This compound belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.
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.
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Application Protocols
Not applicable. No immunoassay or bioanalytical application protocols (e.g., WB, IHC, IF, FC) are provided for this small-molecule reagent.
General lab use suggestions:
For stock solutions, dissolve in dry DMSO, DMF, or dichloromethane depending on downstream use. Filter through a PTFE syringe filter (0.2–0.45 µm) if particulates are observed.
For combinatorial synthesis or screening, document solvent and concentration to ensure reproducibility across lots and assays.
Biological Roles
This product is a synthetic, non-natural small molecule intended for chemical research. It does not have a known intrinsic biological role or function.
General context (for chemists planning bioassays):
Physicochemical profile suggests high hydrophobicity and aromatic character; such scaffolds often exhibit nonspecific binding to proteins, plastics, and membranes. Exercise care when interpreting screening data (stickiness, aggregation) and include appropriate counterscreens and detergents if applicable.
The compound contains no obvious ionizable groups near physiological pH; solubilization for assays typically requires DMSO stocks, followed by dilution into assay buffer with surfactant or carrier protein if permitted.
No biochemical pathway, receptor interaction, or endogenous role is assigned to this structure in the literature. Use is restricted to research and method development; no clinical or diagnostic use is intended or supported.
Buffer Applications
Not typically applicable. Ethyl 4‑phenylsulfanylbenzoate is a neutral, water‑insoluble organic compound and is not used as a buffering agent or buffer component.
Practical note: If preparing assay solutions, dissolve first in anhydrous DMSO to make a concentrated stock (e.g., 10–50 mM), then dilute into the desired buffer with vigorous mixing. Consider adding a small percentage of co‑solvent or nonionic surfactant to minimize precipitation. Verify final organic content is compatible with your biological assay.
Green Alternatives
Greener choices relate primarily to solvent and reagent selection when using this substrate; the molecule itself is a hydrophobic aromatic thioether ester and not inherently “green.”
Greener solvent swaps (literature guidance):
Replace DCM/CHCl3 with EtOAc or cyclopentyl methyl ether (CPME) for extractions and chromatography when feasible.
Use 2‑MeTHF instead of THF for reactions/workups; 2‑MeTHF is bio‑derived and less miscible with water, aiding separations.
Favor toluene or anisole over xylene for high‑temperature operations.
Oxidations at sulfur:
mCPBA is effective but chlorinated waste and peracid hazards are considerations. Alternatives include Oxone (KHSO5) in MeOH/H2O or acetonitrile/water with catalytic TEMPO for certain oxidations; or H2O2 with tungstate catalysts to reach sulfones with improved EHS profiles (literature).
Cross‑couplings via C–S activation:
Nickel catalysis often allows lower catalyst loadings and avoids palladium scarcity; ligand-enabled Ni systems in greener solvents (2‑MeTHF, CPME, anisole) are reported.
Comparison (qualitative):
THF vs 2‑MeTHF: similar performance; 2‑MeTHF offers renewable origin and easier phase separation, but can contain peroxides—monitor and stabilize.
DCM vs EtOAc: EtOAc reduces chlorinated waste and toxicity; may require slightly larger volumes for solubility.
Note: Validate reaction rates, selectivity, and workup compatibility when swapping solvents; small‑scale scouting is recommended.
Pharmaceutical Uses
No pharmacopeial status or excipient function is specified for this item. It is supplied strictly for research use only.
Context for medicinal chemistry workflows (general):
Role: Aromatic thioether benzoate scaffolds are often used as intermediates for SAR exploration. The ester can be hydrolyzed to a carboxylic acid for amide coupling, while the thioether can be oxidized or leveraged for C–S activation to diversify scaffolds.
Formulation (screening stage): If evaluated in biochemical or cell‑based assays, compounds of this class are commonly prepared as DMSO stock solutions. Solubility limits and precipitation should be checked upon dilution.
