N-(4-nitrophenyl)phthalimide

Base Information

• Chemical Name: N-(4-nitrophenyl)phthalimide
• CAS No.: 31604-39-4
• Molecular Formula: C14H8 N2 O4
• Molecular Weight: 268.229
• Hs Code.: 2925190090
• NSC Number: 406342
• UNII: MJN47DN89K
• DSSTox Substance ID: DTXSID70185494
• Nikkaji Number: J308.271G
• Wikidata: Q83056524
• ChEMBL ID: CHEMBL27783
• Mol file: 31604-39-4.mol

Synonyms:N-(4-nitrophenyl)phthalimide;31604-39-4;2-(4-nitrophenyl)isoindoline-1,3-dione;2-(4-nitrophenyl)isoindole-1,3-dione;1H-Isoindole-1,3(2H)-dione, 2-(4-nitrophenyl)-;MJN47DN89K;CHEMBL27783;2-(4-Nitrophenyl)-1H-isoindole-1,3(2H)-dione;N-(4-NITROPHENYL)PHTHALAMIDE;NSC 406342;NSC-406342;AI3-02623;NSC406342;UNII-MJN47DN89K;Oprea1_210160;SCHEMBL1973251;DTXSID70185494;BDBM50488720;STK390545;AKOS001268560;CCG-233794;SB64426;2-(4-Nitro-phenyl)-isoindole-1,3-dione;FT-0629238;FT-0629239;EN300-7142296;2-(4-Nitrophenyl)-1H-isoindole-1,3(2H)-dione #;2-(4-nitrophenyl)-2,3-dihydro-1H-isoindole-1,3-dione;Z198198220

Chemical Property of N-(4-nitrophenyl)phthalimide

Chemical Property:

• Vapor Pressure: 6.56E-10mmHg at 25°C
• Melting Point: 191-192 °C
• Boiling Point: 494.2°C at 760 mmHg
• PKA: -4.92±0.20(Predicted)
• Flash Point: 252.7°C
• PSA: 83.20000
• Density: 1.501g/cm³
• LogP: 2.98360
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 268.04840674
• Heavy Atom Count: 20
• Complexity: 413

Purity/Quality:

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

N-(4-NITROPHENYL)PHTHALIMIDE Aldrich ^*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=C2C(=C1)C(=O)N(C2=O)C3=CC=C(C=C3)[N+](=O)[O-]

Technology Process of N-(4-nitrophenyl)phthalimide

There total 29 articles about N-(4-nitrophenyl)phthalimide 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: 98.0%

phthalic anhydride (85-44-9) + 4-nitro-aniline (100-01-6,104810-17-5) → 2-(4-nitrophenyl)isoindoline-1,3-dione (31604-39-4)

Guidance literature:

With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 130 ℃; for 0.0833333h;

DOI:10.1002/jhet.5570420442

Reference yield: 96.0%

phthalic anhydride (85-44-9) + 4-Nitrophenyl isocyanate (100-28-7) → 2-(4-nitrophenyl)isoindoline-1,3-dione (31604-39-4)

Guidance literature:

In N,N-dimethyl acetamide; for 0.0416667h;

Reference yield: 95.0%

4-nitro-aniline (100-01-6,104810-17-5) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) → 2-(4-nitrophenyl)isoindoline-1,3-dione (31604-39-4)

Guidance literature:

With L-proline; In ethanol; at 30 ℃; for 6h;

DOI:10.1155/2018/5198325

upstream raw materials:

N-phenylphthalimide

oxalic acid

phthalic anhydride

4-nitro-aniline

Downstream raw materials:

4-nitrophthalanilic acid

2-(2-hydroxy-4-nitrophenyl)isoindoline-1,3-dione

p-nitrobenzanilide

2-(4-aminophenyl)isoindoline-1,3-dione

Refernces

• 1、 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.
• 2、 Samanta, Partha Kumar,Biswas, Papu. "Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides". . p. 3968 - 3976. Retrieved 2019/03/26.