4-(4-Ethylphenoxy)aniline - ≥95% , CAS No.41295-21-0

CAS: 41295-21-0 Cat. No.: E1298345 Formule: C₁₄H₁₅NO Poids moléculaire: 213.28 PubChem CID: 7139197

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Expédié en

Normal

Pureté

≥95%

Noms et identifiants

Sourires canoniques

CCC1=CC=C(C=C1)OC2=CC=C(C=C2)N

IUPAC Name

4-(4-ethylphenoxy)aniline

InChIKey

HSZDEKXXWFNXMN-UHFFFAOYSA-N

INCHI

1S/C14H15NO/c1-2-11-3-7-13(8-4-11)16-14-9-5-12(15)6-10-14/h3-10H,2,15H2,1H3

Isomères SMILES

CCC1=CC=C(C=C1)OC2=CC=C(C=C2)N

PubChem CID

7139197

Poids moléculaire

213.28

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Diphenylethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Diphenylethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylethers
• Alternative Parents: Diarylethers Phenoxy compounds Phenol ethers Aniline and substituted anilines Primary amines Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Diphenylether - Diaryl ether - Phenoxy compound - Aniline or substituted anilines - Phenol ether - Ether - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Amine - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
• 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

Propriétés chimiques et physiques

• Poids moléculaire: 213.270 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 213.115 Da
• Monoisotopic Mass: 213.115 Da
• Topological Polar Surface Area: 35.300 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 191.000
• 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

No assay or kit-style application protocols are specified for this item. As a small-molecule building block, usage protocols depend on the intended synthetic transformation. Refer to the Reaction Conditions, Synthetic Utility, and Solvent Selection sections for practical guidance and adapt standard organic synthesis procedures accordingly.

Biological Roles

This product is a synthetic aromatic amine and is not a known endogenous metabolite or cofactor.

• General context (literature/general)
  • Primary anilines can engage in hydrogen bonding and π–π interactions; many serve as pharmacophores or materials motifs, but specific biological roles are structure- and substitution-dependent.
  • The diaryl ether scaffold is common in bioactive molecules and materials, tuning electronics and lipophilicity; however, no specific biological function is ascribed to this compound.
  • Protonation state near physiological pH: largely neutral (anilinium pKa typically ~4.6–5.5), implying limited ionization at neutral pH.

Note: Any biological testing must be conducted under appropriate approvals. This product is supplied strictly for research use only.

Buffer Applications

Not typically used as a buffering agent. As a non-ionic aromatic amine with low aqueous solubility and weak basicity, it is not suited for preparing conventional biological or analytical buffers. For aqueous work, consider standard systems (phosphate, acetate, Tris) and consult the sections on Reaction & Applications and Solvent Selection for relevant organic-phase practices.

Green Alternatives

When planning reactions with 4-(4-ethylphenoxy)aniline, consider solvent and reagent selection to reduce environmental impact while maintaining performance.

• Greener solvent swaps (literature/general)
  • Replace chlorinated solvents (DCM/CHCl3) with ethyl acetate, 2-MeTHF, CPME, or toluene where feasible.
  • For polar aprotic environments, consider propylene carbonate or sulfolane as DMF/NMP substitutes when high-boiling media are acceptable.
• Example comparison (literature/general)
  • DCM vs EtOAc: EtOAc is biodegradable and less toxic; similar polarity for many acylations/sulfonylations; easier waste handling.
  • THF vs 2-MeTHF: 2-MeTHF is bio-based, forms fewer peroxides, and enables biphasic workups; comparable performance in many coupling and protection steps.
  • Toluene vs CPME: CPME offers broad stability window and easy drying; toluene remains widely available and recyclable; choose based on temperature needs and regulatory context.
• Reagent choices
  • Use carbamoylation via organic carbonates (e.g., CDI) as alternatives to phosgene-derived reagents.
  • Employ aqueous nitrite diazotizations with minimal acid excess and efficient quenching to reduce nitrosamine risks.

