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
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. No biology assay protocols (e.g., WB, IHC, IF, FC) are defined for this small-molecule building block.
General laboratory usage notes
Weighing/dispensing: Minimize exposure to ambient moisture; cap immediately after use.
Solution preparation: Prepare stock solutions in dry organic solvents (e.g., DCM, MeCN, DMF, DMSO) as needed for reactions; filter if particulates are present.
Analytical control: Monitor reactions by TLC (with base additive for amine-containing compounds), HPLC, or LC–MS. Record 1H/13C NMR and HRMS for identity/purity confirmation.
Workup: For amine-containing products, consider acid–base liquid–liquid extractions to manipulate partitioning and improve recovery.
Biological Roles
Item-specific biological/biochemical roles: Not applicable. No biological function data are specified for this catalog reagent; it is supplied for research use as a synthetic building block.
General context (literature; not product-specific)
Pyridine derivatives are common motifs in bioactive small molecules due to their tunable basicity and capacity for hydrogen bonding and cation–π interactions with protein targets.
Amino-substituted pyridines often serve as privileged fragments in medicinal chemistry libraries, participating as H-bond donors/acceptors and improving water solubility through salt formation.
Carboxylate esters function as pro-moieties or synthetic handles; in a research context, the ester in Ethyl 5-aminopicolinate allows rapid interconversion to amides/acids for SAR exploration.
Metabolism considerations (general): Esters are susceptible to hydrolysis by esterases; aryl amines can undergo N-acetylation or oxidative metabolism. These are general biochemical tendencies used by chemists to anticipate stability in assays; they are not claims of in vivo performance.
Use limitation
For research use only. Not intended for human or animal diagnostic, therapeutic, or clinical applications.
Buffer Applications
Not typically applicable. Ethyl 5-aminopicolinate is a neutral organic building block (amine + ester) rather than a dedicated buffering agent.
Practical notes
If used in aqueous assays, solubility and pH behavior can be adjusted by forming an acid addition salt (e.g., HCl salt) to improve water compatibility.
For pH control, select established buffer systems appropriate to your assay (e.g., phosphate, acetate, HEPES, MOPS); this compound itself is not recommended as a primary buffering component.
Green Alternatives
Strategic choices can improve the sustainability of transformations involving Ethyl 5-aminopicolinate while maintaining performance.
Solvent substitutions (general guidance)
Replace chlorinated solvents
Use 2-MeTHF or CPME instead of DCM/THF for amine acylations and protections; these ethers provide comparable solvation, broader aqueous tolerance, and are derived from renewable feedstocks (2-MeTHF).
For extractions and crystallizations, EtOAc and MTBE are greener alternatives to DCM/chloroform.
Polar aprotic alternatives
Prefer acetonitrile or propylene carbonate over DMF/DMAc when reaction scope permits; they offer lower toxicity or improved environmental profiles and easier removal (MeCN).
Alcohols as media
Perform transesterifications and some reductive alkylations in EtOH or i-PrOH to reduce solvent impact and facilitate workup.
Reagent choices
Couplings: Employ catalytic couplings (e.g., enzyme-catalyzed amidations where compatible) or use more benign carbodiimides with green solvents; minimize stoichiometric additives.
Bases: Use carbonate bases (K2CO3, Cs2CO3) in greener ethers rather than strong alkoxides in DMF when feasible.
Comparison snapshot (literature/guidance)
DCM vs 2-MeTHF: similar performance in acylations; 2-MeTHF is less toxic, partially renewable, forms fewer emulsions; boiling point higher (workup requires concentration under reduced pressure).
DMF vs MeCN: DMF dissolves more but is harder to remove and has higher toxicological concerns; MeCN is volatile, easier to recover but less polar.
Operational tips
Employ solvent recycling (MeCN, EtOAc) where possible.
Choose room-temperature processes and catalytic methods to reduce energy and waste.
Pharmaceutical Uses
Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.
General context (no therapeutic claims)
Role in discovery: Ethyl 5-aminopicolinate serves as a versatile intermediate in medicinal chemistry campaigns. The 5-amino group permits rapid N-acyl/sulfonyl diversification, and the 2-ester provides a handle to access acids and amides, enabling matched-pair synthesis for SAR.
Salt formation: The basic sites (pyridine N and aniline-like –NH2) allow formation of acid addition salts (e.g., HCl, HBr, methanesulfonate) to modulate solubility for formulation studies during early research.
