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Merck
CN

943576

3-(4-(Piperazin-1-yl)phenyl)piperidine-2,6-dione dihydrochloride

≥95%

Synonym(s):

2,6-Piperidinedione, 3-[4-(1-piperazinyl)phenyl]-, hydrochloride (1:2), Phenyl-glutarimide 4′-piperazine

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SMILES string

O=C1NC(C(CC1)C2=CC=C(N3CCNCC3)C=C2)=O.[2HCl]

InChI key

DUZCAOXBUQOLHN-UHFFFAOYSA-N

InChI

1S/C15H19N3O2.2ClH/c19-14-6-5-13(15(20)17-14)11-1-3-12(4-2-11)18-9-7-16-8-10-18;;/h1-4,13,16H,5-10H2,(H,17,19,20);2*1H

description

Amine Reactivity: The free piperazine nitrogen(s) can undergo alkylation, acylation, or conjugation using standard coupling strategies (e.g., NHS esters, amide bonds). / Linker Compatibility: Ideal for joining target-binding ligands via PROTAC synthetic workflows.

assay

≥95%

form

amorphous solid

reaction suitability

reactivity: amine reactive

color

off-white to gray-brown

functional group

amine (The free piperazine nitrogen(s) can undergo alkylation, acylation, or conjugation using standard coupling strategies (e.g., NHS esters, amide bonds).)

storage temp.

−20°C

Quality Level

100

General description

Phenyl-glutarimide 4′-piperazine is a piperazine-functionalized cereblon (CRBN) ligand, crafted to engage with the E3 ubiquitin ligase cereblon in PROTACs. It’s a member of the PG-PROTAC family, designed to address the hydrolytic instability of traditional IMiD ligands, while maintaining high binding affinity and enabling potent protein degradation activity.

Application

  • PROTAC Assembly: Functions as the E3 ligase ligand, especially in PG-PROTAC systems for targeted protein degradation.
  • Chemical Biology Research: Used in studies of targeted degradation mechanisms and new degrader development.
  • Medicinal Chemistry: Acts as a scaffold for scaffold-based drug design and bifunctional molecule synthesis.

Features and Benefits

  • Reliable cereblon engagement: Binds the CRBN E3 ligase, facilitating PROTAC assembly.
  • Enhanced hydrolytic stability: Outperforms IMiD-based ligands (e.g., thalidomide derivatives) in chemical durability.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2 - Skin Sens. 1B

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000502548
0000502548

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