This compound belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl 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 to this product type.
No tested bioassay applications (e.g., WB, IHC, IF, FC) or recommended dilutions are provided for this chemical building block. Use is case-specific to synthetic or analytical procedures designed by the researcher.
Biological Roles
Item-specific biological data
None provided. This product is supplied for research use only and is not intended for use in humans or animals.
General context (literature)
Pyridine is a core motif in numerous biomolecules and cofactors (e.g., the nicotinamide moiety in NAD+/NADP+), but 5-methoxy-2-methylpyridine itself is not known as a natural metabolite.
Heteroaromatic amines like pyridines can engage in hydrogen bonding and cation–π interactions when protonated, which is why pyridine-containing fragments are widely used in chemical biology and medicinal chemistry discovery to probe binding pockets.
Methoxy substitution modulates electronic properties (donating by resonance, withdrawing by induction on a pyridine ring) and lipophilicity, which can influence permeability and target engagement of derivatives built from this scaffold.
Practical notes for biological research (non-clinical)
When used as a fragment or intermediate for probe synthesis, confirm purity and residual solvent content to avoid confounding assay results.
Protonation state depends on assay pH; the compound will be largely protonated under acidic conditions (enhanced aqueous solubility) and neutral-to-unprotonated near neutral/basic pH, affecting membrane permeability and target binding of downstream constructs.
Compliance
Observe institutional guidelines for handling small-molecule research chemicals; dispose of waste via approved chemical waste streams.
Buffer Applications
Applicability
This compound is a neutral organic building block (weak base) and is not a standard buffering agent.
Guidance
It is not typically used to prepare biological or analytical buffers. If present in buffered systems (e.g., as a component of a reaction mixture), account for potential base protonation near pH ~5–6 (literature pKaH range for related pyridines), which can slightly impact pH in poorly buffered, small-volume systems.
For true buffering needs, choose dedicated buffers (e.g., phosphate, acetate, Tris, HEPES) with appropriate pKa and ionic strength.
Green Alternatives
Context
This item is a fine-chemical building block rather than a process solvent. Greener choices focus on solvents/reagents used with it and synthetic routes to access downstream targets.
Greener solvent choices (general)
Replace chlorinated solvents with 2-MeTHF, CPME, EtOAc, MeCN, or toluene where catalysis/solubility allow.
For metalations, consider 2-MeTHF or CPME in place of THF/diethyl ether to reduce peroxide risk and improve safety; both have better sustainability profiles and higher boiling points.
Reagent substitutions
Demethylation: use BCl3 with scavengers or catalytic methods (e.g., AlCl3/thiols) when compatible, to lower bromine waste versus BBr3; explore iodide-promoted demethylations under milder conditions if selectivity allows.
Oxidations: adopt H2O2 or O2 with appropriate catalysts (e.g., Pd, Cu, nitroxyl-mediated) instead of stoichiometric Cr(VI)/Mn(VII) reagents for benzylic or N-oxidations.
Route design
Leverage N-oxide–mediated C–H functionalization to avoid pre-halogenation steps (step and waste reduction).
Employ micellar catalysis (aqueous surfactant media) for cross-couplings of halogenated derivatives to reduce organic solvent use.
Trade-offs
Greener solvents may alter selectivity/solubility and require re-optimization of catalyst/ligand systems. Some “green” reagents (e.g., H2O2) demand rigorous control to prevent over-oxidation of the heteroaromatic ring.
Documentation
Always document solvent selection and waste minimization in your ELN; validate that any change maintains impurity profiles and yield at scale.
Pharmaceutical Uses
Item-specific status
No pharmacopeial grade or excipient designation is provided for this item. Grade/purity and regulatory status: Not specified for this item; refer to CoA/Spec Sheet.
General, non-clinical context
5-Methoxy-2-methylpyridine is a heteroaromatic fragment used in medicinal chemistry research as a building block to access libraries of drug-like molecules. It may be incorporated into APIs during discovery/early development via N-alkylation, cross-coupling (after halogenation), benzylic oxidation, or ether diversification.
It is not used as an excipient to our knowledge and is provided strictly for research and process development use. Any consideration for GMP manufacture would require full vendor qualification, impurity profiling, and compliance with relevant quality standards.
