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2-(Tributylstannyl)thiazole (CAS No.: 121359-48-6) is a highly valuable organotin compound known for its versatile applications in organic synthesis. With the molecular formula C₁₅H₂₉NSSn and a molecular weight of 374.17 g/mol, it appears as a clear, almost colorless liquid. This compound combines the chemical reactivity of the thiazole ring with the synthetic flexibility of the tributylstannyl group, making it a crucial intermediate in carbon–carbon bond formation reactions, especially Stille coupling.
Physically, 2-(Tributylstannyl)thiazole has a boiling point of 307–309°C, a density of 1.19 g/mL at 25°C, and a refractive index of 1.5200. It has a flash point above 230°F, indicating good thermal stability under standard laboratory conditions. The compound should be stored sealed in a dry environment at 2–8°C, as it is not miscible or is difficult to mix with water. In this blog post, SACH, a high purity organotin compounds manufacturer, will share the synthesis of 2-(Tributylstannyl)thiazole, its key applications, etc.
Chemical Structure and Properties of 2-(Tributylstannyl)thiazole
The structure of 2-(Tributylstannyl)thiazole consists of a thiazole ring substituted at the 2-position by a tributylstannyl group. This configuration introduces both nucleophilic and organometallic characteristics, allowing it to act as a reactive precursor in palladium-catalyzed coupling reactions.
Key physicochemical properties include:
* Appearance: Clear, almost colorless liquid
* Density: 1.1900 g/mL at 25°C
* Melting Point: 224–225°C
* Boiling Point: 307–309°C (lit.)
* Refractive Index: n20/D 1.5200
* Flash Point: >230°F
* Storage: Sealed, dry, 2–8°C
* Acidity Coefficient (pKa): 2.73 ± 0.10 (predicted)
These attributes underline its stability and reactivity balance, making it suitable for controlled laboratory reactions without significant degradation.
Synthetic Routes of 2-(Tributylstannyl)thiazole
Several efficient methods exist for synthesizing 2-(Tributylstannyl)thiazole (CAS No.: 121359-48-6). Among them, the Grignard reagent method and lithium-tin exchange method are most commonly employed due to their high yields and reliability.
1. Grignard Reagent Method
This classical synthesis involves forming a Grignard intermediate from 2-bromothiazole. Under an inert argon atmosphere, a hexane solution of n-butyllithium is added dropwise to an anhydrous ether solution of 2-bromothiazole at 0°C. After stirring for 1 hour and cooling to –78°C, an anhydrous ether solution of tributyltin chloride is added slowly. The mixture is stirred overnight, quenched with water, and extracted with ether. The combined organic layers are dried with magnesium sulfate, and the solvent is removed under vacuum. The yield ranges between 92% and 97%, demonstrating excellent efficiency.
2. Lithium–Tin Exchange Method
In this alternative route, n-butyllithium is added to 2-bromothiazole in anhydrous ether at –78°C, forming a lithiated intermediate. Then, tributyltin chloride in diethyl ether is introduced gradually. The reaction is slowly warmed to room temperature and stirred to completion. Following quenching with water, extraction, drying, filtration, and concentration, the product is purified via silica gel chromatography, yielding about 90% of 2-(Tributylstannyl)thiazole.
3. Alternative Synthetic Approach
Another reported method uses 2-(trimethylsilyl)thiazole as the starting material, reacting it with tributyltin chloride at room temperature. This mild reaction proceeds smoothly, producing the target compound after standard post-treatment. This route may offer better scalability for industrial synthesis due to its simplicity and lower energy requirements.
Applications of 2-(Tributylstannyl)thiazole in Organic Synthesis
2-(Tributylstannyl)thiazole (CAS No.: 121359-48-6) serves as both an organic synthesis intermediate and a key reagent in advanced coupling reactions. Its dual role in pharmaceutical chemistry and organic materials science underlines its importance in modern chemical research.
1. As an Organic Synthesis Intermediate
In pharmaceutical chemistry, 2-(Tributylstannyl)thiazole acts as a precursor for organotin compounds with potential biological activities. These derivatives have been explored for antitumor, antibacterial, and antiviral properties, offering promising avenues for drug discovery and medicinal chemistry.
The thiazole moiety, commonly found in many bioactive molecules, enhances pharmacological stability and binding selectivity, while the organotin fragment contributes to biological activity modulation. Thus, this compound bridges traditional heterocyclic chemistry and metal-organic synthesis.
2. As a Reagent in Stille Cross-Coupling Reactions
2-(Tributylstannyl)thiazole is particularly valuable in Stille coupling, a palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organostannanes and halides or triflates. This reaction enables the construction of polyaryl structures and heteroaromatic compounds with remarkable precision.
In the context of thiazole arylation, 2-(Tributylstannyl)thiazole acts as a stannyl donor, reacting with aryl halides to generate substituted thiazoles. These products find broad use in electronic materials, dyes, OLED components, and bioactive compounds, showcasing the wide synthetic potential of this compound.
Storage, Handling, and Safety of 2-(Tributylstannyl)thiazole
Due to its organotin composition, 2-(Tributylstannyl)thiazole should be handled with care. It should be stored in tightly sealed containers, in a dry environment at 2–8°C, and away from light and moisture. Although relatively stable, it should be kept under an inert gas atmosphere when possible to prevent oxidation.
Direct skin or eye contact should be avoided, and handling should occur in a well-ventilated fume hood. Standard protective laboratory equipment—gloves, goggles, and lab coats—should always be used.
Conclusion
2-(Tributylstannyl)thiazole (CAS No.: 121359-48-6) stands as a cornerstone reagent in modern synthetic chemistry, combining the reactivity of the thiazole ring with the versatility of organotin chemistry. Its high purity, excellent yield from established synthesis methods, and vital role in cross-coupling reactions make it indispensable in both research and industrial applications. From pharmaceutical intermediates to functional material synthesis, this compound exemplifies how precise molecular design can drive innovation across multiple fields of chemistry.
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