4-Ethylphenyl 4-ethylbenzenecarboxylate - ≥90% , CAS No.104899-04-9

CAS: 104899-04-9 Cat. No.: E984597 Summenformel: C₁₇H₁₈O₂ Molekulargewicht: 254.33 PubChem CID: 1490294

GRADE & PURITY ≥90%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥90%

Storage

Room temperature

Reinheit

≥90%

Namen und Kennungen

Kanonisches Lächeln

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

IUPAC Name

(4-ethylphenyl) 4-ethylbenzoate

InChIKey

FOYBYRMCNLYRIS-UHFFFAOYSA-N

INCHI

1S/C17H18O2/c1-3-13-5-9-15(10-6-13)17(18)19-16-11-7-14(4-2)8-12-16/h5-12H,3-4H2,1-2H3

Isomere SMILES

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

PubChem CID

1490294

Molekulargewicht

254.33

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Klasse Depsides and depsidones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Klasse: Depsides and depsidones
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Depsides and depsidones
• Alternative Parents: Phenol esters Benzoic acid esters Phenoxy compounds Benzoyl derivatives Carboxylic acid esters Monocarboxylic acids and derivatives Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Depside backbone - Benzoate ester - Phenol ester - Benzoic acid or derivatives - Phenoxy compound - Benzoyl - Monocyclic benzene moiety - Benzenoid - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 254.320 g/mol
• XLogP3: 5.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 254.131 Da
• Monoisotopic Mass: 254.131 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 271.000
• 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 validated bioassay formats (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic or analytical use, refer to the Reaction Conditions and Solvent Selection sections for general procedural guidance.

Biological Roles

This compound is a synthetic aromatic ester and is not known to occur in biological systems.

• General considerations (research context only):
  • Aromatic benzoate esters can serve as model substrates for studying esterases and lipases in vitro; conversion rates are typically much lower than for aliphatic esters due to decreased electrophilicity and steric/electronic effects.
  • Hydrophobicity and aromaticity may drive nonspecific binding to lipid phases, micelles, or proteins in biophysical studies; such interactions are typically used only as probes in model systems.
  • No known roles in metabolism, signaling, or structural biology have been reported for this specific di-para-ethyl aryl ester.

Caution: Any in vitro biochemical assays using this reagent should be framed as mechanistic or methodological research. It is supplied for research use only and is not intended for food, cosmetic, diagnostic, or therapeutic applications.

Buffer Applications

Not typically applicable. 4-Ethylphenyl 4-ethylbenzenecarboxylate is a hydrophobic aromatic ester with negligible water solubility and no acid/base buffering capacity in the physiological pH range. If aqueous work is required (e.g., biocatalysis), use co-solvent systems or emulsions and refer instead to the Solvent Selection and Reaction & Applications sections.

Green Alternatives

Greener choices relate primarily to solvent and reagent selection when using this aryl ester in synthesis or purification. The compound itself is a benign-by-design candidate only insofar as it avoids halogens; however, it remains hydrophobic and poorly biodegradable.

• Prefer greener solvents when feasible:
  • Replace DCM/CHCl3 with EtOAc, 2-MeTHF, CPME, or toluene depending on polarity needs.
  • For high-temperature steps, anisole or cyclopentyl methyl ether (CPME) can substitute for xylene in some protocols.
• Catalysis choices:
  • Employ catalytic transesterification (e.g., organocatalysts, enzymes/lipases) instead of stoichiometric reagents when compatible.
  • Use nickel-catalyzed C–O activation as an alternative to acid chlorides for cross-couplings, reducing acid chloride handling.

Comparison (general; literature-informed):

• DCM vs EtOAc
  • Worker exposure: DCM (concern) vs EtOAc (lower concern).
  • Waste: Halogenated vs non-halogenated.
  • Polarity: DCM more polar; EtOAc often sufficient for aryl esters.
• THF vs 2-MeTHF
  • Stability: THF forms peroxides; 2-MeTHF slower peroxide formation and higher bp.
  • Sourcing: 2-MeTHF can be bio-based.

Practical steps:

• Employ minimal solvent volumes, recycle where possible, and validate greener eluents (e.g., cyclohexane/EtOAc) for flash chromatography.
• Evaluate enzyme-catalyzed ester transformations in aqueous-organic biphasic systems to reduce organic solvent demand.

