4-(5-Bromo-3-nitropyridin-2-yl)morpholine: Handling & Use Guide

4-(5-Bromo-3-nitropyridin-2-yl)morpholine is a halogenated nitropyridine building block widely employed in medicinal chemistry and heterocyclic synthesis as a versatile electrophilic intermediate for the construction of complex nitrogen-containing scaffolds.

Product Name

4-(5-Bromo-3-nitropyridin-2-yl)morpholine

SKU

B184835

Molecular Formula

C9H10BrN3O3

Functional Groups

Aryl bromide, nitro group, morpholine nitrogen

Primary Application

Electrophilic building block for cross-coupling and nucleophilic aromatic substitution reactions

Storage Condition

Store in a cool, dry place away from light and moisture; seal tightly after use

Chemical Identity and Structure

4-(5-Bromo-3-nitropyridin-2-yl)morpholine (SKU B184835) is a pyridine derivative bearing three key functional handles: a bromine atom at the 5-position, a nitro group at the 3-position, and a morpholine ring attached at the 2-position of the pyridine core. Its molecular formula is C₉H₁₀BrN₃O₃. The combination of an electron-withdrawing nitro group and an aryl bromide on the pyridine ring makes this compound a highly reactive and selective building block for downstream functionalization. The morpholine substituent at C-2 acts as an electron-donating group that modulates the electronic character of the ring, influencing regioselectivity in subsequent reactions.

Synthetic Applications and Reactivity

This compound serves as a versatile intermediate in several key reaction classes:

• Palladium-catalyzed cross-coupling: The aryl bromide at C-5 is an excellent partner for Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and Sonogashira coupling reactions, enabling rapid elaboration of the pyridine scaffold.
• Nucleophilic aromatic substitution (SNAr): The presence of the nitro group at C-3 activates the ring toward SNAr at C-2; however, in this compound the morpholine is already installed at C-2, so researchers may exploit the activated C-4 or utilize the nitro group for further reductive transformations.
• Nitro group reduction: The nitro functionality can be selectively reduced to an amine using standard conditions (e.g., Fe/AcOH, catalytic hydrogenation, or SnCl₂), providing an aminopyridine for further amide coupling or cyclization chemistry.
• Medicinal chemistry scaffold construction: The morpholine-pyridine motif is a privileged structure in drug discovery, and this intermediate is suitable for building kinase inhibitor precursors and other bioactive heterocyclic compounds.

Researchers should evaluate reaction conditions carefully, as the nitro group and aryl bromide may both participate in reactions under certain conditions.

Handling, Safety, and Storage Guidelines

Personal Protective Equipment (PPE): Always wear appropriate PPE including nitrile gloves, a laboratory coat, and safety goggles when handling this compound. Work in a well-ventilated fume hood to minimize inhalation exposure to fine particulates or vapors.

Safety considerations: Nitroaromatic compounds as a class may present irritant or toxic properties. Consult the Safety Data Sheet (SDS) for B184835 before use. Avoid contact with skin, eyes, and mucous membranes. Do not ingest or inhale. Wash hands thoroughly after handling.

Storage: Store in a tightly sealed container in a cool (2–8 °C or room temperature as specified on the product label), dry location protected from light and moisture. Keep away from incompatible materials such as strong reducing agents and strong acids. Check the product label and SDS for the specific recommended storage temperature for your lot.

Disposal: Dispose of waste material in accordance with local, national, and institutional regulations for hazardous chemical waste. Do not pour down the drain.

Quality, Purity, and Procurement

Aladdin Scientific supplies 4-(5-Bromo-3-nitropyridin-2-yl)morpholine (SKU B184835) for research use. Purity specifications and analytical data (such as HPLC purity, NMR characterization, and lot-specific certificates of analysis) are available upon request or on the product detail page. Researchers are encouraged to verify the identity and purity of received material using techniques appropriate to their application, such as ¹H NMR, HPLC, or LC-MS, before committing large-scale synthetic work.

For bulk quantities, custom purity grades, or specialized packaging requirements, contact Aladdin Scientific's sales team. Pricing, availability, and promotions are subject to change; refer to the current Aladdin Scientific catalog or website for up-to-date information.

Frequently asked questions

What cross-coupling reactions are compatible with 4-(5-Bromo-3-nitropyridin-2-yl)morpholine?

The aryl bromide at the 5-position is compatible with palladium-catalyzed Suzuki–Miyaura, Negishi, Sonogashira, and Buchwald–Hartwig coupling reactions under standard conditions. Researchers should optimize catalyst loading and base selection given the electron-deficient nature of the pyridine ring. Reaction yields and conditions should be verified empirically for each specific coupling partner.

How should the nitro group in this compound be selectively reduced to an amine?

Common methods for selective nitro reduction include catalytic hydrogenation (H2/Pd-C or H2/Raney Ni), iron powder in acetic acid (Fe/AcOH), or tin(II) chloride (SnCl2) in ethanol or ethyl acetate. The choice of method should consider compatibility with the aryl bromide — catalytic hydrogenation may also cause hydrodehalogenation, so chemical reductants such as Fe/AcOH or SnCl2 are often preferred when retention of the C–Br bond is required. Reaction conditions should be optimized and validated for each application.

What are the recommended storage conditions for SKU B184835?

Store 4-(5-Bromo-3-nitropyridin-2-yl)morpholine in a tightly sealed container in a cool, dry location protected from light and moisture. Consult the product label and the accompanying Safety Data Sheet for the specific recommended temperature range for your lot. Keep away from strong reducing agents and strong acids.

Is 4-(5-Bromo-3-nitropyridin-2-yl)morpholine suitable for medicinal chemistry applications?

Yes, this compound is well-suited for medicinal chemistry as both the morpholine ring and the pyridine core are privileged structural motifs found in many bioactive molecules and approved drugs. The multiple reactive handles (aryl bromide, nitro group) allow rapid diversification of the scaffold for structure–activity relationship (SAR) studies. It is supplied for research use only and is not intended for therapeutic or clinical applications.

References

1. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference for pyridine and morpholine chemistry)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for cross-coupling and nucleophilic aromatic substitution)
3. Aladdin Scientific Product Page: 4-(5-Bromo-3-nitropyridin-2-yl)morpholine, SKU B184835. (Consult for current purity specifications, certificate of analysis, and safety data sheet.)

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