This compound belongs to the class of organic compounds known as aminopyridines and derivatives. These are organic heterocyclic compounds containing an amino group attached to a pyridine 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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
152.190 g/mol
XLogP3
1.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Exact Mass
152.095 Da
Monoisotopic Mass
152.095 Da
Topological Polar Surface Area
48.100 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
119.000
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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No tested bioanalytical protocols are provided for this item. As a synthetic building block, it does not have standard WB/IHC/IF/FC protocols.
General handling for screening/assays (literature guidance)
Prepare a DMSO stock (e.g., 10–100 mM). Sonicate or warm gently if needed to dissolve.
Filter through 0.2 µm PTFE syringe filter for cell-free assay compatibility.
Dilute into the desired assay buffer to the working concentration, keeping final DMSO ≤1–2% v/v as assay permits.
For chemical reactions, follow the Reaction Conditions section; include appropriate controls and analytical monitoring (HPLC/LC–MS/NMR).
Refer to your lab’s SOPs and the compound’s SDS/CoA for any application-specific instructions.
Biological Roles
Item-specific biological/biochemical roles are not established in the product data.
General context (literature)
2-Aminopyridines are not endogenous metabolites; they serve as privileged motifs in medicinal chemistry due to their capacity to form bidentate H-bonds (as donors/acceptors via –NH2 and ring N) and to tune pKa/lipophilicity through substituents such as ethoxy and methyl.
The 5-ethoxy substituent can enhance lipophilicity and membrane permeability relative to hydroxy analogs, while the 6-methyl substituent adds steric bulk that may influence target selectivity in SAR campaigns.
Protonation states: in physiological pH ranges, the pyridine nitrogen and/or the exocyclic amine may be partially protonated, which affects binding modes, solubility, and distribution in biological assay systems (exact pKa values for this specific compound should be determined experimentally).
Use in discovery workflows: commonly deployed as a core for fragment growth or as a nucleophile for the rapid generation of amide/urea libraries evaluated in biochemical assays. Any biological activity arises from downstream derivatives rather than the starting amine itself.
Note: This product is designated For research use only (from Product Data) and is not intended for use in humans or diagnostics.
Buffer Applications
This compound is not a conventional buffering agent. While its basic nitrogens can be protonated, it lacks the defined buffering range, low UV absorbance, and compatibility profile expected of standard biological buffers.
Practical notes
If used in aqueous assay systems, prepare DMSO stock solutions and dilute into buffered media (e.g., phosphate, HEPES) rather than relying on the compound to provide buffering capacity.
pH adjustment should be achieved with established buffers; confirm that the compound remains in solution at the assay pH, considering possible salt formation under acidic conditions.
Green Alternatives
Context: As a building block rather than a consumable solvent or reagent, “green alternatives” concerns greener media and transformations when using 5-ethoxy-6-methylpyridin-2-amine.
Greener choices for common transformations (literature guidance)
Solvents: replace DMF/NMP/CH2Cl2 with 2-MeTHF, cyclopentyl methyl ether (CPME), ethanol, or water/EtOH mixtures when compatible. For amide couplings, 2-MeTHF or EtOAc can often substitute DCM.
Coupling reagents: prefer greener coupling systems (e.g., CDI, DMTMM, or catalytic thioester approaches) over carbodiimides with hazardous additives. Enabling technologies (microwaves, flow) may reduce solvent and energy use.
Bases: use inorganic carbonates or organic bases with better EHS profiles (e.g., DBU/DIPEA over pyridine for some procedures) while ensuring comparable performance.
Illustrative comparison (general)
DCM vs 2-MeTHF: 2-MeTHF offers lower toxicity, partial bio-sourcing, and favorable recyclability; may require slightly elevated temperatures for equivalent rates.
DMF vs EtOAc/MeCN: EtOAc and MeCN reduce reproductive toxicity concerns relative to DMF; solubility tradeoffs may exist for polar substrates.
Waste minimization
Form crystalline salts of the amine to simplify isolation and reduce chromatographic solvent use.
Employ high-atom-economy reactions (isocyanate additions, direct N-arylation) and telescoped sequences to limit workups.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item. It is supplied for research use only.
