Ethyl 2-(4-phenoxyphenyl)acetate - ≥97% , CAS No.14062-26-1

CAS: 14062-26-1 Cat. No.: E727574 Formula: C₁₆H₁₆O₃ Peso molecolare: 256.3 PubChem CID: 13567666

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥97%

Nomi e identificatori

Sorrisi canonici

CCOC(=O)CC1=CC=C(C=C1)OC2=CC=CC=C2

IUPAC Name

ethyl 2-(4-phenoxyphenyl)acetate

InChIKey

CPYLMUNOJSVCRZ-UHFFFAOYSA-N

INCHI

1S/C16H16O3/c1-2-18-16(17)12-13-8-10-15(11-9-13)19-14-6-4-3-5-7-14/h3-11H,2,12H2,1H3

Isomeri SMILES

CCOC(=O)CC1=CC=C(C=C1)OC2=CC=CC=C2

PubChem CID

13567666

Peso molecolare

256.3

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 Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Diphenylether - Diaryl ether - Phenoxy compound - Phenol ether - Carboxylic acid ester - Monocarboxylic acid or derivatives - Ether - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic homomonocyclic compound
• Descrizione: 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

Proprietà chimiche e fisiche

• Peso molecolare: 256.300 g/mol
• XLogP3: 3.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 256.11 Da
• Monoisotopic Mass: 256.11 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 263.000
• 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 validated bioassay protocols are associated with this small-molecule intermediate for this SKU.

General laboratory protocols (chemistry-focused, literature-based):

• Preparative hydrolysis to acid: dissolve substrate in THF/MeOH/H2O (2:1:1), add 1–2 equiv NaOH, stir at rt 2–4 h; monitor by TLC/HPLC. Acidify to pH ~2; extract with EtOAc.
• LiAlH4 reduction to alcohol: suspend LAH in dry THF under nitrogen, cool to 0 °C, add a THF solution of the ester dropwise, warm to rt 1–2 h; quench cautiously (H2O, NaOH aq., H2O), filter, and concentrate.
• Enolate alkylation: prepare LDA at –78 °C in dry THF, add ester solution slowly, age 30 min, add electrophile; quench with NH4Cl at –20 to 0 °C.

These are generic starting points. For application-specific protocols, consult the primary literature and adjust to your substrate, scale, and safety constraints.

Biological Roles

This product is supplied strictly for research use; no clinical or in vivo use is intended or implied.

General biochemical context (literature-based; not item-specific):

• Ethyl 2-(4-phenoxyphenyl)acetate is a small, neutral, hydrophobic aromatic ester. It does not correspond to a known endogenous metabolite or cofactor in primary metabolism.
• The arylacetic ester motif appears in various synthetic analogs used for structure–activity investigations in chemical biology; however, this specific diaryl ether ester is best regarded as a chemistry intermediate rather than a probe.
• Stability considerations in biological media: esters can undergo enzymatic and chemical hydrolysis to the corresponding acid and ethanol. The diaryl ether is generally stable toward biotic cleavage but may affect lipophilicity and membrane partitioning of derived compounds.
• ADME-relevant features (qualitative): moderate-to-high lipophilicity, low aqueous solubility, and lack of strong H-bond donors; these features influence passive diffusion and binding in model systems but require empirical confirmation per derivative.

If using in biochemical assays:

• Ensure solvent vehicles (e.g., DMSO, EtOH) are compatible with your assay and kept at minimal percentages to avoid artifacts.
• Confirm purity and absence of phenolic/acid contaminants, as these can affect enzyme assays (e.g., esterase background).

No specific biological targets, pathways, or roles are assigned to this compound by Aladdin; consult the literature if you intend to derivatize it into bioactive motifs.

Buffer Applications

Not typically applicable. Ethyl 2-(4-phenoxyphenyl)acetate is a hydrophobic organic intermediate and is not used as a buffering agent.

Practical notes if working in aqueous systems:

• Solubilize in a water-miscible co-solvent (e.g., DMSO, MeCN, EtOH) before dilution into buffers; keep final organic content low (commonly ≤1–2% v/v) to maintain assay integrity.
• Avoid prolonged exposure to strongly basic buffers (risk of saponification) or strongly acidic media at elevated temperature (acidolysis).
• If sustained aqueous work is required, consider converting to the corresponding acid and forming a salt, or employing encapsulation/vehicles (e.g., cyclodextrins) in research contexts.

