2-Ethoxy-4-methylaniline - ≥95% , CAS No.23385-44-6

CAS: 23385-44-6 Cat. No.: E1056189 Formula: C₉H₁₃NO Molecular Weight: 151.21 EC Number: 865-816-9 PubChem CID: 24706534

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CCOC1=C(C=CC(=C1)C)N
• IUPAC Name: 2-ethoxy-4-methylaniline
• InChIKey: QINJFUHLZDSQIC-UHFFFAOYSA-N
• INCHI: 1S/C9H13NO/c1-3-11-9-6-7(2)4-5-8(9)10/h4-6H,3,10H2,1-2H3
• Isomeric SMILES: CCOC1=C(C=CC(=C1)C)N
• PubChem CID: 24706534
• Molecular Weight: 151.21

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenol ethers
      • Subclass Aminophenyl ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenol ethers
• Subclass: Aminophenyl ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Aminophenyl ethers
• Alternative Parents: Phenoxy compounds Aniline and substituted anilines Aminotoluenes Alkyl aryl ethers Primary amines Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aminophenyl ether - Phenoxy compound - Aminotoluene - Aniline or substituted anilines - Alkyl aryl ether - Toluene - Monocyclic benzene moiety - Ether - Primary amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organic oxygen compound - Amine - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 151.210 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 151.1 Da
• Monoisotopic Mass: 151.1 Da
• Topological Polar Surface Area: 35.300 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 116.000
• 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

Application Protocols

Not applicable. No kit-style or bioassay protocols are associated with this small-molecule reagent. For synthetic applications, follow reaction-specific procedures in the literature, adapting stoichiometry, solvent, and temperature to your substrate and scale. Always consult the SDS before handling and the CoA for item-specific quality information.

Biological Roles

This compound is a synthetic organic building block and is not a native metabolite or biochemical cofactor.

• General notes (literature)
  • Aryl amines can interact with biomolecules through hydrogen bonding or cation–π interactions when protonated, but 2-ethoxy-4-methylaniline is not known to have defined physiological roles.
  • In biological matrices, anilines may undergo Phase I oxidation (N-oxidation, ring hydroxylation) and Phase II conjugation (glucuronidation, sulfation) if exposure occurs; such information is provided for context only and not as a use recommendation.

No biological function, target, or pathway relevance is claimed for this product. Use is limited to research and laboratory synthesis.

Buffer Applications

Not typically applicable. 2-Ethoxy-4-methylaniline is not used as a buffering agent. If aqueous work is performed, acid–base extraction may involve temporary formation of its anilinium salts using standard laboratory buffers or mineral acids. For true buffering needs, select established buffer systems (e.g., acetate, phosphate, Tris) appropriate to your pH range.

Green Alternatives

While 2-ethoxy-4-methylaniline itself is a target building block, greener choices can be made in its synthesis and use.

• Greener process choices (general guidance)
  • Avoid nitro reduction with stoichiometric tin/iron in mineral acid; prefer catalytic hydrogenation (H2/Pd, H2/Ni) or transfer hydrogenation to minimize metal salt waste.
  • For acylations/carbamoylations, replace chlorinated solvents (DCM) with EtOAc, 2-MeTHF, or CPME when feasible; use organic bases (DIPEA) to avoid inorganic salt slurries.
  • Oxidation-sensitive handling: store under air-free, amber conditions to reduce need for rework/purification.
• Solvent replacement examples (illustrative; evaluate for your process)
  • DCM → 2-MeTHF or EtOAc (similar polarity, better EHS profile).
  • DMF/NMP → Cyrene, propylene carbonate, or green ethers where catalysis allows.

Comparison snapshot (general)

• DCM: excellent solvating power; high environmental and toxicity concerns.
• 2-MeTHF/CPME: bio-based options; broader flammability range, but lower toxicity and ease of recovery.
• EtOAc: biodegradable, low toxicity; may require higher temperatures for some reactions.

Adopt catalytic, solvent-minimized conditions and in-line purification (e.g., scavengers) to reduce waste. Always validate substitutions for performance and safety.

Pharmaceutical Uses

• Item-specific pharmacopeial status and excipient roles: Not specified for this item; refer to CoA/Spec Sheet.

