N-(Benzoyloxy)succinimide

Base Information

• Chemical Name: N-(Benzoyloxy)succinimide
• CAS No.: 23405-15-4
• Molecular Formula: C11H9NO4
• Molecular Weight: 219.197
• Hs Code.: 2925190090
• European Community (EC) Number: 803-576-9
• DSSTox Substance ID: DTXSID00352011
• Nikkaji Number: J428.417H
• Wikidata: Q72445553
• Mol file: 23405-15-4.mol

Synonyms:N-succinimidyl benzoate

Chemical Property of N-(Benzoyloxy)succinimide

Chemical Property:

• Vapor Pressure: 7.6E-05mmHg at 25°C
• Melting Point: 135.0 to 139.0 °C
• Refractive Index: 1.598
• Boiling Point: 342.3 °C at 760 mmHg
• Flash Point: 160.8 °C
• PSA: 63.68000
• Density: 1.39g/cm³
• LogP: 0.84530
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 219.05315777
• Heavy Atom Count: 16
• Complexity: 304

Purity/Quality:

97% ^*data from raw suppliers

N-(Benzoyloxy)succinimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)C2=CC=CC=C2

Technology Process of N-(Benzoyloxy)succinimide

There total 19 articles about N-(Benzoyloxy)succinimide 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%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + benzoic acid (65-85-0,8013-63-6) → benzoic acid N-hydroxysuccinimide ester (23405-15-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.0c01182

Reference yield: 92.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + benzyl alcohol (100-51-6,185532-71-2) → benzoic acid N-hydroxysuccinimide ester (23405-15-4)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In ethyl acetate; for 0.5h; cooling;

DOI:10.1246/cl.2006.566

Reference yield: 89.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + benzaldehyde (100-52-7) → benzoic acid N-hydroxysuccinimide ester (23405-15-4)

Guidance literature:

With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In ethyl acetate; at 20 - 70 ℃; for 12h;

DOI:10.1002/anie.201205921

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

benzoic acid

benzoyl chloride

sodium benzoate

Downstream raw materials:

N-benzoyl-L-tyrosine

C₅₈H₇₁N₄O₅⁽¹⁺⁾*I^(1-)

1,4-dibenzoylpiperazine

N-Benzoylpiperazine

Refernces

• 1、 Sengle, Gerhard,Jenne, Andreas,Arora, Paramjit S.,Seelig, Burckhard,Nowick, James S.,Jaeschke, Andres,Famulok, Michael. "Synthesis, incorporation efficiency, and stability of disulfide bridged functional groups at RNA 5'-ends". . p. 1317 - 1329. Retrieved 2000.
• 2、 Inomata,K. et al.. "-". . p. 1265 - 1268. Retrieved 1979.
• 3、 Andrews, Charlotte L.,Cardozo, Joaquin M.,Chow, Alyssa S.,Crainic, Jennifer A.,Parsons, William H.,Rutland, Nicholas T.,Sheehan, Brendan K.. "Development of succinimide-based inhibitors for the mitochondrial rhomboid protease PARL". supporting information. . Retrieved 2021/08/04.
• 4、 Dussart-Gautheret, Jade,Deschamp, Julia,Monteil, Maelle,Gager, Olivier,Legigan, Thibaut,Migianu-Griffoni, Evelyne,Lecouvey, Marc. "Formation of 1-hydroxymethylene-1,1-bisphosphinates through the addition of a silylated phosphonite on various trivalent derivatives". . p. 14559 - 14569. Retrieved 2020/12/29.