General development context (literature)
Typical role: heteroaromatic amine building block/intermediate used to synthesize candidate APIs or tool compounds. The 2-aminopyridine motif is common in medicinal chemistry for engaging hinge regions of kinases and other targets when derivatized into amides, ureas, or N-aryl analogs.
Salt formation: formation of hydrochloride or other pharmaceutically relevant salts can improve crystallinity and handling during process development (applies to derivatives as well). Selection of counterion should consider hygroscopicity and polymorphism.
Impurity considerations: oxidative degradation of anilines to nitroso/azo species can occur under harsh conditions; establish appropriate impurity controls and storage to mitigate.
Process notes
For scale-up of derivatives, choose greener solvents and minimize hazardous reagents in line with ICH Q3/Q11 principles. Establish robust analytical methods (HPLC/GC/LC–MS) for identity, assay, and residual solvent monitoring.
Reminder: No therapeutic claims are made here, and this product is not an API nor an excipient.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Density, refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Calculated/literature values (informational; not item specifications)
Molecular formula: C9H12N2O (derived from name; literature/computed)
Molecular weight: ~164.21 g/mol (computed)
Acid–base behavior: the exocyclic aniline-like –NH2 is weakly basic; pyridine ring N is basic but deactivated by adjacent –NH2 and ring substituents. Expected pKa values: conjugate acid of pyridine N typically ~5.0–6.0; anilinium-like –NH3+ typically ~4.5–5.5 (literature ranges for related 2-aminopyridines; exact for this compound not established here).
LogP/solubility (qualitative, literature expectations): heteroaromatic amine with one ether and one methyl group; typically shows good solubility in polar aprotic organics (DMSO, DMF, acetonitrile) and moderate solubility in alcohols; low solubility expected in water at neutral pH but increased in acidic aqueous media via protonation (literature generalization for 2-aminopyridine derivatives).
Melting/boiling points: Not located in primary references for this specific substitution pattern in this context; consult CoA/Spec Sheet or literature for measured values.
Note: For method development or formulation, determine exact thermal and solubility parameters experimentally and confirm against the item’s CoA.
Quality and Grades
Item-specific quality details
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general information)
Research-grade heteroaromatic building blocks are typically supplied with assay (HPLC/GC/NMR) and limits on key impurities (residual solvents, inorganic residues) on the CoA. If “HPLC grade” or “>98%” style purity were declared, that would indicate suitability for sensitive synthesis and screening; absent those declarations, confirm purity on the CoA before use in quantitative studies.
Water and residual solvent levels can influence reactivity of nucleophilic amines (e.g., during acylation or isocyanate coupling). If moisture-sensitive transformations are planned, consider drying the solid under vacuum and verifying Karl Fischer water where relevant.
UV characteristics: for LC-UV workflows, verify background absorbance/impurity profile in your mobile phase; specialized “LC/MS grade” materials minimize nonvolatile residues, but such a grade is not specified here.
Practical recommendations
Review the CoA for assay, impurity profile, and any stabilizer or salt information.
For medicinal chemistry or library synthesis, consider in-house QC (1H/13C NMR, HRMS, HPLC) upon receipt to confirm identity and purity in your solvent system.
Reaction and Applications
Role: 5-Ethoxy-6-methylpyridin-2-amine is a versatile heteroaromatic nucleophile and medicinal chemistry building block. The 2-aminopyridine motif frequently appears in kinase, GPCR, and enzyme inhibitor scaffolds; the 5-ethoxy/6-methyl pattern modulates electronics and lipophilicity.
Representative application areas (literature/general guidance)
Amide/urea/sulfonamide formation: the primary amine undergoes acylation (acyl chlorides, anhydrides, activated esters), carbamoylation/isocyanate additions to give ureas, and sulfonylation (sulfonyl chlorides) to form sulfonamides.
Reductive amination: as the amine component with aldehydes/ketones under NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation to furnish secondary amines.
N-arylation (Buchwald–Hartwig amination): coupling with aryl/vinyl halides/triflates using Pd catalysts and ligands (e.g., BrettPhos, RuPhos) to access N-aryl-2-aminopyridines.
Salt formation/prodrug handles: protonation at pyridine N or amine N affords crystalline salts (e.g., HCl salts) that can improve handling and purification.
Directed metalation/functionalization (on derivatives): the 2-amino group can direct ortho-lithiation on suitably protected variants; 5-ethoxy/6-methyl substituents further tune site selectivity (literature precedents for aminopyridines).