Regulatory and quality notes:
No claims are made regarding GMP, ICH impurity profiling, or suitability for human/animal administration. Not for therapeutic, diagnostic, or in vivo use.
Any stability-indicating methods, impurity thresholds, and residual solvent limits must be established by the user for their specific research application.
Physical Properties
Item-specific physicochemical specifications (mp, bp, density, refractive index, water, metals, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for this scaffold (for informational context only):
Phase at ambient conditions: typically a low-melting solid or high-boiling oil for similar aryl thioether benzoate esters (literature trend; confirm with CoA).
Aqueous solubility: expected to be very low due to two aromatic rings and thioether (literature).
Organic solubility: expected good solubility in chlorinated solvents (DCM, CHCl3), ethers (THF), and medium‑polarity esters (EtOAc) (literature).
Lipophilicity: high (logP likely >3) given aryl–S–aryl and ester functionality (literature/computed trend; no item-specific value assigned).
Acid–base behavior: neutral; no ionizable centers in the typical biological pH range (general chemical knowledge).
Notes:
If precise melting range, residual solvents, or chromatographic purity are critical, request the current Certificate of Analysis, which will supersede literature expectations.
For method development (e.g., HPLC), determine UV characteristics empirically; conjugated aromatics commonly absorb in the 200–280 nm region (literature), but no item-specific cutoff is provided.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications:
In the absence of a stated grade (e.g., “98%,” “AR,” “HPLC grade”), users should rely on the current CoA for assay purity, chromatographic profile, and residual solvent/metals. Aladdin’s CoA typically includes lot-specific purity (GC/HPLC/NMR), identity confirmation, and key limits relevant to the compound class.
Stabilizers: None specified for this item. If stabilizers or antioxidants are present in a specific lot, they will be disclosed on the CoA/SDS. Thioethers generally do not require polymerization inhibitors.
UV/background considerations: If using in photophysical studies or as an internal standard, consider requesting a low-UV-absorbing grade. Without an HPLC/UV grade declaration, assume typical aromatic absorbance.
Metals and water: Not specified for this item; refer to CoA/Spec Sheet.
Recommendations for quality-sensitive work:
For catalytic studies or cross-couplings, request lots screened for low transition-metal contaminants if needed.
For quantitative synthesis, consider verifying purity by 1H NMR and HPLC upon receipt, and, if necessary, purify by flash chromatography or recrystallization from EtOAc/hexanes (general practice for hydrophobic aromatics).
Reaction and Applications
Ethyl 4‑(phenylthio)benzoate is a bifunctional building block combining an aryl thioether and a benzoate ester. This makes it valuable in medicinal chemistry libraries and method development.
Representative transformations (literature):
Functionalization at sulfur:
Oxidation to sulfoxide (mCPBA, ≤1 eq, 0–25 °C) or sulfone (mCPBA or Oxone, excess), enabling polarity tuning and further cross‑couplings.
S‑alkylation/acylation to form sulfonium salts or thioesters (with strong electrophiles), useful as activation handles.
C–S bond activation:
Pd/Ni‑catalyzed cross‑coupling of aryl thioethers to form biaryls or aryl–alkenyl products (C–S activation) under ligand-enabled conditions; thioaryl acts as a pseudohalide.
Kumada‑type couplings (Ni catalysis) with Grignards from the thioether aryl fragment.
Ester manifold:
Saponification (KOH/MeOH or NaOH/THF–H2O) to 4‑(phenylthio)benzoic acid; subsequent amidation (EDC/HOBt, HATU, CDI) or ester exchange.
Reduction to corresponding benzyl alcohol derivatives (DIBAL‑H to aldehyde at −78 °C; LiAlH4/NaBH4 variants for deeper reduction; literature conditions vary).
Electrophilic aromatic substitutions on the external phenyl (limited by deactivation from thioether oxidation state; directing/activating patterns should be considered).
