(2-Bromophenyl)(2,4-dimethylphenyl)sulfane: Properties & Uses
(2-Bromophenyl)(2,4-dimethylphenyl)sulfane: Properties & Uses
(2-Bromophenyl)(2,4-dimethylphenyl)sulfane is a diaryl thioether building block featuring both a reactive aryl bromide handle and a methyl-substituted aryl sulfide motif, making it a versatile intermediate for organosulfur synthesis and transition-metal-catalyzed cross-coupling chemistry.
- IUPAC Name
- (2-bromophenyl)(2,4-dimethylphenyl)sulfane
- Molecular Formula
- C14H13BrS
- Compound Class
- Diaryl thioether (organosulfur)
- Key Functional Groups
- Thioether (C–S–C), aryl bromide (C–Br)
- Primary Application
- Synthetic intermediate for cross-coupling and C–S bond-forming reactions
- SKU
- S734331
- Supplier
- Aladdin Scientific
Chemical Structure and Physicochemical Properties
(2-Bromophenyl)(2,4-dimethylphenyl)sulfane (molecular formula C14H13BrS) is an unsymmetrical diaryl thioether composed of a 2-bromophenyl ring and a 2,4-dimethylphenyl ring linked through a sulfur atom. The thioether sulfur (oxidation state –2) bridges the two arene systems via C–S single bonds. The ortho-bromo substituent on one aryl ring introduces both steric influence and a readily accessible electrophilic site for further functionalization.
As a mid-molecular-weight organosulfur compound, (2-Bromophenyl)(2,4-dimethylphenyl)sulfane is expected to be a low-melting solid or oil at room temperature, with moderate lipophilicity consistent with its aromatic and alkyl substituents. Specific physicochemical data (exact melting point, boiling point, density, and solubility values) should be confirmed from the certificate of analysis supplied with SKU S734331 or from primary literature, as these values are not provided in the current source material.
Synthesis and Preparation Methods
Diaryl thioethers of this structural type are commonly prepared by transition-metal-catalyzed C–S coupling reactions or by nucleophilic aromatic substitution. A representative route to (2-Bromophenyl)(2,4-dimethylphenyl)sulfane involves the coupling of a 2-haloanisole derivative or a 2-bromothiophenol equivalent with a 2,4-dimethylphenyl thiol or vice versa, under copper or palladium catalysis. Alternatively, classical Ullmann-type thioether synthesis using copper powder or copper(I) iodide with an aryl halide and an arene thiol provides a metal-mediated pathway.
The 2-bromo substituent on the phenyl ring is deliberately retained in the final structure, serving as a handle for downstream synthetic transformations. Researchers should note that reaction conditions must be optimized to avoid competitive nucleophilic substitution at the aryl bromide site during thioether formation.
Applications in Synthetic and Medicinal Chemistry
(2-Bromophenyl)(2,4-dimethylphenyl)sulfane serves as a bifunctional synthetic intermediate. The aryl bromide moiety is amenable to a wide range of cross-coupling reactions including Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and lithiation–electrophile trapping sequences, enabling construction of complex biaryl and heteroaryl frameworks containing a thioether linkage.
Diaryl sulfide motifs appear in several pharmacologically relevant scaffolds, including kinase inhibitors, anti-inflammatory agents, and materials for organic electronics such as organic semiconductors and hole-transport layers. The methyl substituents on the second aryl ring modulate both steric and electronic properties of the sulfide, influencing reactivity and binding interactions. Researchers in target synthesis, fragment-based drug discovery, and materials science may find SKU S734331 useful as a starting material or key intermediate.
Handling, Storage, and Safety Considerations
As with all organosulfur compounds containing an aryl bromide, (2-Bromophenyl)(2,4-dimethylphenyl)sulfane should be handled with standard laboratory precautions. Use appropriate personal protective equipment including lab coat, chemical-resistant gloves, and safety goggles. Work in a well-ventilated fume hood to minimize inhalation exposure to any vapor or dust.
Store the compound in a tightly sealed container away from moisture, strong oxidizers, and strong bases. A cool, dry environment (typically 2–8 °C or room temperature as specified on the product label) is recommended to maintain long-term stability. Disposal should comply with local regulations for halogenated organic waste. Consult the Safety Data Sheet (SDS) for SKU S734331 available from Aladdin Scientific for complete hazard and first-aid information before use.
Ordering Information and Quality Specifications
(2-Bromophenyl)(2,4-dimethylphenyl)sulfane is available from Aladdin Scientific under SKU S734331. Researchers should request the certificate of analysis (CoA) for the specific lot number to verify purity (typically assessed by GC or HPLC), identity (confirmed by NMR or MS), and any moisture content data. Aladdin Scientific's quality control protocols help ensure batch-to-batch consistency for reproducible research outcomes.
For bulk quantities, custom packaging, or technical inquiries regarding this reagent, contact Aladdin Scientific's technical support or procurement team. Pricing, availability, and current stock levels can be confirmed through the Aladdin Scientific online catalog or your regional distributor.
Frequently asked questions
What is (2-Bromophenyl)(2,4-dimethylphenyl)sulfane used for in organic synthesis?
It serves as a bifunctional building block combining a diaryl thioether motif with a reactive aryl bromide. The aryl bromide enables cross-coupling reactions (e.g., Suzuki, Negishi, Buchwald–Hartwig) and directed metalation, allowing construction of complex sulfide-containing biaryl frameworks useful in medicinal chemistry and materials science.
How should (2-Bromophenyl)(2,4-dimethylphenyl)sulfane be stored to maintain its stability?
Store the compound in a tightly sealed container in a cool, dry location away from strong oxidizers, strong bases, and moisture. Follow the specific storage temperature indicated on the product label or certificate of analysis for SKU S734331. Always consult the SDS before handling.
What is the molecular formula and key structural feature of this compound?
The molecular formula is C14H13BrS. The key structural feature is an unsymmetrical diaryl thioether with a 2-bromophenyl group and a 2,4-dimethylphenyl group connected through a sulfur atom, providing both a thioether linkage and a halide handle for further derivatization.
Can the aryl bromide in this compound be used in palladium-catalyzed cross-coupling reactions?
Yes. Aryl bromides are well-established partners in palladium-catalyzed cross-coupling reactions including Suzuki–Miyaura (with boronic acids), Negishi (with organozinc reagents), and amination reactions. The ortho-bromo position may introduce steric effects that require optimized ligand and catalyst selection for efficient coupling.
Where can I find purity and analytical data for SKU S734331?
Purity and analytical data are provided in the certificate of analysis (CoA) for each specific lot of SKU S734331. You can request the CoA directly from Aladdin Scientific's website or customer service team when placing your order.
References
- Beletskaya, I. P.; Cheprakov, A. V. Copper in cross-coupling reactions: The post-Ullmann chemistry. Coordination Chemistry Reviews 2004, 248, 2337–2364. doi:10.1016/j.ccr.2004.09.014
- Wolfe, J. P.; Buchwald, S. L. Palladium-catalyzed amination of aryl halides and sulfonates. Journal of Organic Chemistry 2000, 65, 1144–1157. doi:10.1021/jo991699y
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012.
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