Formulation/process notes (non-therapeutic)
When used as a starting material or intermediate, control residual levels in downstream intermediates per ICH Q3A/Q3B impurity guidance. Analytical methods often include GC for residual solvents and HPLC/UPLC with UV detection for assay and related substances.
Salt formation (pyridinium salts) can be leveraged transiently to enhance crystallinity or modify solubility during purification; ensure complete neutralization and removal of counterions as required.
Physical Properties
Item-specific specifications
Boiling point, melting point, density, refractive index, water/peroxide/metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties (for context only; not product specifications)
Physical state: typically a colorless to pale yellow liquid for lower-alkyl/methoxy pyridines of similar substitution.
Basicity: pyridine ring nitrogen is weakly basic; conjugate-acid pKaH for closely related 2-alkyl/methoxypyridines is commonly in the ~5.5–6.5 range (literature, trend-based).
Solubility: expected to be miscible with many polar organic solvents (e.g., alcohols, ethers, chlorinated solvents) and moderately soluble in water due to the heteroaromatic nitrogen and ether oxygen (literature expectation for methoxypyridines).
Volatility: medium; vapor pressure appreciable at room temperature compared with higher-boiling aromatics but lower than small amines (literature trend for C7 pyridines).
Partitioning: logP for analogous methyl/methoxypyridines is typically in the ~1–2 range (literature trend), reflecting moderate polarity.
Practical notes
If precise properties (bp, density, RI) are required for method development or scale-up, obtain the exact values from the CoA/SDS for this catalog item. Do not use literature values as specifications.
Quality & Grades
Item-specific quality information
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance)
Research-grade organics: suitable for most synthetic and method-development work; impurities and UV absorbance are controlled to levels typical for R&D.
“Analytical” or “HPLC” grades (when offered): emphasize low non-volatile residue and low UV background for detection-sensitive techniques.
“Anhydrous” grades (when offered): packaged to limit moisture and stabilized if necessary; verify water content by KF where critical.
Considerations for 5-methoxy-2-methylpyridine
Trace amine/ether impurities, residual solvents, and water can influence base-sensitive reactions, N-alkylations, and metalations. If your application is moisture- or acid-sensitive, verify Karl Fischer water and acidity/basicity indices on the CoA.
UV profile: methoxy-substituted pyridines absorb in the UV; for photometric methods or UV detection, consult spectral data or choose an appropriate blank/solvent.
Stabilizers: None are stated for this item. If a stabilizer is present in a specific lot, it will be declared on the CoA/label because stabilizers can interfere in catalysis and lithiation chemistry.
Documentation
For final purity, assay basis, residual solvents, and other certificate elements, use the lot-specific CoA/Spec Sheet.
Reaction & Applications
Scope (general, literature-based; expand/adapt to your route)
N-functionalization: the pyridine nitrogen undergoes quaternization (alkylation) to pyridinium salts and acylation to N-acylpyridinium intermediates. These can activate adjacent positions for further transformations.
N-oxidation: oxidation to the N-oxide (e.g., mCPBA) increases ring activation toward nucleophilic substitution; subsequent Polonovski-type or Boekelheide rearrangements enable functionalization at benzylic/α-positions.
Demethylation of the methoxy: Lewis acids (BBr3, BCl3) or strong nucleophiles (thiolate, iodide under forcing) can convert the aryl methyl ether to the corresponding 5-hydroxypyridine derivative, opening access to ether diversification via Mitsunobu or alkylation.
Directed metalation: the ring nitrogen coordinates to alkyllithium/bases to enable regioselective deprotonation (often C6 or C3, depending on conditions). Employ LiTMP, LDA, or turbo bases in ethereal solvents at −78 to −20 °C, then trap with electrophiles (CO2, aldehydes, halides).
Cross-coupling (via derivatives): halogenation of the ring (N-oxide-assisted or via electrophilic routes) allows Suzuki, Negishi, or Buchwald–Hartwig couplings to build libraries of substituted pyridines.
Hydrogenation/reduction: selective hydrogenation of the ring (under high pressure and suitable catalysts) can afford piperidine analogs; careful control is required to avoid ether cleavage.
Oxidation at the methyl: benzylic oxidation (e.g., SeO2, TEMPO systems, or metal-catalyzed aerobic methods) can access the corresponding aldehyde or acid at C2.
