This compound belongs to the class of organic compounds known as aminopyridazines. These are organic compounds containing an amino group attached to a pyridazine ring.
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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Recensioni
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Application Protocols
Not applicable (no tested bioassay/antibody protocols provided)
There are no manufacturer-verified application protocols (e.g., WB, IHC, IF, FC) for this small-molecule reagent.
General laboratory usage notes (for chemists)
Prepare stock solutions in dry DMSO or methanol (e.g., 10–100 mM) for screening or synthetic use; filter if particulate is present.
For aqueous studies, form a soluble salt (e.g., HCl salt) or cosolvate with DMSO/EtOH; adjust pH with caution to avoid ether cleavage under strong acid.
Always confirm identity and purity by NMR and LC–MS prior to critical experiments.
Biological Roles
General information (no medical/clinical claims)
6-Ethoxypyridazin-3-amine is a synthetic heteroaromatic amine; it is not a known natural metabolite or cofactor.
The pyridazine ring is a recognized pharmacophore scaffold in medicinal chemistry for modulating hydrogen bonding and electronics; such motifs are frequently explored in target screening and structure–activity relationship studies.
As a basic, small molecule with multiple heteroatoms, it can form salts for in vitro assays and may interact via H-bonding and π–π/π–cation interactions in biochemical systems; any biological evaluation should be performed under appropriate research protocols.
Not specified for this item
Any specific targets, pathways, or bioactivity data. Users should generate primary data or consult the literature for the intended research system.
Buffer Applications
Applicability
This compound is not a conventional buffering agent. It lacks a defined conjugate acid/base pair in the physiological pH range with a narrow, high-capacity buffering window comparable to standard buffers (e.g., phosphate, HEPES, Tris).
Practical note
For aqueous work, the amine can be protonated to form water-soluble salts, but solutions will not provide robust buffering capacity. Use established buffers for pH control and dissolve the compound in a co-solvent (e.g., DMSO) or as a pre-formed salt if needed.
Green Alternatives
Greener solvent choices for typical transformations (literature guidance)
Replace DMF/NMP in acylations or SNAr with 2-MeTHF, CPME, or propylene carbonate when solubility and temperature windows permit.
Prefer ethanol or isopropanol for salt formation and recrystallization over chlorinated solvents.
For Buchwald–Hartwig couplings, use 2-MeTHF or toluene/ethanol mixtures instead of dioxane where applicable.
Comparison (general)
DMF vs 2-MeTHF: 2-MeTHF has lower toxicity, bio-based sourcing, and easier workup (phase split), but offers lower polarity and may reduce solubility for highly polar intermediates.
DCM vs EtOAc: Ethyl acetate provides a safer, biodegradable alternative for extractions and chromatography with comparable elution strength in many systems.
NMP vs propylene carbonate: Propylene carbonate is less hazardous but has higher viscosity; heating/stirring efficiency may be required.
Waste minimization
Use salt-switching crystallizations to avoid chromatographic purification of amine salts.
Opt for catalytic, atom-economical routes (e.g., direct N-arylation) over multi-step protection/deprotection sequences to reduce solvent and reagent consumption.
Notes
The above are general green chemistry practices applicable to heteroaryl amines like 6-ethoxypyridazin-3-amine. Validate solvent/reagent substitutions with small-scale trials.
Pharmaceutical Uses
General formulation/manufacturing context (no therapeutic claims)
As a heteroaryl amine building block, 6-ethoxypyridazin-3-amine may serve as an intermediate in the synthesis of experimental drug candidates during discovery and process development.
Salt formation (e.g., HCl, sulfate, mesylate) can be leveraged to modulate crystallinity and solubility in pre-formulation studies.
Not specified for this item
Any pharmacopeial status (USP/EP/JP), excipient role, or GMP grade. Material supplied is for research use only.
Physical Properties
From Product Data (item-specific)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general expectations for this scaffold; not item specifications)
Estimated molecular formula (see Structure & Identity rationale): C6H9N3O.
Estimated molecular weight: ~139.16 g/mol (literature calculation from elemental composition).
Physical state: small heteroaryl amines of this size are often crystalline solids or low-melting solids; exact MP/BP for this item is not confirmed.
Solubility (qualitative, literature expectation):
Good solubility in polar aprotic solvents (DMSO, DMF, NMP) and moderate in alcohols (MeOH/EtOH).
Limited solubility in nonpolar hydrocarbons; aqueous solubility may increase upon protonation (forming salts).
Acid–base behavior: primary heteroaryl amine; conjugate acid pKa for analogous diazine anilines is typically modest (literature: pKaH often ~2–5 due to ring deactivation), facilitating salt formation with mineral acids.
Not specified for this item; refer to CoA/Spec Sheet
Melting point, boiling point, density, refractive index, water content, residual solvents, UV cutoff, logP/logD.