Practical tips:
Minimize over‑oxidation during selective sulfoxide formation by slow oxident addition at low temperature and monitoring by TLC/NMR.
For C–S activation couplings, remove adventitious thiols (which can poison catalysts) and consider pre‑washing or brief silica pad.
Verify stability under base before long reactions; the ester can slowly transesterify or hydrolyze in strong base.
Reaction Conditions
General literature conditions relevant to this scaffold (not item-specific specifications):
Selective oxidation of thioether to sulfoxide:
Reagents: mCPBA (1.0–1.1 eq) in DCM at 0–5 °C, then warm to rt; 0.5–3 h.
Notes: Control temperature and equivalents to avoid over‑oxidation; quench peracid carefully.
Oxidation to sulfone:
Reagents: mCPBA (2–3 eq) in DCM, or Oxone (3–4 eq) in MeOH/H2O; rt to 40 °C; 2–8 h.
Alternative: H2O2 (30%) with catalytic tungstate in MeOH or AcOH; 25–60 °C.
C–S bond activation cross‑coupling (biaryl formation):
Catalysts: Ni(cod)2 or NiCl2(dppp); Pd2(dba)3 with BrettPhos/Xantphos.
Nucleophiles: Aryl boronates (with Pd), Grignards (Kumada with Ni), or organozincs.
Bases/conditions: K3PO4 or Cs2CO3 in toluene/anisole/2‑MeTHF; 60–120 °C; 2–16 h; 1–5 mol% catalyst.
Ester hydrolysis (to acid):
Conditions: KOH (2–5 eq) in MeOH/THF/H2O (2:2:1), rt to 50 °C, 1–6 h; acidify and extract.
Reduction of ester:
To aldehyde: DIBAL‑H (1.2–1.5 eq) in toluene at −78 °C, then quench at low temperature.
To alcohol: LiAlH4 or excess DIBAL‑H in THF/Et2O, 0 °C to reflux.
Yields: Highly substrate- and method-dependent; consult target literature. Always run small-scale pilots when transferring conditions to this specific substrate.
Safety and Handling
Research use only. Always consult the product SDS for authoritative safety information.
GHS classification, signal word, H‑statements, pictograms: Not specified for this item; refer to SDS.
General handling guidance for aryl thioether esters (informational):
Hazards: Many thioethers and aromatic esters are irritants; some thioethers have strong odors and can cause headaches/nausea at high vapor levels. Avoid inhalation of vapors/aerosols and skin/eye contact.
PPE: Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood when weighing, dissolving, or transferring.
Incompatibilities: Strong oxidizers (risk of exothermic oxidation of the thioether), strong bases or acids under forcing conditions (hydrolysis/transesterification), and strong electrophiles (possible S‑alkylation/acylation).
First aid (overview):
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 contact lenses if easy.
Ingestion: Rinse mouth; seek medical attention.
Spill/cleanup: Absorb with inert material; avoid generating dust/aerosols; ventilate area.
Fire safety: Use CO2, dry chemical, or foam. Combustion may produce SOx and CO/CO2.
Storage per Product Data: Store at room temperature. Ship: Normal.
Keep container tightly closed, away from oxidizers and direct sunlight. Maintain dry conditions to prevent hydrolysis of the ester under adventitious moisture with base/acid.
Solvent Selection
Compound profile: Neutral, hydrophobic, aromatic thioether benzoate; low aqueous solubility; high affinity for medium- to low‑polarity organic solvents.
Poor: Water, very nonpolar alkanes unless warmed or concentrated.
When to choose which solvent:
DCM/CHCl3: Rapid dissolution and room‑temperature workups; strong UV background may impact analytical methods.
EtOAc/hexanes: Useful pair for flash chromatography and recrystallization.
THF/2‑MeTHF: Versatile for reactions (base-compatible) and greener option versus DCM.
Toluene: High‑boiling medium for thermally driven reactions; good for Pd/Ni catalysis.