Tradeoffs: greener solvents may alter rates/solubilities; validate at small scale and track EHS profiles alongside yield and selectivity.

Pharmaceutical Uses

• Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet.
• General formulation/manufacturing context (literature/general)
  • Role: synthetic intermediate/building block for discovery chemistry, enabling preparation of sulfonamides, amides, ureas, and diarylamines.
  • Advantages: electron-rich aniline enables diverse derivatizations; diaryl ether backbone imparts lipophilicity and metabolic stability in lead optimization campaigns.
  • Considerations: control of aromatic amine impurities (nitrosamines, over-acylation byproducts) is critical in GMP settings; robust analytical methods (HPLC/LC–MS) are recommended.

No therapeutic/clinical claims are made. This product is provided for research use only.

Physical Properties

• Item-specific specifications
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula (item): Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight (item): Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general properties for guidance only (not item specifications)
  • Physical state: typically a crystalline aromatic solid for para-substituted diaryl ether anilines.
  • Acid–base: primary anilines are weak bases; pKa of the conjugate acid (anilinium) typically ~4.6–5.5 (literature range), reduced basicity vs aliphatic amines due to resonance with the aromatic ring.
  • Solubility: low in water; good solubility in polar aprotic and aromatic organic solvents (e.g., THF, DMF, DMSO, toluene, EtOAc; literature/general).
  • Lipophilicity: expected moderate lipophilicity (logP in the ~2.5–3.5 range typical for diaryl ether anilines; literature/general).
  • UV: strong π→π* absorption in the UV due to two aromatic rings (literature/general); exact UV cutoff not specified for this item.
  • Thermal behavior: aromatic amines can discolor on air/light exposure; exact MP/BP for this exact compound not specified here.

For definitive limits (e.g., water content, UV absorbance, metal traces), consult the product CoA.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• General guidance on grades (context)
  • Research/technical grade: suitable for most synthetic applications; impurity profiles focus on organic byproducts and residual solvents.
  • High-purity or HPLC grade (if applicable): tighter limits on UV-absorbing impurities and trace metals; advantageous for photophysical measurements or trace analytics.
  • Stabilizers: none specified for this item. Aromatic amines are commonly shipped without stabilizers; if present, stabilizers would be disclosed on the CoA.
• What to check on the CoA
  • Identity confirmation (1H/13C NMR, MS, IR) and assay.
  • Residual solvents, water (Karl Fischer), and known synthetic byproducts.
  • If using for catalysis/materials, review any trace metal data.

Use the CoA/Spec Sheet for exact acceptance criteria relevant to your application.

Reaction and Applications

This compound is a versatile aniline-bearing diaryl ether, serving as a nucleophilic building block and motif donor in organic synthesis and materials chemistry.

• Representative applications (literature/general)
  • Electrophile capture at nitrogen: acylation to amides; sulfonylation to sulfonamides; carbamoylation to ureas/carbamates; phosphorylation to phosphoramidates.
  • N-arylation: Buchwald–Hartwig coupling with aryl halides/triflates to form diarylamines; ligand/base choice tunes selectivity and suppresses O-arylation.
  • Diazotization/azo chemistry: formation of diazonium salts (under cold mineral acid + nitrite), enabling azo dye coupling or Sandmeyer-type transformations on the aniline ring.
  • Redox/functionalization on the aniline ring: oxidative coupling to triarylamines (useful in OLED/OPV), or directed ortho-functionalization via transient anilide directing groups.
  • Protection strategies: formation of Boc/CBz/sulfonyl-protected anilines to modulate reactivity and enable orthogonal transformations.
• Role of the ether and ethyl substituent (literature/general)
  • The aryl–O–aryl linkage is generally inert to many conditions, providing a robust, electron-donating spacer that can modulate electronics and solubility.
  • The para-ethyl group increases lipophilicity and can influence packing/film-forming properties in materials applications.
• Practical notes
  • Dry, oxygen-controlled conditions benefit metal-catalyzed couplings; pre-base with weak inorganic bases for acylations to control selectivity.
  • Monitor for possible over-acylation or O- vs N-arylation in cross-couplings; ligand choice (e.g., BrettPhos, tBuXPhos) can favor N-arylation.

