Tert-Butyldimethylsilyl Chloride CAS 18162-48-6

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Tert-butyldimethylsilyl chloride, commonly abbreviated as TBDMSCl or TBS-Cl, is a versatile and widely used chemical compound in organic synthesis and as a protecting group reagent. With the chemical formula C6H15ClSi, it belongs to the class of organosilicon compounds, specifically silyl chlorides. Its molecular structure features a tertiary butyl group (tert-butyl), two methyl groups, and a silicon atom bearing a chloride substituent.

The tert-butyldimethylsilyl (TBDMS) group is highly valued for its ability to protect hydroxyl, carboxyl, amino, and thiol functionalities in organic molecules under a variety of reaction conditions. This protection is achieved through the formation of stable silyl ethers, esters, and amines, which are resistant to acids, bases, and nucleophiles. The chloride moiety serves as a good leaving group, facilitating the substitution reactions that install the TBDMS group onto the substrate.

Tert-butyldimethylsilyl chloride is typically employed in synthetic chemistry due to its stability, ease of handling, and high yields in protecting group reactions. It can be used in both acidic and basic environments, offering broad compatibility with different reaction media. Furthermore, the removal of the TBDMS group, often referred to as desilylation, can be achieved under mild conditions, such as treatment with tetrabutylammonium fluoride (TBAF) or fluoride ions in acidic solutions, making it a reversible and controlled process.

In addition to its protective role, it finds applications in other areas like cross-linking polymers, modifying surfaces, and as a precursor in the synthesis of other silylating agents. Its low toxicity and relatively benign handling characteristics make it a preferred choice for both laboratory-scale research and industrial-scale manufacturing processes.

Tert Butyldimethylchlorosilane (TBDMSCl or TBSCl) is an important organic silicon compound with the molecular formula C ₆ H ₁₅ ClSi. It usually appears as a white or off white low melting point waxy solid or colorless liquid (pure), with a pungent odor. This compound has a wide range of applications in organic synthesis, pharmaceutical manufacturing, materials science, and other fields.

1. Hydroxyl protecting group
TBSCl is one of the most widely used hydroxyl protecting groups in organic synthesis. It can react with alcohol hydroxyl groups under mild conditions to generate corresponding silicon ethers, thereby protecting the hydroxyl groups from the effects of subsequent reactions. Compared with the common organosilicon protecting group trimethylchlorosilane (TMS), the silicon ether prepared by TBDMSCl has higher chemical stability and can maintain stability under a wider range of reaction conditions, thus having a wider range of applications and generally higher product yields.

Selective protection: In molecules with multiple hydroxyl groups, tert-butyldimethylsilyl chloride can preferentially react with primary alcohols with lower steric hindrance, achieving chemical selective protection. By regulating reaction conditions such as temperature, base, time, etc., protection of secondary alcohols and even phenolic hydroxyl groups can also be achieved. For example, under the combination conditions of CH ₂ Cl ₂ - Et ∝ N-DMAP (dichloromethane triethylamine 4-dimethylaminopyridine), selective protection of primary alcohols in the presence of secondary or tertiary alcohols can be easily achieved.

Deprotection method: Deprotection is the reverse process of upper protection, which involves breaking Si-O bonds and releasing free alcohols. The most commonly used and specific method is to use a THF solution of tetrabutylammonium fluoride (TBAF) and stir it at room temperature for a short period of time to efficiently remove the TBS protecting group. In addition, acid catalyzed removal (such as using dilute acetic acid, p-toluenesulfonic acid, or hydrochloric acid) and silica gel column chromatography removal are also commonly used methods.

2. Silanization reagent
In addition to serving as a hydroxyl protecting group, TBDMSCl can also be used as a silanization reagent to react with other functional groups (such as ketones, esters, amides, etc.) to generate corresponding silicon ethers or silicon esters. For example, in the presence of strong bases such as LDA, KHMDS, etc., TBDMSCl and ketone carbonyl groups can generate TBDMS silyl ethers in high yields. In addition, TBDMSCl can also react with carboxylic acids, carboxylic acid amides, and other compounds to produce corresponding silicone esters or silicone amides.

These reactions not only require the action of strong bases, but also the addition of HMPA (hexamethylphosphoramide) or DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) - pyrimidinone) is beneficial for improving the reaction rate and yield.

 

3. Oxidizing and decyanating agents
TBDMSCl can also be used as an oxidant and decyanation agent. For example, it can cause aromatic acetonitrile to form ketones and achieve decyanation reaction. In addition, TBDMSCl can also participate in other oxidation reactions, such as oxidizing alcohols to aldehydes or ketones.

1. Pharmaceutical intermediates
Tert-butyldimethylsilyl chloride is an important raw material for synthesizing various pharmaceutical intermediates. For example, it can be used to synthesize prostaglandins, certain antibiotics, lipid-lowering drugs (such as lovastatin, simvastatin), etc. During the synthesis of these drugs, TBDMSCl acts as a hydroxyl protecting group or silanizing agent, effectively protecting specific functional groups and avoiding unnecessary chemical changes in subsequent reactions, thereby improving the efficiency and yield of drug synthesis.

