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

Name: 2,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 66134-67-6
Cat. No. CS-0157527
Purity≥97%
MDL No.MFCD00587232

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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2,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate|CS-0157527

Structure of 66134-67-6

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General Information

CAS No. 66134-67-6
Cat. No. CS-0157527
Purity ≥97%
MDL No. MFCD00587232
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₈FNO₄
Molecular Weight 237.18
Synonym(s) Succinimido p-fluorobenzoate
SMILES C1=C(C=CC(=C1)F)C(=O)ON2C(=O)CCC2=O

Description

This activated ester features a 4-fluorobenzoate moiety coupled to a dioxopyrrolidinyl leaving group, enabling efficient amide bond formation under mild conditions. The electron-withdrawing fluorine substituent enhances reactivity while maintaining stability during storage and handling.

Application

2,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate serves as a highly effective acylating agent for amine functionalization, enabling efficient formation of amide bonds under mild conditions. Its bench-stable nature and clean byproduct formation facilitate straightforward purification. The electron-withdrawing fluorophenyl group enhances reactivity while maintaining compatibility with diverse functional groups, making it ideal for peptide coupling and conjugation workflows in medicinal chemistry and materials synthesis.

Synthesis

Route1
- In-stock
  
  6066-82-6
- In-stock
  
  459-56-3
- ~92%
- In-stock
  
  66134-67-6
References
- Wang, Naiwei; Liu, Renhua; Xu, Qing; Liang, Xinmiao Chemistry Letters, 2006 , vol. 35, # 6 p. 566 - 567
Route2
- In-stock
  
  6066-82-6
- In-stock
  
  456-22-4
- ~79%
- In-stock
  
  66134-67-6
References
- Dissoki, Samar; Hagooly, Aviv; Elmachily, Smadar; Mishani, Eyal Journal of Labelled Compounds and Radiopharmaceuticals, 2011 , vol. 54, # 11 p. 693 - 701
Route3
- In-stock
  
  74124-79-1
- In-stock
  
  456-22-4
- ~78%
- In-stock
  
  66134-67-6
References
- Azarian, Vahe; Gangloff, Anne; Seimbille, Yann; Delaloye, Sibylle; Czernin, Johannes; Phelps, Michael E.; Silverman, Daniel H. S. Journal of Labelled Compounds and Radiopharmaceuticals, 2006 , vol. 49, # 3 p. 269 - 283

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 63.68
LogP 1.0465
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Building Blocks for Pharmaceutical Ingredients

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

CAS No. 66134-67-6

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