| Customization: | Available |
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| CAS No.: | 18162-48-6 |
| Formula: | C6h15clsi |
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| Product names | Tert-Butyldimethylsilyl chloride |
| CAS No | 18162-48-6 |
Tert-Butyldimethylsilyl chloride (TBDMS-Cl) is an organosilicon compound with the chemical formula (Me3C)Me2SiCl. It is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols. The compound is commonly used as a protecting reagent in organic synthesis due to its bulky structure, which provides steric hindrance and enhances the stability of the protected groups.
Synthesis
TBDMS-Cl can be synthesized by reacting tert-butyllithium with dichlorodimethylsilane. The reaction involves cooling a pentane solution of dichlorodimethylsilane to 0°C, adding a pentane solution of tert-butyllithium dropwise under nitrogen, and then heating the mixture to 25°C for 48 hours. The product is obtained by distillation, yielding TBDMS-Cl with a 70% yield.
Applications
Protecting Group: TBDMS-Cl is widely used to protect hydroxyl groups in organic synthesis. It reacts with alcohols in the presence of a base (such as imidazole) to form tert-butyldimethylsilyl ethers, which are more stable than trimethylsilyl ethers. This protecting group is particularly useful in the synthesis of prostaglandins, ribonucleosides, and other complex molecules.
Synthesis of Pharmaceuticals: It is used as an auxiliary material in the synthesis of hypolipidemics such as lovastatin and simvastatin.
Gas Chromatography/Mass Spectrometry: TBDMS-Cl is used as a derivatization agent to enhance the volatility and stability of analytes for gas chromatography/mass spectrometry applications.
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