5-Bromo-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
[CAS# 26166-92-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: 5-Bromo-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
• Synonyms: 5-Bromo-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione; 5-Bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
• Molecular Formula: C₁₃H₉BrN₂O₄
• Molecular Weight: 337.13
• CAS Registry Number: 26166-92-7
• EC Number: 885-600-8
• SMILES: C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C=C(C=C3)Br

Properties

• Solubility: Very slightly soluble (0.37 g/L) (25 ºC), Calc.^*
• Density: 1.794±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: >230 ºC^**
• Index of Refraction: 1.668, Calc.^*
• Boiling Point: 564.3±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 295.1±28.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

^** Stewart, Scott G.; Bioorganic & Medicinal Chemistry 2010, V18(2), P650-662.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovory and Applicatios

5-Bromo-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione is a chemical compound that belongs to the class of isoindole derivatives. It has the molecular formula C10H8BrNO3 and is characterized by its distinct structural features, which include a bromine atom attached to the benzene ring and a piperidine ring fused to an isoindole scaffold. The compound has been studied for its chemical reactivity and potential applications in the synthesis of bioactive molecules.

The discovery of 5-Bromo-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione was part of the exploration of isoindole derivatives, which are known for their diverse biological activities. The presence of a piperidine ring and carbonyl groups on the isoindole core suggests the compound could exhibit interesting interactions with biological targets.

While the specific applications of this compound are not as widely documented, its structure suggests it may have utility in medicinal chemistry, particularly in the design of compounds with potential therapeutic activity. The isoindole core is a known scaffold in the development of various bioactive compounds, including those with anticancer, antimicrobial, and neuroactive properties. Therefore, derivatives like 5-Bromo-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione are of interest for further research into their pharmacological potential.

In terms of its chemical reactivity, compounds of this class are often studied for their ability to undergo various types of chemical transformations, which may include nucleophilic substitution or addition reactions. These transformations can be valuable in the development of more complex chemical structures with enhanced biological activity or specificity.

Further exploration of 5-Bromo-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione may involve its synthesis and testing for a variety of pharmacological activities. However, as of the current literature, its widespread application in pharmaceutical development has not yet been established.

References

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Sun, Yang, Zhang, Li et al. Design, synthesis, and evaluation of BTK-targeting PROTACs with optimized bioavailability in vitro and in vivo, RSC Med. Chem.
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Shou-Jie Shen, Le-Mei Wang, Guo-Mei Gong, Yan-Jiao Wang, Jin-Yan Liang, Jun-Wen Wang Construction of sulfur-containing N-vinylimides: N-addition of imides to propargyl sulfonium salts, RSC Adv., 2022, 12, 12671
DOI: 10.1039/D2RA01117D