This compound belongs to the class of organic compounds known as nitroaromatic compounds. These are c-nitro compounds where the nitro group is C-substituted with an aromatic group.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
Not applicable. No biological assay or immunoassay applications (e.g., WB, IHC, IF, FC) are specified for this small-molecule building block. For chemical synthesis, refer to the Reaction Conditions and Synthetic Utility sections for practical guidance.
Biological Roles
Item-specific biological roles: None specified; this product is supplied for research use as a synthetic building block.
General context (literature/biochemistry; not specific to this item):
4-Bromo-3-nitropyridine is a small, non-natural heteroaromatic molecule. It does not have a known endogenous biological role. However, substituted pyridines are frequent motifs in bioactive compounds due to their capacity for hydrogen-bond acceptance (ring nitrogen) and tunable electronics.
The 3-nitro substituent is a strong electron-withdrawing group that modulates pKa and polarity; reduction in situ (chemically or enzymatically in some systems) can yield 3-aminopyridines, which are prevalent in medicinal chemistry scaffolds.
Halopyridines serve as synthetic precursors in SAR programs to access diverse analogs through cross-coupling, enabling exploration of biological targets in enzyme inhibition, receptor modulation, or as ligands in coordination probes. Any biological activity arises from downstream derivatives rather than the starting halonitroheteroarene itself.
Note: No clinical/therapeutic claims are made. For any biological testing, ensure appropriate handling and disposal consistent with institutional safety protocols for nitroaromatics.
Buffer Applications
This compound is a neutral, non-buffering aromatic building block and is not typically used to prepare aqueous buffers. It has no applicable Henderson–Hasselbalch pair and exhibits poor water solubility.
If aqueous work is required (e.g., bioconjugation on derivatives), dissolve the compound in a water-miscible organic cosolvent (DMSO, DMF, acetonitrile) before dilution into buffer, ensuring final organic content does not disrupt the biological system.
For pH control in reactions involving this substrate, choose standard buffer systems (phosphate, acetate, carbonate) as appropriate, but the compound itself does not contribute to buffering capacity.
Green Alternatives
Green chemistry opportunities around 4-bromo-3-nitropyridine focus on solvent/catalyst choices and coupling partners rather than replacing the building block itself.
Solvent substitution (literature guidance):
Replace DMF/DMAc/NMP with 2-MeTHF, CPME, propylene carbonate, or aqueous micellar media where compatible with catalyst/base.
For Suzuki couplings, ethanol/water or 2-MeTHF/water mixtures often provide comparable rates with appropriate ligands.
Catalysis and bases:
Use highly active Pd precatalysts (e.g., Buchwald-type) at low loadings (≤0.5 mol%) to reduce metal footprint.
Consider Ni catalysis for certain couplings to minimize precious metal usage (subject to substrate scope).
Employ inorganic bases with lower hazard profiles (K3PO4, K2CO3) instead of strong alkoxides when feasible.
Use solvent recovery and distillation; choose EtOAc/heptane for greener chromatography eluent systems.
Comparison snapshot (general):
DMF vs 2-MeTHF: 2-MeTHF is biorenewable and lower toxicity; may need temperature optimization and different ligands to match rates.
Dioxane vs CPME: CPME has a favorable peroxide profile and higher boiling point; ensure catalyst/solubility compatibility.
Organic vs aqueous micelles: micellar media (e.g., TPGS-750-M) can reduce organic solvent volumes; may require water-tolerant bases and degassing control.
Note: No item-specific green certifications are provided for this SKU; strategies above are general literature practices.
Pharmaceutical Uses
Item-specific pharmacopeial status and excipient roles: Not specified for this item.
General manufacturing/research context (no therapeutic claims):
4-Bromo-3-nitropyridine is primarily a synthetic intermediate in medicinal chemistry and process development. It enables rapid assembly of aza-heteroaryl frameworks via cross-coupling and subsequent functional-group interconversions (e.g., nitro → amine), facilitating structure–activity relationship (SAR) campaigns.
Potential roles in pharma R&D workflows:
Scaffold diversification for hit-to-lead optimization.
Precursor to heteroaryl amines used in kinase inhibitor cores, GPCR ligands, or antibacterial research series (by analogy to aminopyridine motifs).
Building block for ligand libraries in fragment-based drug discovery after transformation of the nitro/bromo handles.
