Product Manager: Selina Zhang; Email: selina@coreychem.com
| Product Name | BIS(BENZOYLMETHYL) SULFIDE |
| Synonyms | BIS(BENZOYLMETHYL)SULFIDE;Bis(2-phenyl-2-oxoethyl)sulfide;Diphenacylsulfide;α,α’-Thiobisacetophenone;2-(2-oxo-2-phenyl-ethyl)sulfanyl-1-phenyChemicalbookl-ethanone;2-(2-oxo-2-phenylethyl)sulfanyl-1-phenylethanone;2,2-thiobis(1-phenylethan-1-one);2-[(2-keto-2-phenyl-ethyl)thio]-1-phenyl-ethanone |
| CAS NO | 2461-80-5 |
| Purity |
99% |
| Appearance |
/ |
| MF | C16H14O2S |
| MW | 270.35 |
| Contact | selina@coreychem.com |
BIS(BENZOYLMETHYL) SULFIDE (CAS: 2461-80-5), also known as diphenacyl sulfide or 2,2′-thiobis(1-phenylethanone), is a versatile organosulfur compound characterized by two benzoylmethyl groups linked through a central sulfur atom. With the molecular formula C₁₆H₁₄O₂S and a molecular weight of 270.35 g/mol, this compound typically presents as a white to off-white crystalline powder with a melting point between 75°C and 80°C. Its scientific value derives from its unique molecular structure, which features dual electrophilic α-carbonyl and nucleophilic sulfide functionalities. This combination enables a wide range of applications, from serving as a neutral bidentate ligand in coordination chemistry to functioning as an active methylene crosslinker in polymer science. The compound is intended strictly for non-human laboratory research and is not for therapeutic or veterinary use. Its primary applications are outlined below:
1. Coordination Chemistry & Metalloenzyme Modeling
Bis(benzoylmethyl) sulfide functions as a neutral bidentate S,O-chelating ligand, capable of forming stable, crystallographically defined metal complexes. The central sulfur atom and the adjacent carbonyl oxygen atoms coordinate with metal ions, most notably copper(II), to form complexes such as [Cu(BMS)₂]. These well-defined metal chelates are valuable tools for structural and catalytic research, including the modeling of metalloenzyme active sites. The specific electronic character of the thioether bridge, flanked by two electron-withdrawing benzoyl groups, provides a unique ligand field strength and metal-chelating ability that is critical to its performance in these applications.
2. Polymer Chemistry & Epoxy Thermoset Formulation
The compound acts as an active methylene crosslinker for epoxy resins. Its reactivity enables covalent crosslinking with epoxy rings via nucleophilic addition, yielding permanent and thermally stable epoxy thermoset networks. This application is particularly valuable in the formulation of advanced polymer materials where thermal stability and structural integrity are paramount. The high purity of the compound (>99% by GC) is essential for ensuring reproducible crosslinking stoichiometry.
3. Synthetic Organic Chemistry
Bis(benzoylmethyl) sulfide serves as a versatile building block in multi-step organic synthesis. Its dual functionality ensures predictable reactivity in a range of transformations:
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Michael Addition: The compound participates in efficient Michael addition reactions with chalcones, for example under microwave irradiation and solvent-free conditions, to generate symmetrical and unsymmetrical 1,5-diketones.
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Heterocyclic Synthesis: It is a key precursor for constructing complex heterocycles. For instance, its bis(phenylhydrazone) derivatives undergo tandem reactions with the Vilsmeier reagent to yield 3-aroylindoles. It also serves as a precursor in the synthesis of thioamides under Gewald conditions.
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Oxidation, Reduction, and Substitution: The compound can be readily oxidized to sulfoxides and sulfones, reduced to thiols, or undergo substitution reactions at the benzoylmethyl groups, providing access to a diverse array of derivatives.
4. Advanced Materials & Nanomaterials Research
Due to its unique chemical properties, Bis(benzoylmethyl) sulfide is employed in the development of advanced materials, including specialty polymers and nanomaterials. Its ability to act as a ligand and crosslinker makes it a valuable component in creating materials with tailored properties for electronics, coatings, and other industrial applications.
5. Biological & Medicinal Chemistry Research
Derivatives of Bis(benzoylmethyl) sulfide are being explored for their potential biological activities, including antimicrobial and anticancer properties. Ongoing research is investigating its potential therapeutic applications, particularly in drug development. This makes the compound a useful scaffold for generating bioactive compound libraries in medicinal chemistry.
6. Handling & Storage
Storage Conditions: Store in tightly sealed containers at room temperature (15°C or below, in a cool, dry place). Protect from moisture, excessive heat, and direct sunlight.
Purity & Appearance: Commercial grades are available with high purity (>98-99% by GC). The compound appears as a solid (white to off-white or yellow crystalline powder) at 20°C.
Solubility: Insoluble in water but soluble in organic solvents.
Intended Use: This product is intended strictly for non-human laboratory research, including applications in coordination chemistry, polymer science, and organic synthesis. It is not intended for therapeutic, diagnostic, food, or household applications without appropriate regulatory approval.
Summary
The value of BIS(BENZOYLMETHYL) SULFIDE (CAS: 2461-80-5) lies in its unique combination of a neutral bidentate S,O-chelating ligand, an active methylene crosslinker, and a versatile synthetic building block. Its applications span coordination chemistry for metalloenzyme modeling, polymer chemistry for thermally stable epoxy thermosets, and organic synthesis for constructing complex molecules and heterocycles. As a high-purity compound with well-defined reactivity, it is an essential reagent for research in materials science, catalysis, and medicinal chemistry.