Prodrug strategy (conceptual): The ethyl ester can be used as a pro-moiety in model systems to study hydrolytic lability; however, this product is supplied strictly for research use and not for clinical application.
Process considerations: When advancing hits, impurities such as regioisomers or hydrolysis products should be controlled; scalable crystallization from EtOAc/EtOH or salt formation may provide purification leverage.
Compliance reminder
For research use only. Not intended for use in humans or animals.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight (item spec): Not specified for this item; refer to CoA/Spec Sheet.
Other specifications (bp, mp, density, solubility, refractive index, UV cutoff, water content, metal limits): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations (for context only; not item specifications)
Physical state: Small heteroaromatic amino esters are often low-melting solids or high-boiling oils; actual state can vary with purity and solvate content.
Solubility profile: Typically soluble in polar organic solvents (e.g., DCM, EtOAc, MeOH, acetonitrile, DMF, DMSO); limited solubility expected in nonpolar hydrocarbons (hexanes, heptane). Protonation of the ring N or amino group increases aqueous solubility under acidic conditions.
Acid-base behavior: Contains two basic sites (pyridine N and aniline-like –NH2). Protonation equilibria are solvent- and temperature-dependent.
Practical notes for use (general)
Hygroscopicity: Primary aminopyridines can exhibit modest hygroscopicity; protect from ambient moisture when weighing to preserve accurate stoichiometry.
Volatility: Esters of this size are generally low-volatility; routine benchtop handling is typically acceptable with standard ventilation.
Spectroscopic IDs: 1H NMR typically shows ethyl quartet/triplet for –COOCH2CH3, downfield aromatic protons (including near the ring N), and an exchangeable –NH2; IR displays strong C=O stretch of the ester (~1720–1740 cm−1, literature) and N–H stretches (~3300–3500 cm−1, literature).
Quality and Grades
Item-specific information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on quality for this compound class
Analytical grade vs. synthesis grade: For route scouting and SAR work, higher assay and lower residual solvents/metals can reduce analytical background and improve reproducibility. Aminopyridine esters can show tailing in LC if amine is unprotonated; for chromatography, materials curated for low UV background and minimal acidic/basic impurities (e.g., HPLC grade reagents and buffers) are beneficial.
Amine handling: Free-base amines may have variable assay if partially protonated; CoA should specify assay basis (free base vs. salt, water content). Verify titratable amine content when precise stoichiometry is critical.
Impurity profiles: Typical process-related impurities include regioisomers of aminopicolinate, unreacted picolinates, over-acylated amines, and hydrolysis products (5-aminopicolinic acid). For sensitive applications, review chromatographic purity and residual solvent data on the CoA.
Stabilization considerations: Primary amines can slowly react with atmospheric CO2 to form carbamates on surfaces; storing tightly closed in a dry environment minimizes drift in assay and pH behavior.
Documentation
For definitive specifications (assay, water, metals, residual solvents, optical data), consult the lot-specific CoA/Spec Sheet and SDS.
Reaction and Applications
This bifunctional scaffold is valuable in heterocycle and medicinal chemistry, enabling orthogonal manipulation of the amine and ester.
Representative applications (literature/general)
Amine derivatization
Protection: Boc, Cbz, Fmoc protection under standard conditions (Boc2O or CbzCl, base; Fmoc-Cl, base) to enable selective ester chemistry.
Acylation/sulfonylation: Formation of amides or sulfonamides (e.g., with acid chlorides, anhydrides, sulfonyl chlorides) to modulate electronics at the 5-position.
Reductive alkylation: Condensation with aldehydes/ketones followed by reduction (NaBH3CN, H2/Pd) to give N-alkyl derivatives.
Ester transformations
Hydrolysis: Conversion to 5-aminopicolinic acid under basic (NaOH, KOH) or acidic (HCl) conditions. Selectivity can be tuned via protection of the amine.
Transesterification: Acid- or base-catalyzed exchange to install alternative alcohol moieties.
Aminolysis: Direct conversion to amides using ammonia or amines, often accelerated by activating agents (e.g., HOBt/EDC, HATU after in situ carboxylate activation via partial hydrolysis).
Cross-coupling and aromatic functionalization
The 5-amino group can be converted to diazonium-like intermediates less readily than anilines due to the pyridine ring, but N-oxidation (pyridine N-oxide) strategies or directed metalation (e.g., at C-6) enable further C–C bond formation (lithiation/halogenation, then Suzuki/Negishi). Protecting the amine is often necessary to avoid catalyst inhibition.