General context only (no therapeutic claims):

• Substituted anilines like 2-ethoxy-4-methylaniline can serve as intermediates in the synthesis of active pharmaceutical ingredient (API) candidates or advanced intermediates, enabling introduction of ortho-alkoxy/para-alkyl motifs.
• Functionalization pathways include N-acylation to give anilide scaffolds, urea/carbamate formation, or diazotization to diversify the aryl core. Any use in GMP manufacturing requires appropriate qualification, impurity profiling, and supplier change control.

Physical Properties

Item-specific specifications for physical constants are not provided in the Product Data.

• Item-specific values
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general data for the neat compound (reference only; not product specifications)
  • Molecular formula: C9H13NO
  • Formula weight: ~151.21 g/mol
  • Physical state at ambient conditions: substituted anilines of this type are typically low-melting solids or high-boiling liquids; exact MP/BP not specified for this item.
  • Solubility profile: expected to be miscible with many organic solvents (e.g., alcohols, ethers, chlorinated solvents, aromatics). Sparingly soluble in water as the free base; readily water-soluble as its protonated anilinium salt under acidic conditions (literature behavior of anilines).
  • Basicity: primary anilines typically have conjugate acid pKa around 4–6 (literature); electron-donating substituents generally increase basicity modestly. No item-specific pKa is provided.
  • Density, refractive index, logP, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Always consult the product’s CoA/SDS for measured properties of the supplied lot.

Quality & Grades

• Item-specific quality information
  • 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 on typical grades for amine building blocks (general information)
  • Research/Chemical grade: suitable for most synthetic applications; typical assay reported by GC/LC with limits on common impurities (water, residual solvents, related aromatics). UV profile is generally not controlled unless designated “HPLC grade.”
  • High-purity/99%+: beneficial for catalyst-sensitive transformations (e.g., cross-couplings, metal-catalyzed C–N formations) or where color and trace nitro/azo impurities impact downstream quality.
  • Water content: often reported by Karl Fischer for liquid amines; for this item, the specific limit is Not specified for this item; refer to CoA/Spec Sheet.
  • Metals/peroxides/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Practical notes
  • If color develops on storage (common for anilines via air oxidation), a short pass over activated alumina or treatment with a trace of antioxidant/reductant can restore quality; verify purity by GC/1H NMR.
  • For stringent applications, request the latest CoA with detailed impurity profile and recommended analytical methods.

Reaction & Applications

2-Ethoxy-4-methylaniline is a versatile, strongly activating aryl amine useful as a building block and nucleophile.

• Representative transformations (literature/general)
  • N-Acylation/Carbamoylation: Rapid formation of amides, ureas, and carbamates with acyl chlorides, anhydrides, or chloroformates; control exotherm and HCl neutralization with tertiary bases.
  • Schiff base formation: Condenses with aldehydes/ketones to give imines (use molecular sieves or Dean–Stark) that can be reduced to N-alkyl derivatives.
  • Diazotization/Sandmeyer: Conversion of the aniline to the corresponding diazonium salt (typically 0–5 °C, NaNO2/HX) enables Sandmeyer-type substitutions at the amine position, providing access to diverse o-ethoxy-p-tolyl derivatives.
  • Electrophilic aromatic substitution: The combination of –NH2 and –OEt markedly activates the ring; nitration, sulfonylation, or Friedel–Crafts reactions proceed under milder conditions but require regioselectivity control due to multiple activating groups.
  • N-Arylation: Can participate as a nucleophile in Buchwald–Hartwig C–N couplings with aryl (pseudo)halides; ligand/base selection tunes selectivity for primary anilines.
• Application areas (general)
  • Dye and pigment intermediates (coupling to diazonium salts to form azo dyes with tailored electronic properties).
  • Specialty monomers and polymer modifiers (via isocyanate/urethane linkages or amide incorporation).
  • Agrochemical and material science intermediates where ortho-alkoxy/para-alkyl patterns are desired.
• Practical tips
  • Dry before moisture-sensitive steps (azeotrope or molecular sieves). Trace oxidation products can be removed by short-path distillation or alumina.
  • For diazotization, maintain low temperature and exclude phenolic impurities to minimize azo byproducts.

