Ethyl 2-hydrazinonicotinate - ≥97% , CAS No.292155-95-4

CAS: 292155-95-4 Cat. No.: E1031557 PubChem CID: 53404568

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥97%

Storage

Room temperature

Reinheit

≥97%

Namen und Kennungen

• Kanonisches Lächeln: CCOC(=O)C1=C(N=CC=C1)NN
• IUPAC Name: ethyl 2-hydrazinylpyridine-3-carboxylate
• InChIKey: WUTSCQRRPAROJE-UHFFFAOYSA-N
• INCHI: 1S/C8H11N3O2/c1-2-13-8(12)6-4-3-5-10-7(6)11-9/h3-5H,2,9H2,1H3,(H,10,11)
• Isomere SMILES: CCOC(=O)C1=C(N=CC=C1)NN
• PubChem CID: 53404568

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Pyridines and derivatives
      • Subclass Pyridinecarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Pyridines and derivatives
• Subclass: Pyridinecarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyridinecarboxylic acids
• Alternative Parents: Imidolactams Vinylogous amides Heteroaromatic compounds Carboxylic acid esters Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives Hydrazines and derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyridine carboxylic acid - Imidolactam - Vinylogous amide - Heteroaromatic compound - Carboxylic acid ester - Carboxylic acid derivative - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Hydrazine derivative - Organic oxygen compound - Aromatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 181.190 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 181.085 Da
• Monoisotopic Mass: 181.085 Da
• Topological Polar Surface Area: 77.200 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 175.000
• 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

Application Protocols

Not applicable. No immunoassay or biochemical assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the Product Data. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for practical guidance.

Biological Roles

This product is supplied for research use only and is not intended for biological administration. No intrinsic biological role is specified for Ethyl 2-hydrazinonicotinate.

General context (literature/knowledge, not product-specific claims):

• Nicotinate scaffolds are common in bioactive molecules; however, the 2-hydrazino substitution represents a synthetic handle rather than a known metabolite.
• Hydrazino groups can engage in reversible covalent interactions with carbonyl-containing biomolecules in vitro (e.g., hydrazone formation), which is sometimes exploited in bioconjugation method development. Such uses require careful control of pH (typically mildly acidic) and are conducted in research settings only.

No clinical, diagnostic, or therapeutic claims are made for this item.

Buffer Applications

Not typically used as a buffering agent. Ethyl 2-hydrazinonicotinate lacks a conjugate acid/base pair with an appropriate capacity window for standard biochemical buffering systems.

• If aqueous handling is needed (e.g., for bioconjugation research), prepare solutions in a suitable buffer for your system (commonly acetate or phosphate buffers at pH 4–7 for hydrazone chemistry). Selection and recipes should follow your method’s requirements; this item itself is not the buffer component.

Green Alternatives

Opportunities to improve the environmental profile center on solvent choice and coupling reagents, as the substrate itself is defined by the target structure.

• Preferred solvents (greener options):

  • EtOH, i-PrOH, or water/EtOH blends for hydrazone condensations (often effective with catalytic AcOH).
  • 2-MeTHF or EtOAc as alternatives to DCM/THF for acylations when solubility permits.

• Reduce high-EHS reagents:

  • Favor CDI, EDC·HCl, or DMC-based (dimethyl carbonate) methodologies over acid chlorides and phosgene-derivatives for carbamoylations where feasible.
  • Employ organic bases with better EHS profiles (e.g., DIPEA over pyridine) and minimize equivalents.

• Energy efficiency:

  • Many condensations proceed at ambient temperature; apply mild heating or microwave only as needed.

Comparison snapshot (general):

• DCM vs EtOAc: EtOAc is less toxic, biodegradable; may require slightly higher temperature for similar rates.
• DMF/DMSO vs EtOH/2-MeTHF: DMF/DMSO excel in solubility but are higher-boiling and harder to remove; EtOH/2-MeTHF facilitate easier workup but may need co-solvents.

Waste minimization:

• Drive condensations to completion by azeotropic water removal or sieves to reduce excess reagent.
• Crystallize hydrazones from alcohols where possible to avoid chromatographic solvents.

Pharmaceutical Uses

No pharmacopeial status or excipient use is specified for this item. It is supplied for research and laboratory synthesis only.