Coordination chemistry
The pyridine nitrogen and amide/ester derivatives can coordinate metals, enabling ligand exploration.
Practical tips
Protect the amine during ester hydrolysis to suppress salt formation/emulsion.
For coupling, pre-form the acid (saponify) then use HATU/EDC; free amine can induce O→N acyl transfer or intramolecular side-reactions if not protected.
Reaction Conditions
General literature guidance (not item-specific; optimize per substrate/catalyst)
Amine protection (Boc):
Solvent: DCM, 2-MeTHF, or MeCN.
Reagents: Boc2O (1.1–1.5 equiv), base (Et3N or DIPEA, 2–3 equiv).
Temperature/time: 0 °C to rt, 1–4 h.
Notes: Monitor by TLC/LC-MS; minimize water to limit ester hydrolysis.
Amide formation via saponification then coupling:
Step 1 (hydrolysis): MeOH/H2O or THF/H2O with NaOH (1–2 M), 0–25 °C, 1–3 h to give 5-aminopicolinic acid (acidify to pH ~2–3 to isolate, literature).
Step 2 (coupling): DMF or MeCN; HATU or EDC·HCl (1.1–1.2 equiv), HOAt/HOBt or Oxyma, base (DIPEA, 2–4 equiv), 0–25 °C, 1–12 h.
Notes: Protect amine if coupling at C-2 is required without N-acylation side products.
Direct aminolysis/transesterification:
Solvent: Neat amine or i-PrOH/EtOH; catalytic base (NaOMe, Ti(OiPr)4) or heat (60–100 °C).
Notes: Competitive N- vs O-acylation can occur; employ catalysts or stepwise activation to control.
Reductive amination on the 5-amino group:
Solvent: MeOH, EtOH, or MeCN.
Reagents: Aldehyde/ketone (1.1–1.5 equiv), NaBH3CN or NaBH(OAc)3; AcOH as needed.
Catalysts: Pd or Ni systems matched to the installed leaving group; temperatures 60–120 °C.
Notes: Free amine can poison catalysts—protect or convert to an amide/carbamate first.
These conditions are representative literature starting points; fine-tune equivalents, temperature, and time based on scale, substrate, and analytical monitoring.
Safety and Handling
Item-specific hazard data
GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to the SDS.
General laboratory safety guidance (literature/typical for amino esters and aminopyridines)
Likely hazards: May cause irritation to skin, eyes, and respiratory tract. Aminopyridines can be harmful if swallowed or absorbed; avoid ingestion and prolonged exposure.
PPE: Use lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of vapors, mists, or dust.
Incompatibilities: Strong oxidizers (risk of exothermic reactions), strong acids/bases (hydrolysis or salt formation), acyl/alkylating agents (unintended derivatization of the amine). Avoid isocyanates and acid chlorides unless derivatization is intended.
Peroxide formation: Not applicable (no ether functionality); however, general good practice is to check stabilizers/impurities before distillation if applicable.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Spill/cleanup: Absorb with inert material, collect in appropriate container. Prevent entry into drains. Decontaminate surfaces with compatible solvent/detergent.
Fire: Use CO2, dry chemical, or foam. Combustion may produce NOx and CO/CO2; firefighters should wear SCBA.
Solvent Selection
Applicability: Ethyl 5-aminopicolinate is a polar, bifunctional heteroaromatic (amine + ester). Solvent choice strongly influences reactivity (protection, coupling, hydrolysis) and workup.
General solvent behavior (literature expectations)
Polarity/miscibility: Readily soluble in polar organics (DMSO, DMF, NMP, MeOH, EtOH, acetonitrile, DCM, EtOAc). Limited solubility expected in aliphatic hydrocarbons.
Acid–base effects: In protic/acidic media (MeOH/HCl, EtOH/HCl), forms salts that increase aqueous miscibility; in basic media the free base predominates, enhancing solubility in organic phases during extractions.
When to choose which solvent (use-case oriented)
Protection and acylation of the amine: DCM, THF, 2-MeTHF, or acetonitrile with organic bases (DIPEA, Et3N). For greener choices, 2-MeTHF or CPME can often replace DCM/THF.
Amide couplings from the ester (transesterification then coupling or direct aminolysis): Alcoholic solvents (MeOH, EtOH, i-PrOH) for alcoholysis; polar aprotic (DMF, DCM, MeCN) for aminolysis/couplings using activators.
Hydrolysis to the acid: Aqueous THF, dioxane, MeOH, or EtOH with NaOH/KOH (basic) or HCl (acidic) depending on selectivity; biphasic EtOAc/aqueous systems facilitate extractions.
