2,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate
• CAS No.: 66134-67-6
• Molecular Formula: C11H8FNO4
• Molecular Weight: 237.187
• UNII: EGN7SEN5K6
• DSSTox Substance ID: DTXSID00434200
• Nikkaji Number: J428.420H
• Wikipedia: N-Succinimidyl_4-fluorobenzoate
• Wikidata: Q18378723
• Mol file: 66134-67-6.mol

Synonyms:(18F)SFB;N-succinimidyl 4-(18F)fluorobenzoate;N-succinimidyl 4-fluorobenzoate;N-succinimidyl-4-(18F)fluorobenzoate;N-succinimidyl-4-fluorobenzoate;NSM-FB

Chemical Property of 2,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 113-114 °C
• Boiling Point: 354.873oC at 760 mmHg
• Flash Point: 168.422oC
• PSA: 63.68000
• Density: 1.462g/cm3
• LogP: 0.98440
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 237.04373590
• Heavy Atom Count: 17
• Complexity: 333

Purity/Quality:

95% ^*data from raw suppliers

Benzoic acid 4-fluoro-2,5-dioxo-1-pyrrolidinyl ester95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate

There total 12 articles about 2,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate 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: 99.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-Fluorobenzoic acid (456-22-4) → p-fluorobenzoic acid succinimidyl ester (66134-67-6)

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: 91.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-fluorobenzylic alcohol (459-56-3) → p-fluorobenzoic acid succinimidyl ester (66134-67-6)

Guidance literature:

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

DOI:10.1246/cl.2006.566

Reference yield: 85.0%

4-Fluorobenzoic acid (456-22-4) + O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (105832-38-0) → p-fluorobenzoic acid succinimidyl ester (66134-67-6)

Guidance literature:

With sodium carbonate; In acetonitrile; at 50 ℃; for 1h;

DOI:10.1016/j.bmc.2014.11.013

upstream raw materials:

4-Fluorobenzoic acid

O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

di(succinimido) carbonate

1-hydroxy-pyrrolidine-2,5-dione

Downstream raw materials:

N-succinimidyl 4-[18F]fluorobenzoate

Refernces

• 1、 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.
• 2、 Singha, Krishnadipti,Ghosh, Subhash Ch.,Panda, Asit Baran. "N-Doped Yellow TiO2 Hollow Sphere-Mediated Visible-Light-Driven Efficient Esterification of Alcohol and N-Hydroxyimides to Active Esters". . p. 3205 - 3212. Retrieved 2019/09/09.