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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
181.230 g/mol
XLogP3
1.400
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
181.11 Da
Monoisotopic Mass
181.11 Da
Topological Polar Surface Area
44.500 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
141.000
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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Recensioni
Recensioni dei clienti
Application Protocols
No antibody/assay application protocols are applicable to this small-molecule reagent. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for representative procedures and optimization guidance.
Biological Roles
Item-specific (Product Data)
Category path: 生命科学 (Life Science). Research Use Note: For research use only.
General biochemistry context (informational; not a claim for this specific molecule’s physiological role)
Aromatic anilines of this type are not typical endogenous metabolites. They can, however, serve as synthetic precursors to bioactive scaffolds (e.g., diaryl amines, sulfonamides, ureas) used in chemical biology probes and screening libraries.
The primary amine enables conjugation chemistry (amide formation with activated esters, isocyanate/urea linkages) to attach reporter groups, affinity tags, or linkers.
The para 2‑methoxyethoxy unit can increase polarity relative to simple anisidines, potentially modulating solubility and permeability in designed small molecules.
In biochemical assay development, substituted anilines are often employed as building blocks for structure–activity relationship (SAR) exploration, tuning electronic properties and hydrogen-bonding patterns of candidate ligands.
Cautions
No specific biological targets, activities, or pathways are established in the Product Data. Any use should be confined to laboratory research, method development, or synthesis of downstream entities, with no medical or diagnostic application implied.
Buffer Applications
This material is a hydrophobic/aromatic primary amine building block, not a conventional buffering agent.
Applicability
Not typically used to formulate pH buffers or biological buffer systems. It lacks a well-defined pKa/pH range suitable for maintaining physiological buffer capacity in aqueous media.
Practical note
If the compound is temporarily solubilized for biochemical assays, dissolution is usually in organic co-solvents (e.g., DMSO) with subsequent dilution into assay media; pH buffering should be provided by established systems (HEPES, PBS, Tris).
Green Alternatives
While the compound itself is a target building block rather than a solvent, greener choices can be implemented in its use and transformations.
Greener solvent choices (literature guidance)
Prefer 2‑MeTHF or CPME over THF/diethyl ether for many acylations, reductions, and extractions; both offer improved safety (peroxide stability for CPME), higher boiling points, and biorenewable sourcing (2‑MeTHF from hemicellulose).
Use ethyl acetate or propylene carbonate as alternatives to DCM/DMF where feasible; EtOAc is biodegradable and readily recycled.
For reductive aminations, ethanol or isopropanol as hydrogen donors (transfer hydrogenation) can replace hydride reagents in some protocols.
Reagent and process considerations
Couple formation of amides/ureas using organobase-catalyzed coupling agents (e.g., COMU, CDI) to minimize halogenated byproducts from acid chlorides.
Apply continuous flow for diazotization/Sandmeyer steps to enhance safety and minimize excess reagents.
Use aqueous micellar catalysis (surfactant media) for some cross-couplings or acylations to reduce organic solvent volumes.
Tradeoffs
Greener solvents may change solubility and rates; catalyst/ligand and base systems may require re-optimization.
Workup and phase behavior can differ (e.g., propylene carbonate is high-boiling), affecting energy use for solvent recovery.
Mini comparison (qualitative)
DCM vs EtOAc: EtOAc greener, but less effective for very low-temp acylations; consider cooling and base adjustments.
THF vs 2‑MeTHF: Similar performance; 2‑MeTHF offers renewability and better water immiscibility aiding separations.
Pharmaceutical Uses
Item-specific (Product Data)
No pharmacopeial grade, excipient role, or GMP status is provided. Research Use Only.
General formulation/manufacturing context (informational)
Substituted anilines such as this are commonly used as intermediates in the synthesis of active pharmaceutical ingredient (API) candidates and reference standards. Typical transformations include formation of amide/sulfonamide/urea linkages or incorporation into more complex heteroaromatic frameworks.
The 2‑methoxyethoxy substituent can serve as a solubilizing handle in medicinal chemistry, improving chromatographic behavior and enabling prodrug-like modifications (e.g., carbonate/carbamate linkages) during route scouting.
