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
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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 in the sense of immunoassays or bioanalytical antibody protocols. For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for general procedural guidance.
If preparing stock solutions for screening chemistry:
Dissolve in anhydrous DMSO or DMF to a convenient concentration (e.g., 10–100 mM), filter (PTFE, 0.2 µm) under inert gas if needed, and store aliquots protected from light at −20°C. Exact solution stability is not specified for this item; confirm by LC/MS before use.
Biological Roles
This product is supplied strictly for research use; no biological or clinical claims are made.
General biochemical considerations (literature/guidance):
Hydrazines react with carbonyls (aldehydes/ketones) to form hydrazones under mild conditions. This chemistry is exploited in bioconjugation and metabolite derivatization workflows, although specific biological compatibility of 2-hydrazinyl-3-nitropyridine has not been established.
The pyridine ring can participate in metal coordination (through ring N), which may be relevant in designing probes or chelating ligands; however, binding constants and selectivity for this specific ligand are not established here.
Nitroaromatic groups can influence redox behavior, but this compound is not intended for cellular work unless appropriately evaluated by the researcher for cytotoxicity and compatibility.
Item-specific biological data (pKa, logP, permeability, metabolic fate, enzyme inhibition/activation): Not specified for this item; refer to primary literature if contemplating biochemical experiments.
Caution: Hydrazine-containing molecules can be reactive toward biomolecules; handle with appropriate containment and do not assume biocompatibility. Any use in biological systems should be preceded by rigorous toxicity and stability assessments under the relevant conditions.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare pH buffers.
Practical note:
If employed in aqueous media (e.g., for hydrazone formation with water-soluble carbonyls), choose an external buffer system appropriate for the reaction (e.g., acetate buffer pH 4–5.5 to catalyze condensation). The compound itself does not define a standard buffer pair nor a validated buffering range.
For standard buffer preparations (PBS, acetate, citrate, HEPES, etc.), refer to dedicated buffering agents instead of this heteroaromatic building block.
Green Alternatives
Greenness considerations focus on solvent choice and reduction methods rather than the substrate itself.
2-Methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME): greener ethers with better safety profiles; may require co-solvent or base to solubilize hydrazines.
Propylene carbonate or dimethyl carbonate for some condensations; watch for basicity limits and reactivity with nucleophiles.
Replace dichloromethane with:
Ethyl acetate or Me-THF for extractions and medium-polarity reactions.
Aqueous/ethanol media:
Many hydrazone formations proceed in EtOH/H2O with catalytic acetic acid; reduces VOC impact and simplifies workup.
Greener reductions (for nitro → amine):
Catalytic hydrogenation (H2/Pd, H2/Pt) in alcohol or EtOAc is generally cleaner than stoichiometric metal reductions (Fe, SnCl2), minimizing inorganic waste. Monitor for over-reduction of the hydrazino group.
Trade-offs:
Hydrazine functionality may be less stable in strongly basic green solvents (e.g., carbonate media) and could undergo side reactions with cyclic carbonates.
2-MeTHF and CPME offer improved safety but may not dissolve this substrate as effectively as DMF/DMSO; small percentages of alcohol or DMSO can help.
Summary table (qualitative):
DMF/NMP: excellent solvency, poor EHS profile.
DMSO: strong solvency, acceptable EHS but odor and workup challenges.
2-MeTHF/CPME: greener, good handling, may need cosolvent.
EtOH/H2O: green, compatible with condensations, limited solubility control.
Pharmaceutical Uses
No pharmacopeial or excipient status is provided. This product is for research use only.
General context (synthetic/pharmaceutically relevant chemistry):
Potential role as an intermediate: hydrazino and nitro functionalities enable convergent routes to drug-like heterocycles (e.g., pyrazoles, pyridyl hydrazides) and to bifunctional linkers after reduction of the nitro group.
Derivatization handle: formation of hydrazones can serve as protecting/activating groups for carbonyl-containing fragments during medicinal chemistry campaigns.
Item-specific regulatory/quality information:
USP/EP/JP monographs: Not specified for this item; refer to regulatory databases.
Residual solvents, elemental impurities (ICH Q3D), and other GMP-relevant metrics: Not specified for this item; refer to CoA/Spec Sheet if pursuing process development.
Important: No claims are made regarding safety, efficacy, or suitability for human or veterinary use. All uses are confined to laboratory research by qualified professionals.