Developability considerations: nitro groups can raise toxicological flags in final APIs; thus, they are commonly transformed (e.g., to amines, amides, sulfonamides) during lead optimization. Halide is typically replaced through coupling to adjust lipophilicity and polarity.
Note: There are no pharmacopeial monographs for this specific compound to our knowledge. Use strictly for laboratory research and process development.
Physical Properties
Item-specific physico-chemical specifications: Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for 4-bromo-3-nitropyridine (for reference only; not item-specific specifications):
Physical state: typically a crystalline solid (heteroaryl bromonitro compounds are commonly low-melting solids). Exact appearance for this catalog item is not specified.
Polarity/character: electron-deficient heteroaromatic; moderately polar relative to simple bromobenzenes due to the nitro and ring nitrogen.
Solubility (qualitative, literature):
Good solubility in polar aprotic organic solvents (DMF, DMSO, NMP, acetonitrile)
Moderate solubility in ethyl acetate, dichloromethane, THF
Low solubility in alkanes and water
Acid-base: ring nitrogen is weakly basic; nitro group is strongly electron withdrawing. No ionizable protons.
Partitioning: aryl bromides with nitro substituents usually show elevated logP relative to unsubstituted pyridines but remain workable in polar organics. Specific logP for this item is not specified.
Optical properties: no specific UV cutoffs provided for this item; nitro-heteroarenes generally absorb in the near-UV; use a reference blank when performing analytical UV detection.
Note: For exact melting point, boiling point, density, refractive index, and aqueous solubility limits, consult the Certificate of Analysis or Specification Sheet for this batch.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications (general guidance):
In the absence of a declared grade (e.g., “97%,” “98%,” or “HPLC grade”), users should consult the batch-specific Certificate of Analysis for purity, residual solvents, and assay methods (GC, HPLC, or NMR).
For cross-coupling and nucleophilic aromatic substitution chemistry, trace metal or halide impurities usually have limited impact, but moisture and peroxides in solvents may affect performance. Because this item is supplied under argon and light protection, it is intended to preserve chemical integrity and minimize adventitious hydrolysis or photodegradation.
UV-Vis background and LC baseline characteristics are not specified; for analytical applications (e.g., as a reference standard), request a chromatographic purity trace if needed.
Stabilizers/inhibitors: none are specified for this item. If your process is sensitive to stabilizers, confirm the absence/presence on the CoA.
Reproducibility: for scale-up or medicinal chemistry campaigns, we recommend verifying identity by 1H/13C NMR and MS upon receipt, and confirming water content (Karl Fischer) if moisture-sensitive steps are planned, as storage is under inert gas.
Reaction and Applications
As an electron-deficient aryl bromide bearing a 3-nitro substituent, 4-bromo-3-nitropyridine is highly versatile for heteroaryl diversification.
Cross-coupling platform (literature):
Suzuki–Miyaura: couples with aryl/heteroaryl/alkenyl boron reagents under Pd catalysis. The 4-bromo handle is typically reactive under mild–moderate conditions; the 3-nitro group is retained, enabling subsequent orthogonal chemistry.
Buchwald–Hartwig amination: installation of anilines or aliphatic amines using bulky electron-rich ligands (e.g., BrettPhos, XPhos) and bases such as NaOtBu or Cs2CO3.
Stille/Negishi/Kumada: viable using appropriate organostannanes, organozinc, or Grignard reagents; the electron-poor ring often enhances oxidative addition rates to Pd/Ni.
Nucleophilic aromatic substitution (SNAr): the nitro at C-3 is ortho to the aryl bromide at C-4, increasing ring activation. Under strong nucleophiles and elevated temperatures, displacement at C-4 can occur, particularly with amines or alkoxides, providing an alternative to Pd catalysis for certain nucleophiles.
Nitro group as a handle:
Reductive transformations: chemoselective reduction to the 3-aminopyridine (Fe/AcOH, SnCl2, catalytic hydrogenation), enabling diamino/bromo intermediates for further cross-coupling or cyclizations.
Denitration or N-oxide routes (via pyridine N-oxidation, then rearrangement) can alter substitution patterns in advanced synthesis.
Applications (general): medicinal chemistry scaffold hopping, building electron-poor biaryls and diaryl amines, ligand synthesis for catalysis, and precursors to aza-heterocycle libraries.
