2,5-Dioxopyrrolidin-1-yl 2-cyanoacetate

Name: 2,5-Dioxopyrrolidin-1-yl 2-cyanoacetate
Brand: ChemScene
Availability: InStock
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CAS No. 56657-76-2
Cat. No. CS-M3397
Purity≥98%
MDL No.MFCD00798802

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2,5-Dioxopyrrolidin-1-yl 2-cyanoacetate|CS-M3397

Structure of 56657-76-2

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General Information

CAS No. 56657-76-2
Cat. No. CS-M3397
Purity ≥98%
MDL No. MFCD00798802
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₆N₂O₄
Molecular Weight 182.13
Synonym(s) None
SMILES O=C(ON1C(CCC1=O)=O)CC#N

Description

This activated ester features a pyrrolidinone ring that enhances hydrolytic stability while enabling efficient coupling to amines under mild conditions. The cyanoacetate moiety provides a reactive handle for conjugation, delivering high yields in amide bond formation without racemization. Ideal for peptide synthesis and bioconjugation workflows requiring precise control and clean reaction profiles.

Application

2,5-Dioxopyrrolidin-1-yl 2-cyanoacetate serves as a highly effective activated ester for amide bond formation, enabling efficient coupling of carboxylic acids with amines under mild conditions. Its stability in storage and ease of purification make it ideal for peptide synthesis and medicinal chemistry applications. The cyano group provides additional reactivity for downstream transformations, such as nucleophilic additions or heterocycle formation.

Synthesis

Route1
- In-stock
  
  6066-82-6
- 372-09-8
- ~24%
- In-stock
  
  56657-76-2
References
- Stefanowicz, P.; Siemion, I. Z. Polish Journal of Chemistry, 1992 , vol. 66, # 1 p. 111 - 118

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 87.47
LogP -0.49272
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Key Words

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2,5-Dioxopyrrolidin-1-yl 2-cyanoacetate

CAS No. 56657-76-2

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