Quality and Grades
From Product Data
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grades (general guidance)
Research grade: Suitable for synthetic and analytical R&D; impurity profiles may not meet pharmacopeial monographs.
Purity reporting: For heteroaryl amines, purity is commonly reported by HPLC/GC and supported by NMR/HRMS; water and residual solvent levels may be stated when relevant. If not shown here, consult the CoA.
Stabilizers: None specified for this item; if present in a specific lot, stabilizers would be listed on the CoA and may influence downstream reactions (e.g., base-sensitive steps).
Practical considerations
If using in metal-catalyzed couplings (e.g., Buchwald–Hartwig), trace metal content and halide levels can affect reactivity; check CoA if catalyst sensitivity is a concern.
If performing quantitative biological assays, confirm counter-ions, salt form, and exact purity method (area% vs weight%).
For chromatography-sensitive applications (e.g., LC–MS method development), prefer material with documented low non-volatile residue and known UV background; otherwise, pre-purify as needed.
Reaction and Applications
Role in synthesis (general, literature)
Heteroaryl primary amine useful as a nucleophile and ligand motif in medicinal chemistry and agrochemical scaffold elaboration.
The pyridazine ring is electron-deficient, enabling SNAr on appropriately activated/halogenated derivatives; the present amine itself is a handle for downstream functionalization.
Typical transformations of 6-ethoxypyridazin-3-amine (examples)
Acylation and carbamoylation: Formation of amides, ureas, and carbamates using acyl chlorides, CDI, or isocyanates.
Sulfonylation: Reaction with sulfonyl chlorides to give sulfonamides.
N-arylation (Buchwald–Hartwig): Coupling with aryl/vinyl halides/triflates under Pd catalysis to introduce aryl groups on the exocyclic amine.
Reductive amination (on aldehyde/ketone partners): Formation of secondary/tertiary amines if the exocyclic amine is used as the amine component.
Ether modification: Under acidic or nucleophilic conditions, ethoxy substituents on electron-deficient diazines can sometimes be exchanged (e.g., to –OH or –NR2) via SNAr or hydrolysis pathways; conditions must be optimized to avoid ring degradation.
Application contexts
Library synthesis and SAR exploration: The exocyclic amine allows rapid introduction of diversity (acyls, sulfonyls, aryls), while the ethoxy substituent tunes electronics and lipophilicity.
Fragment-to-lead chemistry: The small, polar scaffold offers multiple vectors for growth and H-bonding in enzyme/receptor active sites (general medicinal chemistry rationale; not a claim of activity).
Practical tips
Protecting strategies: Boc/CBz/Fmoc protection can moderate basicity during cross-couplings or multi-step sequences.
Purification: Basic silica or addition of a base modifier (e.g., 0.1–1% Et3N) can improve chromatographic behavior of amines.
Reaction Conditions
General conditions (literature guidance; optimize per substrate)
Acylation (amide formation):
Reagents: acid chlorides or EDCI/HOBt or HATU with base (DIPEA/Et3N).
Solvents: DCM, THF, 2-MeTHF, or DMF.
Temperature: 0–25 °C for acid chloride routes; 20–40 °C for carbodiimide couplings.
CDI (1.1–1.5 equiv) with amine partner, or reaction with isocyanates/isocyanates generated in situ.
Solvents: THF, DCM, DMF; 0–25 °C, then warm to 40–60 °C as needed.
Buchwald–Hartwig N-arylation:
Catalysts: Pd2(dba)3 (1–2 mol%) or Pd(OAc)2 (2–5 mol%) with ligands such as XPhos/BrettPhos.
Base: NaOtBu, Cs2CO3, or K3PO4 (2–3 equiv).
Solvent: toluene, dioxane, or 2-MeTHF; 80–110 °C, 4–16 h.
SNAr on diazine ethers (for O/N exchange on related substrates):
Nucleophile: amines/alkoxides.
Solvent: DMF/DMSO; 80–140 °C; sometimes requires halogen or additional activation on the ring.
Workup/purification tips
Quench acylation/sulfonylation with aqueous base to remove acid byproducts; extract into EtOAc; wash with brine.
For basic products, add a few drops of Et3N to chromatography eluents to reduce tailing; consider isolating as crystalline salts.
Not specified for this item
Specific yields, kinetic data, or catalyst loadings validated for this exact substrate.
Safety and Handling
From Product Data
Storage conditions: Room temperature
Shipped: Normal
GHS/Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature/standard practice; defer to SDS for authoritative details)
Likely hazards: Aromatic/heteroaromatic amines commonly cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid dust formation and inhalation.
PPE: Wear lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors/dust.
Handling: Avoid contact with strong oxidizers and strong acids/bases unless intended; amines can react with acylating agents, acid chlorides, and isocyanates. Prevent prolonged exposure to air/moisture if purity is critical.