Pharmaceutical Uses

No item-specific pharmacopeial status, excipient grade, or formulation role is provided. This reagent is supplied for research use only.

• General context (literature/industry practice):
  • Aromatic benzoate esters are sometimes used in flavors/fragrances or as pro-moieties in medicinal chemistry research; however, this specific di-para-ethyl derivative is not a common pharmaceutical excipient.
  • In discovery chemistry, aryl esters may be employed as masked acids or phenols, or as lipophilicity modulators on screening compounds (internal R&D use).

If a GMP or compendial grade is required for any manufacturing-related study, request full regulatory documentation and confirm grade, residual solvents, and impurity profile. Do not use this item for therapeutic, diagnostic, or clinical applications.

Physical Properties

Item-specific specifications are not provided in the Product Data for this SKU. Do not treat the following as specifications; consult the CoA/Spec Sheet for authoritative values.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature/computed value for this structure: ~254.32 g/mol.)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature/computed: C17H18O2.)
• Boiling point, melting point, density, refractive index, viscosity, UV cut-off, water content, residual metals: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general expectations for aryl esters; literature):
  • Poorly soluble in water.
  • Readily soluble in nonpolar and moderately polar organic solvents (e.g., toluene, dichloromethane, THF, ethyl acetate, acetone).
• Partitioning (literature expectation): logP likely high due to two ethyl substituents and diaryl ester framework.

Notes for handling measurements (general):

• If determining purity or identity, GC/FID or HPLC (UV at ~230–280 nm) typically gives strong absorbance for aromatic esters; confirm wavelength empirically.
• For solid vs liquid state at room temperature: diaryl esters may be low-melting solids or high-boiling liquids; confirm actual state from the CoA prior to planning operations.

Quality and Grades

• Item-specific 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 grades and what they imply (general):

• Research grade reagents for synthetic chemistry are typically supplied at high purity suitable for reaction development, method validation, and materials research. If your application requires chromatographic or spectroscopic baselines (e.g., HPLC/GC reference), request an HPLC-grade or assay-by-GC verified lot.
• For photochemical or analytical applications, low-UV-absorbing solvent residues and low peroxide content can be important. Verify by CoA if these are critical, especially when using gradient HPLC/UV detection.
• Trace metal content can affect catalytic transformations (e.g., Ni/Pd-catalyzed C–O activation of aryl esters). If ppm metal limits are important, request ICP results for the lot.

Recommendations:

• If using in catalysis or kinetic studies, obtain a CoA including assay method (e.g., 1H NMR, GC, or HPLC), water content (Karl Fischer), and residual solvents.
• For reproducibility across campaigns, retain a sample of the received lot and record its baseline chromatographic behavior (retention time, UV spectrum) for internal QC.

Reaction and Applications

As a di-para-ethyl–substituted aryl ester, this compound serves as a hydrophobic, well-defined model substrate and intermediate in synthetic methodology and materials studies.

• Representative uses (literature/general):
  • Hydrolysis and transesterification kinetics as a sterically/electronically tuned aryl benzoate.
  • Nucleophilic acyl substitution to form amides (ester-to-amide conversion) under activated or catalytic conditions.
  • Metal-catalyzed C–O bond activation of aryl esters (Ni, Pd) enabling cross-coupling, decarbonylative couplings, and acyl transfer to nucleophiles.
  • Fries-type rearrangements under Lewis/Brønsted acidic conditions to generate acylated phenols (requires rigorous optimization).
• Practical tips:
  • Moisture control is important for base- or acid-catalyzed transesterifications and amidations; use dry solvent and glassware.
  • Electron-donating para-ethyl groups modestly increase aryl electron density, which can influence rates in metal-catalyzed C–O activation and in solvolysis.
  • Monitor reactions by GC or HPLC-UV (aromatic esters show strong absorbance near 230–280 nm); confirm identity by 1H/13C NMR and HRMS.
• Purification:
  • Silica gel chromatography with hexanes/EtOAc or toluene/EtOAc gradients typically separates unreacted starting materials from more polar products (amides, phenols, acids).
• Applications in materials/analytical contexts:
  • Hydrophobic probe in partitioning studies or as a GC retention-time marker within a homologous aryl-ester series (research use only).

Always tailor conditions to the specific catalyst/reagent system and verify compatibility with the ester functionality.

Reaction Conditions

Guidance below is literature-informed and general for aryl esters; optimize for your system. These are not item specifications.

