3-(6-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione
[CAS# 2304513-76-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: 3-(6-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione
• Synonyms: 3-(5-bromo-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione
• Molecular Formula: C₁₃H₁₁BrN₂O₃
• Molecular Weight: 323.14
• CAS Registry Number: 2304513-76-4
• EC Number: 893-749-5
• SMILES: C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=C(C=C3)Br

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.651, Calc.^*
• Boiling Point: 575.3±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 301.8±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

The development of 3-(6-bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione (often abbreviated as BOPD) stems from the study of isoindolinone derivatives, which are well known for their medicinal potential. The synthesis of BOPD involves bromination of an isoindolinone precursor followed by the introduction of the piperidinedione group. This step-by-step approach highlights the precision required in modern organic chemistry to create such complex molecules. BOPD is characterized by its crystalline solid form and remarkable chemical stability, which is attributed to the synergistic effects between the bromine atom, the isoindolinone core, and the piperidinedione ring.

BOPD is expected to be a scaffold for anticancer drug development. The unique structure of the compound enables it to interact with a variety of biological targets, making it a candidate for inhibiting cancer cell growth and inducing apoptosis. Researchers focus on optimizing BOPD derivatives to enhance their efficacy against different types of cancer.

BOPD has also been explored as an enzyme inhibitor. Its structure, especially the bromine atom, contributes to the compound's ability to bind to enzyme active sites, providing a potential treatment for diseases associated with enzyme regulation, such as cancer and metabolic disorders.

Research on BOPD includes its use as a scaffold for anti-inflammatory agents. The compound's ability to modulate inflammatory pathways provides an opportunity to develop new therapeutics for diseases such as arthritis and other inflammatory diseases. Modifications to the BOPD structure are designed to improve its selectivity and minimize side effects, making it a promising candidate for the development of anti-inflammatory drugs.

BOPD is a versatile organic synthesis intermediate. The combination of its isoindolinone core and piperidinedione ring provides a platform for a variety of chemical transformations, which is essential for creating complex molecular structures in pharmaceuticals and fine chemicals.

The compound is used as a building block for the synthesis of heterocyclic compounds. The isoindolinone and piperidinedione rings have structural diversity that enables the creation of heterocycles with potential biological activity. Such applications are essential for the development of new chemical entities for drug discovery and materials science.

As a precursor, BOPD can be further functionalized to introduce additional substituents, resulting in derivatives with tailored properties. This versatility allows the synthesis of a wide range of compounds with specific electronic and steric properties for use in pharmaceuticals and advanced materials.