Overview
test-Butyldimethylsilyl chloride, commonly abbreviated as TBSCl or TBDMSCl, is an organosilicon compound widely used in organic synthesis for the protection of alcohols and amines. Known for its effectiveness in forming silyl ethers, TBSCl is essential in various chemical processes. This blog post explores the chemical properties, applications, and safety measures associated with tort-butyldimethylsilyl chloride, providing a thorough overview for researchers and industry professionals.
Description
test-Butyldimethylsilyl chloride is a colorless to pale yellow liquid, notable for its reactivity with alcohols and amines to form stable silyl ether and silyl amine derivatives. This organosilicon compound is a popular protecting group in organic synthesis due to its stability under a wide range of conditions.
Product Information
- IUPAC Name: tert-Butyldimethylsilyl chloride
- Common Name: TBSCl or TBDMSCl
- CAS Number: 18162-48-6
- Molecular Formula: C₆H₁₅ClSi
- Molecular Weight: 150.72 g/mol
- Appearance: Colorless to pale yellow liquid
- Boiling Point: 125-126°C
- Density: 0.865 g/cm³
- Solubility: Soluble in organic solvents like dichloromethane, toluene, and ether; reacts with water
Applications
- Protecting Group in Organic Synthesis
- TBSCl is widely utilized to protect alcohols and amines by forming stable silyl ether and silyl amine derivatives, which can withstand a variety of reaction conditions.
- Peptide Synthesis
- In peptide synthesis, TBSCl is used to protect functional groups during the synthesis process, ensuring high-purity and high-yield peptide production.
- Drug Development
- The pharmaceutical industry employs TBSCl in the synthesis of various drug compounds, especially those requiring the protection of hydroxyl and amino groups during multiple-step synthesis processes.
- Material Science
- TBSCl is used in the functionalization of surfaces and in the preparation of silicon-based materials.
Physicochemical Information
- Molecular Formula: C₆H₁₅ClSi
- Molecular Weight: 150.72 g/mol
- Boiling Point: 125-126°C
- Density: 0.865 g/cm³
- Solubility: Soluble in organic solvents; reacts with water
Safety Information According to GHS
- Hazard Statements:
- H225: Highly flammable liquid and vapor
- H302: Harmful if swallowed
- H314: Causes severe skin burns and eye damage
- H335: May cause respiratory irritation
- Precautionary Statements:
- P210: Keep away from heat, hot surfaces, sparks, open flames, and other ignition sources. No smoking.
- P280: Wear protective gloves/protective clothing/eye protection/face protection.
- P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
- P303+P361+P353: IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower.
- P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
Safety Information
- Hazards: TBSCl is flammable and corrosive, causing severe burns to skin and eyes. Inhalation of vapors can lead to respiratory irritation.
- Protective Measures: Use appropriate personal protective equipment (PPE) such as gloves, safety goggles, and lab coats. Work with TBSCl should be conducted in a well-ventilated area, preferably in a fume hood.
- Storage: Store in tightly sealed containers made of compatible materials, away from ignition sources and moisture.
Storage and Shipping Information
- Storage Conditions: Store in a cool, dry place in tightly sealed containers. Keep away from sources of ignition and moisture.
- Shipping Information: Transport according to local regulations. Ensure containers are secure and upright during transit to prevent leaks.
Transport Information
- UN Number: 2920
- Hazard Class: 8 (Corrosive substances)
- Packing Group: II
- Proper Shipping Name: Corrosive liquid, flammable, n.o.s. (contains tert-Butyldimethylsilyl chloride)
Specifications
- Purity: Typically >98%
- Appearance: Colorless to pale yellow liquid
- Boiling Point: 125-126°C
- Density: 0.865 g/cm³
Related Products & Applications
- Triisopropylsilane (TIPS): Used similarly to TBSCl in organic synthesis and peptide synthesis.
- Trimethylsilyl Chloride (TMSCl): Another silylating agent used to protect hydroxyl groups in organic synthesis.
- Di-tert-butylsilyl Chloride (DTBSCl): Employed in organic synthesis for the protection of alcohols and amines.
- Silicon-based Reagents: Various reagents used in organic synthesis and material science to impart desirable properties.