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
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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
No immunoassay or bioconjugation application data are provided for this small-molecule reagent. Typical uses are in synthetic chemistry (couplings, esterifications), coordination chemistry, and as a heteroaromatic building block.
General handling suggestions (research use; non-validated):
Stock solution preparation: dissolve at 10–100 mM in DMSO, DMF, or ethanol; filter (0.2 μm PTFE) if particulates are present.
For aqueous work: titrate with NaOH to form the sodium salt, then dilute into buffer; confirm pH and ionic strength.
Metal complex formation: adjust pH to 6.5–7.0, combine with metal salt under stirring, and characterize complexes by UV–Vis, IR (C=O shifts), and 1H NMR (paramagnetic effects may apply).
For any assay-specific protocol, validate concentration, vehicle composition, and stability independently. Refer to the SDS for safe handling during any procedure.
Biological Roles
Item is designated for research use only (from Product Data). No clinical or therapeutic claims are made.
General context (literature; not specific to this derivative):
Picolinic acid (pyridine-2-carboxylic acid) is a known chelating agent in biological systems and a metabolite in the kynurenine pathway of tryptophan catabolism. It can bind divalent cations and has been studied for roles in metal transport and coordination.
For 6-ethylpicolinic acid specifically:
This is a synthetic derivative; no established endogenous biological role is known.
The N,O-chelating motif is retained, making it of interest in bioinorganic model studies, metal sensing ligands, and as a heteroaromatic fragment for medicinal chemistry discovery programs.
Practical laboratory considerations:
For biochemical assays, solubilize in DMSO or ethanol to prepare concentrated stocks, then dilute into buffered media while monitoring final DMSO/EtOH content (<1–2% v/v preferred for many assays).
Be mindful that metal chelation can sequester essential cations in enzyme assays; include appropriate metal controls and buffering of ionic strength.
Data gaps:
No pharmacopoeial monograph or standardized biological activity metrics are known for this derivative. If biological evaluations are intended, generate full characterization and purity data, and control for solvent, pH, and metal content effects.
Buffer Applications
This compound is not a standard buffering agent. However, as a weak carboxylic acid on a pyridine scaffold, it can participate in pH-dependent equilibria and metal-binding in buffered systems.
Practical notes (general/literature):
pKa context: picolinic acid derivatives typically show carboxylic acid pKa in the ~4.5–5.8 range; thus, mixtures of the free acid and its conjugate base can provide limited buffering capacity near pH ~5. Specific pKa for 6-ethylpicolinic acid is not provided here.
Metal chelation: in MES, MOPS, or phosphate buffers at pH 6–7.4, partial deprotonation enables N,O-chelation to divalent metals. This may perturb metal-dependent assays. Use metal-free buffers or add defined metal concentrations to control speciation.
Solubility management: dissolve in minimal DMSO or adjust pH with dilute base (NaOH) to form the sodium salt for aqueous work. Back-titrate to the desired pH.
If a true buffer is required:
Prefer established systems (acetate pH 3.6–5.6, citrate pH 3.0–6.2, phosphate pH 6.0–8.0). Use this compound as an analyte or chelator rather than as the buffering species.
Item-specific buffer specifications: Not specified for this item; refer to CoA/Spec Sheet.
Green Alternatives
Greener choices relate primarily to solvent and reagent selection for transformations of 6-ethylpicolinic acid.
Solvent substitution (literature guidance):
Replace DMF/NMP with safer alternatives like 2-MeTHF, CPME, or ethyl acetate for extractions and some couplings when solubility allows.
For esterifications, use the corresponding bio-derived alcohol (EtOH) with azeotropic water removal rather than chlorinated solvents.
Aqueous or water-lean micellar media (e.g., TPGS-750-M) can support amide formation with reduced solvent burdens.
Coupling reagents and activation:
Favor EDC·HCl with catalytic HOBt alternatives (e.g., Oxyma Pure) or DMTMM in aqueous/EtOAc biphasic systems instead of uronium reagents that generate problematic waste.
Enzymatic esterification amid mild conditions is feasible for some substrates, reducing energy input and hazardous byproducts.
Comparison of common choices (general):
DMF vs 2-MeTHF: DMF offers higher solubility but has toxicity and difficult removal; 2-MeTHF is bio-based and distillable but may need warming or co-solvent for full solubilization.
DCM vs EtOAc: DCM provides rapid dissolution but is a chlorinated solvent; EtOAc is a greener drop-in for extractions and some reactions.