General formulation context (not specific to this product):

• Nicotinate esters and hydrazine derivatives may appear as intermediates in medicinal chemistry programs, enabling SAR exploration around the pyridine core and facilitating prodrug or linker strategies.
• Any use in GMP or clinical contexts would require separate qualification and regulatory assessment beyond the scope of this research-grade listing.

Physical Properties

Item-specific physical specifications (bp, mp, density, etc.) are not provided for this SKU. Values below are general/literature guidance for the named structure and should not be taken as specifications for this lot.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: ~181.20 g/mol (literature/computed for C8H11N3O2)
• Molecular formula: C8H11N3O2 (literature/computed)
• Acid/base character (literature):
  • Basic sites: pyridine N (weak base), hydrazino nitrogens (moderate bases)
  • Expected to be polyfunctional with potential for salt formation under acidic conditions
• Solubility (literature/experience-based generality):
  • Likely good solubility in polar aprotic solvents (DMF, DMSO) and alcohols (MeOH, EtOH)
  • Limited solubility in nonpolar hydrocarbons (hexanes, toluene)
  • Can form salts with mineral acids to improve aqueous solubility
• LogP/logD (qualitative, literature expectation): moderate polarity due to hydrazino and ester; logP likely in the low-to-moderate positive range; exact value not specified for this item.
• pKa (qualitative, literature expectation): hydrazino N–H typically pKa (conjugate acid) in the 4–6 range; pyridine N (conjugate acid) around 5–6; exact values not specified for this item.
• Refractive index, melting/boiling point, density, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance for interpretation (general):

• When offered as “research grade,” material is intended for synthetic and analytical research, not for clinical or diagnostic use.
• If an HPLC or LC-MS grade were specified, that would imply low UV background/particulate and strict control of non-volatile residues; no such designation is listed for this SKU.
• If a metal content, water content (Karl Fischer), or residual solvent specification is important for your application (e.g., cross-couplings or moisture-sensitive condensations), consult the lot-specific CoA.

Stabilizers/impurities:

• No stabilizer is indicated in the Product Data. If present, stabilizers would be listed explicitly on the CoA/SDS.

Fit-for-use notes:

• For condensations (hydrazone formation), trace acids/bases can influence kinetics and selectivity. Consider pre-drying and, if needed, purifying (e.g., recrystallization or silica plug) to meet your performance criteria.
• For analytical needs, verify identity by 1H/13C NMR and HRMS; hydrazino protons often appear as exchangeable signals and may require D2O shake to confirm.

Reaction and Applications

As a 2-hydrazino-substituted nicotinate, this reagent serves as a versatile nucleophilic building block and condensation partner for heterocycle construction and derivatization.

• Condensations (literature):
  • Hydrazone formation with aldehydes/ketones to give azomethines/hydrazones; useful for carbonyl protection, derivatization, and as precursors to heterocycles.
  • Reaction with 1,3-dicarbonyls to access pyrazole frameworks after cyclocondensation.
• N-acylation/carbamoylation:
  • Selective acylation at the terminal NH2 vs the internal –NH– can be steered by base strength, acylating agent reactivity, and temperature. Carbamates, ureas, and amide libraries can be prepared.
• Heterocycle synthesis on the pyridine scaffold:
  • Intramolecular or tandem condensations can furnish fused N-heterocycles; the nicotinate ester can participate in further transformations (e.g., amidation to nicotinamide analogs).
• Functional handles:
  • Ester group enables downstream modifications: hydrolysis to acid, conversion to acid chlorides, or amidation for library synthesis.
  • Hydrazino unit can capture electrophiles (chloroformates, sulfonyl chlorides) to modulate basicity and solubility.
• Coordination chemistry:
  • The pyridine N plus hydrazino N donors can chelate metals in situ, sometimes influencing catalysis or enabling ligand development (literature precedent for related hydrazinopyridines).

Practical tips:

• Dry solvents and maintain anhydrous conditions for acylations/couplings; hydrazones typically tolerate protic media.
• Use mild acid catalysis (e.g., AcOH, p-TsOH, 0.1–10 mol%) for sluggish carbonyl condensations; remove water (Dean–Stark or molecular sieves) to drive equilibrium.
• Monitor by TLC/LC-MS; hydrazones exhibit characteristic UV and MS shifts (M–18 upon dehydration is common).