First aid (overview):
Inhalation: Move to fresh air; seek medical advice if symptoms persist.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Organic heteroaromatics are typically combustible. Use dry chemical, CO2, or foam. Fire may produce NOx and CO/CO2.
Spills: Contain and collect with inert absorbent; avoid dust; ventilate area; dispose according to regulations.
Always consult the current SDS for this catalog item for definitive hazard classification and response measures.
Solvent Selection
Compound type and polarity (general)
6-Ethoxypyridazin-3-amine is a small, polar heteroaromatic base with H-bond donor/acceptor functionality. It typically dissolves well in polar aprotic solvents and alcohols; protonated salts improve water solubility.
Reaction media: DMSO, DMF, NMP, dioxane, MeCN, ethanol, 2-MeTHF. Choose based on downstream compatibility and catalyst system.
Analytical preparation: DMSO or MeOH stock solutions (10–100 mM) are common for bioassay screening; dilute with buffer post-neutralization or as salts.
Workup/recrystallization: Ethyl acetate/hexanes or EtOAc/MTBE for neutral forms; ethanol/water for salts.
Comparative notes
DMSO vs DMF: DMSO offers better safety/tox profile for handling and often greater solubility; DMF can be advantageous for high-temperature SNAr but raises regulatory flags.
Alcohols: EtOH/IPA can be greener alternatives and facilitate salt crystallization; water content may protonate the amine and alter solubility.
Aqueous systems: Form hydrochloride or other salts in situ to enhance water solubility for processing; adjust pH carefully to avoid hydrolysis of aryl ethers under strongly acidic conditions.
Not specified for this item
Measured solubilities, partition coefficients, or dielectric properties; consult experimental data if solvent choice is critical to your process.
Storage and Reconstitution
From Product Data
Storage: Room temperature
Shipped: Normal conditions
General guidance (literature/standard practice)
Keep tightly closed in a dry, well-ventilated place; protect from excessive heat and moisture. Desiccation is recommended for long-term storage to maintain purity of amines.
If preparing solutions:
Solvents: Dry DMSO, DMF, MeOH, or EtOH are typical. For biological testing, prepare concentrated DMSO stocks and dilute into buffer immediately before use.
Concentrations: 10–100 mM stocks are common; filter through 0.22 µm if needed.
Stability: Amines and aryl ethers are generally stable at ambient temperature; avoid prolonged exposure to strong acids/bases in solution.
Freeze–thaw: If aliquoted solutions are frozen (e.g., at −20 °C), minimize freeze–thaw cycles by preparing single-use aliquots.
Not specified for this item
Exact solubility limits, solution stability timelines, and reconstitution volumes; refer to CoA/Spec Sheet or perform small-scale solubility/stability checks for your application.
Structure and Identity
From Product Data
SKU: E184272
Product name: 6-Ethoxypyridazin-3-amine
CAS: 39614-78-3
CID: 3084748
InChIKey: 105691 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general identity and structural features)
Approximate molecular formula (literature inference for 6-ethoxypyridazin-3-amine): C6H9N3O
2D description: a six-membered aromatic ring with adjacent N atoms at positions 1 and 2; –NH2 para to N1 (at C3), and –OEt meta to the –NH2 (at C6), giving a polar, H-bond-donor/acceptor-rich heteroaromatic.
Notes
The above structural description reflects typical nomenclature of 6-ethoxypyridazin-3-amine. Exact identifiers (canonical SMILES/InChIKey string) are not specified in the Product Data and should be confirmed from the CoA/SDS or primary databases.
Synthetic Utility
Functional group reactivity (general)
Primary amine: readily acylated, sulfonylated, carbamoylated; engages in reductive amination and N-arylation (Pd-catalyzed). Can be protected as Boc/CBz/Fmoc for multistep synthesis.
Aryl ether (ethoxy on electron-deficient pyridazine): potential site for substitution or hydrolysis under SNAr/acidic conditions, enabling diversification to amino- or hydroxy-analogs.
Diazine ring: electron deficiency facilitates further substitution on activated positions if halogenated/activated derivatives are prepared.
Retrosynthetic value
Serves as an aniline-equivalent on a pyridazine core, allowing rapid access to ureas/sulfonamides/amides that project into binding pockets.
The ethoxy substituent provides an electronics/lipophilicity knob; late-stage modification (e.g., deprotection/exchange) can fine-tune ADME-relevant properties.
Named reaction relevance (literature)
Buchwald–Hartwig amination for N-arylation.
Schotten–Baumann acylation for amide synthesis.
CDI-mediated urea formation with amines/isocyanates.
SNAr on electron-deficient diazines for O/N substitution (when appropriately activated).
Target Specificity
Not applicable for this product type
This catalog item is a small-molecule reagent, not a biological affinity reagent (e.g., antibody, enzyme, or probe). No target/epitope specificity is provided or implied for this item.
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