Practical tips
Pre-dry the substrate if moisture-sensitive reagents are used; amines can retain adventitious water.
For acylations, add base (DIPEA, Et3N, pyridine) to scavenge HX and suppress overacylation; low temperatures minimize side reactions.
For Pd-catalyzed couplings, protect or account for the basic heteroatoms (which may coordinate Pd); ligand/base choice is key to high conversion.
Manufacturer applications
Not provided in product data; the above represent common literature uses of 2-aminopyridine derivatives.
Reaction Conditions
General literature guidance for common transformations of 2-aminopyridines; adjust to this substrate and verify experimentally.
Amide formation
Reagents: acid chlorides, anhydrides, or carboxylic acids with coupling agents (EDC·HCl/HOBt alternatives like HOAt, or DMTMM/CDI for greener profiles).
Solvents: DCM, THF, 2-MeTHF, EtOAc, or MeCN; DMF/DMSO for challenging couplings.
Base: DIPEA, Et3N, or NaHCO3.
Temperature/time: 0–25 C (acyl chlorides) to 40–60 C (CDI/DMTMM) for 1–16 h.
Notes: control stoichiometry to avoid overacylation; monitor by LC–MS.
Urea formation (isocyanates or CDI route)
Reagents: aryl/alkyl isocyanates; or generate in situ via CDI from the corresponding amine/carboxylic acid derivatives.
Solvents: THF, MeCN, toluene.
Temperature: 0–80 C depending on reactivity; 1–6 h typical.
Buchwald–Hartwig N-arylation
Catalyst/ligand: Pd2(dba)3 (1–2 mol%) with BrettPhos/RuPhos (2–4 mol%).
Base: NaOtBu, Cs2CO3, or K3PO4.
Solvent: toluene, dioxane, or CPME; 80–110 C, 4–16 h.
Considerations: basic heteroatoms may chelate Pd; ligand choice and additive bases modulate activity.
Reductive amination
Conditions: carbonyl (1.0 eq), amine (1.2–2.0 eq), NaBH(OAc)3 in DCE/MeCN/THF with AcOH (cat.); 25–40 C, 2–18 h.
Salt formation/crystallization
Acid: HCl or p-TsOH in Et2O/IPA/EtOAc to form crystalline salts; optimize solvent pairs for isolation.
Yields: dependent on substrates and conditions; consult the primary literature for closely related aminopyridines when planning.
Safety and Handling
Item-specific hazard information
Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to SDS.
General safety guidance for substituted aminopyridines (literature/similar-compound guidance; not a substitute for the SDS)
Likely hazards: aromatic amines can cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid dust formation and inhalation of particulates. Some aminopyridines may be sensitizers.
PPE: wear lab coat, safety glasses or chemical splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to control vapors/particulates.
Storage incompatibilities: separate from strong oxidizers and strong acids/bases when possible. Amines readily form salts with acids; avoid unintended acid exposure unless salt formation is desired.
First aid (overview; consult 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 attention for persistent irritation.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Fire fighting: use CO2, dry chemical, or alcohol-resistant foam. Combustion may produce NOx and CO/CO2.
Waste: dispose according to local regulations for organic amines/heteroaromatics; avoid release to the environment.
Always defer to the product’s SDS for authoritative hazard classification and response measures.
Solvent Selection
Applicability: This compound is a small heteroaromatic amine/ether; solvent selection generally concerns dissolution for reactions or screening rather than use as a solvent itself.
General solubility/polarity guidance (literature expectations)
Likely good solubility: polar aprotic solvents (DMSO, DMF, NMP, acetonitrile), chlorinated solvents (DCM, CHCl3), and alcohols (MeOH, EtOH).
Moderate to low solubility: nonpolar hydrocarbons (hexanes, heptane) due to polar functionalities.
Aqueous media: limited solubility at neutral pH; solubility increases upon protonation in acidic buffers (formation of ammonium salt). For basic media, free base may precipitate as pH rises.
When to choose particular solvents
Synthesis (acylations, sulfonylations, urea formation): dry DCM, THF, MeCN, or toluene often suitable; for less reactive electrophiles, DMF/DMSO improve rates.
Metalation/cross-coupling on derivatized analogs: dioxane, toluene, CPME, or MeTHF with a co-solvent base system can be effective (literature for aminopyridine derivatives).
