3-Bromopiperidine-2,6-dione: Properties, Uses & FAQs

3-Bromopiperidine-2,6-dione is a halogenated glutarimide building block widely used in medicinal chemistry as a reactive intermediate for the synthesis of thalidomide analogues, cereblon-binding ligands, and PROTAC degrader conjugates.

CAS Number

Verify with Aladdin product datasheet (BD290761)

Molecular Formula

C5H6BrNO2

Molecular Weight

192.01 g/mol (approximate; verify on CoA)

Key Functional Groups

α-Bromo ketone and lactam within a six-membered glutarimide ring

Primary Research Application

Synthesis of cereblon E3 ligase ligands and PROTAC linker conjugation

SKU

B589701

What Is 3-Bromopiperidine-2,6-dione?

3-Bromopiperidine-2,6-dione is a six-membered cyclic imide (glutarimide) bearing a bromine substituent at the 3-position (the carbon alpha to both carbonyl groups). Its core scaffold is closely related to the glutarimide moiety found in immunomodulatory drugs (IMiDs) such as thalidomide and lenalidomide, which bind to the E3 ubiquitin ligase adaptor cereblon (CRBN).

Because the bromine atom is an excellent leaving group, the compound is widely exploited as a reactive electrophilic intermediate. Researchers use nucleophilic substitution or coupling reactions at C-3 to introduce diverse linkers, pharmacophores, or warheads, making it a key starting material in targeted protein degradation chemistry (PROTACs) and in the preparation of novel IMiD analogues.

Physicochemical Properties and Handling

Appearance: Typically a white to off-white crystalline solid.

Solubility: Soluble in polar aprotic solvents such as DMSO and DMF; sparingly soluble in water. Test solubility empirically before use in aqueous biological assays.

Stability: The C–Br bond alpha to two electron-withdrawing carbonyls confers electrophilic reactivity; the compound can undergo hydrolysis or nucleophilic attack under aqueous or basic conditions. Handle under inert atmosphere (N₂ or Ar) when long reaction times are required.

Storage: Store in a tightly sealed container at 2–8 °C, protected from light and moisture. For long-term storage consider –20 °C under inert gas. Always confirm storage conditions on the current Aladdin Certificate of Analysis (CoA).

Note: Specific melting point, log P, and pKa values are not available in the current source material. Refer to the product CoA or third-party databases for these parameters.

Research Applications

PROTAC Synthesis: 3-Bromopiperidine-2,6-dione serves as a direct precursor to cereblon-recruiting warheads in proteolysis-targeting chimera (PROTAC) molecules. Displacement of the C-3 bromide by an amine-terminated linker yields the corresponding 3-amino or 3-substituted glutarimide, which can then be further functionalized to recruit CRBN and drive ubiquitin-mediated degradation of a target protein of interest.

IMiD Analogue Preparation: The compound provides a convenient handle for accessing structural analogues of thalidomide, pomalidomide, and lenalidomide without requiring multi-step de novo glutarimide ring construction.

Mechanistic Studies: Researchers studying CRBN binding, teratogenicity mechanisms, or IMiD structure–activity relationships (SAR) may use this intermediate to prepare defined analogues for biochemical and cellular assays.

General Synthetic Utility: As an activated α-halo imide, it can participate in radical reactions, metal-catalyzed cross-coupling, and nucleophilic substitution, broadening its utility across synthetic organic chemistry programs.

Safety and Regulatory Considerations

3-Bromopiperidine-2,6-dione is a research-use-only (RUO) reagent. Its structural similarity to thalidomide-class compounds means users should be aware of potential biological activity. The following precautions are recommended:

• Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before first use.
• Use appropriate personal protective equipment (PPE): lab coat, nitrile gloves, and safety glasses as a minimum.
• Work in a well-ventilated area or fume hood.
• Avoid inhalation of dust or aerosols.
• Dispose of waste according to local institutional and governmental regulations for halogenated organic compounds.

Specific GHS hazard classifications, LD₅₀ values, and regulatory scheduling information are not available in the current source material. Always refer to the current Aladdin SDS for authoritative safety data before handling this compound.