Physical Properties
Item-specific numerical specifications are not provided in the Product Data. Consult the CoA/Spec Sheet for definitive values.
General/literature expectations for this class of compound (for planning only):
Physical state: typically a crystalline solid for nitro-substituted aminopyridines/hydrazinopyridines.
Molecular formula and MW (literature): C5H6N4O2; ~154.13 g/mol.
Polarity: moderately polar due to one ring nitrogen, one hydrazino (two nitrogens), and one nitro group; capable of hydrogen bonding (donor and acceptor sites).
Solubility (qualitative, literature/guidance):
Good in polar aprotic solvents (DMSO, DMF, NMP).
Often soluble in alcohols (MeOH, EtOH) and partially in acetonitrile and ethyl acetate.
Low solubility expected in nonpolar solvents (hexanes, toluene) unless derivatized.
Acid–base behavior (general): hydrazino nitrogen(s) are basic; protonation increases aqueous solubility. The ring nitrogen also contributes to basicity; overall pKa values depend on substitution and are not specified for this item.
UV-vis: aromatic heterocycle with nitro substituent typically shows strong absorbance in the 250–380 nm region (literature, qualitative); exact cutoffs/epsilon not specified for this item.
Do not treat the above as specifications. For exact melting point, purity, water/peroxide/metal content, refractive index, or logP: Not specified for this item; refer to CoA/Spec Sheet.
Quality & Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general):
Research grade: suitable for most synthetic and exploratory work. Purity typically specified on CoA.
High-purity/98–99%+ materials: favored for multistep synthesis, SAR studies, or analytical uses; often accompanied by tight controls on residual solvents and related impurities.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Given the hydrazino functionality, materials are typically supplied without stabilizers but may be packaged under inert gas to limit oxidative degradation (as indicated: Argon charged).
Analytical quality considerations for this class of compound:
Identity confirmation: 1H/13C NMR (aromatic signals and hydrazino NH/NH2), IR (N–H stretches ~3300–3200 cm−1; NO2 asym/sym ~1530/1350 cm−1), HRMS/EI/ESI for exact mass, and HPLC/UPLC purity profile.
Residual moisture/peroxides/metals/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
What is item-specific here:
Storage profile is defined by the Product Data (−20°C, under argon, protected from light) and should be considered part of the quality-preservation strategy from production to use.
Reaction & Applications
As a 2-hydrazinyl-3-nitropyridine, this reagent combines a nucleophilic, derivatizable hydrazine with a strongly deactivating nitro group on a pyridine ring, enabling diverse transformations.
Hydrazone formation with aldehydes/ketones (analytical tagging, intermediates to heterocycles). Mild acid catalysis (AcOH) in MeOH/EtOH or DMSO, rt–reflux.
Acylhydrazide synthesis via acyl chlorides/anhydrides; subsequent cyclizations (e.g., to 1,3,4-oxadiazoles) after further elaboration.
Reductive interconversions:
Nitro-to-amine reduction (e.g., Fe/AcOH, SnCl2/EtOH, catalytic hydrogenation) to access 2-hydrazinyl-3-aminopyridine, unlocking cross-couplings (Buchwald–Hartwig, Suzuki after further halogenation) and diazotization pathways.
Heterocycle construction:
Condensation of the hydrazine with 1,3-dicarbonyls, α,β-unsaturated carbonyls, or isothiocyanates to form pyrazoles, hydrazides, and thiosemicarbazide-derived rings attached to a pyridyl handle.
Electrophile capture and protection:
Temporary protection of carbonyls via hydrazones, enabling umpolung strategies (e.g., Shapiro-type chemistry after appropriate activation, literature-dependent).
Practical tips:
Maintain inert atmosphere (argon/nitrogen) and exclude light, consistent with the storage recommendations.
Titrate base/acid carefully; over-acidification can protonate both ring and hydrazino nitrogens, suppressing nucleophilicity.
For condensations, remove water azeotropically (Dean–Stark) or add molecular sieves to drive equilibrium.
Manufacturer Applications: Not provided in Product Data; the above are typical uses inferred from functional groups (literature/generic guidance).
Reaction Conditions
Typical conditions (literature/guidance; adjust per substrate and scale):
Hydrazone formation (with aldehydes/ketones):
Solvent: EtOH, MeOH, or DMSO; optional toluene for azeotropic water removal.
