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
methoxybenzene
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.
Solubility in water: Practically Insoluble; Degree of Solubility in water: 4.7 g/l 25 °C; Soluble in Benzene,Alcohol,Ether; Very slightly soluble in Chloroform
Sensibilité
Air Sensitive
Point d'éclair (°F)
230.0 °F - closed cup
Point d'éclair (°C)
110 °C - closed cup
Point d'ébullition (°C)
235°C
Point de fusion (°C)
52℃
Poids moléculaire
137.180 g/mol
XLogP3
1.700
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
137.084 Da
Monoisotopic Mass
137.084 Da
Topological Polar Surface Area
35.300 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
105.000
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
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Application Protocols
No assay or bioanalytical application protocols are specified for this small-molecule reagent. For synthetic applications, see the Reaction Conditions tab for class-based procedural guidance and adjust to your specific transformation.
Biological Roles
No endogenous biological role is expected for 2-methoxy-5-methylaniline; it is a synthetic aromatic amine used as a chemical intermediate.
General notes (class-based)
Aromatic amines can interact with biomolecules via hydrogen bonding (–NH2) and π–π interactions, and some may undergo metabolic N-acetylation or N-oxidation in vivo (literature). However, this product is provided for research use only and is not intended for biological administration.
Some anisidine derivatives have been studied as dye precursors and may display chromophoric properties upon azo coupling; such behavior is exploited in materials research rather than biology.
Research use restriction: For research use only (per Product Data). No clinical or diagnostic claims are made or implied.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biochemical buffers. If aqueous handling is required (e.g., diazotization), the anilinium salt may be generated in mineral acid media, but dedicated buffer systems (phosphate, acetate, citrate) should be used separately as appropriate to the reaction.
Green Alternatives
Process choices
Prefer catalytic C–N bond formations (e.g., Pd-catalyzed Buchwald–Hartwig or Cu-catalyzed Ullmann-type couplings) over stoichiometric nucleophilic aromatic substitutions when feasible, reducing waste.
For demethylation, consider catalytic or milder reagents (e.g., AlCl3/thiols, oxidative demethylations) rather than high-equivalents of BBr3 or HI, balancing selectivity vs. waste and safety.
Solvent substitutions (general guidance)
Replace chlorinated solvents with greener options when compatible:
2-MeTHF or CPME vs THF/DCM for many transformations (better safety/renewable feedstocks).
Toluene/EtOAc mixtures vs DCM for acylations/extractions.
Workup and waste minimization
Use pH-switch crystallization or salt formation to avoid extensive chromatography.
Recycle aqueous acid/base streams when feasible; employ in-line scavengers for amine salts.
Comparison snapshot (general)
DCM: excellent acylation medium, low bp; environmental and toxicity concerns.
2-MeTHF: bio-based, higher bp, good for couplings and organometallic steps; may form peroxides over time (monitor, inhibit as needed).
CPME: hydrophobic, azeotrope-friendly, low peroxide tendency, good for water-sensitive steps; higher bp affects removal energy.
Pharmaceutical Uses
Role in pharma workflows (general)
Substituted anilines like 2-methoxy-5-methylaniline are commonly used as intermediates in the synthesis of APIs and advanced intermediates through acylations, sulfonylations, diazotizations, and cross-couplings.
They can serve as precursors to diarylamines, anilide motifs, and heterocycles after further functionalization.
Regulatory status
No pharmacopeial monograph is indicated for this specific isomer in the Product Data. Any use in GMP settings would require appropriate qualification and supplier QA oversight.
Formulation/excipient
Not used as an excipient. Any pharmaceutical relevance is as an intermediate in chemical synthesis only.
Physical Properties
Item-specific physical constants were not provided in the Product Data. Refer to the CoA/SDS for definitive specifications.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point, melting point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general/literature expectations for substituted anisidines)
Organic solvents: typically miscible or highly soluble in common organics (e.g., alcohols, ethers, chlorinated solvents, aromatics).
Water: limited solubility as the free base; markedly increased solubility upon protonation (e.g., in dilute mineral acids) forming the anilinium salt.
Acid–base behavior (general)
Aryl amines are weak bases; pKa of the conjugate acid for anisidine analogs is typically in the 4–6 range (literature, compound-class guidance), giving a mostly unprotonated free base at neutral pH.
Partitioning (general)
Presence of –OMe and –NH2 confers moderate polarity; logP for close analogs generally around 1.5–2.0 (literature, class value). Actual measured value for this specific isomer is not provided here.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Analytical documentation
For precise assay, impurity profile, and residual solvent limits, consult the lot-specific Certificate of Analysis (CoA). UV cutoff, trace metals, and stabilizers are not specified for this item.
Stabilizers
No stabilizer is specified in the Product Data. If present, stabilizers (e.g., trace BHT) would be declared on the CoA; absence of such notation typically indicates neat material.