Green Alternatives

While Ethyl 2-(4-phenoxyphenyl)acetate is a substrate rather than a solvent, greener choices can be made for its processing and transformations.

Greener solvent options (literature-based guidance):

• Replace chlorinated solvents (e.g., DCM) with ethyl acetate or 2-methyltetrahydrofuran (2-MeTHF) where feasible.
• Use propylene carbonate or Cyrene for certain polar-aprotic needs in place of DMF/DMSO, noting solubility and reactivity tradeoffs with enolate chemistry.
• Prefer toluene over benzene; use heptane/EtOAc gradients for chromatography instead of hexane/DCM.

Sample comparison (general):

• DCM vs EtOAc: EtOAc is biodegradable and less toxic; may require temperature adjustment due to higher bp.
• THF vs 2-MeTHF: 2-MeTHF is bio-derived, forms fewer peroxides, and enables easier biphasic workups; note slightly different polarity and water content.
• DMF vs CPME/EtOAc: CPME/EtOAc reduce reproductive toxicity concerns; assess base solubility for enolate chemistry.

Process intensification:

• Employ catalytic transesterification and flow saponification to minimize solvent and energy use.
• Use micellar catalysis (aqueous surfactant media) for some coupling/functionalization steps when compatible with the hydrophobic substrate.

Waste minimization:

• Select bases with easier neutralization (e.g., carbonate) for hydrolysis when possible; recover and recycle ester-rich organic phases.

All substitutions should be validated by solubility and reaction outcome; greener choices must not compromise selectivity or safety.

Pharmaceutical Uses

No excipient or pharmacopeial status is specified for this item. This product is sold for research use only.

Formulation/manufacturing context (general, non-clinical):

• As a synthetic intermediate, Ethyl 2-(4-phenoxyphenyl)acetate may be transformed to acids, amides, or alcohols that are subsequently evaluated in medicinal chemistry workflows. The compound itself is not presented for therapeutic use.
• If handled in a development laboratory, typical considerations include solvent selection for reaction and crystallization, solid–liquid separation strategies (if crystalline), and control of residual solvents in downstream intermediates.
• Analytical controls suitable for pre-formulation research include orthogonal purity assessment (HPLC/GC/NMR) and stability studies under forced conditions (acid/base, oxidative, thermal) to inform handling of derived candidates.

Regulatory note:

• No claims are made regarding GMP manufacture, compendial compliance, or suitability as an active or inactive pharmaceutical ingredient. For any regulated application, synthesis and testing must be requalified under appropriate quality systems.

Physical Properties

Item-specific specifications (this listing):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Storage Conditions: Room temperature (item-specific).
• Other physico-chemical specifications (bp/mp, density, refractive index, elemental/trace specs): Not specified for this item; refer to CoA/Spec Sheet.

General properties (literature/computed guidance — not item specifications):

• Typical formula and FW (literature): C16H16O3; ~256.30 g/mol.
• Physical state: aromatic ester/diaryl ether that is often a low-melting solid or high-boiling liquid near ambient temperature; exact state depends on batch/crystallinity.
• Polarity/solubility: expected to be sparingly soluble in water and readily soluble in common organic solvents (e.g., dichloromethane, ethyl acetate, toluene, THF, acetone) due to the lipophilic diaryl ether and ester functionalities.
• Volatility: lower volatility than simple ethyl benzoates; high-boiling behavior typical for diaryl ethers/arylacetates.
• Acid–base: neutral compound (no strongly ionizable groups); benzylic acidity is modestly enhanced by the adjacent carbonyl but remains weak under neutral conditions.

Notes for handling based on physicochemical profile (general):

• Ensure complete dissolution in chosen organic solvent before use; gentle warming and/or sonication can assist with poorly soluble matrices.
• Avoid prolonged heating at elevated temperatures to limit ester hydrolysis or transesterification in the presence of alcohols/bases.
• If necessary, assess crystallinity by DSC or simple melting behavior to plan purification (recrystallization vs. chromatography).

