N-Hydroxyphthalimide

Base Information

• Chemical Name: N-Hydroxyphthalimide
• CAS No.: 524-38-9
• Molecular Formula: C8H5NO3
• Molecular Weight: 163.133
• Hs Code.: 29251995
• European Community (EC) Number: 208-358-1
• NSC Number: 770
• UNII: BXI99M81X0
• DSSTox Substance ID: DTXSID7060170
• Nikkaji Number: J26.847J
• Wikipedia: N-Hydroxyphthalimide
• Wikidata: Q26296355
• ChEMBL ID: CHEMBL276057
• Mol file: 524-38-9.mol

Synonyms:N-hydroxyphthalimide

Chemical Property of N-Hydroxyphthalimide

Chemical Property:

• Appearance/Colour: yellow moist powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 233 °C (dec.)(lit.)
• Refractive Index: 1.646
• Boiling Point: 370.3 °C at 760 mmHg
• PKA: 6.10±0.20(Predicted)
• Flash Point: 177.8 °C
• PSA: 57.61000
• Density: 1.638 g/cm³
• LogP: 0.60970
• Storage Temp.: Store at RT.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 163.026943022
• Heavy Atom Count: 12
• Complexity: 215

Purity/Quality:

99.8 % ^*data from raw suppliers

N-Hydroxyphthalimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Rings
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)O
• Uses: N-Hydroxyphthalimide，additives in to DCC method of peptide synthesis used to improve yield of optically pure product. Catalyst for oxidation reactions. 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.

Technology Process of N-Hydroxyphthalimide

There total 85 articles about N-Hydroxyphthalimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.34%

phthalic anhydride (85-44-9) → N-hydroxyphthalimide (524-38-9)

Guidance literature:

With hydroxylamine hydrochloride; In glycerol; at 200 ℃; for 12h; Solvent; Temperature;

Reference yield: 96.0%

N-acetoxyphthalimide (17720-64-8) → N-hydroxyphthalimide (524-38-9)

Guidance literature:

With methanol; potassium permanganate; at 25 ℃; chemoselective reaction;

DOI:10.1039/d0nj04321d

Reference yield: 95.0%

tert-butyl 1,3-dioxoisoindoline-2-carboxylate (150220-29-4) → N-hydroxyphthalimide (524-38-9)

Guidance literature:

With hydroxylamine; In acetonitrile; at 20 ℃;

DOI:10.1081/SCC-100103264

upstream raw materials:

phthalic anhydride

phthalimide

hydroxyimino-phthalide

N-(benzyloxy)phthalimide

Downstream raw materials:

N-dimethoxythiophosphoryloxy-phthalimide

O,O-diethyl-phthalimido phosphorothioate

N-2-nitrophenylsulfenylphthalimide

N-(mesyloxy)phthalimide

Refernces

• 1、 Zhou, Wei,Yao, Lan,Liu, Yongxiurong,Shen, Lichun,Chen, Jie,Deng, Hongmei,Shao, Min,Zhang, Hui,Tang, Xiaojun,Cao, Weiguo. "A Catalyst-Free Synthesis of Fused Perfluoroalkylated 2,3-Dihydroisoxazoles via Oxa-Michael-Aldol Annulation". supporting information. p. 429 - 438. Retrieved 2021/10/01.
• 2、 Akunuri, Ravikumar,Veerareddy, Vaishnavi,Kaul, Grace,Akhir, Abdul,Unnissa, Tanveer,Parupalli, Ramulu,Madhavi,Chopra, Sidharth,Nanduri, Srinivas. "Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains". supporting information. . Retrieved 2021/08/27.