3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

Name: 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 827026-45-9
Cat. No. CS-M1824
Purity≥98%
MDL No.MFCD11977267

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3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione|CS-M1824

Structure of 827026-45-9

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General Information

CAS No. 827026-45-9
Cat. No. CS-M1824
Purity ≥98%
MDL No. MFCD11977267
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₁N₃O₅
Molecular Weight None
Synonym(s) 3-(4-Nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
SMILES O=C(C(CC1)N(CC2=C3C=CC=C2[N+]([O-])=O)C3=O)NC1=O

Description

This piperidine-2,6-dione scaffold features a fused isoindolone ring bearing a para-nitro substituent, delivering enhanced electron deficiency and rigidity. The conjugated system enables efficient integration into bioactive scaffolds, while the diketone moiety provides versatile coordination sites for metal complexes or coupling reactions under standard conditions.

Application

3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione serves as a versatile building block for heterocyclic synthesis, enabling efficient access to complex scaffolds via standard amide coupling and cyclization protocols. The ortho-nitroaryl moiety facilitates subsequent reduction and functionalization, while the diketone framework offers multiple points for derivatization. Bench-stable and compatible with common reaction conditions, it functions reliably in medicinal chemistry and process R&D workflows.

Synthesis

Route1
- In-stock
  
  98475-07-1
- In-stock
  
  2353-44-8
- ~77%
- In-stock
  
  827026-45-9
References
- CELGENE CORPORATION; LI, Ying; XU, Jean; KLOPFER, Kevin, J. Patent: WO2013/126394 A1, 2013 ; Location in patent: Paragraph 00123-00125 ;
Route2
- 1198299-72-7
- ~80%
- In-stock
  
  827026-45-9
References
- NANJING CAVENDISH BIO-ENGINEERING TECHNOLOGY CO., LTD.; YAN, Rong; YANG, Hao; XU, Yongxiang Patent: WO2010/139266 A1, 2010 ; Location in patent: Page/Page column 55 ;
Route3
- In-stock
  
  24666-56-6
- In-stock
  
  98475-07-1
- ~94%
- In-stock
  
  827026-45-9
References
- RANBAXY LABORATORIES LIMITED; KAPOOR, Munish; KUMAR, Saridi, Madhava, Dileep; MURUGESAN, Balaguru; SATHYANARAYANA, Swargam; THAPER, Rajesh, Kumar; PRASAD, Mohan Patent: WO2011/27326 A1, 2011 ; Location in patent: Page/Page column 11 ;

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

Quality Control

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Computational Chemistry Data

TPSA 112.3
LogP -0.9826
H_Acceptors 7
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

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3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

CAS No. 827026-45-9

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