Tip: Exploit orthogonality—perform Pd coupling first (bromide), then reduce nitro to amine for subsequent acylation/sulfonylation or intramolecular cyclizations.
Reaction Conditions
General literature guidance for typical transformations of 4-bromo-3-nitropyridine (non-item-specific; optimize per substrate and scale):
Suzuki–Miyaura coupling (C–B):
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-precatalysts with Buchwald ligands (e.g., XPhos, SPhos 0.5–2 mol%)
Base: K2CO3 or K3PO4 (2–3 equiv); Cs2CO3 for challenging partners
Solvent: 1,4-dioxane/H2O (4:1) or THF/H2O; DMF/H2O for polar substrates
Temperature: 60–100 °C; time: 2–16 h
Notes: Electron-deficient aryl bromides generally couple readily; water improves boronate activation.
Buchwald–Hartwig amination (C–N):
Catalyst/ligand: Pd2(dba)3 (1 mol% Pd) with BrettPhos/XPhos or Pd-PEPPSI-type precatalysts; alternative Ni catalysts for certain amines
Base: NaOtBu, KOtBu, or Cs2CO3
Solvent: toluene, dioxane, or DMAc
Temperature: 80–110 °C; time: 4–20 h
Notes: Use bulky electron-rich ligands to accelerate oxidative addition on electron-poor substrates and suppress dehalogenation.
Notes: Ortho activation by the 3-nitro group facilitates substitution; Pd-free route to aryl amines/ethers.
Nitro reduction to amine:
H2 (1–5 bar) with Pd/C (5–10%) in EtOH/EtOAc at rt–50 °C; or Fe/AcOH or SnCl2/HCl stoichiometric reductions
Chemoselectivity: C–Br may hydrogenolyze under forcing H2/Pd conditions; milder conditions or alternative reductants preserve the bromide.
Always monitor reactions by LC/MS or TLC; dry and degas solvents when using air- or moisture-sensitive catalysts.
Safety and Handling
Research use: For research use only (per Product Data). Not for human or veterinary use.
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to the SDS for authoritative hazard information.
Likely hazards (general guidance for nitro- and bromo-heteroarenes; not item-specific): may cause skin/eye/respiratory irritation; harmful if swallowed or inhaled. Nitro aromatics can present methemoglobinemia risk upon significant exposure—avoid inhalation/ingestion.
Storage (item-specific from Product Data):
Store at −20 °C
Protect from light
Keep under argon (argon charged)
Shipping condition (item-specific): shipped in an ice chest with ice pads.
Handling recommendations (general lab best practice):
Work in a certified chemical fume hood; avoid dust/aerosol formation.
Wear appropriate PPE: lab coat, safety glasses or splash goggles, and chemical-resistant gloves (e.g., nitrile). Consider double-gloving for extended handling in DMF/DMSO.
Avoid contact with strong bases or nucleophiles unless intended (substrate is activated for substitution); avoid strong oxidants and reducing agents in storage.
For weighing, minimize light exposure and promptly recap under inert gas to preserve material integrity.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention immediately.
Spill/leak: avoid dust; collect with inert absorbent; dispose according to institutional and local regulations.
Solvent Selection
4-Bromo-3-nitropyridine is an electron-poor heteroaryl halide that dissolves best in polar aprotic solvents commonly used in cross-coupling and SNAr.
Polarity class (general): moderately polar, electron-deficient aromatic.
Practical solvent choices (general guidance):
Excellent: DMF, DMAc, NMP, DMSO, acetonitrile (good for SNAr/coupling and analytical prep)
Good: 1,4-dioxane, THF, ethyl acetate, dichloromethane (for workups, extractions, and some couplings)
Limited: toluene, MTBE (solubility may be modest; can be improved by heating)
Poor: alkanes, water
Choosing among common media:
Pd-catalyzed Suzuki/Negishi/Stille: 1,4-dioxane/H2O or THF/H2O, or polar aprotics (DMF, DMAc). Water co-solvent improves base solubility for Suzuki.
Buchwald–Hartwig amination: toluene, dioxane, or DMAc depending on ligand/base system.
SNAr with amines/alkoxides: DMF, DMSO, or NMP to enable higher temperatures and solvation of nucleophiles.
Workup considerations: nitro-heteroarenes can partition into moderately polar organics (EtOAc, DCM); salting-out assists phase separation. Avoid basic aqueous washes if product is base-labile.