Use areas (non-clinical)
Employed as a heteroaromatic building block for agrochemical, materials, and medicinal chemistry discovery programs where dual electron-donating (OMe) and basic (pyridine N) features are desirable.
Reaction Conditions
General conditions (literature guidance; adjust to your system)
N-oxidation: mCPBA (1.1–1.5 equiv) in DCM or CHCl3 at 0–25 °C, 1–4 h, giving N-oxides typically in good yields. Monitor for over-oxidation.
Directed metalation: LiTMP or LDA (1.2–1.5 equiv) in dry THF or 2-MeTHF at −78 to −40 °C, 0.5–2 h; trap with electrophiles (e.g., CO2, RX, aldehydes). Zincate or magnesiate bases can improve functional group tolerance.
Demethylation: BBr3 (1–3 equiv) in DCM at −78 to 0 °C, then warm to rt, 1–16 h; quench with MeOH/H2O to give 5-hydroxypyridine derivatives. BCl3 is milder but may require longer times.
Halogenation (via N-oxide): POCl3 or SOCl2 systems at 0–80 °C can install chloro substituents regioselectively; follow with cross-coupling in toluene/1,4-dioxane/MeTHF using Pd catalysts (e.g., XPhos/SPhos systems) at 60–110 °C.
Benzylic oxidation: TEMPO/bleach (NaOCl) biphasic systems or MnO2 under solvent like DCM/EtOAc can oxidize the 2-methyl to the corresponding aldehyde; alternative methods include Ru- or Cu-catalyzed aerobic oxidations.
Solvents and atmosphere
Dry, oxygen-free conditions (argon/nitrogen) recommended for strong-base and metal-catalyzed steps. Protic solvents/proton sources should be excluded until quench.
Yields
Typical yields for these transformations in the literature range from 60–90% depending on substitution and conditions; optimization of base, temperature, ligand, and solvent is often decisive.
Safety
Manage exotherms when adding strong Lewis acids (BBr3) or peracids; ensure appropriate quench protocols and temperature control.
Safety & Handling
Item-specific hazard data
GHS classification, signal word, hazard statements, pictograms: Not specified for this item; refer to the SDS for authoritative safety information.
General safety information for pyridine derivatives (literature/analog-based; not product-specific)
Likely hazards: may cause skin/eye irritation; vapors can be irritating to the respiratory tract. Many pyridines have noticeable odor and can be harmful if swallowed or inhaled.
Peroxide formation: aromatic ethers can slowly form peroxides upon prolonged air/light exposure, especially after opening; test and manage peroxides as appropriate when concentrating old samples.
Incompatibilities: strong oxidizers (risk of exotherm), strong acids (forms pyridinium salts; potential heat evolution), alkali metals/strong bases for neat material (risk of side reactions), and acyl halides (reactive at the pyridine nitrogen).
Fire safety: combustible liquid; use CO2, dry chemical, or foam. Avoid ignition sources; ensure adequate ventilation.
PPE and handling practices
Wear safety glasses, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to control vapors/odors.
First aid (overview): rinse skin/eyes with water for several minutes; remove contaminated clothing; move person to fresh air if inhaled; seek medical attention as needed. Refer to SDS for detailed instructions.
Storage
Follow item-specific guidance: Room temperature (per Product Data). Keep tightly closed in a dry, well-ventilated place away from strong oxidizers and acids.
Solvent Selection
Applicability
This product is a heteroaromatic building block, not generally used as a bulk solvent. The section below discusses choosing solvents for reactions/workups involving this compound.
Polarity and miscibility (literature/general)
Polarity: moderate (heteroaromatic with ether). Expected to dissolve well in polar aprotic solvents (DMF, DMSO, MeCN), ethers (THF, 2-MeTHF, MTBE), esters (EtOAc), and chlorinated solvents (DCM, chloroform). Moderate aqueous solubility is typical for methoxypyridines.
Acid–base behavior: the pyridine nitrogen can be protonated; protonation strongly increases aqueous solubility and can aid extractions (acid–base partitioning).
Selection guidance by use-case
N-alkylation/acylation: use dry polar aprotic solvents (MeCN, DMF, DCM) with a suitable base; exclude moisture to minimize side reactions.
Directed metalation/ortholithiation: ethereal solvents (THF, 2-MeTHF, CPME) at low temperature improve control; consider mixed solvent systems for solubility.