• Hydrolysis (saponification):
  • Base: KOH or NaOH (1–2 M) in ethanol/water or THF/water, 20–60 °C; hours to completion depending on substrate and conditions.
  • Acid: H2SO4 or HCl (1–3 M) in aqueous-organic mixtures, reflux as needed.
• Transesterification:
  • Acid-catalyzed: p-TsOH (1–10 mol%) in toluene or xylene with azeotropic water removal, 80–130 °C.
  • Base-catalyzed: Alkoxide (NaOEt, KOtBu, 5–20 mol%) in corresponding alcohol solvent, 0–60 °C; exclude moisture.
  • Enzymatic: Lipases (e.g., CAL-B) in nonaqueous media or biphasic systems, rt–60 °C.
• Amidation of aryl esters:
  • Ni-catalyzed systems (literature): Ni(cod)2 (5–10 mol%), bidentate phosphine (e.g., dppp, dcype), amine (1.2–2.0 equiv), base (e.g., K3PO4), solvent (toluene, dioxane), 80–120 °C, 6–24 h.
  • Alternative activation: Use of catalytic DMAP with more reactive ester systems; aryl esters may require stronger activation or catalysts.
• Metal-catalyzed C–O activation / decarbonylative coupling:
  • Ni(0) or Pd(0) catalysts with bulky phosphines, base (Cs2CO3/K3PO4), 100–150 °C in anisole, toluene, or dioxane; inert atmosphere.
• Analytical monitoring:
  • HPLC-UV at 230–280 nm, GC-FID/MS after suitable temperature program; confirm with NMR and HRMS.

Safety and workup:

• Quench bases/acids carefully; separate organic/aqueous phases; wash to remove catalysts; use chelators (e.g., EDTA) if needed to scavenge metals before chromatography.

Safety and Handling

Item-specific GHS data are not provided in the Product Data. Always consult the SDS for definitive hazard, classification, and first-aid guidance.

• GHS/Classification (item-specific): Not specified for this item; refer to SDS.
• Likely hazard profile (general for aryl esters; literature): May cause skin/eye irritation; harmful if swallowed or inhaled. Low volatility typically reduces acute inhalation exposure versus lighter solvents.
• PPE (good laboratory practice):
  • Wear lab coat, safety glasses/goggles, and appropriate chemical-resistant gloves (e.g., nitrile).
  • Use in a fume hood to avoid inhalation of mists or vapors during heating or aerosol-generating operations.
• Handling tips:
  • Avoid prolonged heating above decomposition temperatures; ester hydrolysis can occur under strong acid/base and elevated temperature.
  • Keep away from strong bases, strong acids, and strong nucleophiles that promote transesterification or saponification.
  • Avoid strong oxidizers.
• First aid (overview; defer to SDS):
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek attention if respiratory symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
• Storage incompatibilities (general): Separate from alkali metals, strong oxidants, and reactive bases/acids. Use amber containers if prolonged light exposure is expected (aromatic esters can undergo slow photooxidation).
• Spill/cleanup: Absorb with inert material, collect in compatible container for disposal; ventilate area.

Solvent Selection

This product is an aromatic ester and is itself typically used as a substrate or intermediate rather than as a solvent. Selection of solvents for its handling or reactions should consider hydrophobicity and ester stability.

• Polarity/miscibility (general behavior of diaryl esters):
  • Essentially insoluble in water.
  • Highly soluble in nonpolar and moderately polar organic solvents (toluene, xylene, DCM, chloroform, THF, EtOAc, acetone, acetonitrile).
• Typical choices by operation:
  • Purification: Hexanes/EtOAc or toluene/EtOAc mixtures for flash chromatography; recrystallization (if solid) from ethanol, isopropanol, or toluene/hexanes blends as determined experimentally.
  • NMR: CDCl3 or DMSO-d6 provide well-resolved aromatic and aliphatic resonances; residual water signals minimal in CDCl3.
  • Reactions: Toluene, dioxane, THF, CPME, or anisole for transesterifications and metal-catalyzed C–O activation; DMF/DMAc/NMP for amidation with amines (if base required).
• When to choose alternatives:
  • For greener processing, prefer 2-MeTHF, CPME, or EtOAc over DCM/CHCl3.
  • For high-temperature catalysis, anisole or xylene provides thermal robustness.

