This compound belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene 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.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
Not applicable. No tested bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic procedures involving this compound, refer to the Reaction & Applications and Reaction Conditions sections for general laboratory guidance.
Biological Roles
This product is supplied strictly for research use; no biological testing data are provided for this item.
General context (literature; not specific to this product):
Aromatic amines can undergo metabolic N-acetylation and N-oxidation in biological systems, mediated by N-acetyltransferases and cytochrome P450 enzymes. Ortho-methoxy substitution can influence electron density and potential sites of metabolism (e.g., O-demethylation to phenolic anilines).
Protonation: At physiological pH, anilines are largely unprotonated (weak bases), but can form anilinium ions in acidic environments, altering solubility and transport.
Reactivity: Aromatic amines may participate in diazotization under nitrosative stress in vivo; this underlies caution with nitrosating agents.
No in vitro/in vivo potency, target affinity, or biological activity data are claimed or implied for this catalog item. For biochemical or toxicological studies, consult primary literature and perform your own validation.
Buffer Applications
Not typically applicable. 2-Methoxy-4-methylaniline is a hydrophobic aromatic amine used as a synthetic building block rather than a buffering agent. If used in aqueous experiments, it may be dissolved in a compatible co-solvent (e.g., DMSO, ethanol) and then diluted into the buffer, taking into account solubility limits and potential amine protonation at low pH.
Green Alternatives
While the reagent itself is the target substrate, greener choices can be made for the processes in which it participates.
Greener solvent and condition considerations (literature/guidance):
Replace chlorinated solvents (DCM/DCE) with EtOAc, toluene, 2-MeTHF, CPME, or Me-THF/toluene blends when performing acylations or extractions.
For Buchwald–Hartwig couplings, use bio-derived 2-MeTHF or CPME, or propylene carbonate where compatible, and consider heterogeneous Pd/C under flow to minimize metal residues.
Conduct diazotizations in aqueous ethanol or water-lean systems with precise temperature control to reduce organic solvent use; ensure safe nitrite handling and quench strategies.
Employ organocatalytic or enzyme-mimetic methods for certain transformations (e.g., acylations) when feasible to avoid heavy metals.
Compact comparison (process solvent choices):
Chlorinated solvents: Excellent solvency; high EHS impact; prioritize only if required for selectivity.
Toluene/xylene: Good solvency; moderate EHS; recyclable; watch worker exposure.
EtOAc/IPA/MeOH: Broad utility; lower toxicity; readily recoverable; check amine salt formation in protic media.
2-MeTHF/CPME: Hydrophobic ether alternatives; good for moisture-sensitive couplings; form fewer peroxides than THF/Et2O; biomass-derived (2-MeTHF).
Waste minimization:
Convert amine to isolable salts for crystallization-based purifications.
Use catalytic over stoichiometric reagents where possible; design telescoped sequences to reduce solvent changeovers.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item.
General context (literature; not item-specific claims):
Function in drug R&D: 2-Methoxy-4-methylaniline serves as a versatile intermediate for building anilide, sulfonamide, diarylamine, and azo-containing motifs frequently encountered in medicinal chemistry scaffolds.
Advantages of this substitution pattern: The ortho-methoxy and para-methyl groups modulate basicity, lipophilicity, and electronic properties of downstream amide/urea/sulfonamide derivatives, enabling fine-tuning of ADME-relevant attributes during SAR exploration.
Process considerations: Availability of both free base and protonated salt forms can facilitate crystallization-based purifications; protecting-group strategies (Boc, acetyl) may be applied for multistep campaigns.
Note: This product is for research use only and is not intended for human or veterinary use, as a drug substance, or as an excipient in finished dosage forms.
Physical Properties
Item-specific specifications (this lot):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
General/literature properties for 2-methoxy-4-methylaniline (reference only; not item specifications):
Physical state: Typically a pale to amber liquid at ambient temperature (literature, aromatic anilines of similar substitution are liquids near RT).
Boiling point: Commonly reported in the ~235–245 °C range at 1 atm (literature; varies with measurement and purity).
Melting point: Often reported below room temperature (literature; many anisidine/toluidine isomers are low-melting liquids).
Density: Expected around 1.00–1.08 g/mL at 20–25 °C (literature estimates for substituted anilines).
