Ethyl Phenyl Sulfide: Properties, Uses & Lab Handling Guide
Ethyl Phenyl Sulfide: Properties, Uses & Lab Handling Guide
Ethyl Phenyl Sulfide is a versatile aromatic thioether reagent widely employed in organic synthesis as a sulfur-containing building block and precursor for sulfinyl and sulfonyl derivatives.
- Chemical Name
- Ethyl Phenyl Sulfide (Phenyl Ethyl Sulfide)
- Molecular Formula
- C₈H₁₀S
- Molecular Weight
- 138.23 g/mol
- CAS Number
- 622-38-8
- Appearance
- Colorless to pale yellow liquid with a characteristic sulfurous odor
- SKU
- E101809
- Functional Class
- Thioether / Organosulfur Reagent
Physicochemical Properties
Ethyl Phenyl Sulfide (CAS 622-38-8, MW 138.23 g/mol, molecular formula C₈H₁₀S) is a simple diaryl/alkyl thioether consisting of a phenyl group linked to an ethyl group through a divalent sulfur atom. At ambient conditions it presents as a colorless to pale yellow, mobile liquid with a distinctive sulfurous odor. Key physicochemical characteristics include moderate lipophilicity (log P approximately 2.8), low water solubility, and miscibility with common organic solvents such as dichloromethane, ethyl acetate, diethyl ether, and toluene. The boiling point is reported in the range of 184–188 °C at atmospheric pressure, and the density is approximately 1.02 g/mL at 20 °C. The thioether sulfur center is nucleophilic and can be oxidized stepwise to the corresponding sulfoxide and sulfone, providing a chemically tunable handle for downstream transformations.
Note: Exact physical constants should be verified against the current Aladdin product certificate of analysis (CoA) for lot-specific values.
Synthetic Applications and Research Uses
Ethyl Phenyl Sulfide is a broadly useful building block and reagent in modern synthetic organic chemistry. Its principal applications include:
- Oxidation chemistry: Controlled oxidation with reagents such as mCPBA, Oxone®, or hydrogen peroxide affords ethyl phenyl sulfoxide and ethyl phenyl sulfone in a stepwise manner, enabling access to chiral sulfoxide motifs relevant to pharmaceutical synthesis and asymmetric catalysis.
- C–S bond formation studies: It serves as a model substrate for evaluating transition-metal-catalyzed C–S coupling reactions, including palladium-, copper-, and nickel-catalyzed cross-coupling methodologies.
- Electrophilic sulfenylation precursor: Activated forms derived from Ethyl Phenyl Sulfide can participate in sulfenylation reactions for the introduction of sulfur-containing functionality onto aromatic and heteroaromatic cores.
- Ligand and material science: Thioether motifs present in Ethyl Phenyl Sulfide are explored as soft donor ligands in coordination chemistry and as structural components in functional organic materials.
- Flavour and fragrance research: Low-concentration thioethers are studied as sulfur-containing aroma compounds, making this compound relevant to food chemistry research.
Researchers should consult primary literature for reaction-specific conditions, catalyst loadings, and yields.
Safe Handling, Storage, and Waste Disposal
General Precautions: Ethyl Phenyl Sulfide should be handled in a well-ventilated fume hood at all times. Personal protective equipment (PPE) including chemical-resistant gloves (nitrile or neoprene), safety goggles, and a laboratory coat is mandatory. Avoid inhalation of vapors; the compound has a strong, persistent sulfurous odor detectable at very low concentrations.
Flammability: As a combustible organic liquid, keep away from open flames, sparks, and hot surfaces. Ensure earthing of containers when transferring larger quantities.
Storage: Store in a tightly sealed container under inert atmosphere (nitrogen or argon) in a cool, dry, well-ventilated area away from oxidizing agents and strong acids. Recommended storage temperature is 2–8 °C or as specified on the product label. Protect from light to minimize discoloration.
