Introduction：Basic information about N-Hydroxyphthalimide CAS 524-38-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 |
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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 |
| Major Application | peptide synthesis |
| InChI | 1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4,12H |
| InChIKey | CFMZSMGAMPBRBE-UHFFFAOYSA-N |
| SMILES | ON1C(=O)c2ccccc2C1=O |
| 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) |
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 Class | 11 - Combustible Solids |
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 |
| reaction suitability | reaction type: Addition Reactions |
| Synthesis | One 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 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 |