For any consideration beyond discovery research (e.g., scale-up, impurity profiling), establish specifications for assay, residual solvents, elemental impurities, and nitrosamine risk assessments per ICH guidance. For this catalog item, such specifications are Not specified and must be confirmed on the lot-specific CoA/Spec Sheet if relevant.
Physical Properties
Item-specific (Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computational expectations for analogous substituted anilines (informational; not specifications)
Physical state: Typically a low-melting solid or high-boiling liquid for aryl anilines bearing ether chains of this size.
Boiling point: Often in the 260–320 °C range for comparably substituted anisidine derivatives (literature trends), with potential decomposition on distillation in air.
Melting point: Frequently low or oily at room temperature when bearing flexible ether chains; many analogs are liquids or low-melting solids.
Density: Aromatic amines with ether substituents commonly fall around 1.00–1.12 g/mL at 25 °C (literature ranges).
Solubility profile: Sparingly soluble in water; freely soluble in common organic solvents (EtOAc, ether, MTBE, THF, DCM, toluene, MeOH, EtOH, acetonitrile). The aniline N can form H-bonds, improving solubility in polar protic/aprotic solvents.
Acid–base: The anilinium conjugate acid pKaH for electron-rich anilines is typically ~5.2–6.0 (literature), reflecting weak basicity relative to aliphatic amines (due to aniline resonance).
LogP: Electron-rich anilines with one ether chain and a methyl generally exhibit logP ~1.5–2.5 (calculated/literature ranges for close analogs).
UV–Vis: Aromatic π–π* absorption typically λmax ~200–230 nm with a weaker band near 275–300 nm; anilines/anisoles may show modest bathochromic shifts (literature).
Refractive index, UV cutoff, residual water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific (Product Data)
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for professional use
When selecting an aniline intermediate for synthesis, consider impurity classes that commonly affect performance: residual aniline isomers, phenolic impurities (from ether cleavage), residual solvents, and trace metals from upstream steps.
For chromatography or photophysical studies, low UV-absorbing solvent residues and tight control of non-UV-active impurities are critical; HPLC-grade solvents during workup help minimize background.
If available grades include “98%+” or “purified,” higher assay typically correlates with improved coupling efficiency (e.g., in amide/urea/sulfonamide formations) and reduced byproduct profiles.
Water and peroxide specifications are particularly important when the material will be used in moisture- or radical-sensitive transformations (e.g., organometallics); for this item, such specifications are Not specified and should be confirmed on the CoA if critical.
If stabilizers are present for some catalog lots (e.g., trace BHT in ethers), assess compatibility with downstream reactions; absence/presence of stabilizer is Not specified for this item—verify on the lot-specific documentation.
Reaction and Applications
As a 3-methyl, 4-(2-methoxyethoxy) substituted aniline, this molecule is an electron-rich, nucleophilic building block suitable for diverse transformations.
Typical application families (literature/general)
N‑Derivatization: Formation of amides (acid chlorides/coupling reagents like EDCI/HATU), sulfonamides (sulfonyl chlorides), ureas/carbamates (phosgene equivalents, CDI, triphosgene), isocyanates via Curtius/urea routes.
Reductive amination/N‑alkylation: Condensation with carbonyls followed by reduction (NaBH3CN, BH(OAc)3, H2/Pd); or direct alkylation with alkyl halides (use hindered base to limit O‑alkylation).
Diazotization/Sandmeyer/Meerwein: Convert the aniline to the diazonium salt (NaNO2/HX, 0–5 °C) enabling aryl–X installation (X = Cl, Br, CN, OAr, etc.). The para ether and meta methyl generally increase diazotization rate.
Electrophilic aromatic substitution on the ring: Strongly activated by –NH2 and –OR (both o/p‑directing). Protecting or moderating N basicity (e.g., acetylation to acetanilide) can improve regioselectivity and limit overreaction.
Cross-coupling as nucleophile: Buchwald–Hartwig amination (as amine partner) to form aryl–N bonds with aryl/vinyl halides under Pd/ligand catalysis.
Practical tips
Competing O‑ vs N‑acylation/alkylation: For selective N‑functionalization, use non-nucleophilic bases (DIPEA), aprotic solvents, and controlled temperature. For O‑functionalization, more forcing conditions/phase-transfer catalysts can be leveraged.
Protecting groups: Acetyl, Boc, or sulfonamide PGs reduce aniline basicity and can steer EAS. Deprotection conditions should be chosen to preserve the aryl ether linkage.