What the grade implies (general)
Research-grade aromatic amines are typically qualified by GC/HPLC purity, identity by NMR/IR/MS, and appearance/color limits. If HPLC or GC grade is specified elsewhere, it generally indicates low UV background and low trace nonvolatile residues, relevant for analytical applications.
Item-specific storage handling noted by Aladdin Scientific
Storage: Room temperature, under argon (per Product Data), to mitigate oxidative discoloration and maintain chemical integrity.
Reaction and Applications
2-Methoxy-5-methylaniline is a versatile building block in aromatic amine chemistry. While no manufacturer application notes were provided, the following reflect common uses for methoxy/methyl-substituted anilines (literature/general guidance):
Electrophilic aromatic substitution (EAS)
Strong activation by –NH2 and –OMe enables regioselective nitration, halogenation, and Friedel–Crafts-type reactions at remaining ortho/para positions (subject to steric constraints from substituents). Controlled protection of –NH2 (e.g., acylation) can tune directing effects.
Functional group interconversions
O-Demethylation to yield the corresponding ortho-phenol aniline (e.g., with BBr3 or HI), expanding access to aminophenol derivatives useful in dyes and ligands.
N-acylation/sulfonylation to form amides/sulfonamides for subsequent transformations or as protecting groups.
Diazonium chemistry
Diazotization of the aniline permits Sandmeyer-type substitutions (Ar–Cl/Br/CN) or azo coupling to make azo dyes/pigments. The strong ring activation aids high coupling efficiency with activated phenols/anilines.
Cross-coupling as amine nucleophile
Engages in Buchwald–Hartwig C–N coupling to craft diarylamines/arylamides; electron-rich anilines often react under milder conditions with appropriate ligands (e.g., BrettPhos, XPhos systems, literature).
Redox/metalation
Directed ortho-metalation adjacent to –OMe/–NH– protecting groups can be leveraged for lithiation–electrophile trapping sequences (under cryogenic, anhydrous conditions).
Application domains
Intermediates for dyes, agrochemical scaffolds, polymer additives, and heteroaromatic frameworks where electron-donating substituents modulate electronics.
Reaction Conditions
General, literature-style guidance for substituted anilines; adapt to your substrate and consult primary sources.
N-Acylation
Solvent: DCM, MeCN, or toluene. Base: Et3N, DIPEA, or pyridine. Temp: 0–25 °C. Typical completion: 0.5–4 h.
Sulfonamide formation
Reagents: sulfonyl chloride (1.0–1.2 eq), base (2.0–3.0 eq). Solvent: DCM or THF. 0–25 °C, 1–3 h.
Diazotization and Sandmeyer
Medium: 2–6 M HCl or HBF4 at 0–5 °C; NaNO2 (1.1 eq). Subsequent Cu-catalyzed substitution in MeCN/H2O at 0–25 °C. Azo coupling with phenols in mildly basic aq/alcoholic media.
Catalyst: Pd2(dba)3 (0.5–2 mol%) with dialkylbiaryl phosphine (e.g., BrettPhos 1–4 mol%). Base: NaOtBu, K3PO4, or Cs2CO3 (2–3 eq). Solvent: toluene, dioxane, 2-MeTHF, or t-BuOH. 60–110 °C, 2–16 h. Electron-rich anilines often couple efficiently at the lower end of the range.
O-Demethylation
BBr3 (1–3 eq) in DCM at −78 to 0 °C; quench with MeOH/H2O. Alternatively, HI (48%) reflux. Selectivity depends on substitution; strictly anhydrous conditions improve outcomes with BBr3.
Note: Conditions above are literature generalities for this class; optimize for this specific isomer.
Safety and Handling
GHS information
Signal word: Not specified for this item; refer to SDS.
Hazard statements, classification, pictograms: Not specified for this item; refer to SDS.
General hazards (class-based guidance)
Aromatic amines may be harmful if swallowed, inhaled, or absorbed through skin and may cause irritation to skin, eyes, and respiratory tract. Some anilines can induce methemoglobinemia upon significant exposure. Treat unknowns conservatively.
PPE and engineering controls
Use in a fume hood with splash protection.
Wear safety glasses or goggles, lab coat, and suitable chemically resistant gloves (e.g., nitrile). Consider double-gloving for extended handling.
Handling guidance
Avoid breathing vapors/aerosols; prevent contact with skin/eyes.
Keep away from strong oxidizers and acylating/sulfonylating agents unless intended for reaction; amines can react vigorously.
Anilines can darken on air exposure due to slow oxidation; minimize air/illumination exposure during storage and handling.
First aid (overview; consult SDS for authoritative instructions)
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eyes: rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire and reactivity
Combustible organic; use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and nitrogen oxides. Secure containers from heat/sparks/open flames.
Solvent Selection
This is an organic reagent rather than a solvent; however, solvent choice is central to its use in synthesis and purification.