Solubility: Sparingly soluble in water; miscible with most organic solvents (alcohols, ethers, esters, chlorinated, and aromatic hydrocarbons) (literature).
LogP (octanol/water): Typically in the ~1.8–2.2 range for comparable methoxy/methyl anilines (literature).
pKa: Anilinium conjugate acids typically pKa ~4.5–5.5 in water; basicity slightly reduced by intramolecular H-bonding/ortho effects (literature for 2-methoxyaniline derivatives).
UV-vis: Aromatic amines show strong absorbance in the UV (ca. 200–280 nm) with bathochromic shifts from electron-donating substituents (literature).
Notes:
Exact numeric values for this catalog item are Not specified; consult the CoA/SDS for authoritative data and handling limits.
Impurity-sensitive applications (e.g., spectroscopy) should confirm UV cutoff and absorbance on the supplied CoA before use.
Quality and Grades
Supplied grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grades (general guidance for this class of reagent):
Research/technical grade: Suitable for synthesis and general lab use. May have higher residual solvents and broader impurity profile.
Purified/97–99%: Suitable for most synthetic transformations; verify residual water/amine stabilizers if relevant to your reaction.
High-purity/GC or HPLC assay: Preferred for analytical or photophysical studies; typically features lower UV background and tighter impurity limits.
Key quality aspects for 2-methoxy-4-methylaniline:
Color and absorbance: Electron-rich anilines can oxidize to colored species; check color/APHA or UV specs if your application is color- or UV-sensitive.
Amino content: Assay by GC/LC or NMR typically verifies identity and purity; trace aniline isomers or nitro/azo byproducts may be monitored depending on synthesis route.
Water and residual solvents: Not specified for this item; refer to CoA/Spec Sheet. For moisture-/acid-sensitive couplings, confirm by KF and residual solvent analysis.
Metal content: Not specified for this item; refer to CoA/Spec Sheet. If used in metal-catalyzed cross-couplings downstream, low baseline metals are advantageous.
Documentation: Each lot should be confirmed against the CoA for assay, identity (NMR/GC/MS/IR), and any stabilizer or inhibitor content (if applicable). Contact Aladdin Scientific for additional analytical data packages upon request.
Reaction and Applications
As an electron-rich, ortho-methoxy/para-methyl substituted aniline, 2-methoxy-4-methylaniline is a versatile intermediate in dye, pigment, agrochemical, and pharmaceutical research synthesis.
Common transformations (literature/general):
N-Acylation and N-sulfonylation: Formation of amides and sulfonamides under Schotten–Baumann or coupling conditions (acid chlorides/anhydrides, sulfonyl chlorides; bases like Et3N, pyridine, or aqueous Na2CO3; 0–25 °C).
Diazotization and azo coupling: Conversion to diazonium salts (NaNO2/HX at 0–5 °C) followed by coupling to activated aromatics or heterocycles to access azo dyes/pigments; ortho-methoxy can influence coupling orientation and stability.
N-Arylation (Buchwald–Hartwig): Cross-coupling with aryl halides/triflates using Pd catalysts (e.g., Pd2(dba)3, BrettPhos/XPhos ligands), bases (NaOtBu, Cs2CO3), and solvents (toluene, dioxane, 2-MeTHF) to build diarylamines.
Electrophilic aromatic substitution: The –NH2/–OMe/–CH3 strongly activate the ring; SEAr (e.g., nitration, sulfonation, formylation) proceeds with regioselectivity favoring residual ortho/para positions relative to –NH2 (sterics from –OMe at C2 guide outcomes).
Reductive transformations: Formation of N-alkyl anilines via reductive amination (aldehydes/ketones + H2/Pd or NaBH3CN), or catalytic hydrogenation of diazonium-derived intermediates.
Protection strategies: Temporary protection as acetanilide/carbamate (Boc, Cbz) to modulate reactivity in multi-step synthesis.
Practical tips:
Drying: If needed, dry over K2CO3 or molecular sieves to reduce moisture before sensitive couplings.
Oxidation control: Work under inert gas as supplied; minimize air/light to limit color formation.
Workup: Formation of water-soluble anilinium salts enables efficient phase separations; basify to recover the free base.