Quality and Grades

Item-specific quality/grade:

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret common grades for this compound class (general guidance):

• Research grade: typically suitable for synthetic chemistry and method development. Purity often ≥95% by HPLC/GC/NMR unless otherwise noted. Trace residual solvents or synthesis by-products may be present.
• High-purity or ≥98% grade: preferred for structure–activity studies, analytical reference work, or reactions sensitive to impurities (e.g., metal-catalyzed couplings where phenolic/acidic impurities poison catalysts).
• HPLC grade (if offered): emphasizes low UV background and low non-volatile residue; relevant when using the compound as a chromatography standard or analyte.

Analytical expectations and controls (general):

• Identity confirmation: 1H/13C NMR consistent with diaryl ether signals, benzylic –CH2– singlet, and ethyl ester quartet/triplet; HRMS consistent with [M+H]+ for C16H16O3 (literature) if applicable.
• Purity assessment: integration of NMR, area% by HPLC/GC (orthogonal methods), and water/RS testing as needed.
• Stabilizers/antioxidants: none are typically required for this structure; if present in a specific lot, they will be declared on the CoA.

Documentation:

• For definitive specifications (assay, residual solvents, elemental analysis, water, metals, UV cutoff), consult the lot-specific CoA/Spec Sheet. If your application is impurity-sensitive, request analytical details prior to use.

Reaction and Applications

Use this diaryl ether arylacetate as a versatile building block for aromatic and benzylic transformations. Typical applications (literature-based; not item-specific):

• Hydrolysis (saponification) to the corresponding acid: base- or acid-catalyzed conversion to 2-(4-phenoxyphenyl)acetic acid, a common intermediate for amide couplings or further derivatization.
• Transesterification: exchange of the ethyl group under acidic (Fischer) or basic conditions to tailor protecting/solubility properties (e.g., tert-butyl, benzyl).
• Reduction: LiAlH4 or DIBAL-H reduction to the corresponding primary alcohol (benzylic hydroxymethyl) or, under milder conditions, to the aldehyde.
• Alpha-functionalization: deprotonation of the benzylic methylene (adjacent to the carbonyl) with strong, non-nucleophilic base (e.g., LDA) for alkylation, acylation, or carbon–carbon bond formation (e.g., aldol-type additions, Michael additions to activated acceptors).
• Oxidation of the benzylic position: controlled oxidation to aldehyde/acid (e.g., using SeO2 or TEMPO systems) after appropriate functional group management.
• Ether manipulations: aryl–O–aryl bonds are robust; however, targeted ether cleavage to unveil a p-hydroxyphenyl unit can be achieved under harsh Lewis-acidic conditions (e.g., BBr3 or AlCl3), enabling late-stage diversification.
• Cross-coupling compatibility: while lacking a direct cross-coupling handle, the diaryl ether and ester groups are generally compatible with Pd-catalyzed couplings performed on other partners in multistep sequences.

Application domains:

• Synthesis of advanced intermediates for materials, agrochemistry, and structure–property studies where a para-phenoxy substituent modulates electronic and steric profiles.
• Preparation of analog libraries by variation at the benzylic alpha position (diversity-oriented synthesis).

Reaction Conditions

General conditions from literature (guidance only; optimize for your system):

• Saponification to acid:

  • Reagents: NaOH or K2CO3 (aqueous), EtOH/THF/H2O mixture.
  • Conditions: 0.5–2 M base, rt to reflux, 1–6 h depending on solvent/base strength.
  • Workup: acidify to pH ~2, extract with EtOAc, dry, and concentrate.

• Ester reduction to alcohol/aldehyde:

  • Alcohol: LiAlH4 (THF, 0–25 °C, 1–3 h). Caution: exothermic; quench carefully.
  • Aldehyde: DIBAL-H (toluene or CH2Cl2, –78 to –50 °C, 1–2 equiv), then low-temperature quench.