Specific application: In the synthesis of lovastatin and simvastatin, TBDMSCl is used to protect the hydroxyl groups of alcohols, ensuring that the hydroxyl groups are not oxidized or undergo other reactions during the synthesis process.

By precisely controlling the reaction conditions, a highly selective reaction between TBDMSCl and alcohol hydroxyl groups can be achieved, resulting in high-purity intermediates that lay the foundation for subsequent drug synthesis.

2. Drug analysis
In the field of drug analysis, TBDMSCl also plays an important role. It can be used as a derivatization reagent to react with specific functional groups (such as hydroxyl, carboxyl, etc.) in drug molecules to generate stable derivatives, thereby improving the sensitivity and accuracy of drug detection. For example, in gas chromatography-mass spectrometry (GC-MS) analysis, TBDMSCl can react with hydroxyl groups in drug molecules to generate corresponding silicon ether derivatives, thereby improving the volatility and thermal stability of the drug, and enhancing the accuracy and reliability of the analysis.

1. Synthesis of polymer materials
TBDMSCl can be used to synthesize various organic silicon polymer materials, such as silicone rubber, silicone oil, silicone grease, etc. In the synthesis process of these materials, TBDMSCl acts as a silane or crosslinking agent, which can react with other monomers or polymers to form stable silicon oxygen or silicon carbon bonds, thereby endowing the materials with excellent physical and chemical properties. For example, in the synthesis of silicone rubber, TBDMSCl can react with polydimethylsiloxane (PDMS) to form a cross-linked silicone rubber network structure, improving the strength and elasticity of silicone rubber.

2. Surface modification of materials
TBDMSCl can also be used for surface modification of materials. By combining with other reagents such as fluorides, silane coupling agents, etc., TBDMSCl can form a stable siloxane film or silicon fluoride compound film on the surface of the material, thereby improving the surface properties of the material (such as wetting, wear resistance, corrosion resistance, etc.). For example, in the surface treatment of metal materials, TBDMSCl can react with fluoride to form a dense silicon fluoride compound film, improving the corrosion resistance and wear resistance of the metal material.

1. Coatings, adhesives, and sealants
Tert-butyldimethylsilyl chloride can be used as an additive in coatings, adhesives, and sealants to improve the weather resistance and adhesion of products. In these products, TBDMSCl can react with other components to form stable chemical bonds or network structures, thereby enhancing the physical and chemical properties of the product. For example, adding TBDMSCl to coatings can improve their water resistance, chemical corrosion resistance, and wear resistance; Adding TBDMSCl to the adhesive can improve its bonding strength and weather resistance.

2. Analytical Chemistry
In analytical chemistry, TBDMSCl can be used as a silanization reagent for sample derivatization. For example, when combined with reagents such as MTBSTFA (N-methyl-N - (tert butyldimethylsilyl) trifluoroacetamide), TBDMSCl can provide stable tert butyldimethylsilane (TBDMS) derivatization for hydroxyl, carboxyl, thiol, and amine compounds. This derivatization method can significantly enhance the volatility and thermal stability of these compounds, thereby improving their separation efficiency and detection sensitivity in gas chromatography (GC) or liquid chromatography (LC).

The synthesis methods of tbdmsci mainly include dimethyl tert butyl silane chlorination method, dimethyl tert butyl silanol chlorination method, tert butyl chloroform reagent method, etc. there is no raw material source of dimethyl tert butyl silane in China, and the yield of dimethyl tert butyl silanol method is low (about 50%), and the raw material comes from the deprotection by-product of tbdmsci. Therefore, the preparation of tbdmsci by tert butyl chloroform reagent method is an ideal synthesis method. The synthetic route is as follows.

In a four neck flask equipped with nitrogen protection device, agitator, reflux condenser and constant pressure dropping funnel (CaCl2 drying pipe is installed on the top of the reflux condensing pipe), after removing the air in the flask with nitrogen, add 19.4 g (o. 15 mol) of dimethyldichlorosilane and 80 ml of tetrahydrofuran, an appropriate amount of cuprous chloride catalyst, stir, heat, control the temperature at about 60 C, and drop tert butyl magnesium chloride Grignard reagent into the reaction system within 45 minutes. After 4.5 hours of reaction, add 150 ml of petroleum ether and stir. Natural cooling, suction filtration and collection of filtrate. Wash the filter cake with 30ml petroleum ether for 2-3 times and combine it with the filtrate. First evaporate most of the solvents under normal pressure, and then evaporate the residual low boiling point substances under vacuum. Collect colorless transparent solid at 124-126 C by atmospheric distillation, weigh 16.79 g (0.111 mol), and the yield is 74.2%. The purity of the product is 99.3% (GC).

The common catalysts for the synthesis of tert butyl dimethylchlorosilane are cuprous chloride, sodium thiocyanate and cuprous cyanide. Under the same conditions of using tetrahydrofuran as solvent, n (dimethyldichlorosilane): n (tert butyl magnesium chloride) =1:1, reaction temperature 60C and reaction time 4.5H, using cuprous cyanide as catalyst has the best effect and highest yield, while the product synthesized with sodium thiocyanate as catalyst has odor and low yield.

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