3-Bromopiperidine-2,6-dione
3-Bromopiperidine-2,6-dione (also known as 3-bromoglutarimide) is a brominated heterocyclic compound with the molecular formula C₅H₆BrNO₂ and molecular weight 192.01 g/mol. It has the CAS number 62595-74-8.
Core Properties
- Structure: A piperidine-2,6-dione (glutarimide) ring with a bromine atom at the 3-position.
- Physical form: White to off-white crystalline powder.
- Solubility: Insoluble in water; soluble in polar organic solvents (DMF, DMSO).
- Melting point: ~107 °C.
- Storage: 2–8 °C, protected from light.
Key Features & Applications
- Reactive handle: The 3-bromo group enables nucleophilic substitution for further functionalization.
- Synthetic intermediate: Critical building block for preparing immunomodulatory imide drugs (IMiDs) (e.g., thalidomide analogs) and PROTACs.
- Medicinal chemistry: Used in the design of anticancer and immunomodulatory agents.
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