Operational tips:
Maximize atom economy by using catalytic activators and in-situ dehydrating agents (e.g., molecular sieves) rather than stoichiometric chlorinating agents where feasible.
Implement solvent recycling (EtOAc, 2-MeTHF) and minimize halogenated waste streams.
Pharmaceutical Uses
No pharmacopeial grade, excipient role, or GMP status is provided in the Product Data for this item. For research use only.
General, non-clinical context (literature):
Heteroaromatic carboxylic acids like 6-ethylpicolinic acid are commonly used as synthetic intermediates to generate amide/ester derivatives during medicinal chemistry lead optimization.
The N,O-chelating motif can be incorporated into metal-binding pharmacophores or coordination complexes used as research tools (e.g., imaging agents, catalysts for prodrug activation) in preclinical settings.
Formulation and handling considerations (research stage):
Salt forms: transient formation of alkali metal salts (e.g., sodium salt) can improve aqueous solubility for in vitro dosing; convert back to free acid for isolation if needed.
Vehicle selection: DMSO, PEG400, or ethanol/cremophor/water mixtures are typical for small-scale dosing solutions in discovery research—validate compatibility and stability empirically.
Analytical control: monitor purity and identity by HPLC-UV and HRMS; track potential decarboxylation or N-oxide formation during stress testing.
Regulatory note:
Absence of pharmacopoeial monographs and GMP documentation means this material should not be used in human or veterinary applications. For any scale-up or translational work, source or qualify material to appropriate standards and compile full CMC documentation.
Physical Properties
Item-specific specifications for this product are not provided in the Product Data. Refer to the CoA/Spec Sheet for definitive values relevant to this lot.
Literature/typical information (for reference; not product specification):
Physical state: crystalline solid (typical for substituted picolinic acids).
Acid/base: weak carboxylic acid; pyridine N is a weak base but generally unprotonated under neutral conditions.
Solubility (qualitative, literature):
Sparingly soluble in water at neutral pH; higher solubility in basic aqueous media due to carboxylate formation.
Readily soluble in polar organic solvents (e.g., methanol, ethanol, acetone) and in high-dipole aprotic media (e.g., DMF, DMSO).
pKa (qualitative, literature): carboxylic acid pKa in the approximate range 4.5–5.8 for picolinic acid derivatives; 6-alkyl substitution is weakly electron-donating and may slightly increase acidity pKa relative to picolinic acid. Specific value for this compound is not established here.
Partitioning (qualitative): ethyl substitution increases hydrophobicity relative to picolinic acid; expect moderate logP compared to the parent acid.
Thermal behavior: substituted pyridinecarboxylic acids typically exhibit melting in the 100–200 °C range before decomposition; exact melting point for this compound is not provided here.
Notes:
Do not use literature values as quality specifications. Verify critical parameters (e.g., melting point, water content, residual metals) on the supplied CoA for your lot.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades and analytical expectations (general):
If provided as “research grade,” typical controls include identity (1H/13C NMR), purity by HPLC/GC, and mass confirmation. For heteroaromatic acids, IR (C=O stretch) and elemental analysis are also common.
Low-residual solvent and low water content are often important for moisture-sensitive transformations (e.g., acid chloride formation); verify Karl Fischer and residual solvent data on the CoA when applicable.
Trace metal content may matter if the compound is intended for coordination chemistry studies where background metals can interfere; check ICP-MS/ICP-OES data if provided.
Stabilizers: none are typically required for pyridinecarboxylic acids; no stabilizer information is provided for this item.
Documentation and traceability:
Request the lot-specific Certificate of Analysis for measured purity, analytical methods, and spectral data.
If using in regulated workflows (e.g., reference standard preparation), document chain-of-custody and store copies of CoA and SDS with the material.
Reaction and Applications
6-Ethylpicolinic acid combines a pyridine nitrogen with an ortho-carboxyl group, enabling bidentate N,O-chelation and versatile derivatization.
Representative application areas (literature/general):
Ligand/chelator: forms neutral or anionic N,O-chelates with transition metals (e.g., Cu, Zn, Fe, rare earths). The 6-ethyl substituent modulates sterics and lipophilicity relative to picolinic acid, potentially tuning complex stability/solubility.
Ester and amide libraries: readily converted to esters (Fischer or Steglich) and amides (EDC/HOBt, HATU, or CDI protocols) for SAR exploration in heteroaromatic scaffolds.