Catalyst: AcOH (0.1–1.0 equiv) or p-TsOH (1–10 mol%).
Temperature/time: rt to reflux (20–80°C), 1–16 h; monitor by TLC/HPLC.
Tips: add 3Å molecular sieves or employ Dean–Stark to drive equilibrium; avoid strong mineral acids which can over-protonate the pyridine nitrogen.
Acylation to hydrazides:
Reagents: acyl chlorides/anhydrides (1.0–1.5 equiv), base (pyridine, NEt3, DIPEA, or Na2CO3).
Solvent: DCM, THF, or DMF; 0–25°C to control exotherm.
Notes: chemoselectivity between terminal vs internal N may be tuned by base and temperature.
Nitro reduction to amine (3-aminopyridyl derivative):
Transfer hydrogenation: ammonium formate/Pd-C in MeOH, 25–40°C.
Stoichiometric: Fe/AcOH or SnCl2·2H2O in EtOH; 50–80°C. Workup removes inorganic salts.
Caution: preserve hydrazino moiety; milder conditions and careful monitoring recommended.
Downstream couplings (after nitro→amine or halogenation):
Buchwald–Hartwig: Pd(0)/biaryl phosphine, NaOtBu or Cs2CO3, toluene/DME, 80–110°C.
Suzuki–Miyaura (if aryl/heteroaryl halide installed): Pd(PPh3)4 or Pd(dppf)Cl2, K2CO3, dioxane/H2O or EtOH/H2O, 60–100°C.
Yields are substrate dependent and not specified for this item; consult primary literature and optimize on small scale.
Safety & Handling
Hazard classification and pictograms are not specified in the Product Data. Always consult the product SDS for authoritative safety information.
General safety considerations for hydrazine- and nitro-substituted heteroarenes (guidance):
Potential hazards: toxic if swallowed/inhaled; skin/eye irritation or sensitization possible. Hydrazines can be reducing and reactive toward carbonyls; nitroaromatics may present additional toxicological concerns.
Stability notes: per Product Data, protect from light, store under argon at −20°C; this suggests sensitivity to air/oxidation and/or photodegradation. Keep tightly sealed; minimize headspace oxygen and moisture.
Incompatibilities: strong oxidizers (risk of vigorous reaction), strong electrophiles and acylating agents (exothermic acylation of hydrazines), nitrosating agents (risk of N-nitrosamine formation), and carbonyl compounds (spontaneous condensation possible under acidic conditions).
PPE: lab coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a properly functioning fume hood; avoid inhalation of dust.
Handling tips:
Open vials briefly and under inert gas when possible; recap promptly.
Weigh quickly to limit air/light exposure; consider amber glassware.
Avoid grinding that produces dust; wet with compatible solvent first if needed.
First aid (overview; defer to SDS): move to fresh air if inhaled; rinse skin/eyes with water for at least 15 minutes upon contact; seek medical attention after ingestion or significant exposure.
Waste: collect hydrazine-containing waste separately; avoid mixing with oxidizing wastes. Follow institutional and regulatory disposal procedures.
Solvent Selection
This compound is a moderately polar, multifunctional heteroaromatic (hydrogen-bond donor/acceptor). Choose solvents that stabilize both hydrogen-bonding and polar interactions while preserving reactivity of the hydrazino group.
DMSO, DMF, NMP: excellent solvating power for hydrazines and nitroheteroarenes; ideal for stock solutions and SNAr/coupling setups.
Alcohols (MeOH, EtOH, i-PrOH): good for condensations (hydrazone formation) and recrystallization in some cases.
Conditional choices:
Acetonitrile, ethyl acetate: moderate solubility; good for workups and some catalytic hydrogenations.
Aqueous mixtures (pH-controlled): protonated forms increase water solubility, useful during extractions or for bioconjugation-type condensations.
Avoid/limited:
Nonpolar solvents (hexanes, heptane): poor solubility likely; reserve for antisolvent precipitation or trituration.
When to choose vs alternatives:
For condensation with aldehydes/ketones: alcohol solvent with catalytic acid (AcOH, TsOH) or mixed MeOH/DMSO for difficult substrates.
For reductions or metal-catalyzed couplings after functional-group interconversion: DMF or THF/EtOH mixtures under inert atmosphere.