Spill Management: Contain spills immediately with an inert absorbent material (vermiculite or dry sand). Avoid letting the material enter drains or waterways due to potential ecotoxicity and persistent odor. Transfer absorbed material to a sealed waste container.
Waste Disposal: Dispose of Ethyl Phenyl Sulfide and contaminated materials in accordance with local, national, and institutional hazardous waste regulations. Do not flush to sewer. Consult your institution's Environmental Health and Safety (EH&S) office for approved disposal routes.
Always consult the current Safety Data Sheet (SDS) for Ethyl Phenyl Sulfide (E101809) before use.
Quality, Purity, and Procurement Guidelines
Purity Considerations: For sensitive synthetic applications, particularly asymmetric oxidation or catalytic reactions where trace impurities may influence enantioselectivity or catalyst turnover, it is critical to use high-purity Ethyl Phenyl Sulfide. Aladdin Scientific's E101809 is supplied with a certificate of analysis (CoA) specifying purity determined by GC or HPLC. Researchers should request the CoA for their specific lot and confirm that purity meets experimental requirements prior to use.
Packaging and Quantities: Ethyl Phenyl Sulfide (E101809) is available in research-scale quantities suitable for laboratory use. Contact Aladdin Scientific's sales team or consult the product page for current packaging options, pricing, and availability.
Verification on Receipt: Upon receipt, inspect the container for integrity, confirm the label matches the ordered SKU (E101809), and check that the odor and appearance are consistent with the expected properties. Store immediately under recommended conditions.
Shelf Life: Shelf life is indicated on the product label and CoA. To maximize stability, minimize exposure to air, moisture, light, and heat. Reseal immediately after use under inert gas.
Frequently asked questions
What is Ethyl Phenyl Sulfide used for in organic synthesis?
Ethyl Phenyl Sulfide is primarily used as a thioether building block that can be oxidized to the corresponding sulfoxide or sulfone, serving as a key intermediate in pharmaceutical and agrochemical synthesis. It also functions as a model substrate in C–S bond-forming reactions and transition-metal-catalyzed coupling studies.
How should Ethyl Phenyl Sulfide be stored to maintain its quality?
Ethyl Phenyl Sulfide should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C, away from oxidizing agents, strong acids, light, and moisture. Always reseal the container immediately after use to prevent degradation and odor release.
Is Ethyl Phenyl Sulfide hazardous, and what PPE is required?
Yes, Ethyl Phenyl Sulfide is a combustible liquid with a strong sulfurous odor and poses risks through inhalation and skin contact. Required PPE includes chemical-resistant gloves (nitrile or neoprene), safety goggles, and a lab coat. All handling should be conducted in a well-ventilated fume hood. Consult the current SDS for full hazard information.
Can Ethyl Phenyl Sulfide be used as a chiral sulfoxide precursor?
Yes. Ethyl Phenyl Sulfide can be enantioselectively oxidized using chiral oxidants or metal-catalyzed asymmetric oxidation systems to afford chiral ethyl phenyl sulfoxide, a motif found in bioactive compounds and asymmetric synthesis auxiliaries. Reaction conditions should be optimized based on the specific catalytic system employed.
How do I confirm the purity of Ethyl Phenyl Sulfide (E101809) received from Aladdin?
Request the Certificate of Analysis (CoA) for your specific lot from Aladdin Scientific. The CoA provides purity data determined by GC or HPLC analysis. Compare the lot-specific values against your experimental requirements and visually inspect the product for the expected appearance upon receipt.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General thioether chemistry and oxidation)
- Fernández, I.; Khiar, N. Recent Developments in the Synthesis and Utilization of Chiral Sulfoxides. Chem. Rev. 2003, 103, 3651–3705. doi:10.1021/cr990372u
- Beletskaya, I. P.; Ananikov, V. P. Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions. Chem. Rev. 2011, 111, 1596–1636. doi:10.1021/cr100347k
- Aladdin Scientific Product Page: Ethyl Phenyl Sulfide, SKU E101809. https://www.aladdin-e.com (accessed 2024).
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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