Reaction Conditions

General, literature-based guidance for common transformations of 4-(4-ethylphenoxy)aniline. These are not product specifications; optimize per application.

• Acylation/sulfonylation (to amides/sulfonamides)
  • Solvent: DCM, THF, EtOAc, or MeCN.
  • Base: Et3N, DIPEA, pyridine, or Na2CO3 (aqueous biphasic).
  • Temperature: 0–25 °C for additions; 25–60 °C for completion.
  • Typical time: 0.5–4 h; monitor by TLC/HPLC.
• Carbamoylation/urea formation
  • Reagents: CDI or triphosgene substitutes; or isocyanates for unsymmetrical ureas.
  • Solvent: THF, toluene, or DMF; 0–25 °C addition, then 25–60 °C.
• Buchwald–Hartwig N-arylation (as amine coupling partner)
  • Catalyst: Pd2(dba)3 (1–2 mol%) with biaryl phosphines (e.g., XPhos, tBuXPhos, BrettPhos 2–6 mol%).
  • Base: NaOtBu, KOtBu, or Cs2CO3.
  • Solvent: toluene, dioxane, or tBuOH; 80–110 °C.
  • Typical time: 4–18 h under inert atmosphere.
• Diazotization and azo coupling
  • Diazotization: 0–5 °C in 2–6 M HCl or H2SO4 with NaNO2 (1.0–1.1 eq) until positive nitrite test.
  • Coupling: weakly basic media (pH 8–10) in EtOH/H2O with phenol/aniline partners; 0–25 °C.

Yields are substrate- and condition-dependent; consult primary literature for analogous anilines and scale appropriately.

Safety and Handling

• Item-specific hazard data
  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.
• General safety considerations for aromatic amines and diaryl ethers (literature/general)
  • Potential hazards: many aromatic amines can be harmful if swallowed, in contact with skin, or inhaled; may cause skin/eye irritation and sensitization. Avoid dust formation.
  • PPE: use lab coat, safety glasses/goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dust or vapors.
  • Incompatibilities: strong oxidizing agents; strong acids may form anilinium salts; nitrosating agents form N-nitroso species; electrophiles may react at the amine.
  • First aid (general): in case of skin contact, wash with soap and water; eye contact, rinse cautiously with water for several minutes and seek medical attention; inhalation, move to fresh air; ingestion, rinse mouth and seek medical attention. Always follow institutional protocols.
  • Environmental: avoid release to the environment; collect spills with inert absorbents and dispose according to regulations.
• Peroxide formation: diaryl ethers are generally less prone to peroxide formation than dialkyl ethers, but routine peroxide testing is not typically required.

Authoritative safety information is provided in the SDS; consult it before use.

Solvent Selection

• Solubility/miscibility profile (literature/general)
  • Poorly water-soluble; readily soluble in common organic solvents: DCM, CHCl3, EtOAc, toluene, THF, 1,4-dioxane, DMF, DMSO, MeCN.
  • The basic aniline can form salts in strong acids, increasing aqueous solubility transiently.
• Polarity considerations
  • Neutral form is moderately lipophilic; polar aprotic solvents (DMF/DMAc/DMSO/NMP) aid in nucleophilic or coupling chemistry; aromatic solvents (toluene/xylene) are useful for high-temperature operations and minimizing hydrogen bonding to the amine.
• Practical selection
  • For acylations/sulfonylations: DCM, THF, MeCN, or pyridine as base/solvent.
  • For diazotization/azo coupling: mixed aqueous mineral acid for diazotization; coupling in ethanol/acetate buffer or basic aqueous-organic mixtures.
  • For Pd-catalyzed N-arylation (when used as nucleophile): toluene, dioxane, or tBuOH with bases like NaOtBu or Cs2CO3.
• Comparison (literature/general)
  • Toluene vs dioxane: toluene enables higher temperatures and easy removal; dioxane offers better polarity but regulatory considerations may apply.
  • DMF/DMSO: excellent solvation but difficult removal; consider 2-MeTHF or CPME as greener, more volatile alternatives where feasible.

