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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
202.990 g/mol
XLogP3
1.400
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Exact Mass
201.938 Da
Monoisotopic Mass
201.938 Da
Topological Polar Surface Area
58.700 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
136.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Application Protocols
Not applicable. No validated bioassay or immunoassay protocols (WB, IHC, IF, FC) are associated with this small-molecule building block in our catalog entry.
Chemical synthesis guidance instead:
For cross-coupling or reductions, see the Reaction Conditions tab for representative setups and starting parameters.
For purification, normal-phase silica gel chromatography using EtOAc/hexanes or DCM/MeOH gradients is commonly effective; monitor by TLC or LC–MS.
For analytical control, use 1H/13C NMR, LC–MS (ESI+), and HPLC purity assessment. Confirm identity versus a reference standard when available.
Biological Roles
This product is a synthetic heteroaromatic building block intended for chemical research. It does not possess an intrinsic biological role.
General notes (literature):
Pyridine derivatives are common motifs in bioactive molecules due to their hydrogen-bond-accepting ring nitrogen and tunable electronics. However, 4-bromo-2-nitropyridine itself is best regarded as a reactive intermediate rather than a probe.
The nitro group and aryl bromide confer electrophilicity and reactivity but are typically transformed (e.g., nitro → amine, Br → C–C/C–N bond) before any biological testing of final targets.
Nitro-arenes can show nonspecific reactivity and potential cytotoxicity at high concentrations; therefore, this compound should not be used in biological systems except as a chemical intermediate under controlled laboratory conditions.
For any biological evaluation of derivatives synthesized from this material, appropriate purification and characterization are required, along with toxicity and off-target profiling of the final compounds. This product itself is supplied strictly for research and laboratory use.
Buffer Applications
Not typically applicable. 4-Bromo-2-nitropyridine is a neutral organic building block, not a buffering agent. It is not used to control pH in aqueous systems.
Practical note: If handling this compound in aqueous workflows (e.g., extractions or bioconjugation of downstream derivatives), select buffers that are compatible with organic solvents used for dissolution (e.g., phosphate or acetate buffers with controlled ionic strength). Avoid strong basic buffers if unintentional SNAr or hydrolysis would be detrimental.
Green Alternatives
While the substrate itself is fixed, greener choices can be made in solvents, bases, and catalysts for its common transformations (literature/general):
Solvent selection:
Prefer 2-MeTHF or CPME over THF/dioxane for Pd-catalyzed couplings; they offer better safety profiles and often comparable rates.
Aqueous ethanol or water/ethanol blends can support Suzuki couplings with suitable ligands and bases, reducing reliance on amide solvents.
Replace DMF/DMAc/NMP where possible due to reproductive toxicity concerns; consider propylene carbonate or Cyrene when compatible.
Base and reagent choices:
Use K3PO4, K2CO3, or Na2CO3 in water or aqueous alcohols for Suzuki to minimize hazardous waste from strong alkoxides.
For reductions of –NO2, catalytic hydrogenation (H2, Pd/C) in green solvents (EtOH, EtOAc) is preferable to stoichiometric tin or iron salts.
Catalyst systems:
Employ modern Pd catalysts with high turnover numbers (e.g., Pd–NHC, dialkylbiaryl phosphine systems) at ppm–level loadings to reduce precious metal usage.
Explore nickel catalysis for certain couplings as a lower-cost alternative; verify scope as electron-poor heteroaryl bromides can be challenging.
Greener: 2-MeTHF/H2O or EtOH/H2O, K3PO4, 50–500 ppm Pd–NHC or Pd–SPhos; or Ni/bipyridine where feasible.
Trade-offs: Greener media may alter solubility and kinetics; re-optimize temperature, base strength, and water content accordingly.
Pharmaceutical Uses
No excipient or pharmacopeial role is specified for this item; it is provided for research use only. Do not use for human or veterinary applications.
General formulation/manufacturing context (literature/general):
4-Bromo-2-nitropyridine can serve as an intermediate in multi-step syntheses en route to heteroaryl APIs or advanced intermediates. Typical transformations include Pd-catalyzed cross-coupling at C4 and reduction of the nitro group to introduce an aniline-like handle at C2.
Process considerations when used as an intermediate:
Control residual palladium/nickel after couplings (metal scavengers, carbon treatment).
Monitor nitro reduction endpoints to avoid over-reduction or ring hydrogenation.
Choose greener solvents for scale (2-MeTHF, EtOAc, aqueous ethanol) and robust crystallization endpoints for impurity purge.
