n-(o-Hydroxyphenyl)phthalimide

Base Information

• Chemical Name: n-(o-Hydroxyphenyl)phthalimide
• CAS No.: 6307-13-7
• Molecular Formula: C14H9NO3
• Molecular Weight: 239.23
• Hs Code.: 2925190090
• NSC Number: 41070
• DSSTox Substance ID: DTXSID00285214
• Nikkaji Number: J1.172.424H
• Wikidata: Q82020509
• ChEMBL ID: CHEMBL1450411
• Mol file: 6307-13-7.mol

Synonyms:N-(o-hydroxyphenyl)phthalimide

Chemical Property of n-(o-Hydroxyphenyl)phthalimide

Chemical Property:

• Vapor Pressure: 6.25E-08mmHg at 25°C
• Boiling Point: 428.1°C at 760 mmHg
• Flash Point: 212.7°C
• PSA: 57.61000
• Density: 1.448g/cm³
• LogP: 2.25780
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 239.058243149
• Heavy Atom Count: 18
• Complexity: 344

Purity/Quality:

≥99% ^*data from raw suppliers

2-(2-Hydroxyphenyl)-1H-isoindole-1,3(2H)-dione Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)C3=CC=CC=C3O

Technology Process of n-(o-Hydroxyphenyl)phthalimide

There total 11 articles about n-(o-Hydroxyphenyl)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: 93.0%

phthalic anhydride (85-44-9) + 2-amino-phenol (95-55-6) → 2-(2-hydroxyphenyl) isoindoline-1,3-dione (6307-13-7)

Guidance literature:

In acetic acid; for 1h; Heating;

DOI:10.1002/ardp.19903230206

Reference yield: 84.0%

trimethylsilyl cyanide (7677-24-9) + 2-Iodobenzoic acid (88-67-5) + 2-amino-phenol (95-55-6) → 2-(2-hydroxyphenyl) isoindoline-1,3-dione (6307-13-7)

Guidance literature:

With copper(I) oxide; water; at 100 ℃; for 8h; Green chemistry;

DOI:10.1039/d1ob00073j

Reference yield: 82.0%

N-phenylphthalimide (520-03-6) → 2-(2-hydroxyphenyl) isoindoline-1,3-dione (6307-13-7)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; ammonium peroxydisulfate; In trifluoroacetic acid; at 80 ℃; for 15h; Reagent/catalyst; Solvent; Temperature; regioselective reaction; Catalytic behavior; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.8b02899

upstream raw materials:

phthalic anhydride

2-amino-phenol

Phthaloyl dichloride

2-phenoxyisoindol-1,3-dione

Downstream raw materials:

N-(2-methoxyphenyl)phthalimide

2-methoxy-phenylamine

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

2-(benzyloxy)-N-(3-(4-methoxytetrahydro-2H-pyran-4-yl) benzyl) aniline

Refernces

• 1、 Zhang, Kan,Liu, Jia,Ohashi, Seishi,Ishida, Hatsuo,Liu, Xiaoyun,Han, Zhewen. "Synthesis of high thermal stability polybenzoxazoles via ortho-imide-functional benzoxazine monomers". . p. 1330 - 1338. Retrieved 2015.
• 2、 Akai, Shuji,Ikawa, Takashi,Masuda, Shigeaki. "One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols". . . Retrieved 2020/03/23.