Reaction Conditions
General literature guidance for typical transformations using 2-methoxy-4-methylaniline (optimize per your system):
N-Acylation (to anilides):
Reagents: Acyl chloride or anhydride; base (Et3N, DIPEA, pyridine, NaHCO3/Na2CO3).
Solvent: DCM, EtOAc, MeCN, or toluene.
Temperature/time: 0–25 °C, 0.5–4 h.
Notes: Control exotherm; quench to form amine hydrochloride, wash, and basify.
Sulfonamide formation:
Reagents: Sulfonyl chloride; base (pyridine, Et3N) or biphasic Na2CO3.
Solvent: DCM, EtOAc, or toluene.
Temperature/time: 0–25 °C, 1–6 h.
Buchwald–Hartwig C–N coupling (as nucleophile):
Catalyst/ligand: Pd2(dba)3 or Pd(OAc)2 (1–3 mol% Pd) with BrettPhos/XPhos/RuPhos (2–6 mol%).
Base: NaOtBu, KOtBu, Cs2CO3, or K3PO4.
Solvent: Toluene, 1,4-dioxane, 2-MeTHF, CPME.
Temperature/time: 80–110 °C, 4–18 h.
Notes: Exclude air/moisture; the electron-rich amine is typically highly reactive.
Diazotization/azo coupling:
Reagents: NaNO2 in water; HX (HCl/H2SO4) at 0–5 °C to form diazonium; couple with activated aromatics.
Solvent: Aqueous ethanol or mixed aqueous/organic.
Notes: Strict temperature control; handle diazonium salts with caution.
Electrophilic ring functionalization:
Bromination: NBS or Br2 under controlled conditions (solvent: AcOH, MeCN, or CHCl3), 0–25 °C.
Formylation: Vilsmeier–Haack (POCl3/DMF), 0–80 °C.
Yields: Depend on substrate/catalyst; many literature examples report good to excellent isolated yields after optimization. Verify on small scale first.
Safety and Handling
Item-specific hazard classification:
GHS Classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the product SDS.
General safety information for aromatic amines (literature/good practice; not item-specific):
Hazards: Aromatic amines may be harmful if swallowed, inhaled, or absorbed through skin; may cause skin/eye irritation and respiratory irritation. Some anilines can cause methemoglobinemia upon significant exposure. Avoid aerosol generation and prolonged skin contact.
PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles. In case of potential vapor/aerosol, use appropriate local exhaust; handle in a fume hood.
First aid (general):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Remove contaminated clothing, wash with soap and water.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if easy; continue rinsing; seek medical attention.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Handling/engineering: Keep containers tightly closed under inert gas as provided. Prevent contact with oxidizers and strong acids. Minimize exposure to light per storage guidance.
Incompatibilities: Strong oxidizing agents; strong acids (can form anilinium salts with exotherm). Nitrosating agents can form N-nitroso compounds; avoid.
Stability considerations: Aromatic amines can gradually darken on air/light exposure due to oxidative byproducts; argon blanket and light protection help maintain quality.
Always consult the SDS for authoritative hazard, exposure limits, and spill/firefighting guidance.
Solvent Selection
This product is a reactive aromatic amine building block, not a process solvent. Solvent selection therefore concerns dissolving it for reaction or analysis.
Polarity/miscibility (literature): Sparingly soluble in water; readily soluble in many organic solvents (MeOH, EtOH, i-PrOH, acetone, MTBE/Et2O, THF/2-MeTHF, CPME, toluene, DCM/DCE, DMF/DMAc/DMSO, acetonitrile).
Selection guidance by use case:
N-acylation/sulfonylation: Use aprotic solvents (DCM, CH2Cl2 alternatives like EtOAc or toluene) or mild alcohols; include base (Et3N, DIPEA, NaHCO3).
Metal-catalyzed arylation: Polar aprotic media (toluene, dioxane, 2-MeTHF, CPME, tert-amyl alcohol, or greener esters) frequently used with Pd/Cu catalysts.
Diazotization/azo coupling: Acidic aqueous-organic biphasic or alcoholic media at 0–5 °C; ensure sufficient solubility of the free base or use its salt.
Salt formation/extractions: Protonation (e.g., HCl) increases water solubility for workup; liberate the free base for organic-phase operations.
Analytical prep: For HPLC/UPLC, dissolve in ACN, MeOH, or IPA; filter through 0.2 µm PTFE/RC. Confirm UV background for detector compatibility.
