3-(3-Bromophenyl)-1,2,4-oxadiazole: Properties & Lab FAQ

3-(3-Bromophenyl)-1,2,4-oxadiazole is a halogenated heteroaromatic building block widely used in medicinal chemistry and materials science as a versatile synthetic intermediate for the construction of more complex oxadiazole-containing scaffolds.

Product Name

3-(3-Bromophenyl)-1,2,4-oxadiazole

SKU

B178912

Molecular Formula

C8H5BrN2O

Heterocycle Class

1,2,4-Oxadiazole

Key Functional Handle

Aryl bromide (C–Br) enabling cross-coupling reactions

Primary Application

Synthetic intermediate and building block in drug discovery and materials research

What Is 3-(3-Bromophenyl)-1,2,4-oxadiazole?

3-(3-Bromophenyl)-1,2,4-oxadiazole (SKU B178912) is a five-membered heteroaromatic compound containing one oxygen and two nitrogen atoms arranged in the 1,2,4-positions of the ring. A 3-bromophenyl substituent is attached at the 3-position of the oxadiazole core, providing an aryl bromide handle that is highly amenable to palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings.

The 1,2,4-oxadiazole ring is a bioisostere of ester and amide functional groups and is recognized for its metabolic stability relative to its carbonyl-based analogs. This makes the scaffold attractive in medicinal chemistry programs where improved pharmacokinetic profiles are desired.

Solubility, Storage, and Handling

Solubility: 3-(3-Bromophenyl)-1,2,4-oxadiazole is expected to be soluble in common organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), dichloromethane (DCM), and ethyl acetate. Solubility in aqueous systems is anticipated to be low due to the lipophilic bromophenyl group and the aromatic heterocyclic core. Researchers should prepare stock solutions in DMSO and dilute into aqueous buffers immediately before use if aqueous conditions are required.

Storage: Store the compound in a tightly sealed container under cool, dry conditions away from light and moisture. Refrigerated storage (2–8 °C) is typically recommended for long-term stability of halogenated heteroaromatic compounds. Always confirm specific storage conditions on the product certificate of analysis.

Handling: Standard laboratory precautions for handling halogenated organic compounds apply. Use appropriate personal protective equipment (PPE) including gloves, safety glasses, and a lab coat. Work in a well-ventilated area or fume hood.

Synthetic Applications and Reactivity

The aryl bromide substituent in 3-(3-Bromophenyl)-1,2,4-oxadiazole serves as a versatile electrophilic partner in transition-metal-catalyzed reactions. Key synthetic utilities include:

• Suzuki–Miyaura coupling: Reaction with aryl or heteroaryl boronic acids in the presence of a palladium catalyst and base to generate biaryl and heteroaryl–aryl products bearing the oxadiazole pharmacophore.
• Buchwald–Hartwig amination: Introduction of amine groups via palladium-catalyzed C–N bond formation, enabling access to aminoaryl-oxadiazole derivatives relevant to drug discovery.
• Negishi and Kumada couplings: Use of organozinc or organomagnesium reagents to install alkyl or aryl groups.
• Lithiation/metal–halogen exchange: Treatment with n-BuLi or other organolithium reagents can generate the aryllithium species for subsequent electrophilic trapping.

The electron-withdrawing nature of the 1,2,4-oxadiazole ring may influence the reactivity of the aryl bromide and should be considered when optimizing reaction conditions.

Relevance in Medicinal Chemistry and Drug Discovery

The 1,2,4-oxadiazole ring system has attracted sustained attention in pharmaceutical research due to its role as a bioisostere of amide and ester bonds, its resistance to metabolic hydrolysis, and its favorable physicochemical properties. Compounds incorporating this heterocycle have been investigated across a broad range of biological targets.

The 3-bromophenyl substitution pattern introduces additional synthetic flexibility, enabling rapid library synthesis through parallel cross-coupling chemistry. This is particularly valuable in fragment-based drug discovery and lead optimization campaigns where rapid analog synthesis is required.

Researchers should note that biological activity data specific to 3-(3-Bromophenyl)-1,2,4-oxadiazole itself are not provided in this document; its primary value is as a synthetic building block rather than as a final active compound.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 3-(3-Bromophenyl)-1,2,4-oxadiazole under SKU B178912. Each lot is accompanied by a Certificate of Analysis (CoA) detailing purity, analytical data (typically including NMR and/or HPLC), and physical characterization. Customers are encouraged to request the CoA for their specific lot prior to use in critical applications.

For bulk quantities, custom synthesis inquiries, or technical support regarding this compound, please contact Aladdin Scientific customer service. Procurement teams should reference SKU B178912 when placing orders to ensure correct product fulfillment.

Frequently asked questions

What is the molecular formula and molecular weight of 3-(3-Bromophenyl)-1,2,4-oxadiazole?

The molecular formula of 3-(3-Bromophenyl)-1,2,4-oxadiazole is C8H5BrN2O. The molecular weight is approximately 225.04 g/mol. Researchers should verify exact values against the product Certificate of Analysis supplied with each lot.

Which solvents are recommended for dissolving 3-(3-Bromophenyl)-1,2,4-oxadiazole?

Based on the compound's lipophilic aromatic structure, DMSO and DMF are recommended as primary solvents for preparing concentrated stock solutions. DCM and ethyl acetate are suitable for synthetic work. Aqueous solubility is expected to be low; any aqueous dilutions should be prepared fresh and tested for precipitation before use.

Can 3-(3-Bromophenyl)-1,2,4-oxadiazole be used in palladium-catalyzed cross-coupling reactions?

Yes. The aryl bromide (C–Br) group present in 3-(3-Bromophenyl)-1,2,4-oxadiazole is well-suited for palladium-catalyzed cross-coupling reactions including Suzuki–Miyaura, Buchwald–Hartwig, and Negishi couplings, making it a useful building block for constructing diverse oxadiazole-containing compound libraries. Reaction conditions should be optimized taking into account the electron-withdrawing effect of the oxadiazole ring.

What are the recommended storage conditions for 3-(3-Bromophenyl)-1,2,4-oxadiazole?

The compound should be stored in a tightly sealed container under cool and dry conditions, protected from light and moisture. Refrigerated storage at 2–8 °C is generally recommended for long-term stability of halogenated heteroaromatic compounds. Always refer to the specific storage conditions stated on the product label and Certificate of Analysis.

Is 3-(3-Bromophenyl)-1,2,4-oxadiazole a biologically active compound or primarily a synthetic intermediate?

3-(3-Bromophenyl)-1,2,4-oxadiazole is primarily valued as a synthetic building block and intermediate, enabling the construction of more complex oxadiazole-bearing molecules for pharmaceutical and materials research. Specific intrinsic biological activity data for this compound are not documented in the current source material; researchers pursuing bioactivity screening should consult primary literature on related oxadiazole analogs.

References

1. General reference: Textbook-level knowledge of 1,2,4-oxadiazole chemistry and cross-coupling reactions. No specific primary literature citation available from source material.
2. Aladdin Scientific product listing: 3-(3-Bromophenyl)-1,2,4-oxadiazole, SKU B178912.

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