• Alpha-alkylation (benzylic position):

  • Base: LDA or lithium bis(trimethylsilyl)amide (LiHMDS) in dry THF at –78 to –40 °C.
  • Electrophiles: primary alkyl halides, aldehydes (for aldol-like additions), or Michael acceptors (via related strategies).
  • Notes: ensure anhydrous conditions; slow addition of electrophile improves selectivity.

• Transesterification:

  • Acidic: catalytic p-TsOH in the target alcohol (reflux, Dean–Stark as needed) or solid acid resins.
  • Basic: NaOEt or TBD in the corresponding alcohol at 25–60 °C; remove ethanol byproduct.

• Ether demasking (to phenol, if desired):

  • Reagents: BBr3 (1–3 equiv per aryl–O–aryl site) in CH2Cl2 at –78 to 0 °C, then warm to rt. Yields and feasibility depend on substitution pattern; diaryl ethers are tougher than aryl–OMe.

Typical yields vary widely (50–90%) depending on substitution and conditions; run small-scale screenings to refine reagents, stoichiometry, and temperature profiles.

Safety and Handling

Item-specific hazard data for this SKU:

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety guidance for aromatic esters/diaryl ethers (literature-based; not item-specific):

• Likely hazards: combustible liquid/solid; may cause mild skin/eye irritation; harmful if swallowed in quantity. Actual classification must be confirmed on the SDS.
• PPE: wear lab coat, safety glasses or splash goggles, and suitable gloves (e.g., nitrile). Use in a fume hood to minimize inhalation of vapors/aerosols.
• Handling: avoid inhalation of dust/vapors and contact with skin/eyes. Keep away from ignition sources. Do not heat with strong base or strong acid without controls (ester cleavage risk).
• Incompatibilities: strong bases (saponification/transesterification), strong acids (acidolysis), strong oxidizers (oxidation of benzylic position/aryl ether). Moisture and alcohols can promote slow transesterification under basic conditions.
• First aid (overview; defer to SDS):
  • Inhalation: move to fresh air; seek medical advice if symptoms persist.
  • Skin: wash with soap and water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; remove contacts if present and easy.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire: use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and irritating fumes from aromatic residues.

Always consult the product-specific SDS for authoritative hazard classifications and response measures.

Solvent Selection

This product is a synthetic intermediate, not a solvent. Solvent selection pertains to dissolving/processing it in reactions or analyses.

General solvent compatibility (literature-based):

• Expected solubility: high in nonpolar and moderately polar organic solvents (e.g., dichloromethane, chloroform, toluene, THF, acetone, ethyl acetate, acetonitrile); very low in water.
• Polarity profile: predominantly hydrophobic (diaryl ether plus arylacetate). A modest dipole arises from the ester and ether oxygens, aiding solubility in medium-polarity solvents.

Practical selection by task:

• Reaction medium (base-sensitive chemistry minimized): toluene, DCM, or EtOAc; avoid protic alcohols if transesterification is a concern.
• Strong base enolate chemistry (alpha-functionalization): anhydrous THF or DME at sub-ambient temperatures with LDA/LHMDS.
• Hydrogenation/reductions (if applicable to other functionalities): ethyl acetate, THF, or alcohols under neutral conditions; avoid strong base with esters unless intended.
• Purification by flash chromatography: hexanes/EtOAc or toluene/EtOAc gradients provide good ring/ester separation behavior.
• Analytical HPLC: reversed-phase (C18) with MeCN/H2O or MeOH/H2O; anticipate late retention; add 0.1% acid modifier for peak shape if needed.

Comparison hints:

• Versus more polar benzylic esters, this compound may require less polar eluents for chromatography.
• Versus non-ether diaryl esters, the ether oxygen slightly increases polarity, improving solubility in THF/EtOAc without dramatically increasing water solubility.

Storage and Reconstitution

Item-specific storage information:

• Storage Conditions: Room temperature (as provided in Product Data).
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance/Physical state: Not specified for this item; refer to CoA/Spec Sheet.

General storage guidance for aromatic esters:

• Keep container tightly closed in a dry, well-ventilated place. Protect from excessive heat and direct sunlight.
• Avoid prolonged exposure to strong acids/bases and moisture if cap integrity is compromised; ester functions can slowly hydrolyze under harsh conditions.
• If long-term storage is planned, storing under inert gas (e.g., nitrogen) and in amber glass can help minimize oxidative discoloration of aromatic materials, though the diaryl ether/ester is generally stable.

