N-Phenylphthalimide

Base Information

• Chemical Name: N-Phenylphthalimide
• CAS No.: 520-03-6
• Molecular Formula: C14H9NO2
• Molecular Weight: 223.231
• Hs Code.: 2925190090
• European Community (EC) Number: 208-282-9
• NSC Number: 2769
• UNII: LA29QA196M
• DSSTox Substance ID: DTXSID3060166
• Nikkaji Number: J6.598F
• Wikidata: Q72498194
• ChEMBL ID: CHEMBL9020
• Mol file: 520-03-6.mol

Synonyms:N-phenylphthalimide

Chemical Property of N-Phenylphthalimide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.99E-06mmHg at 25°C
• Melting Point: 204-207 °C
• Refractive Index: 1.667
• Boiling Point: 388.8 °C at 760 mmHg
• PKA: -0.54±0.20(Predicted)
• Flash Point: 182.6 °C
• PSA: 37.38000
• Density: 1.338 g/cm³
• LogP: 2.55220
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 223.063328530
• Heavy Atom Count: 17
• Complexity: 309

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Phenylisoindole-1,3-dione 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3C2=O

Technology Process of N-Phenylphthalimide

There total 261 articles about N-Phenylphthalimide 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: 100.0%

phthalic anhydride (85-44-9) + aniline (62-53-3) → N-phenylphthalimide (520-03-6)

Guidance literature:

phthalic anhydride; aniline; In N,N-dimethyl acetamide; at 20 ℃; for 24h;

In N,N-dimethyl acetamide; xylene; at 140 ℃; for 48h;

DOI:10.1021/ma049232z

Reference yield: 97.0%

1,2-Diiodobenzene (615-42-9) + carbon monoxide (201230-82-2) + aniline (62-53-3) → N-phenylphthalimide (520-03-6)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon; In toluene; at 120 ℃; for 2h; under 4654.46 Torr; Autoclave;

DOI:10.1002/adsc.201100460

Reference yield: 96.0%

inden-1-one (83-33-0) + aniline (62-53-3) → N-phenylphthalimide (520-03-6)

Guidance literature:

With manganese(IV) oxide; oxygen; In tetrahydrofuran; at 100 ℃; for 24h; under 15001.5 Torr; Reagent/catalyst; Solvent; Pressure; Temperature; Catalytic behavior; Autoclave;

upstream raw materials:

aniline

(+/-)-phthaloylaspartic acid

pyridine

phthalic anhydride

Downstream raw materials:

(3aR,8aS,8bS)-6,6-Dimethyl-2-phenyl-hexahydro-dipyrrolo[1,2-b;3',4'-d]isoxazole-1,3-dione

(3aR,8aR,8bS)-6,6-Dimethyl-2-phenyl-hexahydro-dipyrrolo[1,2-b;3',4'-d]isoxazole-1,3-dione

1,3-Bistrimethylsiloxy-isoindol

3-(p-bromophenylethynyl)-2,3-dihydro-3-hydroxy-2-phenyl-1H-isoindol-1-one

Refernces

• 1、 Sato, Masaru,Ebine, Seiji,Akabori, Sadatoshi. "Condensation of Halobenzenes and Haloferrocenes with Phthalimide in the Presence of Copper(I) Oxide; A Simplified Gabriel Reaction". . p. 472 - 473. Retrieved 1981.
• 2、 Wang, Hai,Wu, Xiao-Feng. "Palladium-Catalyzed Carbonylative Dearomatization of Indoles". . p. 5264 - 5268. Retrieved 2019.
• 3、 Bourel, Line,Tartar, Andre,Melnyk, Patricia. "Improved synthesis of pyridazinediones under microwave irradiation". . p. 4145 - 4148. Retrieved 1996.
• 4、 Iwakura et al.. "-". . p. 351,355,361. Retrieved 1975.
• 5、 Mali, Anil S.,Indalkar, Krishna,Chaturbhuj, Ganesh U.. "Solvent-free, Efficient Transamidation of Carboxamides with Amines Catalyzed by Recyclable Sulfated Polyborate Catalyst". . p. 369 - 378. Retrieved 2021/07/26.
• 6、 Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang. "“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides". supporting information. p. 1738 - 1743. Retrieved 2021/03/14.