Workup: Protonation/deprotonation cycles help partition the amine between organic and aqueous phases for purification.
Reaction Conditions
General literature guidance for similar aniline substrates (non-binding; optimize per substrate and scale):
Amide formation (acid chloride route)
Solvent: DCM or THF; Base: DIPEA or pyridine (1.5–2.0 equiv).
Temperature: 0 °C to rt; Time: 0.5–4 h.
Notes: Cool during addition to control exotherm; wash with bicarbonate then acid if needed.
Amide formation (carbodiimide/uronium coupling)
Solvent: DMF, DCM, or 2‑MeTHF; Reagents: EDCI/HOBt, HATU, or T3P.
Base: DIPEA (2–3 equiv); Temperature: rt to 40 °C; Time: 1–12 h.
Sulfonamide synthesis
Reagents: R–SO2Cl (1.05–1.2 equiv), Base: Et3N or NaHCO3.
Solvent: DCM/MeCN; Temperature: 0–25 °C; Time: 0.5–3 h.
Reductive amination
Solvent: MeOH, EtOH, or MeCN; Reagents: NaBH3CN (1.2–2.0 equiv) or NaBH(OAc)3.
Acid catalyst: AcOH (0.5–1.0 equiv); Temperature: rt; Time: 2–16 h.
Diazotization / Sandmeyer
Conditions: NaNO2 (1.1 equiv) in water; HX (HCl/HBr, 2–4 M); 0–5 °C.
Subsequent substitution: CuX or other mediators; maintain low temp initially, then warm as required.
Base: NaOtBu or Cs2CO3; Solvent: toluene, dioxane, or tBuOH; 80–110 °C, 4–18 h.
Workup and isolation
Partition between organic solvent and aqueous acid/base to shuttle the amine; dry organic layers over Na2SO4; concentrate under reduced pressure. Add Et3N to silica eluent to avoid tailing.
All parameters are representative literature ranges; substrate- and scale-dependent optimization is recommended.
Safety and Handling
Item-specific (Product Data)
Storage conditions: Room temperature.
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
General safety guidance for substituted anilines and aryl ethers (informational; consult the product SDS for authoritative data)
Hazards: Aromatic amines can be harmful if swallowed, inhaled, or in contact with skin; may cause skin/eye irritation and can be sensitizers in some cases. Many anilines show methemoglobin-forming potential; handle to minimize exposure.
PPE: Lab coat, nitrile gloves (change regularly), safety goggles; handle in a fume hood to avoid inhalation.
Handling: Avoid heat and open flames. Prevent aerosol/mist formation. Do not breathe vapors. Avoid contact with oxidizing agents and strong acids unless intended for reaction.
Incompatibilities: Strong oxidizers (risk of exotherm), nitrosating agents under acidic conditions (risk of N‑nitrosamine formation), and acid halides/anhydrides (acylation) unless controlled synthetically.
First aid overview: Eye/skin contact—rinse with water for at least 15 minutes; remove contaminated clothing. Inhalation—move to fresh air; seek medical attention if symptoms persist. Ingestion—rinse mouth; do not induce vomiting; seek medical attention.
Spills and disposal: Absorb small spills with inert material; collect for disposal according to local regulations. Prevent entry into drains. Decontaminate surfaces with suitable solvent/detergent.
Firefighting: Use CO2, dry chemical, or foam. Combustion may release irritating nitrogen oxides and phenolic/anisole-type vapors.
Solvent Selection
This product is a functionalized aromatic amine (moderately polar, weakly basic). It behaves well in a variety of organic media.
Polarity and miscibility (literature-based behavior of similar anilines)
Highly soluble in polar aprotic solvents (DMF, DMSO, NMP, MeCN) and polar protic solvents (MeOH, EtOH).
Good solubility in moderately polar ethers (THF, 2‑MeTHF, CPME) and halogenated solvents (DCM, chloroform).
Limited water solubility expected, but sufficient for biphasic extractions upon protonation (e.g., with HCl).
Practical selection guidance
N‑acylation/sulfonylation: Use DCM, THF, MeCN, or toluene with base (DIPEA, pyridine, or triethylamine). Low temperatures in DCM help suppress overacylation.