Item-specific pharmacopeial status, residual solvent limits, and impurity thresholds: Not specified for this item; refer to internal specifications if used in process development.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general physical data for 4-bromo-2-nitropyridine (for method planning; verify experimentally):
Appearance: Typically a pale yellow to light brown crystalline solid (literature/general for nitro-aryl bromides). Exact appearance may vary with lot and purity.
Molecular formula: C5H3BrN2O2 (literature)
Formula weight: ~203.0 g/mol (literature/computed)
Acid/base: Weakly basic heteroaromatic nitrogen; overall molecule is deactivated by –NO2 and –Br. Conjugate acid pKa of pyridinium typically ~5 (literature, parent pyridine pKaH ≈ 5.2); substituents lower basicity further.
Solubility (literature/general trends):
Low in water.
Good in polar aprotic organics: DMSO, DMF, NMP, acetonitrile.
Moderate in ethyl acetate, dichloromethane, THF; lower in hexanes/toluene unless warmed.
Volatility: Low; behaves as a non-volatile solid under ambient conditions.
Stability: Aromatic nitro and aryl bromide are stable under neutral, dry conditions; hydrolysis and reduction are possible under basic/reducing environments.
Instrumental parameters such as melting point, boiling point, density, refractive index, logP, UV cutoff, metals content, residual solvents: Not specified for this item; consult CoA/Spec Sheet or determine empirically for your application.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and any stabilizers.
Appearance: Not specified for this item; confirm on CoA/Spec Sheet.
General guidance on quality for this building block:
Research grade heteroaryl halides are commonly qualified by:
Identity: 1H NMR/13C NMR, MS (ESI/CI), and matching of retention time by HPLC/GC where applicable.
Purity: HPLC area % or GC area %, typically ≥95% for reliable cross-coupling and SNAr. Residual halide/nitro isomers are common related substances.
Inorganics: Residual metal content (if produced via catalytic halogenation or nitration) may be reported; if critical to your application (e.g., catalyst screening), request ICP data.
Water/volatiles: KF moisture and residual solvents may be listed; low moisture is beneficial for air/moisture-sensitive transformations.
UV characteristics: For chromatographic applications, low UV background is helpful; specific UV cutoff is Not specified for this item.
Stabilizers: Not typically required for this class; this item is provided argon charged per listing, which helps preserve quality by limiting hydrolysis/oxidation during storage.
Recommendation: For sensitive catalytic couplings (Suzuki–Miyaura/Buchwald–Hartwig), select lots with high area % purity and low moisture; review the lot-specific CoA to match your process needs.
Reaction and Applications
4-Bromo-2-nitropyridine is a bifunctional heteroaryl electrophile with orthogonal reactivity at C4–Br and transformability of the C2–NO2 group. Typical uses (literature/general):
Cross-coupling at C4–Br:
Suzuki–Miyaura: Install aryl/heteroaryl/alkenyl substituents using Pd(0/II) catalysts and boron partners; base/water mix enhances transmetalation.
Buchwald–Hartwig amination: Convert C4–Br to anilines/anilides with amines under Pd catalysis and dialkylbiaryl phosphines; choice of base (NaOtBu, Cs2CO3) tunes scope.
Stille/Negishi/Kumada: Alternative couplings using organostannanes, organozinc, or Grignard reagents respectively when boron chemistry is unsuitable.
Nitro group manipulations at C2:
Reductive conversion to 2-aminopyridines (e.g., H2/Pd–C, Fe/NH4Cl, SnCl2/HCl), enabling access to diamino, urea, or amide motifs.
Nucleophilic aromatic substitution (SNAr) at positions activated by –NO2 and the ring N; strong nucleophiles (alkoxides, amines) can displace hydrogen (vicarious) or add to activated carbons depending on conditions.
Sandmeyer-like sequences after reduction to anilines for further diversification (diazotization then substitution).
Directed metalation/functionalization:
The ring N and –NO2 reduce electron density; halogen–metal exchange at C4 is feasible at low temperature with iPrMgCl·LiCl or nBuLi (with caution), enabling alternative C–C bond constructions.
Applications:
Synthesis of N-heteroaryl libraries, ligands, and intermediates for materials and agrochemical research.
Orthogonal handles allow sequential functionalization (e.g., first Suzuki at C4–Br, then reduction of –NO2 to reveal nucleophilic amine for further coupling).