Activation: formation of acid chlorides (SOCl2, oxalyl chloride, (COCl)2/DMF catalyst) enables coupling to hindered amines/alcohols; mixed anhydrides (pivaloyl or isobutyl chloroformate) are milder alternatives.
Directed C–H functionalization (chelation assistance): the 2-carboxyl group (as amide) can serve as a directing group for metal-catalyzed C–H activation on the pyridine ring; the 6-ethyl group provides regiocontrol/steric bias in further elaboration (literature precedent in picolinamide systems).
Decarboxylative strategies: under photoredox or silver catalysis, pyridine-2-carboxylates can undergo decarboxylative cross-coupling; substituents like 6-ethyl influence radical stability and product profiles.
N-oxidation/reduction: pyridine N-oxide formation (mCPBA) alters electronics and can be leveraged in subsequent rearrangements or as a temporary directing handle; N-oxide can be reduced back (PCl3, Zn/AcOH).
Practical tips:
Drying: for coupling, dry reagents/solvents and remove adventitious water to improve conversion.
Base choice: tertiary amines (DIPEA, TEA) minimize salt formation issues and aid in-situ activation.
Metal complexation: adjust pH near 6–7 to favor mono-deprotonated ligand state for robust N,O-chelation.
Reaction Conditions
The following conditions are general literature guidance for heteroaromatic carboxylic acids like 6-ethylpicolinic acid; verify and optimize for your system.
Conditions: 0 °C to reflux until gas evolution ceases (1–4 h). Evaporate volatiles under inert atmosphere.
N-oxidation of pyridine:
Reagent: mCPBA (1.1–1.5 equiv) in DCM or CHCl3 at 0–25 °C; 1–6 h. Quench with Na2SO3; wash thoroughly.
Metal complexation (N,O-chelate formation):
Prepare ligand as sodium salt (NaOH, pH 6.5–7.0). Mix with metal salt (e.g., Cu(II) acetate) in water/EtOH at rt to 60 °C; 0.5–4 h. Adjust pH to optimize complexation and isolate by filtration.
Photoredox: Ir/Ru photocatalyst (1–2 mol%), base (Cs2CO3), blue LEDs, MeCN or DMA, rt to 40 °C; 4–24 h, provides arylation/alkylation partners depending on conditions.
Always conduct small-scale trials and monitor by TLC/HPLC. Adjust base equivalents to manage simultaneous protonation states (acid vs pyridine N).
Safety and Handling
GHS classification and detailed hazard statements for this specific item are not provided in the Product Data. Always consult the product SDS for authoritative safety information.
General safety considerations for pyridinecarboxylic acids (informational; not item-specific):
Expected hazards: may cause skin/eye irritation; harmful if swallowed or inhaled at sufficient doses. Dust may be irritating to the respiratory tract.
PPE: wear appropriate laboratory PPE—lab coat, safety glasses or goggles, and chemical-resistant gloves (e.g., nitrile). Use a dust mask or work in a fume hood to avoid dust exposure.
Handling: avoid creating and breathing dust. Use in a well-ventilated area or fume hood. Prevent contact with eyes and skin. Wash hands thoroughly after handling.
Incompatibilities: strong oxidizers and strong bases/acids (may lead to salt formation or decomposition under extreme conditions). Forms salts with bases; neutralization liberates heat.
First aid (overview):
Skin/eye contact: rinse with copious water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: move to fresh air; seek medical advice if symptoms develop.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: organic solid; combustible. Use water spray, dry chemical, CO2, or foam. Combustion may produce NOx and COx.
Environmental: avoid release to the environment. Collect spillage to prevent entry into waterways.
Storage and transport (from Product Data):
Storage conditions: room temperature.
Shipped in: normal conditions.
For research use only (from Product Data).
Solvent Selection
As a heteroaromatic carboxylic acid, 6-ethylpicolinic acid exhibits mixed polarity: an aromatic pyridine ring with an acid group capable of hydrogen bonding and ionization.
General solvent behavior (literature/typical; not item-specific):
Water: limited solubility at neutral pH; solubility increases markedly in basic aqueous solutions (carboxylate formation).
Protic organics: methanol, ethanol, isopropanol typically dissolve the neutral acid well, especially on warming.
Aprotic polar: DMSO, DMF, NMP offer high solubility and are preferred for coupling reactions or when high concentrations are needed.
Less polar: acetone and acetonitrile often provide moderate solubility; ethyl acetate varies. Hydrocarbons (hexanes, toluene) generally poor unless converted to esters or salts.
When to choose specific solvents:
Spectroscopic work or stock solutions: DMSO for high concentration; methanol/ethanol for routine handling and precipitation control.