Reaction Conditions

General conditions below are literature-style guidance for related substrates; optimize for your system. They are not product specifications.

• Hydrazone formation with aldehydes/ketones:

  • Solvent: EtOH, MeOH, or EtOH/H2O (4:1 to 9:1). Optional 0.5–5 mol% AcOH or p-TsOH.
  • Temperature: rt to 60 °C.
  • Time: 0.5–12 h depending on substrate.
  • Workup: Concentrate, triturate, or crystallize; neutralize acid if used.

• N-acylation (selective on terminal NH2):

  • Solvent: DCM, THF, or DMF (anhydrous).
  • Base: DIPEA (2–3 equiv) or NaHCO3/Na2CO3 (aqueous-organic biphasic for acid chlorides).
  • Electrophile: Acyl chlorides, anhydrides, carbamoyl chlorides, or activated esters (e.g., NHS esters).
  • Temperature: 0 °C to rt; control addition to manage exotherm.

• Amidation at the ester (to convert –CO2Et):

  • Method A: Direct aminolysis with excess amine in EtOH or toluene, 60–110 °C; removal of EtOH byproduct drives conversion.
  • Method B: Activate as acid chloride (SOCl2, catalytic DMF), then couple with amines in DCM/THF with base.

• Cyclizations to pyrazoles (with 1,3-dicarbonyls):

  • Solvent: EtOH or EtOH/AcOH.
  • Temperature: 50–90 °C.
  • Typical outcome: formation of N–N heterocycles; isolate by crystallization or chromatography.

• Inert atmosphere: Recommended for moisture/air-sensitive acylations; hydrazone condensations usually tolerate air.

• Monitoring: TLC (UV-active pyridine), LC-MS; hydrazones often show characteristic mass shift (M + electrophile − H2O).

Note: Expected yields vary widely (50–90% typical for well-matched condensations). Optimize stoichiometry and water removal to improve conversions.

Safety and Handling

Hazard classification details for this specific item are not provided. Always consult the SDS for authoritative information before use.

• GHS information (item-specific):

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H-codes): Not specified for this item; refer to SDS.
  • Pictograms/GHS classification: Not specified for this item; refer to SDS.

• General hazards for hydrazine-bearing pyridines (literature/general):

  • May be harmful if swallowed, inhaled, or in contact with skin; can cause irritation to skin, eyes, and respiratory tract.
  • Hydrazino functionality can be sensitive to strong oxidizers; avoid oxidizing agents and nitrosating conditions.
  • May be combustible; keep away from ignition sources and heat.

• PPE and engineering controls (good laboratory practice):

  • Wear lab coat, safety glasses (or goggles), and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to avoid inhalation exposure.
  • Avoid aerosol formation; use closed systems or local exhaust when feasible.

• First-aid overview (general):

  • Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; obtain medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed; seek medical attention.

• Incompatibilities (general): strong oxidizers, strong acids/bases for extended periods (can lead to decomposition or transesterification), nitrosating agents.

• Waste: Collect organic waste containing hydrazines in compatible containers; dispose according to institutional and local regulations.

Solvent Selection

Ethyl 2-hydrazinonicotinate is a polar, bifunctional heteroaromatic. Solvent choice should balance solubility, reactivity (particularly for condensations), and stability of the hydrazino group.

• Polarity class (general): polar protic/aprotic compatible; typically more soluble in polar aprotics and alcohols.
• Miscibility/solubility (literature/typical):
  • High: DMSO, DMF, NMP, MeOH, EtOH.
  • Moderate: acetonitrile, ethyl acetate.
  • Low: toluene, MTBE, hexanes.
• Water: Free base exhibits limited aqueous solubility; formation of mineral-acid salts (e.g., HCl) increases water solubility for workups.

Selection by task:

• Hydrazone formation with aldehydes/ketones: EtOH, MeOH, or EtOH/water mixtures often give clean conversions; catalytic acid (AcOH) can accelerate.
• N-acylation or carbamoylation: Use anhydrous polar aprotic solvents (DCM, THF, DMF) with base (e.g., DIPEA) to control selectivity between terminal and internal nitrogen.
• Metal-catalyzed transformations on the ring (if applicable): NMP/DMF or mixed solvent systems under inert atmosphere.