Notes:
This item is shipped cold and stored under argon; dry and deoxygenate solvents before use to minimize oxidative degradation of the hydrazino moiety.
Exact solubility values for this item: Not specified; evaluate empirically or consult CoA if available.
Storage & Reconstitution
Item-specific storage (from Product Data):
Store at −20°C.
Protect from light.
Supplied argon charged (maintain an inert atmosphere to minimize oxidation/decomposition).
Shipped in an ice chest with ice pads.
General handling and reconstitution guidance:
Upon receipt: allow the sealed container to equilibrate to room temperature before opening to prevent moisture condensation. Open quickly, preferably in a glovebox or under a dry inert gas purge.
Solid handling: if clumping occurs, gently break up under inert gas; avoid prolonged exposure to air and light.
Stock solutions: prepare in dry, oxygen-free solvents (e.g., anhydrous DMSO, DMF, or alcohols). Use amber vials; sparge solutions with argon/nitrogen if practical. Typical working concentrations vary by application; item-specific solubility is not specified.
Aliquoting: divide into single-use portions to minimize freeze–thaw cycles and headspace oxygen.
Stability: long-term stability data and solution stability: Not specified for this item; refer to CoA/Spec Sheet. As a precaution, re-check purity (HPLC/LC–MS) after extended storage.
Research Use Note: For research use only. Handle and store according to best practices for hydrazine-containing, light/air-sensitive heteroaromatics.
Structure & Identity
A bifunctional, heteroaromatic building block featuring a pyridine ring bearing a hydrazino group at C-2 and a nitro group at C-3.
SKU: H708748
Product Name: 2-Hydrazinyl-3-nitropyridine
CAS: 15367-16-5; PubChem CID: 3578935
InChIKey (as provided): 302814
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet. (typical literature assignment: C5H6N4O2)
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet. (literature value for C5H6N4O2 ≈ 154.13 g/mol)
Structural features (general description):
Core ring: six-membered aromatic pyridine (one ring nitrogen at position 1).
Substituents: 2-hydrazinyl (–NH–NH2) at the ortho position to the ring N; 3-nitro (–NO2) adjacent to the hydrazino group.
Functional groups: basic hydrazine (nucleophilic, can be acylated/condensed) and strongly electron-withdrawing nitro (can be reduced; modulates ring electronics).
2D arrangement (verbal): starting from the ring nitrogen (position 1), position 2 bears –NH–NH2, position 3 bears –NO2, positions 4–6 are unsubstituted carbons with aromatic hydrogens.
Notes:
The juxtaposition of a nucleophilic hydrazino donor and a nitro acceptor on a pyridine scaffold makes this a useful divergent intermediate for heterocycle synthesis and late-stage derivatization. All identifiers not explicitly provided above should be confirmed against the product CoA.
Synthetic Utility
Functional group leverage:
Hydrazino group (–NH–NH2):
Nucleophilic at terminal and internal N; undergoes acylation, sulfonylation, and carbonyl condensation to hydrazones/azines.
Can serve as a linchpin for building N–N-containing heterocycles (e.g., pyrazoles via condensation with 1,3-dicarbonyls, followed by cyclization/oxidation; 1,3,4-oxadiazoles from acylhydrazides after dehydrative cyclization).
Nitro group (–NO2):
Modulates ring electronics (strong −M/−I), potentially enabling SNAr at suitably activated positions in related substrates.
Versatile handle for reduction to the aniline (3-aminopyridine derivative), opening cross-coupling (Buchwald–Hartwig, Chan–Lam after appropriate activation) and diazotization/sandmeyer-type diversifications.
Retrosynthetic value:
Acts as a bifunctional node: the hydrazino end can be diversified first (e.g., install acyl/aryl/alkyl groups), with the nitro later unmasked to amine for further coupling; or vice versa, allowing orthogonal, stepwise elaboration.
Protecting group strategy:
The hydrazino may be selectively protected (e.g., Boc, benzyl, or acyl) to control chemoselectivity. Acidic workups should balance stability vs. desired deprotection pathway.
Practical notes:
Control protonation state (pH/base selection) to maximize nucleophilicity of the targeted nitrogen.
Because the material is stored under argon and light-protected, maintain inert conditions during sensitive steps; use dry solvents and minimize heating in air.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent or antibody. No antigen/epitope specificity, clone, isotype, or species reactivity applies.
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