Esterification (Fischer): use anhydrous ROH (e.g., MeOH/EtOH) with acid catalysis; remove water to drive equilibrium.
Amide coupling: DMF, DCM, or MeCN with carbodiimides or uronium reagents; add base (DIPEA) carefully to control carboxylate formation.
Metal complexation studies: water/alcohol mixtures or buffered aqueous media at pH 6–8 to balance solubility and ligand deprotonation.
Comparison (typical):
DMSO vs DMF: DMSO gives higher solubility; DMF offers easier removal. Choose per downstream needs.
Storage and Reconstitution
Storage conditions (from Product Data): Room temperature. Store tightly closed, in a dry place, and protect from excessive humidity.
Shipped in (from Product Data): Normal conditions.
Research Use Note: For research use only.
Reconstitution and solution handling (general guidance; not item-specific):
Solubility: dissolve in polar organics (DMSO, DMF, methanol, ethanol). For aqueous solutions, prepare the sodium or potassium salt by neutralization with dilute base.
Stock solutions: prepare 10–100 mM in DMSO or ethanol; aliquot to minimize freeze–thaw if storing below ambient.
Stability: aromatic carboxylic acids are generally stable at ambient conditions; avoid prolonged exposure to strong light/oxidants to minimize unintended N-oxide formation.
Storage of solutions: store organic solutions at 2–8 °C in amber vials when possible; bring to room temperature before use and check for precipitation or degradation by HPLC.
Item-specific specifications (water content, residual solvents, assay): Not specified for this item; refer to CoA/Spec Sheet.
Disposal: follow local regulations for organic acids and heteroaromatics; segregate halogenated and non-halogenated solvent waste.
Structure and Identity
6-Ethylpicolinic acid is a pyridine-2-carboxylic acid bearing an ethyl substituent at the 6-position of the pyridine ring, giving a bidentate donor set (pyridine N and carboxylate O) for metal coordination.
Item-specific identifiers (from Product Data):
SKU: E193287
Product name: 6-Ethylpicolinic acid
CAS: 4080-48-2
CID: 11360564
InChIKey: 279541 (as provided; truncated—refer to CoA/Spec Sheet for full identifier)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and features (for reference; not specification):
Core structural motifs: substituted pyridine (heteroaromatic ring), carboxylic acid (–CO2H) at the 2-position, ethyl at the 6-position; no stereocenters.
2D structural description (general):
A six-membered aromatic ring containing one ring nitrogen (pyridine). The carboxylic acid is ortho to the ring nitrogen (picolinic acid skeleton), and an ethyl group is located at the position para to the carboxyl group and ortho to the ring nitrogen (ring position 6), introducing modest lipophilicity while retaining the chelating N,O motif.
Synthetic Utility
Functional handles and their reactivity (literature/general):
Carboxylic acid (–CO2H):
Coupling to amines via EDC/HOBt alternatives (e.g., Oxyma) or HATU to give amides.
Esterification (Fischer, Steglich using DCC/DMAP) to access diverse esters.
Conversion to acid chloride (SOCl2, (COCl)2/DMF cat.) for subsequent acylations.
Curtius or Schmidt rearrangements via acyl azide formation to access amines or carbamates.
Pyridine nitrogen:
N-oxidation (mCPBA) for electronic activation, enabling ipso-substitution or directed C–H functionalization; reducible back to pyridine.
Quaternization (e.g., MeI) to form pyridinium salts for phase-transfer or as reactive intermediates.
Aromatic core:
Electrophilic substitution is deactivated by the ring N; functionalization often proceeds via metal-catalyzed C–H activation using the amide of the 2-carboxyl group as a directing group.
Radical and cross-coupling manifolds (after halogenation) enable diversification around the ring; the 6-ethyl group imposes steric bias and can serve as a blocking group.
Retrosynthetic value:
Serves as a convergent node: install the 6-ethyl group early (via alkylated pyridine routes) and diversify the acid into amides/esters late-stage.
The N,O-chelating topology provides access to stable metal complexes useful as catalysts or precursors for further ligand elaboration.
Practical notes:
Control water content for coupling steps; use molecular sieves or azeotropic drying.
For acid chloride formation, remove excess thionyl chloride thoroughly to avoid downstream side reactions.
Target Specificity
Not applicable. This product is a small-molecule heteroaromatic acid, not an antibody, protein, or nucleic acid. No antigen/epitope, species reactivity, clone, or isotype data apply.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