Reaction Conditions

The following are literature/general conditions for common transformations of primary anilines like 2-ethoxy-4-methylaniline; they are guidance only and not specifications for this item.

• N-Acylation (anilide formation)
  • Solvent: DCM, THF, toluene, or EtOAc. Base: triethylamine or DIPEA (1.1–2.0 equiv). Temperature: 0 °C to rt. Typical times: 0.5–4 h. Monitor by TLC/LC.
• Carbamate/Urea formation
  • With chloroformates or CDI-activated alcohols in DCM/THF; base scavenges HX. 0–25 °C, 1–6 h.
• Schiff base and reductive amination
  • Carbonyl partner (1.0 equiv), amine (1.2 equiv), 3 Å molecular sieves in toluene or MeOH; reduce with NaBH3CN or catalytic hydrogenation. 20–60 °C, 2–16 h.
• Diazotization/Sandmeyer
  • 2–3 M HCl or HBF4 at 0–5 °C; NaNO2 (1.05–1.2 equiv) added slowly; subsequent Cu-catalyzed substitution with X− (Cl−/Br−/CN−) or thermal decomposition to phenol/aryl fluoride (with HBF4). Maintain cold to stabilize diazonium.
• Buchwald–Hartwig C–N coupling (as nucleophile)
  • Catalyst: Pd2(dba)3 or Pd(OAc)2 (1–3 mol%), ligand: BINAP/XPhos/BrettPhos (2–6 mol%), base: NaOtBu/K3PO4, solvent: toluene/dioxane/THF, 60–110 °C, 4–24 h. Air/moisture exclusion beneficial.

Always optimize conditions for your substrate set. Confirm identity/purity of this item before use via NMR/GC/LC as appropriate.

Safety & Handling

• Item-specific hazard data
  • Signal Word: Not specified for this item; refer to SDS.
  • GHS Classification: Not specified for this item; refer to SDS.
  • Hazard (H-) Statements and Pictograms: Not specified for this item; refer to SDS.
• General safety considerations for aryl amines (literature/guidance; not product-specific classification)
  • Primary anilines can be harmful if swallowed, in contact with skin, or inhaled; may cause skin/eye irritation and methemoglobinemia with significant exposure. Avoid aerosols and prolonged skin contact.
  • Many anilines are combustible; keep away from ignition sources. Use in a fume hood due to odor and potential vapor toxicity.
• Incompatibilities and reactive hazards (general)
  • Strong oxidizers (risk of exothermic reaction/oxidation).
  • Acid chlorides/anhydrides and isocyanates (will react to form amides/ureas). Manage heat evolution.
  • Nitrosating agents under acidic conditions may form N-nitroso species.
• PPE and handling
  • Wear lab coat, nitrile gloves, and splash goggles. Use a chemical fume hood.
  • In case of skin contact: wash with soap and water. Eye contact: rinse cautiously with water for several minutes; seek medical attention as needed. Inhalation: move to fresh air; obtain medical advice. Ingestion: rinse mouth; do not induce vomiting; seek medical help.
• Spill/Fire
  • Absorb small spills with inert material; dispose per regulations. For fire, use CO2, dry chemical, or foam. Refer to SDS for authoritative guidance.

Solvent Selection

This product is a reactive aryl amine building block rather than a solvent. However, selecting appropriate solvents for its handling and reactions is important.

• Polarity/miscibility (general behavior)
  • Expected to dissolve well in moderately polar aprotics (THF, DCM, acetonitrile, DMF, DMSO) and aromatics (toluene).
  • Sparingly soluble in water as the free base; fully soluble in dilute mineral or organic acids as the anilinium salt.
• Choosing media for common operations
  • Salt formation/extractions: Partition into organic phase as free base; drive into aqueous phase by protonation (HCl, H2SO4, AcOH). Back-extract with base.
  • N-acylations/carbamoylations: Use DCM, THF, or toluene with non-nucleophilic bases (DIPEA, pyridine) to control HCl/acid scavenging.
  • Electrophilic aromatic substitutions (EAS): Often run in acetic acid, nitrobenzene, or polar solvents that stabilize cationic intermediates; note that –NH2 and –OR activate the ring strongly.
  • Metal-catalyzed couplings (if used as nucleophile or directing group transformations): Anhydrous toluene/THF/dioxane are typical.
• Comparison notes
  • Relative to more hydrophobic anilines, the ethoxy group can increase solubility in polar organics and facilitate homogeneous reaction conditions.