Analytical solvents: acetonitrile or methanol are preferred for HPLC sampling; DMSO-d6 or CD3CN for NMR if solubility in CDCl3 is insufficient.
Note: No item-specific solubility specifications are provided for this SKU; adjust solvent choice based on the intended reaction and preliminary solubility tests.
Storage and Reconstitution
Item-specific storage (from Product Data):
Store at −20 °C
Protect from light
Maintain under inert atmosphere (argon charged)
Shipped in an ice chest with ice pads
Container handling: After opening, promptly purge headspace with inert gas (Ar or N2), recap tightly, and return to cold, dark storage to minimize degradation.
Solubility and preparation (general guidance):
Prepare stock solutions in dry, oxygen-free polar aprotic solvents (DMF, DMSO, acetonitrile) immediately before use if possible. For long-term stock solutions, store in sealed, inerted vials at −20 °C and protect from light.
Filter stock solutions (0.2 µm PTFE) prior to use for sensitive catalytic reactions.
Stability notes: Item-specific stability data are not provided. Nitro-heteroarenes and aryl bromides are generally shelf-stable as solids when protected from light and air; prolonged exposure to heat, light, or moisture may promote decomposition or hydrolysis.
Freeze–thaw: Minimize freeze–thaw cycles. If preparing solution aliquots, dispense into small inerted vials to avoid repeated warming.
For definitive stability limits, retest periods, and any impurity specifications, consult the batch CoA/Specification Sheet and the SDS.
Structure and Identity
4-Bromo-3-nitropyridine is a halogenated, nitro-substituted pyridine useful as an electron-deficient heteroaryl building block.
Item-specific identifiers (from Product Data):
CAS: 23056-44-2
CID: 2762920
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and features (for reference only):
Molecular formula (literature): C5H2BrN2O2
Molecular weight (literature): ~201.99 g/mol
Core scaffold: pyridine (six-membered aromatic ring with one ring nitrogen)
Substitution pattern: bromo at the 4-position (para to ring N), nitro at the 3-position (meta to ring N); overall ring is significantly electron-deficient due to the nitro and ring nitrogen.
Functional groups: aryl bromide (cross-coupling handle), nitro group (strong −I/−M deactivator; convertible to amine), heteroaromatic N (basic site with reduced basicity versus anilines).
2D structural description (general): a planar pyridine ring with the ring nitrogen at position 1; adjacent carbons at positions 2–6. A nitro group (–NO2) is attached at position 3 (meta to N), and a bromine substituent at position 4 (para to N; ortho to the nitro), creating an activated aryl bromide suitable for SNAr and Pd-catalyzed cross-couplings.
Synthetic Utility
Key functional handles and reactivity:
Aryl bromide at C-4:
Excellent handle for Pd- or Ni-catalyzed cross-couplings (Suzuki, Stille, Negishi, Kumada, Heck) and Buchwald–Hartwig amination.
Electron-poor ring accelerates oxidative addition and can enable couplings at lower temperatures versus electron-rich analogs.
Nitro group at C-3:
Chemoselective reduction to an aniline enables subsequent acylation/sulfonylation/urea formation, or intramolecular cyclizations to N-heterocycles.
Can direct SNAr by increasing ring activation, especially ortho/para to the nitro (here, C-4 is ortho to NO2).
Ring nitrogen:
Influences coordination to catalysts and bases; N-oxide chemistry (oxidation → rearrangement) can alter substitution patterns.
Strategic applications (literature):
Orthogonal two-point diversification: perform cross-coupling at C-4 first, then reduce nitro to amine and derivatize; or invert the sequence if chemoselectivity is controlled (e.g., use chemoselective hydrogenation conditions that spare C–Br when needed).
Late-stage functionalization: install complex aryl/heteroaryl groups via Suzuki, then access diamino or amide derivatives post-reduction for property tuning (pKa, solubility).
Cyclization manifolds: after nitro reduction, intramolecular SNAr or condensation with carbonyl partners affords fused aza-systems relevant to medicinal chemistry.
Overall, the combination of an activated aryl bromide and a transformable nitro group provides exceptional flexibility for parallel synthesis and SAR exploration.
Target Specificity
Not applicable. This product is a small-molecule synthetic building block and is not an antibody, oligonucleotide, enzyme, or affinity reagent. No target, epitope, clone, isotype, or species reactivity information applies.
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