Biological assays: DMSO stock solutions (10–100 mM) with subsequent dilution into buffered aqueous systems are typical. Filter sterilize if required.
Comparison note
Compared with anilines, 2-aminopyridines are generally more polar and dissolve better in polar aprotics, but may exhibit lower solubility in pure hydrocarbons due to the ring nitrogen and the ethoxy functionality.
Storage and Reconstitution
Item-specific storage conditions
Storage Conditions: Room temperature (from Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (for heteroaromatic amines; supplementing item-specific conditions)
Keep container tightly closed in a dry, well-ventilated place. Protect from strong oxidizers and acids unless salt formation is intended.
If long-term storage is planned, consider storing in amber glass to reduce light exposure and in a desiccator to limit moisture uptake. Purge headspace with inert gas after opening when feasible.
Label date of opening; periodically verify purity by NMR/HPLC if used for quantitative synthesis.
Reconstitution/dissolution
For stock solutions, DMSO, DMF, MeCN, or alcohols typically dissolve aminopyridines well (literature guidance). Filter to remove particulates if needed.
Prepare single-use aliquots to avoid repeated freeze–thaw of solutions; store solutions at 2–8 C or −20 C as appropriate to solvent stability and project needs. Confirm solution stability experimentally.
Always consult the product’s CoA and SDS for definitive handling and storage recommendations.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Calculated/literature structural details (for context; not item specifications)
Molecular formula (by interpretation of the IUPAC name): C9H12N2O (literature/structure-derived)
Molecular weight: ~164.21 g/mol (calculated from C9H12N2O; literature/computed)
Core scaffold: substituted pyridine (aza-heteroaromatic, 1,4-dihydrogen-deficient six-membered ring bearing a ring nitrogen)
Functional groups: primary aromatic amine at C-2 (ortho to ring N), ethoxy substituent at C-5 (–O–CH2–CH3), methyl substituent at C-6.
Substitution pattern (described 2D topology): relative to the ring nitrogen as position 1, the amine is at position 2 (adjacent to N), an ethoxy group at position 5 (meta to ring N), and a methyl at position 6 (ortho to ring N). This creates a 2,5,6-trisubstituted pyridine with one exocyclic –NH2 and two alkoxy/alkyl groups that modulate electron density and sterics.
Stereochemistry: none (achiral, no stereogenic centers).
Synthetic Utility
Key reactive elements
Primary amine (exocyclic): nucleophilic at nitrogen; undergoes acylation, sulfonylation, carbamoylation, alkylation, and condensation (Schiff base formation, then reduction).
Pyridine ring nitrogen: basic/ligating site; can be selectively protonated or alkylated under controlled conditions (N-oxide formation with mCPBA affords a handle for further functionalization; literature for pyridine chemistry in general).
Ether (ethoxy) and methyl substituents: tune electronics and sterics; the ethoxy group can be transformed via O-dealkylation (e.g., BBr3/AlCl3 for aryl ethers in some systems; substrate-dependent) or oxidative pathways in late-stage diversification.
Retrosynthetic value
Serves as a node for SAR exploration at the amide/urea vector (from the –NH2). The 5-ethoxy position offers potential for subsequent O→functional group interconversions on designed derivatives, while the 6-methyl blocks ortho positions and can influence regioselectivity in further ring functionalization of advanced intermediates.
Named/typical transformations (literature)
Buchwald–Hartwig N-arylation to install biaryl-aminopyridines.
Curtius/Schmidt approaches to isocyanates followed by capture by this amine to form ureas/carbamates.
SuFEx and sulfuryl fluoride chemistry to craft sulfonamides using this amine as the nucleophile.
Reductive amination and alkylation sequences for secondary/tertiary amines.
Purification considerations
Amines often streak on silica; pre-treat silica with base or elute with basic modifiers (0.1–1% Et3N) to improve recovery. Salt formation/crystallization can be advantageous.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, enzyme, or ligand with defined biological specificity). No antigen/epitope, clone, isotype, or species reactivity information is associated with this item.
Domande frequenti
What is the purity of this product?
This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 73101-79-8, the molecular formula is C8H12N2O, and the molecular weight is 152.19 g/mol. InChIKey BATUATIMONERQY-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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