N‑alkylation/Reductive amination: Polar aprotics (DMF/MeCN) aid SN2; alcohol solvents may be used for hydrogenative reductive amination with supported catalysts.
Diazotization/Sandmeyer: Aqueous mineral acid media at 0–5 °C, followed by copper-mediated substitution; co-solvents (MeCN, DCM) can assist phase transfer for lipophilic products.
Metal-catalyzed couplings (e.g., Buchwald–Hartwig as nucleophile counterpart): Toluene, dioxane, or tBuOH often balance solubility and base compatibility.
Comparison snapshot (qualitative)
THF/2‑MeTHF: Excellent balance of polarity and volatility; ethers facilitate dissolution and easy removal.
DCM: Superior for acyl/sulfonyl chloride handling at low temp; consider environmental profile.
DMF/DMSO: Maximize solubility for challenging transformations; harder to remove, higher boiling.
Storage and Reconstitution
Item-specific (Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for substituted anilines (informational)
Storage: Keep tightly closed in a dry, well-ventilated place. Protect from excessive heat and light. If long-term storage is anticipated, consider inert atmosphere (argon/nitrogen) to limit oxidative discoloration.
Moisture/air sensitivity: Typically stable, but prolonged exposure to air and light may cause gradual darkening due to oxidation. Store in amber glass if possible.
Reconstitution/solubility: Freely soluble in common organic solvents (DMSO, DMF, MeOH, EtOH, THF, DCM, toluene). For biological assays, prepare concentrated DMSO stock solutions (e.g., 10–100 mM) and dilute into assay buffer with appropriate cosolvent control.
Freeze–thaw: Not generally required for neat solids/liquids. If preparing solutions, aliquot to avoid repeated freeze–thaw cycles that can introduce moisture and contaminants.
Label compliance: For research use only. Consult the lot-specific CoA and SDS for definitive storage and handling instructions.
Structure and Identity
Brief overview: 4-(2-Methoxyethoxy)-3-methylaniline is an electron-rich, substituted aniline bearing a para 2-methoxyethoxy side chain and a meta methyl group.
Item-specific (Product Data)
Product name: 4-(2-Methoxyethoxy)-3-methylaniline
CAS: 946741-63-5
CID: 26189999
InChIKey: 212419 (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.
Substitution pattern: meta-CH3 (3-position relative to –NH2) and para –O–CH2–CH2–OCH3 (2‑methoxyethoxy) at the 4‑position.
Functional groups: primary aniline (weak base), anisole-type aryl ether (–O–R), internal ether (–CH2–CH2–O–), and an alkyl substituent (–CH3).
2D description: A benzene ring bears –NH2 at C1, –CH3 at C3, and –OCH2CH2OCH3 at C4. The para ether oxygen links the ring to an ethoxy chain terminating in a methoxy group. No stereocenters are present; the molecule is achiral.
Notes
Structural features predict increased electron density on the ring (two oxygen substituents and an aniline), enhancing electrophilic aromatic substitution (EAS) reactivity and directing effects (overall ortho/para directors relative to each substituent).
Aryl ether (para –O–CH2–CH2–OCH3): electron-donating, activating the ring for electrophilic substitution; potential site for ether cleavage under strong Lewis/Brønsted acids if desired.
Meta methyl: weakly activating and ortho/para-directing relative to itself; provides steric bias in EAS and can be oxidized (harsh) or benzylicly functionalized under radical conditions.
Retrosynthetic value
Serves as a convergent node for constructing substituted diarylamines (via N‑arylation) or benzanilide-type motifs (via N‑acylation followed by further elaboration).
The diazonium strategy allows late-stage diversification of the aryl ring without disturbing the ether chain.
Named reactions and tactics (literature)
Buchwald–Hartwig amination (as amine partner) to forge C–N bonds.
Schotten–Baumann and Steglich amidations for rapid amide library synthesis.
Sulfonylation with aryl/alkyl sulfonyl chlorides to generate sulfonamide probes.
Balz–Schiemann (via tetrafluoroborate diazonium) for aryl fluorination, when applicable to substrate stability.
Purification/handling
Protonation with HCl to form water-soluble salts for extraction; basify to recover free base. Silica gel chromatography generally effective; add 0.1–1% Et3N to mobile phase to minimize streaking of basic compounds.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biologic or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.
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