N-Benzoylphthalimide

Base Information

• Chemical Name: N-Benzoylphthalimide
• CAS No.: 4583-50-0
• Molecular Formula: C15H9NO3
• Molecular Weight: 251.241
• Hs Code.: 2925190090
• NSC Number: 137566
• DSSTox Substance ID: DTXSID70196626
• Nikkaji Number: J50.513G
• Wikidata: Q83069652
• Mol file: 4583-50-0.mol

Synonyms:N-Benzoylphthalimide;Phthalimide, N-benzoyl-;2-benzoylisoindole-1,3-dione;4583-50-0;1H-Isoindole-1,3(2H)-dione, 2-benzoyl-;NSC 137566;BRN 0199407;1H-Isoindole-1,3(2H)-dione, 2-benzoyl- (9CI);5-21-10-00427 (Beilstein Handbook Reference);C15H9NO3;phthaloyl benzamide;NSC137566;Oprea1_769831;Oprea1_798983;WLN: T56 BVNVJ CVR;1H-Isoindole-1, 2-benzoyl-;SCHEMBL9686147;DTXSID70196626;AKOS003788899;NSC-137566;LS-109439;2-Benzoyl-1H-isoindole-1,3(2H)-dione #;SR-01000312446;SR-01000312446-1

Chemical Property of N-Benzoylphthalimide

Chemical Property:

• Vapor Pressure: 1.13E-07mmHg at 25°C
• Boiling Point: 432.2°C at 760 mmHg
• Flash Point: 205.8°C
• PSA: 54.45000
• Density: 1.398g/cm³
• LogP: 2.06090
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 251.058243149
• Heavy Atom Count: 19
• Complexity: 388

Purity/Quality:

99% ^*data from raw suppliers

N-BENZOYLPHTHALIMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of N-Benzoylphthalimide

There total 12 articles about N-Benzoylphthalimide 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: 88.0%

diphenyl (1,3-dioxoisoindolin-2-yl)phosphonate (80824-98-2) + benzoic acid (65-85-0,8013-63-6) → 2-benzoylisoindoline-1,3-dione (4583-50-0)

Guidance literature:

With triethylamine; In acetonitrile; for 3h; Heating;

DOI:10.1055/s-1981-29675

Reference yield: 80.0%

phthalimide (136918-14-4,85-41-6) + benzoyl chloride (98-88-4) → 2-benzoylisoindoline-1,3-dione (4583-50-0)

Guidance literature:

With triethylamine; In N,N-dimethyl acetamide; at 0 ℃; for 1.5h;

DOI:10.1021/acs.orglett.7b02877

Reference yield: 80.0%

phthalimide (136918-14-4,85-41-6) + benzoic acid anhydride (93-97-0) → 2-benzoylisoindoline-1,3-dione (4583-50-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 9h; Heating;

upstream raw materials:

pyridine

phthalimide

benzoyl chloride

benzaldehyde

Downstream raw materials:

4-Methylbenzophenone

N-methyl-N-phenyl-benzamide

Cyclohexyl phenyl ketone

4-methoxylbiphenyl

Refernces

• 1、 Bisz, Elwira,Chen, Hao,Dziuk, B?a?ej,Ejsmont, Krzysztof,Lalancette, Roger,Pyle, Daniel J.,Rahman, Md. Mahbubur,Szostak, Michal,Szostak, Roman,Wang, Qi. "Evaluation of Cyclic Amides as Activating Groups in N-C Bond Cross-Coupling: Discovery of N-Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions". . p. 10455 - 10466. Retrieved 2021/07/31.
• 2、 Karthik, Shanmugam,Gandhi, Thirumanavelan. "Palladium(II)/N-heterocyclic carbene-catalyzed direct C-H acylation of heteroarenes with N-acylsaccharins". supporting information. p. 5486 - 5489. Retrieved 2017/11/06.