Specifications Table

Product Name – tert-Butyldimethylsilyl chloride, 50 wt.% solution in toluene, AcroSeal®
Quantity/Pack Size – 100ML
Form – Liquid (toluene solution)
Grade – Laboratory Reagent
Application – Silylating agent for alcohols, phenols, and carboxylic acids

Product Overview

tert-Butyldimethylsilyl chloride (TBDMS-Cl) in 50% toluene solution is a highly reactive silylating agent designed for selective protection of hydroxyl and carboxyl groups in organic synthesis. The AcroSeal® packaging ensures minimal moisture exposure, preserving reagent integrity for consistent performance in lab applications. This solution offers enhanced solubility compared to neat TBDMS-Cl, making it ideal for reactions requiring homogeneous conditions. The bulky tert-butyl group provides steric hindrance, enabling selective protection of primary alcohols over secondary ones. With a molecular weight of 150.78 g/mol (neat), this reagent forms stable silyl ethers that can withstand a wide range of reaction conditions. The toluene solvent system allows for easy handling and precise dosing via syringe or pipette. Store under inert atmosphere at 2-8°C to maintain optimal reactivity. The reagent’s high purity (typically >97%) minimizes side reactions, while the standardized 50% concentration simplifies reaction stoichiometry calculations for synthetic chemists.

FAQs

1. What is the typical reaction time when using this TBDMS-Cl solution?

Reaction times vary based on substrate and conditions, but most silylation reactions complete within 1-4 hours at room temperature when using this 50% solution with imidazole or DMAP as base.

2. Can this solution be used for protecting amines?

This reagent is not suitable for amine protection as it primarily reacts with hydroxyl and carboxyl groups. For amine protection, consider using tert-butyldimethylsilyl triflate instead.

3. How does the toluene solvent affect the reaction?

The toluene solvent improves reagent solubility and allows for better mixing in organic reactions. It also helps moderate the reaction rate compared to using neat TBDMS-Cl.

4. What is the shelf life of this solution when stored properly?

When stored unopened at 2-8°C under inert atmosphere, this solution maintains its specified purity for at least 12 months from the date of manufacture.

5. Is this solution compatible with aqueous workups?

No, the silyl ethers formed are typically hydrolyzed under acidic or basic aqueous conditions. Use mild, non-aqueous quenching methods to preserve the protecting groups.