Always verify solvent compatibility with your specific reaction and consult the SDS for safety-driven solvent choice.

Storage & Reconstitution

• Item-specific storage/shipping
  • Storage Conditions: Room temperature (per Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
  • Physical form/Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• General handling and stability (literature guidance)
  • Primary anilines can slowly oxidize in air/light to colored impurities. Store tightly closed in a dry place, preferably under inert gas and protected from light to maintain assay and color.
  • If solid, keep desiccated to prevent caking; if liquid, minimize headspace oxygen and moisture.
• Reconstitution/Preparation for use
  • No reconstitution is required for neat material. For solution preparation, use anhydrous solvents when moisture-sensitive chemistry is planned. Filter through a PTFE syringe filter if particulate forms.
• Freeze–thaw guidance
  • Not generally necessary. If frozen for long-term storage, allow to reach room temperature before opening to avoid moisture uptake/condensation.

Always refer to the current CoA and SDS for lot-specific handling advice and stability information.

Structure & Identity

A substituted aniline bearing an ortho ethoxy and para methyl group on the phenyl ring.

• Item-specific (from Product Data)
  • CAS: 23385-44-6
  • SKU: E1056189
  • InChIKey (as provided): 297882
  • Storage: Room temperature
  • Research Use: For research use only
• Literature/computed identifiers (for reference; not item specifications)
  • Preferred name: 2-Ethoxy-4-methylaniline (o-ethoxy-p-toluidine)
  • Molecular formula: C9H13NO (literature)
  • Molecular weight: ~151.21 g/mol (literature)
  • SMILES (literature): CCOc1cc(C)ccc1N
  • InChIKey (literature): MWQXSRITQYVYBL-UHFFFAOYSA-N
• Structural features (general description)
  • Aromatic ring (benzene) bearing: an aniline moiety (–NH2) at C1, an ethoxy substituent (–OCH2CH3) at C2 (ortho), and a methyl group (–CH3) at C4 (para).
  • Functional groups: primary aryl amine (basic, nucleophilic), aryl ether (ethoxy, relatively electron-donating), and alkyl substituent (methyl, weakly activating).
  • Electronic character: overall ring is activated toward electrophilic substitution by the combined +M effects of –NH2 and –OR; directs further substitution primarily to ortho/para positions relative to each activator (subject to steric bias).

Synthetic Utility

• Functional group reactivity (general)
  • –NH2: nucleophilic at nitrogen (acylation, sulfonylation, carbamoylation), forms imines/enamines, and serves as a handle for diazotization to aryl diazonium salts.
  • –OEt (aryl ether): resonance-donating, enhances ring activation; relatively inert under many conditions but can direct EAS and participate in metal-catalyzed C–O activation under specialized conditions (e.g., Ni-catalyzed ether cleavage).
  • –CH3: weak activator; provides benzylic C–H that can be oxidized or halogenated under radical conditions.
• Named/typical transformations
  • Buchwald–Hartwig amination (as amine coupling partner) with aryl halides.
  • Sandmeyer/Meerwein reactions from the diazonium salt to access halo-, cyano-, or hydroxy- derivatives.
  • Schotten–Baumann and Mukaiyama-type acylations to form anilides.
  • Reductive amination to install N-alkyl substituents after imine formation.
• Retrosynthetic value
  • Orthogonal handles allow late-stage diversification at N (acyl/alkyl), ring (EAS), and benzylic positions. The ortho-ethoxy/para-methyl pattern can tune electronics for downstream steps.
• Practical orchestration
  • Protect –NH2 when harsh electrophilic conditions are required (e.g., as acetamide/carbamate) to control regioselectivity and suppress overreaction.
  • Use acid–base extraction toggling to simplify workups and purifications.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or biological targeting reagent. No antigen/epitope or species reactivity applies.