Quick comparison (general guidance):

• EtOH: green, effective for hydrazone formation; reversible equilibria manageable by water removal.
• DMF/DMSO: excellent solubilizers; consider greener alternatives where possible and ensure rigorous workup to remove high-boiling residues.
• 2-MeTHF/EtOAc: better EHS profile; may need co-solvent or mild heating for complete dissolution.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Protect from moisture and strong light; store tightly closed.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/solution preparation (general guidance):
  • Prepare stock solutions in dry solvents (e.g., DMSO, DMF, EtOH) as needed. For maximum stability, use anhydrous solvent and store aliquots to minimize headspace and freeze–thaw.
  • Aqueous solutions are not recommended for long-term storage unless converted to a stable salt; prepare fresh as needed.
  • Filtration through 0.2 µm PTFE or PES is recommended for assay-ready solutions.
• Stability considerations (general):
  • Hydrazino groups can slowly oxidize; minimize exposure to air/oxidants. Avoid prolonged contact with strong acids/bases which can promote hydrolysis or transesterification of the ester.
  • If long-term storage is required, consider refrigeration in inert atmosphere for solutions; verify stability by LC-MS/NMR prior to critical use.

Always refer to the product’s CoA/SDS for lot-specific handling and stability information.

Structure and Identity

Ethyl 2-hydrazinonicotinate is a heteroaromatic building block: a nicotinate (pyridine-3-carboxylate) ethyl ester bearing a 2-hydrazino substituent on the pyridine ring.

• Item-specific identifiers (from Product Data):

  • CAS: 292155-95-4
  • PubChem CID: 53404568
  • InChIKey (as provided): 408619 (note: appears truncated/non-standard; consult CoA/SDS for the full InChIKey)
  • Storage: Room temperature
  • Research use: For research use only

• Structure description (general/literature):

  • Core ring: pyridine (one ring nitrogen at position 1)
  • Substitution pattern: 2-position = hydrazino (–NH–NH2); 3-position = ethyl ester of the carboxylate (–C(=O)OCH2CH3)
  • Functional groups: heteroaromatic pyridine, hydrazine (nucleophilic, bifunctional), ethyl ester (electrophilic at carbonyl)
  • Stereochemistry: none (achiral)

• Formula and mass (computed/literature for the named structure):

  • Molecular formula: C8H11N3O2 (literature/computed)
  • Molecular weight: ~181.20 g/mol (literature/computed)

• Structural strings:

  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChI: Not specified for this item; refer to CoA/Spec Sheet.

• 2D structure in words: A six-membered aromatic ring with a ring nitrogen (pyridine). Adjacent (ortho) to the ring nitrogen lies an –NH–NH2 substituent; at the meta position relative to the ring nitrogen is an ethoxycarbonyl group (–C(=O)OCH2CH3).

Synthetic Utility

Key functional elements define the reactivity profile of Ethyl 2-hydrazinonicotinate and make it a versatile node in retrosynthesis:

• Hydrazino functionality (–NH–NH2):

  • Acts as a bifunctional nucleophile toward acyl, sulfonyl, and carbonyl electrophiles.
  • Enables formation of hydrazones/azines and subsequent cyclizations to pyrazoles, 1,2,4-triazines (with appropriate partners), and other N-rich heterocycles.
  • Differential protection of the two nitrogens allows stepwise elaboration (e.g., Boc on terminal NH2 to direct acylation to the internal N).

• Ethyl ester (–CO2Et):

  • Convertible to the acid (hydrolysis), amides (aminolysis), or acid chlorides (oxalyl chloride, SOCl2) for downstream coupling.
  • Participates in Claisen-type condensations after conversion to the corresponding acid/activated derivatives in ring-fusion strategies.

• Pyridine core:

  • Coordinates to metals, offering avenues for catalyst-directed C–H functionalization or cross-coupling at other ring positions if appropriately halogenated.

• Retrosynthetic leverage:

  • Disconnection to a 2-halonicotinate followed by nucleophilic substitution with hydrazine derivatives, or direct electrophilic amination on 2-aminonicotinate followed by N–N bond construction.

Overall, the scaffold balances nucleophilicity (hydrazine) with an electrophilic handle (ester), facilitating divergent library synthesis.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or species reactivity is defined for this item.