2,5-Dioxopyrrolidin-1-yl 6-(2-(propan-2-ylidene)hydrazinyl)nicotinate

Name: 2,5-Dioxopyrrolidin-1-yl 6-(2-(propan-2-ylidene)hydrazinyl)nicotinate
Brand: ChemScene
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CAS No. 362522-50-7
Cat. No. CS-0132369
Molecule weight290.27
Purity≥97%
MDL No.MFCD06411383

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2,5-Dioxopyrrolidin-1-yl 6-(2-(propan-2-ylidene)hydrazinyl)nicotinate|CS-0132369

Structure of 362522-50-7

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General Information

CAS No. 362522-50-7
Cat. No. CS-0132369
Purity ≥97%
MDL No. MFCD06411383
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₄N₄O₄
Molecular Weight 290.27
Synonym(s) 2,5-dioxopyrrolidin-1-yl 6-(2-(propan-2-ylidene)hydrazinyl)nicotinate (S-SANH)
SMILES O=C(C1=CC=C(N/N=C(C)\C)N=C1)ON2C(CCC2=O)=O

Description

This pyrrolidinone ester features a hydrazinyl-substituted nicotinate core, enabling efficient coupling in peptide and biomolecule conjugation. The dioxopyrrolidinyl leaving group ensures high reactivity under mild conditions, while the tert-butylidene hydrazine moiety imparts stability and selective functionalization potential.

Application

This compound serves as a versatile acylating agent for amine functionalization, leveraging the reactive 2,5-dioxopyrrolidin-1-yl ester moiety. It facilitates efficient amidation under mild conditions, with the hydrazine-containing nicotinate group enabling downstream derivatization in heterocyclic synthesis. The tert-butylidene substituent enhances stability and aids in purification, making it suitable for bench-scale applications in medicinal chemistry and API intermediate development.

Synthesis

Route1
- In-stock
  
  6066-82-6
- In-stock
  
  133081-24-0
- 67-64-1
- ~68%
- In-stock
  
  362522-50-7
References
- Grotzky, Andrea; Nauser, Thomas; Erdogan, Huriye; Schlueter, A. Dieter; Walde, Peter Journal of the American Chemical Society, 2012 , vol. 134, # 28 p. 11392 - 11395

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 100.96
LogP 1.1101
H_Acceptors 7
H_Donors 1
Rotatable_Bonds 4

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Key Words

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2,5-Dioxopyrrolidin-1-yl 6-(2-(propan-2-ylidene)hydrazinyl)nicotinate

CAS No. 362522-50-7

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