Storage and Reconstitution

• Storage conditions (from Product Data)
  • Store at room temperature.
  • Shipped: normal (ambient) conditions.
• General handling
  • Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to air and light to minimize discoloration/oxidation of aromatic amines.
  • If hygroscopicity or caking is observed (not typical but possible for some amines), handle quickly and reseal with desiccant.
• Reconstitution
  • Not applicable as a buffer/biological reagent. For solution preparation in the lab, dissolve in a suitable dry organic solvent (e.g., DCM, toluene, THF, DMF, or DMSO) appropriate to the intended application.
• Stability
  • Long-term stability is formulation- and storage-dependent. For definitive retest/expiry dating and any stabilizer information, refer to the CoA/Spec Sheet and SDS.

Research use only; not for human or animal use.

Structure and Identity

A para-aminophenyl ether bearing a para-ethyl substituent on the distal ring; an aniline linked through oxygen to a 4-ethylphenyl ring.

• Item-specific identifiers (from Product Data)
  • SKU: E1298345
  • Product name: 4-(4-Ethylphenoxy)aniline
  • CAS: 41295-21-0
  • CID: 7139197
  • InChIKey: 130246 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed identifiers and description (informational)
  • Typical SMILES (literature): Nc1ccc(Oc2ccc(CC)cc2)cc1
  • 2D structural features: two para-substituted benzene rings connected by an ether oxygen (Ar–O–Ar′); one ring bears a para–NH2 (aniline) and the other bears a para–ethyl group (–CH2CH3). No stereocenters; fully aromatic system.
  • Functional groups: primary aromatic amine (aniline), aryl–aryl ether (diaryl ether), ethyl substituent.
• Composition (literature/computed)
  • Molecular formula (literature/computed): C14H15NO
  • Molecular weight (literature/computed): ~213.28 g/mol

Note: Where item-specific identifiers are missing, consult the CoA/Spec Sheet for definitive values.

Synthetic Utility

Key functional groups and their synthetic leverage:

• Aniline nitrogen (nucleophilic center)
  • Acylation to amides, sulfonylation to sulfonamides, carbamoylation (CDI, chloroformates) to ureas/carbamates.
  • N-arylation via Buchwald–Hartwig coupling to generate diarylamines; careful ligand/base selection minimizes O-arylation of the ether oxygen.
  • Protection (Boc, Cbz, tosyl) enables orthogonal chemistry on the aromatic rings (e.g., electrophilic substitution, metalation).
• Aromatic rings (electrophilic/nucleophilic substitution)
  • Para-substituted rings limit further para EAS; ortho positions can be targeted under directed metalation using N-acyl anilide as a directing group.
  • Diazotization of the aniline ring allows Sandmeyer-type transformations (Ar–N2+ to Ar–X, CN) and azo coupling to phenols/anilines.
• Ether linkage
  • Generally inert; survives many oxidative and basic conditions; can participate in SNAr only under forcing conditions on highly activated partners, not typically at this scaffold.

This scaffold is also used to install electron-donating aryl-amine motifs in optoelectronic materials (triarylamine derivatives), dyes, and ligands (literature/general).

Target Specificity

Not applicable. This product is a small-molecule chemical reagent, not a biological targeting reagent (e.g., antibody, inhibitor with defined target). No item-specific target, epitope, or species reactivity information is provided.

Foire aux questions

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 41295-21-0, the molecular formula is C14H15NO, and the molecular weight is 213.28 g/mol. InChIKey HSZDEKXXWFNXMN-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.