Small comparison (general):

• Toluene: good solvency for aryl esters; high bp; low polarity.
• EtOAc: medium polarity; facilitates transesterification but can co-react under strong base.
• 2-MeTHF/CPME: greener ethers; good for moisture-sensitive/base-catalyzed steps with improved safety vs THF.

Storage and Reconstitution

• Storage (item-specific from Product Data): Store at room temperature.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance/state: Not specified for this item; verify on CoA before planning handling steps.

General guidance:

• Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and strong light during long-term storage.
• If solid, gently warm (30–40 °C) or use minimal solvent (e.g., toluene, EtOAc) to dissolve prior to dispensing. If liquid or low-melting, pre-warm to ensure homogeneity before aliquoting.
• Avoid repeated heating/cooling cycles to minimize degradation; prepare working aliquots if frequent use is anticipated.
• Inert atmosphere is not typically required but may improve shelf life for samples subjected to high temperature or prolonged storage.
• Reconstitution: Not applicable; compound is supplied neat. For stock solutions, prepare in a compatible anhydrous organic solvent (e.g., toluene, DCM, THF, EtOAc) at a convenient concentration, label with solvent, concentration, and date, and store according to solvent stability and lab policy.

Always consult the product CoA/SDS for lot-specific handling and stability information.

Structure and Identity

Overview: 4-Ethylphenyl 4-ethylbenzenecarboxylate is a symmetrical, di-para-ethyl–substituted aromatic ester (a 4-ethylbenzoate of 4-ethylphenol). It contains two benzene rings connected through a phenyl ester linkage (Ar–O–C(=O)–Ar′).

• Item-specific registry data (from Product Data)

  • Product name: 4-Ethylphenyl 4-ethylbenzenecarboxylate
  • CAS: 104899-04-9
  • PubChem CID: 1490294
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identifiers and features (for reference; not item specifications)

  • Typical molecular formula (literature/computed from structure): C17H18O2
  • Typical molecular weight (literature/computed): ~254.32 g/mol
  • Representative SMILES (literature): O=C(Oc1ccc(CC)cc1)c1ccc(CC)cc1

• Structural features (general description)

  • Functional groups: aromatic ester (aryl–O–C(=O)–aryl), two ethyl substituents para to the linking positions on each ring.
  • Rings: two benzene rings; no heteroaromatic systems.
  • Stereochemistry: none (achiral under standard conditions).
  • 2D motif: a central ester carbonyl flanked by an aryl carbonyl carbon and an aryl ether oxygen; both aryl rings bear para-ethyl groups, giving increased hydrophobicity and reduced polarity compared to unsubstituted phenyl benzoate.

Synthetic Utility

Key reactivity arises from the aryl ester functional group and the electronically donating para-ethyl substituents on both rings.

• Transformations (literature/general):
  • Ester-to-amide conversion with amines under catalytic activation (e.g., Ni/Pd-catalyzed amidation of aryl esters, or using activating agents such as DMAP with carbodiimides for related systems).
  • Transesterification with alcohols (acid- or base-catalyzed); para-ethyl substituents may modestly retard reaction vs unsubstituted phenyl benzoate.
  • Hydrolysis (acidic or basic) to give 4-ethylbenzoic acid and 4-ethylphenol (or their salts), enabling access to both fragments.
  • Metal-catalyzed C–O activation: Ni(0)/phosphine ligands can enable cross-coupling, acylative coupling, or decarbonylative aryl–aryl formations from aryl esters.
  • Fries rearrangement (Lewis acids, strong conditions) to acylated phenols (positional control required).
• Retrosynthetic value:
  • Functions as a protected form of 4-ethylbenzoic acid (masked as aryl ester) and 4-ethylphenol (masked as aryl carbonate analogue), allowing orthogonal deprotection planning in multi-step routes.
• Analysis and ID:
  • 1H NMR: two sets of para-disubstituted aromatic patterns plus two ethyl groups (quartet/triplet aliphatic signals).
  • 13C NMR: ester carbonyl ~165–170 ppm; aromatic carbons ~115–150 ppm; ethyl carbons ~15–30 ppm.

These features make it a useful, lipophilic benchmark substrate in method development for ester activation and C–O cleavage chemistry.

Target Specificity

Not applicable. This product is a small-molecule aromatic ester and is not an antibody, protein, or nucleic acid reagent. No antigen/epitope/clone/isotype data apply.