Notes:
Avoid strong protic acids in presence of oxidants to prevent nitrosation.
Where possible, prefer greener solvents (2-MeTHF, CPME, EtOAc, MeTHF/toluene blends) over chlorinated media without compromising performance.
Storage and Reconstitution
Item-specific storage/shipping (as provided):
Storage: Store at 2–8 °C, protected from light, under argon (argon charged).
Shipping: Shipped on wet ice.
Best practices (general):
Container: Keep tightly closed in an amber glass bottle with PTFE-lined cap to minimize light/oxygen ingress.
Headspace: Maintain inert gas blanket (argon or nitrogen) after each use; purge headspace before resealing.
Handling: Warm gently to room temperature before opening to avoid moisture condensation. Dispense under inert gas if possible.
Stability: Aromatic amines can slowly oxidize/discolor on exposure to air/light; follow the above precautions to preserve assay and color.
Long-term: For multi-month storage, periodic GC or NMR check is recommended for critical applications.
Reconstitution:
This product is supplied neat; no reconstitution is required. For solution preparation, dissolve in a compatible, dry solvent (e.g., toluene, EtOAc, MeCN, 2-MeTHF, DCM, alcohols) at the desired concentration. Filter through 0.2 µm PTFE for analytical use.
Disposal: Collect waste and contaminated materials as halogen-free organic amine waste per institutional and regulatory guidelines.
Structure and Identity
Brief overview: 2-Methoxy-4-methylaniline (also called 4-methyl-2-methoxyaniline; an anisidine/toluidine isomer) is an ortho-methoxy, para-methyl substituted aniline used as an electron-rich aromatic amine building block.
Item identifiers (as supplied):
CAS: 39538-68-6
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identifiers (for reference only; not item-specific specs):
Representative SMILES (literature): COc1cc(N)ccc1C (one of several equivalent representations)
Computed/literature composition:
Molecular formula: C8H11NO (literature)
Molecular weight: ~137.18 g/mol (literature)
Structural features (general description):
Core ring: Benzene ring bearing an aniline –NH2 at position 1.
Substituents: –OCH3 at the 2-position (ortho to –NH2) and –CH3 at the 4-position (para to –NH2).
Functional groups: Primary aromatic amine (nucleophilic nitrogen), methoxy ether (–OMe), and an electron-donating methyl group.
Electronic effects: Strongly activated ring (ortho/para-directing substituents); the –OMe and –CH3 increase electron density; –NH2 is the most activating and can serve as a directing group and ligand.
2D description: An aniline ring with the amino group at the top (position 1); moving clockwise, methoxy at position 2, hydrogen at 3, methyl at 4, and hydrogens at 5 and 6.
Synthetic Utility
Functional group leverage:
Nucleophilic amine (–NH2): Readily acylated, sulfonylated, carbamoylated, or engaged in C–N bond formation (Buchwald–Hartwig, Ullmann–Goldberg).
Electron-rich ring: With –OMe and –CH3 donors, the ring is highly activated for SEAr (e.g., halogenation, nitration under milder conditions, Vilsmeier–Haack formylation).
Ortho effects: The 2-methoxy group introduces potential intramolecular H-bonding and steric bias that can steer regioselectivity and stabilize certain intermediates (e.g., diazonium salts, o-quinone imine formation pathways).
Retrosynthetic value:
As a masked anisidine/toluidine unit that can be diversified via: (i) N-functionalization (amides, sulfonamides, ureas), (ii) ring functionalization (bromination/iodination for subsequent cross-coupling), and (iii) oxidative transformations (O-demethylation to 2-hydroxy-4-methylaniline when phenols are desired).
Named/representative reactions (literature):
Buchwald–Hartwig amination with aryl bromides (Pd/BrettPhos, NaOtBu, toluene or 2-MeTHF, 80–110 °C).
Pre-form the anilinium salt to enhance crystallinity/purification.
Protect –NH2 (e.g., Boc) to direct electrophilic substitution onto the ring selectively when needed.
Target Specificity
Not applicable. This product is a small-molecule reagent (aromatic amine) and is not an antibody, enzyme, or biological probe with defined target specificity. No antigen, epitope, clone, isotype, or species reactivity information applies.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
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.
H2328552