3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine: Properties & Uses
3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine: Properties & Uses
3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine is a halogenated, nitrogen-rich pyridine building block widely employed in medicinal chemistry and drug discovery as a versatile intermediate for the construction of complex heterocyclic scaffolds.
- Chemical Name
- 3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine
- SKU
- B179104
- Molecular Formula
- C8H8BrN3O2
- Functional Groups
- Aryl bromide, nitro group, secondary amine (cyclopropyl)
- Primary Application
- Heterocyclic synthesis, cross-coupling reactions, medicinal chemistry
- Supplier
- Aladdin Scientific
Chemical Identity and Structure
3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine (SKU B179104) is a substituted pyridine derivative bearing three key functional handles on the aromatic ring: a bromine atom at the 3-position, a nitro group at the 5-position, and a cyclopropylamino substituent at the 2-position. Its molecular formula is C8H8BrN3O2.
The combination of an electron-withdrawing nitro group and an aryl bromide on the electron-deficient pyridine ring creates a highly reactive scaffold. The cyclopropyl moiety attached to the ring nitrogen contributes conformational rigidity and modulates the electronic density of the amine nitrogen, properties that are valuable in the design of biologically active molecules.
The compound is typically encountered as a solid at ambient temperature. Researchers should consult the product Safety Data Sheet (SDS) for precise physical constants, handling guidance, and storage requirements.
Synthesis and Reactivity
The structural features of 3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine make it a highly versatile intermediate in synthetic chemistry. The aryl C–Br bond at the 3-position is well-suited for participation in palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, and Negishi couplings, enabling the introduction of diverse aryl, heteroaryl, vinyl, or amino substituents.
The nitro group at the 5-position can be selectively reduced to a primary amine under standard catalytic hydrogenation or chemical reduction conditions (e.g., Fe/AcOH, Zn/NH4Cl), providing access to 2,5-diaminopyridine intermediates that are important precursors for cyclization reactions yielding imidazopyridines, pyrimidines, and related fused ring systems.
The cyclopropylamine group at the 2-position contributes to the compound's profile as a directed metalation substrate and may itself serve as a handle for further elaboration under appropriate conditions. The overall reactivity profile positions this compound as a privileged three-point diversification intermediate in library synthesis.
Applications in Drug Discovery and Medicinal Chemistry
Substituted aminopyridines and bromonitropyridines are recognized privileged scaffolds in drug discovery programs. The presence of the cyclopropyl group in 3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine is particularly noteworthy: cyclopropyl rings are frequently incorporated into drug candidates to improve metabolic stability, enhance binding affinity through conformational restriction, and modulate lipophilicity.
This compound serves as a starting material or key intermediate in the preparation of kinase inhibitors, GPCR ligands, and other bioactive small molecules that contain pyridine-based cores. The 2-aminopyridine motif embedded in the structure is a common pharmacophore found across multiple therapeutic areas including oncology, inflammation, and infectious disease.
Researchers engaged in fragment-based drug design, structure–activity relationship (SAR) studies, or diversity-oriented synthesis will find this building block useful for rapidly accessing novel chemical space around the aminobromonitropyridine scaffold.
Handling, Storage, and Safety Considerations
As with all aromatic nitro compounds and organobromine reagents, 3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine should be handled with appropriate laboratory precautions. Personnel should wear suitable personal protective equipment (PPE), including chemical-resistant gloves, safety glasses, and a laboratory coat, when handling this material.
The compound should be stored in a cool, dry, well-ventilated location, away from incompatible materials such as strong reducing agents and strong bases. Researchers are strongly advised to consult the full Safety Data Sheet (SDS) supplied by Aladdin Scientific prior to use for detailed hazard classifications, first-aid measures, and disposal instructions.
Waste containing this material should be disposed of in accordance with applicable local, regional, and national regulations governing chemical waste disposal.
Frequently asked questions
What cross-coupling reactions are compatible with 3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine?
The aryl bromide at the 3-position makes this compound a suitable substrate for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura (with boronic acids), Buchwald–Hartwig (amination), and Negishi (organozinc) couplings. Reaction optimization may be required to preserve the nitro group and secondary amine under coupling conditions.
How can the nitro group in this compound be converted to an amine for further synthesis?
The nitro group at the 5-position can be reduced to a primary amine using standard methods such as catalytic hydrogenation (H2/Pd-C) or chemical reduction with reagents like iron in acetic acid (Fe/AcOH) or zinc with ammonium chloride. Care should be taken to maintain chemoselectivity in the presence of the aryl bromide, as hydrogenation conditions may also cause dehalogenation.
What are the recommended storage conditions for B179104?
3-Bromo-N-cyclopropyl-5-nitropyridin-2-amine (B179104) should be stored in a cool, dry, and well-ventilated area, away from strong reducing agents and incompatible materials. Always refer to the Aladdin Scientific SDS for the most current and product-specific storage guidance.
Why is the cyclopropyl group valuable in drug discovery applications?
The cyclopropyl group is a bioisostere widely used in medicinal chemistry because it imparts conformational rigidity to a molecule, which can improve target selectivity and binding affinity. It also tends to enhance metabolic stability compared to linear alkyl substituents and can favorably tune lipophilicity and permeability, making it a popular motif in the design of clinical drug candidates.
References
- Roughley, S. D.; Jordan, A. M. The Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates. J. Med. Chem. 2011, 54, 3451–3479. doi:10.1021/jm200187y
- Lovering, F.; Bikker, J.; Humblet, C. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success. J. Med. Chem. 2009, 52, 6752–6756. doi:10.1021/jm901241e
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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