference(s) | Tetrahedron Letters, 37, p. 2035, 1996 DOI: 10.1016/0040-4039(96)00211-0 | | 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.] |
| | N-Hydroxyphthalimide Preparation Products And Raw materials |
| Raw materials | 2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, 1,1-dimethylethyl ester-->1,3-dioxoisoindolin-2-yl acetate-->Benzenebutanoic acid, α-methylene-, ethyl ester-->Benzoic acid, 2-[(hydroxyamino)carbonyl]--->2,4-DIPHENYL-1-BUTENE-D5-->Fmoc-Phe-OH-->2-phenylmethoxyisoindole-1,3-dione-->2,4-Diphenyl-4-methyl-1-pentene-->Phthaloyl dichloride | | Preparation Products | O-(2,3,4,5,6-PENTAFLUOROBENZYL)HYDROXYLAMINE HYDROCHLORIDE-->1,3-Adamantanediol-->TERT-BUTYL N-(BENZYLOXY)CARBAMATE-->1-Adamantanol-->synthetic tanning agent HV-->synthetic tanning agent No.742-->5-Hydroxy-1,4-naphthalenedione-->1H-Isoindol-1-one, 3-hydroxy--->N-(METHYLTHIO)PHTHALIMIDE 97 |
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