Reconstitution/Preparation for use:

• Dissolve the compound in an appropriate anhydrous organic solvent (e.g., THF, DCM, EtOAc, toluene) to the desired concentration. Gentle warming and sonication can aid dissolution.
• Filter solutions through PTFE syringe filters (0.2–0.45 μm) prior to moisture/air-sensitive reactions.
• For analytical stocks, prepare solutions in high-purity solvents; document concentration gravimetrically or by quantitative NMR where precision is required.

Always follow the lot-specific CoA/SDS for any additional storage or handling instructions.

Structure and Identity

Ethyl 2-(4-phenoxyphenyl)acetate is an aromatic ether–containing arylacetic ester useful as a synthetic building block.

• SKU: E727574
• Product Name: Ethyl 2-(4-phenoxyphenyl)acetate
• CAS: 14062-26-1 (item-specific)
• CID: 13567666 (item-specific)
• InChIKey: 50644 (item-specific; truncated/abbreviated 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.

Structural features (general description):

• Core scaffold: a di-aryl ether (phenyl–O–phenyl) unit, where the “receiving” ring bears a benzylic acetate ester side chain (–CH2–CO2Et) para to the ether linkage.
• Functional groups: aryl ether (Ph–O–Ph) and ethyl arylacetate ester (–CH2–CO2Et).
• Aromatic system: two conjugated phenyl rings separated by an ether oxygen; the benzylic methylene (–CH2–) connects the ester to the para position of one ring.
• Stereochemistry: achiral; no stereogenic centers expected in the neutral molecule.

Literature identifiers (for reference only; not item-specific):

• Representative SMILES (literature): CCOC(=O)Cc1ccc(cc1)Oc2ccccc2
• Representative molecular formula (literature): C16H16O3
• Representative formula weight (literature): ~256.30 g/mol

2D structure in words: an ethyl ester of phenylacetic acid whose benzylic carbon is attached to a para-phenoxyphenyl ring; the para-oxygen further links to a second phenyl ring, forming a diaryl ether motif.

Synthetic Utility

Functional group leverage (literature-based):

• Ester handle (–CO2Et):
  • Hydrolysis to acid; subsequent coupling (amide/ester) with HATU, EDCI, DIC/DMAP, or via acid chlorides.
  • Reduction to alcohol (LiAlH4/DIBAL-H) or aldehyde (DIBAL-H, –78 °C).
  • Transesterification (acid or base catalysis) to tune protecting group and solubility.
  • Enolate generation at the benzylic position (LDA/LHMDS) for alkylation/acylation or aldol condensations.
• Diaryl ether (Ar–O–Ar):
  • Enhances lipophilicity and modulates electronics of the aryl system; stable under many conditions used for cross-couplings on other partners.
  • Can be cleaved to unveil phenols under forcing Lewis-acidic conditions (e.g., BBr3) enabling phenol-based derivatization.

Retrosynthetic value:

• Traceably connects to two common fragments: 4-hydroxyphenylacetic acid (or its esters) and chlorobenzene/phenol derivatives via nucleophilic aromatic substitution or Ullmann-type/Chan–Lam ether formation in earlier steps.
• The benzylic acetate unit provides a strategic branching point for C–C bond formation to build substituted diarylmethyl motifs.

Representative transformations:

• Knoevenagel-type condensations after conversion to the corresponding aldehyde or via active methylene chemistry under basic conditions with suitable electrophiles.
• Decarboxylative protocols (after hydrolysis/activation) to access diarylmethyl frameworks.
• Late-stage diversification through selective oxidation/reduction at the benzylic position.

Purification considerations:

• Aromatic esters with diaryl ethers often purify well by silica gel with hexanes/EtOAc; watch for tailing due to π–π interactions—add 0.1–1% TEA if acidic impurities cause streaking.

Target Specificity

Not applicable. This product is a small-molecule chemical intermediate and is not an antibody, enzyme, or affinity reagent. No antigen targets, epitopes, species reactivity, clone, or isotype information applies.