SNAr on N-oxides or cross-couplings of halogenated analogs derived from this substrate: toluene/1,4-dioxane/MeTHF with Pd or Ni catalysts are common choices.
Workup/extraction: leverage protonation with dilute HCl to move the amine into the aqueous phase; basify to back-extract into organic solvent.
Small comparison (general)
THF vs 2-MeTHF: 2-MeTHF offers greener profile and higher boiling point, benefiting low-temperature metalations and extractions; THF often provides higher solubility but forms peroxides more readily.
Storage & Reconstitution
Item-specific storage and shipping
Storage conditions: Room temperature (per Product Data). Protect from moisture and strong oxidizers. Keep container tightly closed in a cool, well-ventilated area.
Shipped in: Normal (per Product Data).
General guidance (literature/best practice)
If long-term storage is anticipated after opening, consider blanketing the headspace with inert gas and storing in amber glass to minimize light/air exposure. Periodically check for discoloration or precipitate formation.
If the material partially solidifies/crystallizes at low ambient temperatures, gently warm to room temperature and mix thoroughly before use.
Reconstitution: Not applicable; this item is supplied neat. For solution preparation, use dry, oxygen-free solvents where moisture-sensitive chemistry is intended, and record concentrations and solvent identity on secondary labels.
Documentation and stability
For definitive shelf-life, impurity limits, and any stabilizers/additives, refer to the lot-specific CoA/SDS. Re-test or re-qualify material before use in critical applications if stored for extended periods.
Structure & Identity
Item-specific facts (from Product Data)
SKU: M185173
Product name: 5-Methoxy-2-methylpyridine
CAS: 55270-47-8
InChIKey: 206042 (as provided)
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.
Literature/computed identifiers and structural description (for reference only)
Structural features: a six-membered aromatic pyridine ring (one ring nitrogen) bearing a methyl substituent at C2 (adjacent to N) and a methoxy substituent at C5 (meta to N relative to position 2). Functional groups include a heteroaromatic tertiary amine (pyridine) and an aryl methyl ether (–OCH3).
2D description in words: Start from the ring nitrogen (position 1). At position 2 is a –CH3 group; positions 3 and 4 are unsubstituted carbons; position 5 carries a –OCH3 substituent; position 6 is unsubstituted. The –OCH3 is para to C3 and meta to the ring nitrogen.
Notes
The identifiers and structure description under “Literature/computed” are provided for general chemical context only. Please consult the item’s CoA/Spec Sheet for definitive structural identifiers used for this specific lot.
Synthetic Utility
Reactivity highlights (literature)
Pyridine nitrogen: nucleophilic center for N-alkylation and acylation; N-oxide formation activates the ring toward SNAr and enables rearrangements (Boekelheide/Polonovski).
Aryl methyl ether (–OMe): a traceless protecting group convertible to phenolic (pyridinol) functionality via demethylation (BBr3, BCl3) or displacement under specific conditions; can serve as a handle for SNAr on activated systems.
Benzylic methyl (at C2): susceptible to oxidative or radical functionalization, enabling access to aldehydes, alcohols, or cross-coupled products.
Retrosynthetic value
Serves as a substituted pyridine core allowing orthogonal diversification at N, O (via demethylation and re-alkylation), and ring carbons (after selective activation). Useful in scaffold hopping where modulation of basicity and electronics is needed.
Named/typical transformations
N-oxidation with mCPBA; Boekelheide rearrangement with acyl anhydrides.
Directed orthometalation using LiTMP/LDA in THF or 2-MeTHF, then trapping with electrophiles.
Demethylation to 5-hydroxypyridine followed by Mitsunobu or Williamson ether synthesis to vary O-alkyl groups.
Halogenation (N-oxide assisted) followed by Suzuki/Negishi/Buchwald–Hartwig couplings.
Practical considerations
Exclude moisture for strong-base chemistry; quench carefully to avoid exotherms.
The methoxy group can coordinate/compete in metal-catalyzed reactions; ligand and base choice may need adjustment.
Control protonation state during extractions and crystallizations to improve isolations.
Target Specificity
Not applicable to this product type.
This catalog item is a small-molecule chemical building block, not a biological reagent (e.g., antibody, enzyme, or ligand with defined biological target specificity). No antigen/epitope/clone/isotype information applies.
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