Polarity/miscibility profile (class-based)
Free base is moderately polar and typically dissolves well in ethers (Et2O, THF), alcohols, chlorinated solvents (DCM, CHCl3), aromatics (toluene), and polar aprotics (MeCN, DMF, DMSO). Aqueous solubility is limited as base but high as protonated salts in dilute mineral acids.
Choosing a solvent by transformation
Acylation/sulfonylation: DCM, CH2Cl2/pyridine, or acetonitrile with base (Et3N, DIPEA) are common.
Diazotization/azo coupling: aqueous mineral acid for diazotization, then coupling in alcoholic or aqueous buffer media.
Cross-coupling (C–N formation as nucleophile): polar aprotics (toluene, dioxane, CPME, or t-BuOH with base) for Buchwald–Hartwig amidation/arylation.
Demethylation to the phenol: protic acids (HBr, HI) or BBr3 in DCM/CH2Cl2 at low temperature (strictly anhydrous).
Workup hints
Partition into organic phase as the free base; for aqueous handling, temporarily protonate to anilinium salt to move into water, then basify to re-extract.
Small comparison (general)
DCM: easy workups, low bp, good for acylations; environmental concerns.
THF/2-MeTHF: good for metalations/cross-couplings; 2-MeTHF preferred for greener profile and better phase-splitting.
Storage and Reconstitution
Storage conditions (item-specific)
Store at room temperature under an argon atmosphere (per Product Data). Maintain tightly closed in an inerted container to minimize oxidative discoloration/polymerization.
Light and air sensitivity
Aromatic amines can slowly oxidize and darken upon air/light exposure; inert gas blanket and minimal headspace are beneficial. Use amber glass where feasible.
Moisture considerations
Generally not highly hygroscopic as a free base, but keep dry to prevent acid/base contamination and maintain assay.
Reconstitution
Supplied neat unless otherwise noted. If solidified or viscous, gently warm and dissolve in a suitable dry solvent (e.g., DCM, MeCN, THF) under inert gas. No aqueous reconstitution is required unless forming salts for specific procedures.
Shipping
Shipped via FedEx DG Service (per Product Data).
Shelf life
Refer to CoA for retest date. Periodic inspection for color changes is recommended; mild discoloration does not necessarily indicate loss of purity but may warrant a quick QC check (e.g., GC).
Structure and Identity
2-Methoxy-5-methylaniline is a substituted aniline (anisidine derivative) bearing both a methoxy and a methyl group on the aromatic ring.
Chemical identity
Product name: 2-Methoxy-5-methylaniline (aka 5-methyl-2-anisidine; positional isomer of methyl–anisidines)
CAS: 120-71-8 (per Product Data)
PubChem CID: 8445 (per Product Data)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Composition
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general/literature description)
Functional groups: primary aryl amine (–NH2), methoxy ether (–OCH3), and an aryl methyl (–CH3) on a benzene ring.
Aromatic ring is strongly activated toward electrophilic substitution by the ortho/para-directing –NH2 and –OMe groups; the methyl is weakly activating/ortho–para directing.
2D structure (verbal): an aniline where adjacent (ortho) to the –NH2 is a methoxy substituent; a methyl substituent resides meta to the –NH2 and para to the –OMe (relative position nomenclature per name). No stereocenters; planar aromatic core.
Synthetic Utility
Reactivity highlights
Nucleophilicity at nitrogen enables formation of amides, sulfonamides, carbamates, ureas, and C–N coupled products.
Electron-donating –OMe and –NH2 groups activate the ring for EAS and can direct ortho/para substitution; methyl adds mild steric/electronic bias.
Strategic manipulations
Protect –NH2 (e.g., acylation with Ac2O) to modulate directing effects before performing ring substitutions; deprotect via hydrolysis afterward.
Demethylate –OMe to phenol for divergent synthesis (access to aminophenols), then further elaborate via O-alkylation, ether formation, or metal–ligand assembly.
Convert –NH2 to diazonium for Sandmeyer substitutions (Ar–X, –CN) or azo couplings to generate dyes/pigments.
Retrosynthetic value
Readily accessible from corresponding nitro precursor via reduction, or from anisidine scaffolds by regioselective functionalization, making it a convenient node in dye, agrochemical, and materials chemistry routes.
Polymer/materials context
Forms part of chromophoric systems upon azo coupling; the electron-rich ring is suitable for donor segments in push–pull motifs.
Target Specificity
Not applicable. This product is a small-molecule aromatic amine, not a biological macromolecule or targeting reagent. No antigen, clone, isotype, or species reactivity information applies.
Foire aux questions
What is the purity of this product, and how is it determined?
This product is supplied at ≥98% purity, determined by gas chromatography (GC). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature under argon. It is supplied under an argon blanket; reseal under inert gas after each use.
How is this product shipped?
This product is classified as dangerous goods and ships via FedEx DG Service. Ground and other economy services are not available, and delivery to some destinations or address types may be restricted.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 120-71-8, the molecular formula is C8H11NO, and the molecular weight is 137.18 g/mol. InChIKey WXWCDTXEKCVRRO-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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