Note: Sequence planning should account for the –NO2 sensitivity to strong bases/reductants and the coordinating ring N, which can influence catalyst selection.
Reaction Conditions
General literature conditions (illustrative; optimize for your system):
Solvent: 1,4-dioxane/H2O (4:1), 2-MeTHF/H2O, or DMAc/H2O.
Temperature/time: 70–100 °C, 2–16 h.
Notes: Electron-poor heteroaryl bromides often couple efficiently; water improves boronate activation. Maintain inert atmosphere to limit hydrolysis.
Buchwald–Hartwig amination (C4–Br → C4–NR2):
Catalyst: Pd2(dba)3 (0.5–1 mol%) with BrettPhos/SPhos (1–2 mol%) or Pd-PEPPSI–IPr (0.5–1 mol%).
Base: NaOtBu or KOtBu (2 equiv) in toluene/CPME; Cs2CO3 in dioxane/DMAc for milder conditions.
Temperature: 80–110 °C, 4–18 h.
Notes: The pyridine N can bind Pd—bulky electron-rich ligands mitigate inhibition.
Nitro reduction (C2–NO2 → C2–NH2):
H2 (1–4 bar) with Pd/C (5–10 wt% relative to substrate) in EtOH or EtOAc; 20–50 °C, 2–8 h.
Alternative: Fe/NH4Cl or SnCl2·2H2O in EtOH or EtOH/H2O at reflux (workup generates waste; less green).
Notes: Protect sensitive halides/coupling products if needed; check for dehalogenation under hydrogenation.
Halogen–metal exchange at C4:
Reagent: iPrMgCl·LiCl (2–3 equiv) in THF, −40 to 0 °C; quench with electrophiles (CO2, DMF, B(OMe)3).
Notes: The –NO2 group limits strong basicity; temperature control essential.
These are representative starting points from the literature; conduct small-scale scouting to define optimal ligands, bases, and temperatures for your substrates.
Safety and Handling
Item-specific hazard statements/classification: Not specified for this item; refer to the SDS for authoritative safety data.
General GHS considerations for nitro-heteroaromatics and aryl bromides (literature/general):
Potential hazards: May cause skin/eye irritation and respiratory irritation; harmful if swallowed or inhaled. Nitro-arenes can exhibit methemoglobin-forming potential upon significant exposure; handle to minimize dust.
Recommended PPE: Lab coat, nitrile gloves (change regularly), splash goggles. Use in a chemical fume hood.
Handling tips:
Avoid dust formation; handle solids gently.
Keep container tightly closed; product is shipped under inert gas—maintain an argon or nitrogen blanket to minimize oxidative or hydrolytic degradation.
Avoid contact with strong reducing agents (risk of exothermic reduction of –NO2), strong bases (may promote SNAr or decomposition), and strong nucleophiles unless intended.
Storage incompatibilities (general): Strong bases, strong reducing agents, reactive metals; segregate from oxidizers when storing mixed classes.
First-aid overview (general):
Inhalation: Move to fresh air, seek medical attention if symptoms occur.
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy.
Ingestion: Rinse mouth; seek medical advice.
Fire response: Use CO2, dry chemical, or foam. Combustion may generate HBr, NOx.
Always defer to and follow the product SDS and institutional safety protocols.
Solvent Selection
As a moderately polar, heteroaryl bromide bearing a strongly electron-withdrawing nitro group, 4-bromo-2-nitropyridine dissolves best in polar aprotic solvents.
Polarity/miscibility (literature/general):
Water: Poor solubility; consider cosolvents.
Polar aprotic: DMSO, DMF, NMP, and acetonitrile offer high solubility and support cross-coupling and SNAr chemistry.
Ethers: THF/2-MeTHF provide moderate solubility and are suitable for many Pd-catalyzed couplings (with base) and reductions (under hydrogenation conditions).
Chlorinated: DCM/DCE provide moderate solubility; useful for electrophilic substitutions or protection steps, less common for couplings requiring base.
Esters: Ethyl acetate often affords workable solubility for workups and chromatography.
Choosing solvents by application:
Cross-coupling (Suzuki/Negishi/Stille): 1,4-dioxane/water, THF/water, or DMAc/EtOH/water are common; base and water improve boronate activation.
Buchwald–Hartwig amination: Toluene, dioxane, or CPME with bulky dialkylbiaryl phosphines; DMAc/DMF when higher solubility needed.
SNAr at C3/C5 positions (activated by –NO2): DMF/DMSO/NMP at elevated temperature.