Acetonitrile: Compatible with many catalysts and electrochemical setups; moderate solubility anticipated.
DMSO/DMF: Maximum solubility for screening; consider difficult removal and odor retention with thioethers.
Comparison snapshot:
DCM vs EtOAc: DCM dissolves faster and more; EtOAc is greener and easier to remove but may need warming.
THF vs Toluene: THF offers polarity and room‑temp kinetics; toluene supports higher‑temp operations and lower coordinating character useful for some metal catalysis.
Tip: Pre‑dry ethers/esters when moisture‑sensitive transformations (e.g., amidations after hydrolysis) are planned.
Storage and Reconstitution
Storage conditions (from Product Data):
Store at room temperature. Shipped under normal conditions.
General handling:
Keep tightly sealed under dry, inert atmosphere if long-term storage is planned, especially if frequent opening is expected. Protect from strong light and oxidizers to preserve the thioether functionality.
If supplied as a solid, gently break up agglomerates before weighing. If supplied as an oil, use positive‑displacement pipettes for accurate dosing.
Reconstitution/solution preparation:
Not supplied lyophilized; no reconstitution needed. For solution preparation, dissolve in anhydrous organic solvent (e.g., DCM, THF, EtOAc, toluene, DMF, or DMSO) to the desired concentration.
For bioassay stocks, prepare in dry DMSO (e.g., 10–50 mM), aliquot to minimize freeze–thaw, and store at −20 °C to −80 °C if long-term solution stability is required (general best practice; confirm solution stability empirically).
Stability notes:
The ester is generally stable under neutral, dry conditions; avoid prolonged exposure to strong acids/bases and oxidants. Periodic NMR or LC checks are recommended for long-term stored solutions.
Specifications such as water content, residual solvents, or stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Ethyl 4-phenylsulfanylbenzoate is an aromatic thioether-bearing benzoate ester, useful as a hydrophobic building block for synthesis.
Topology: Two phenyl rings linked through sulfur; the carbonyl carbon is sp2; no stereocenters.
2D structure in words: An ethyl benzoate where the benzene ring’s para position relative to the ester is substituted by a phenylthio group, i.e., Ph–S–(p‑C6H4–CO2Et).
Synthetic Utility
Key functional groups and reactivity:
Aryl thioether (Ph–S–Ar): tunable via oxidation (sulfoxide/sulfone), S‑alkylation, and metal-catalyzed C–S bond activation for cross‑couplings.
Benzoate ester (Ar–CO2Et): convertible to acid (saponification), amide (after hydrolysis/activation), alcohol/aldehyde (selective reductions), or alternative esters (transesterification).
Retrosynthetic perspectives (literature):
Constructed via C–S coupling of 4‑halobenzoates (e.g., 4‑bromobenzoate esters) with thiophenol under Pd/Cu catalysis, followed by esterification if needed.
Alternatively, thioether formation from 4‑mercaptobenzoate derivatives with aryl electrophiles (diazonium, iodonium, or aryl halides) under suitable conditions.
Value in diversification:
Post‑oxidation to sulfone enhances polarity and can switch directing effects and metabolic stability in analog series.
C–S activation provides a route to biaryls without using aryl halides in the final coupling step, complementing Suzuki/Negishi chemistry.
The para‑relationship between the ester and thioaryl substituent offers predictable electronics for electrophilic/nucleophilic aromatic manipulations on the second ring.
Practical advice:
Maintain low thiol/thiolate impurities prior to Pd/Ni catalysis; they can bind and deactivate catalysts.
For ester hydrolysis, mixed solvent systems (THF/MeOH/H2O) improve rate and handling of hydrophobic substrates; monitor by LC/MS or 1H NMR (disappearance of ethyl triplet ~1.2 ppm).
Target Specificity
Not applicable. This product is a small-molecule chemical and does not possess biological target specificity information such as antigen, epitope, clone, or isotype.
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