3-(4-Bromo-3-methyl-2-oxo-2,3-dihydro-1h-benzo[d]imidazol-1-yl)piperidine-2,6-dione
[CAS# 2304754-51-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 3-(4-Bromo-3-methyl-2-oxo-2,3-dihydro-1h-benzo[d]imidazol-1-yl)piperidine-2,6-dione
• Molecular Formula: C₁₃H₁₂BrN₃O₃
• Molecular Weight: 338.16
• CAS Registry Number: 2304754-51-4
• SMILES: CN1C2=C(C=CC=C2Br)N(C1=O)C3CCC(=O)NC3=O

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.647, Calc.^*
• Boiling Point: 516.6±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 266.2±30.1 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

3-(4-bromo-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-2,6-dione, commonly abbreviated as BMBIPD, is a compound that combines a benzo[d]imidazole structure with a piperidinedione ring and a bromine atom. The discovery of BMBIPD stems from the study of benzo[d]imidazole derivatives that have diverse biological activities and structural stability. BMBIPD combines the 4-bromo-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole moiety with a piperidine-2,6-dione ring. The bromine atom and benzo[d]imidazole backbone enhance its reactivity and potential as a pharmacophore, while the piperidinedione group provides additional stability and functional diversity.

BMBIPD is synthesized via a multistep process that first forms the benzo[d]imidazole core, followed by bromination, methylation, and incorporation of the piperidinedione ring. The compound is a crystalline solid with remarkable stability and reactivity due to the electron-withdrawing bromine atom and the electron-donating methyl group. These properties make BMBIPD an attractive candidate for various chemical transformations.

BMBIPD is expected to be a scaffold for the development of anticancer agents. Its benzo[d]imidazole core can interact with a variety of biological targets, offering the potential for designing drugs that inhibit cancer cell proliferation and induce apoptosis. The unique structure of the compound, especially the bromine and methyl groups, provides a basis for the development of enzyme inhibitors. BMBIPD derivatives can effectively bind to enzyme active sites, providing potential treatments for diseases involving enzyme dysfunction, such as cancer and inflammation. BMBIPD and its derivatives have also been intensively studied for their antimicrobial activity. The interaction of the benzo[d]imidazole moiety with microbial proteins suggests the potential to create compounds that are effective against bacterial and fungal infections. The goal is to optimize these derivatives to improve their efficacy and safety as antimicrobial agents.

BMBIPD is a versatile organic synthesis intermediate. Its benzo[d]imidazole and piperidinedione rings provide multiple functionalization sites, enabling the construction of complex molecular structures that are critical for pharmaceuticals and advanced materials. This compound can serve as a building block for the synthesis of a wide range of heterocycles. Its unique structure allows for a variety of transformations that aid in the development of new chemical entities with potential biological activity. The structure of BMBIPD allows for further functionalization, making it a valuable precursor for the introduction of additional substituents. This versatility can be used to create molecules with specific electronic and steric properties to suit a variety of applications in chemical synthesis and industry.

References

2021. Compounds and methods for the targeted degradation of irak-4. WO-2022266258-A1

2021. Egfr degraders and associated methods of use. WO-2022228556-A1

2020. Irak degraders and uses thereof. WO-2022147465-A1