Reductions of –NO2: Alcohols (EtOH/iPrOH) or ethyl acetate under catalytic hydrogenation; avoid basic aqueous media unless desired downstream.
Practical tips:
Dry, oxygen-free solvents improve reproducibility in Pd-catalyzed reactions.
For scale-up, prefer higher-boiling, safer solvents (e.g., 2-MeTHF, CPME, propylene carbonate) where compatible with kinetics and base selection.
Storage and Reconstitution
Item-specific instructions (from Product Data):
Storage: Store at 2–8 °C, argon charged.
Shipping: Shipped on wet ice.
General handling and preparation (literature/general):
Upon receipt: Allow container to equilibrate to room temperature before opening to minimize moisture condensation. Maintain an inert gas blanket after each use.
Solid handling: Minimize exposure to ambient humidity. If necessary for moisture-sensitive reactions, dry the solid under high vacuum at ambient temperature prior to use (avoid heating unless stability is verified).
Solution preparation: Prepare stock solutions in dry, oxygen-free solvents (e.g., anhydrous DMSO, DMF, THF, 2-MeTHF). Typical lab stocks are 0.1–1.0 M depending on solubility and intended use.
Storage of solutions: Store in sealed, inerted vials at 2–8 °C or −20 °C as appropriate. Check for precipitation or degradation before use; avoid repeated freeze–thaw of DMSO solutions by aliquoting.
Stability: Nitro-heteroaryl bromides are generally stable when dry and protected from light and moisture. Avoid prolonged exposure to strong light or base.
For lot-specific shelf-life and re-test dates, consult the CoA/label. Research use only.
Structure and Identity
Brief: 4-Bromo-2-nitropyridine is a brominated, nitro-substituted pyridine used as an electrophilic heteroaryl building block.
Item-specific identifiers (from Product Data):
CAS: 909712-10-3
CID: 23436857
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Storage note (item-specific): Store at 2–8 °C under argon; shipped on wet ice.
Structural features (literature/general):
Core ring: Aromatic pyridine (six-membered heteroaromatic, one ring nitrogen).
Substitution pattern: Nitro group at C2 (adjacent to ring N) and bromo at C4 (para to ring N).
Functional groups: Aryl–Br (cross-coupling handle), strongly electron-withdrawing –NO2 (activates ring toward SNAr at adjacent positions; convertible to amine).
2D description: A planar pyridine ring bearing –NO2 ortho to the ring N and –Br para to the ring N; no stereocenters.
Empirical formula and formula mass (literature/computed):
Notes: Structural identifiers not explicitly provided in the item listing should be confirmed against the product CoA/SDS for this specific lot.
Synthetic Utility
Key functional elements and reactivity (literature/general):
Aryl bromide at C4: Excellent handle for Pd-catalyzed cross-coupling (Suzuki, Stille, Negishi, Heck) and Buchwald–Hartwig amination. Electron-poor ring often enhances oxidative addition rates to Pd(0).
Nitro at C2: Strongly deactivating; directs ring electronics and can be chemoselectively reduced to the corresponding 2-aminopyridine. Also contributes to activation for SNAr at adjacent carbons.
Ring nitrogen: Coordinates to transition metals and bases; may require ligand/base selection to prevent catalyst inhibition (use of dialkylbiaryl phosphines, NHCs, or additive pyridine scavengers).
Strategic sequences:
Two-directional diversification: First functionalize C4 via coupling (tolerant to –NO2), then reduce –NO2 to amine for further acylation/sulfonylation/urea formation. Alternatively, protect amine after reduction and perform subsequent metalation at remaining positions.
Halogen–metal exchange on C4–Br (with iPrMgCl·LiCl or nBuLi at −78 to −20 °C) followed by electrophile trapping (formylation, carboxylation) when cross-coupling partners are unavailable.
Reductive cyclizations or intramolecular couplings after nitro reduction to access bicyclic aza-heterocycles.
Selectivity considerations:
The –NO2 group is typically retained during Pd couplings but can be reduced under hydrogenation; use transfer hydrogenation or chemoselective catalysts if both groups must survive.
Base-sensitive pathways: Strong bases may trigger SNAr or degrade nitro; carbonate/phosphate bases are often safer in couplings.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and does not have biological target specificity, antigen reactivity, clone, or isotype. For applications that require target specificity (e.g., antibodies, inhibitors), use this compound only as a synthetic intermediate to construct the desired active molecules.
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