3-Bromo-5-morpholinophenylboronic Acid: Key Facts & FAQs

3-Bromo-5-morpholinophenylboronic acid is a difunctional arylboronic acid building block bearing both a bromo substituent and a morpholino group on the phenyl ring, making it a versatile reagent for sequential cross-coupling reactions and medicinal chemistry synthesis.

Product Name

3-Bromo-5-morpholinophenylboronic acid

SKU

B180658

Molecular Formula

C10H13BBrNO3

Functional Groups

Boronic acid (–B(OH)2), Bromo (–Br), Morpholino (–N(C2H4)2O)

Primary Application

Suzuki–Miyaura cross-coupling and sequential palladium-catalyzed reactions

Supplier SKU Source

Aladdin Scientific, catalog number B180658

What Is 3-Bromo-5-morpholinophenylboronic Acid?

3-Bromo-5-morpholinophenylboronic acid (Aladdin SKU B180658) is an arylboronic acid in which the phenyl ring carries three distinct substituents at the 1-, 3-, and 5-positions: a boronic acid group (–B(OH)₂), a bromo atom (–Br), and a morpholino ring (–N(C₂H₄)₂O). This combination of functional groups in a single molecule provides orthogonal reactivity: the boronic acid participates in palladium-catalyzed Suzuki–Miyaura coupling under mild conditions, while the C–Br bond is available for a second, independent cross-coupling step or other metal-mediated transformations. The morpholino moiety improves aqueous solubility and is widely used in medicinal chemistry to modulate pharmacokinetic properties of drug candidates.

Chemical Properties and Structure

The compound possesses a symmetric 1,3,5-trisubstituted benzene core. The boronic acid group is a mild Lewis acid capable of forming reversible covalent bonds with diols and is the reactive handle exploited in Suzuki coupling. The aryl bromide provides a site for oxidative addition to palladium(0) complexes, enabling sequential or one-pot diversification strategies. The morpholino nitrogen is tertiary and non-nucleophilic under typical coupling conditions, minimizing side reactions. Arylboronic acids of this class are generally stable solids at room temperature but can slowly undergo protodeboronation or oxidative degradation upon prolonged exposure to air and moisture; therefore, proper storage is essential.

Handling, Storage, and Safety

As with most organoboron reagents, 3-Bromo-5-morpholinophenylboronic acid should be stored in a cool, dry place, away from direct light, preferably under an inert atmosphere (nitrogen or argon) or with a desiccant to prevent moisture uptake. Standard laboratory personal protective equipment—including nitrile gloves, safety glasses, and a laboratory coat—should be worn when handling the compound. Users should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for authoritative hazard classifications, GHS pictograms, first-aid measures, and disposal guidance before use. The compound contains an aryl bromide, which warrants the same general precautions applied to halogenated aromatic compounds.

Applications in Synthesis and Drug Discovery

The dual electrophilic/nucleophilic-equivalent reactivity of this building block makes it particularly valuable in fragment-based drug discovery and library synthesis. Researchers can first engage the boronic acid in a Suzuki coupling to install one aryl or heteroaryl fragment, then exploit the retained C–Br bond in a second coupling, amination (Buchwald–Hartwig), or other transition-metal-catalyzed reaction to introduce additional diversity. The morpholino group itself is a bioisostere commonly found in kinase inhibitors, antifungals, and CNS-active compounds, lending the scaffold direct relevance to medicinal chemistry programs. It is also useful as an intermediate in the synthesis of terphenyl or multi-aryl systems encountered in materials science and supramolecular chemistry.

Ordering and Availability from Aladdin Scientific

3-Bromo-5-morpholinophenylboronic acid is available from Aladdin Scientific under catalog number B180658. Procurement teams and lab managers can obtain current pricing, available pack sizes, purity certificates (CoA), and lead times directly through the Aladdin Scientific website or by contacting customer service. When placing an order, quote the SKU B180658 to ensure correct product identification. For bulk quantities or custom packaging, inquire with the Aladdin sales team. All shipments are accompanied by a batch-specific Certificate of Analysis confirming identity and purity.

Frequently asked questions

What reactions can 3-Bromo-5-morpholinophenylboronic acid (B180658) be used in?

The compound is primarily used in Suzuki–Miyaura palladium-catalyzed cross-coupling reactions via its boronic acid group. The intact aryl bromide provides a second reactive handle for additional cross-coupling (e.g., another Suzuki, Buchwald–Hartwig amination, or Negishi coupling), enabling sequential functionalization in a single synthetic sequence.

How should 3-Bromo-5-morpholinophenylboronic acid be stored to maintain stability?

The reagent should be stored in a cool, dry environment, protected from light, and ideally under an inert gas atmosphere or with a desiccant to prevent moisture-induced protodeboronation. Sealing the container tightly after each use and returning it to cold storage promptly will extend shelf life.

What is the significance of the morpholino group in this boronic acid?

The morpholino group is a biologically relevant pharmacophore that enhances aqueous solubility and is a common structural motif in kinase inhibitors and other bioactive small molecules. In a synthetic context, the tertiary morpholino nitrogen is non-nucleophilic under standard coupling conditions, making it compatible with a wide range of palladium- and copper-catalyzed reactions without requiring protection.

Is a Certificate of Analysis (CoA) available for B180658?

Yes. Aladdin Scientific provides a batch-specific Certificate of Analysis for B180658 confirming the compound's identity, purity, and other quality parameters. The CoA can be requested through the Aladdin Scientific website or by contacting customer service with your lot number.

Can this compound be used as a building block in fragment-based drug discovery?

Yes. The orthogonal reactivity of the boronic acid and aryl bromide groups, combined with the drug-like morpholino pharmacophore, makes 3-Bromo-5-morpholinophenylboronic acid well suited for fragment-based drug discovery and parallel library synthesis, where multiple points of diversification are required from a single scaffold.

References

1. Hall, D. G. (Ed.) Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. Wiley-VCH, 2011.
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95, 2457–2483. doi:10.1021/cr00039a007
3. Aladdin Scientific product page for 3-Bromo-5-morpholinophenylboronic acid, SKU B180658.

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