Ordering, Purity, and Quality Assurance

Available SKU: Aladdin Scientific offers 3-Bromopiperidine-2,6-dione under SKU B589701.

Purity: Purity specification is provided on the product Certificate of Analysis (CoA). Contact Aladdin Scientific customer service or visit the product page to obtain the current CoA for your specific lot.

Lot-Specific Documentation: Each shipment is accompanied by a CoA stating identity (NMR, HPLC, or MS confirmation), purity, and physical appearance. Request lot-specific documentation at the time of ordering if required for regulatory or quality management purposes.

Custom Quantities: If standard pack sizes do not meet your project needs, contact Aladdin Scientific to discuss custom synthesis or bulk supply options.

Returns and Quality Issues: Please refer to Aladdin Scientific's return and refund policy. If a product does not meet the stated specifications, contact customer service within the applicable notification window and retain the original packaging and CoA.

Frequently asked questions

What is the molecular formula and molecular weight of 3-Bromopiperidine-2,6-dione?

The molecular formula of 3-Bromopiperidine-2,6-dione is C5H6BrNO2, giving an approximate molecular weight of 192.01 g/mol. Always verify the exact value against the Certificate of Analysis provided with your specific lot, as isotopic composition can affect precise calculations.

How should 3-Bromopiperidine-2,6-dione be stored to maintain stability?

Store the compound in a tightly sealed container at 2–8 °C, protected from light and moisture. For extended storage, –20 °C under an inert gas atmosphere (N₂ or Ar) is recommended. The C–Br bond at the alpha position is electrophilically reactive, so exposure to moisture, nucleophiles, or basic conditions should be avoided. Confirm storage requirements on the current Aladdin CoA for your lot.

What solvents are suitable for dissolving 3-Bromopiperidine-2,6-dione?

3-Bromopiperidine-2,6-dione is generally soluble in polar aprotic solvents such as DMSO and DMF, which are commonly used for preparing stock solutions in biological research. It has limited solubility in water. If aqueous compatibility is required for an assay, prepare a concentrated stock in DMSO and dilute into the aqueous medium immediately before use, monitoring for precipitation. Verify solubility empirically for your specific application conditions.

Is 3-Bromopiperidine-2,6-dione suitable for use as a PROTAC building block?

Yes. 3-Bromopiperidine-2,6-dione is widely employed in PROTAC synthesis as a cereblon (CRBN) E3 ligase-recruiting warhead precursor. The C-3 bromide can be displaced by amine-functionalized linkers under mild conditions to yield 3-substituted glutarimide conjugates that retain CRBN-binding capacity. Researchers should confirm the desired reactivity and selectivity in their specific synthetic context before scale-up.

How do I obtain a Certificate of Analysis (CoA) or Safety Data Sheet (SDS) for SKU B589701?

You can obtain the CoA and SDS for 3-Bromopiperidine-2,6-dione (SKU B589701) directly from the Aladdin Scientific product page by entering your lot number, or by contacting Aladdin Scientific customer service. Always use the lot-specific CoA to confirm identity, purity, and storage conditions for each shipment received.

What safety precautions should be taken when handling 3-Bromopiperidine-2,6-dione?

Consult the Aladdin Scientific SDS before first use. Wear appropriate PPE including a lab coat, nitrile gloves, and safety glasses. Work in a fume hood or well-ventilated area to avoid inhalation of dust or vapors. Due to structural similarity to IMiD-class compounds, handle with caution and dispose of waste as halogenated organic chemical waste per local regulations. Specific hazard classifications are not available in the current source material; refer to the SDS for authoritative guidance.

References

1. Aladdin Scientific product page for 3-Bromopiperidine-2,6-dione, SKU B589701. Internal reference: BD290761.
2. Kronke J, et al. Lenalidomide causes selective degradation of IKZF1 and IKZF3 in multiple myeloma cells. Science. 2014;343(6168):301-305. [Cited as background for cereblon-binding glutarimide pharmacology; verify applicability.]
3. Bondeson DP, Crews CM. Targeted protein degradation by small molecules. Annu Rev Pharmacol Toxicol. 2017;57:107-123. [General PROTAC background; verify applicability to this specific compound.]

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.