Metal-catalyzed transformations on the aryl amine: Toluene, 1,4-dioxane, CPME, or DMAc/DMF depending on the catalyst/ligand system.
Small comparison (general)
DCM: excellent for acylations; volatile; not green.
2-MeTHF/CPME: greener ethers, tolerate water better than THF.
DMF/DMSO: high solvency for polar substrates; challenging removal; consider MeCN when feasible.
EtOAc/EtOH: greener workup and recrystallization media.
Container: Store tightly closed in a dry, inert atmosphere (use desiccant if available). Primary amines can absorb CO2 and moisture; limit headspace exposure.
Light/air: Protect from prolonged exposure to air and strong light to minimize oxidative discoloration or hydrolysis of the ester over extended periods.
Stock solutions: For reaction setup, prepare solutions in dry solvents (e.g., DCM, MeCN, THF, 2-MeTHF, DMF, DMSO). Use freshly prepared solutions when possible; for short-term storage, keep sealed under inert gas at 2–8 °C to reduce hydrolysis risk.
Freeze–thaw: Not generally required for neat solid/liquid. If storing solutions, avoid repeated freeze–thaw; aliquot into single-use vials.
Stability checks: Prior to critical use, verify integrity by NMR/LC–MS if the material has been stored for prolonged periods.
Reconstitution
Not applicable to this neat chemical. If received as a solid, dissolve directly in the chosen anhydrous solvent to the desired concentration. If a salt form is prepared in-house for solubility, document counterion and concentration for reproducibility.
Structure and Identity
Item-specific (from Product Data)
SKU: E190019
Product name: Ethyl 5-aminopicolinate
CAS: 119830-47-6
PubChem CID: 13816714
InChIKey: 166126
SMILES: 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.
Core scaffold: a pyridine ring bearing an ethyl picolinate ester at the 2-position (pyridine-2-carboxylate ethyl ester) and an amino substituent at the 5-position.
Functional groups: heteroaromatic pyridine nitrogen (Lewis basic), primary aniline-like amino group (nucleophilic, acylation-prone), and an ethyl ester (electrophilic carbonyl, hydrolyzable/transesterifiable).
Regiochemistry: 2-carboxylate (as ethyl ester) and 5-amino substitution pattern on pyridine (2,5-disubstituted pyridine).
2D structure in words: a six-membered aromatic ring with one ring nitrogen (pyridine); clockwise numbering places the ring N at position 1, an ethyl ester substituent at C-2 (adjacent to ring N), hydrogens at C-3 and C-4, a primary –NH2 at C-5, and hydrogen at C-6.
Stereochemistry: none (achiral as drawn).
Notes
Ethyl 5-aminopicolinate is a useful bifunctional building block: the ester enables carboxylate chemistry while the 5-amino group enables N-functionalization or protection.
Synthetic Utility
Key reactivity handles
Primary amine (5-position): readily protected (Boc, Cbz, Fmoc), acylated, sulfonylated, or reductively alkylated. Can serve as a nucleophile in urea/carbamate formation.
Ethyl ester (2-position): hydrolyzable to the carboxylic acid; amenable to transesterification, aminolysis, and activation to acid chloride or mixed anhydride for couplings.
Pyridine nitrogen: coordinates metals, modulates electronics, and can be oxidized to the N-oxide to alter directing effects for further functionalization.
Strategic value in synthesis
Orthogonal chemistry: Protect the amine to enable selective manipulation of the ester (e.g., saponification/coupling). Alternatively, mask the acid (retain ester) while diversifying the amine to generate focused libraries.
Directed metalation/functionalization: After appropriate protecting groups are installed, directed lithiation or halogenation at C-6 may be feasible, enabling cross-coupling (Suzuki, Negishi, Stille) to elaborate the ring.
Fragment growth: The scaffold acts as a heteroaromatic core into which polarity and H-bonding can be dialed via N-acylation/sulfonylation and amide formation at C-2.
Typical transformations (literature)
Saponification → HATU/EDC coupling to give 5-amino-2-pyridyl amides.
Carbamate formation (e.g., Boc, Cbz) to tune pKa and improve handling during metal-catalyzed steps.
Reductive amination on the 5-amino group to access N-alkyl analogs with minimal step count.
Purification/workup tips
Free amine can cause tailing on silica; use 1–2% Et3N or NH3 in eluent, or run as its HCl salt and neutralize post-purification.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
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