tert-Butyldimethylsilyl chloride
[CAS# 18162-48-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Silane
• Name: tert-Butyldimethylsilyl chloride
• Synonyms: TBSCl; tert-Butylchlorodimethylsilane; t-Butyldimethylsilyl chloride; t-Butyldimethylchlorosilane; TBDMCS; t-Butyl Dimethyl Chlorsilane
• Molecular Formula: C₆H₁₅ClSi
• Molecular Weight: 150.72
• CAS Registry Number: 18162-48-6
• EC Number: 242-042-4
• SMILES: CC(C)(C)[Si](C)(C)Cl

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.81 g/mL (Expl.)
• Melting point: 86-89 ºC (Expl.)
• Index of Refraction: 1.411, Calc.^*, 1.46 (Expl.)
• Boiling Point: 125.0±0.0 ºC (760 mmHg), Calc.^*, 125 ºC (Expl.)
• Flash Point: 22.8±0.0 ºC, Calc.^*, 22 ºC (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07;GHS09 Danger
• Hazard Statements: H228-H314-H318-H335-H411
• Precautionary Statements: P210-P240-P241-P260-P261-P264-P264+P265-P271-P273-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P321-P363-P370+P378-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable solids	Flam. Sol.	1	H228
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin corrosion	Skin Corr.	1A	H314
Skin corrosion	Skin Corr.	1C	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable solids	Flam. Sol.	2	H228
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - single exposure	STOT SE	3	H336
Acute toxicity	Acute Tox.	4	H302
Aspiration hazard	Asp. Tox.	1	H304
Flammable liquids	Flam. Liq.	2	H225

Discovory and Applicatios

tert-Butyldimethylsilyl chloride (TBDMSCl) is a widely used reagent in organic chemistry, known for its ability to protect hydroxyl and amine groups in the synthesis of complex molecules. Its chemical structure consists of a silicon atom bonded to a tert-butyl group and two methyl groups, with a chlorine atom attached to the silicon. The compound's molecular formula is C6H15ClSi, and it is typically used as a silylating agent to introduce the tert-butyl dimethylsilyl (TBDMS) group into molecules. This protective group is highly stable under a variety of conditions, making it an ideal choice for use in multi-step synthetic routes.

The discovery and application of tert-butyldimethylsilyl chloride can be traced back to the increasing need for selective protection in organic synthesis. The use of silyl groups as protecting groups was first explored in the mid-20th century, and the advent of tert-butyldimethylsilyl chloride provided chemists with a more stable and efficient alternative to other silylating agents. The compound was first synthesized and introduced into the scientific community in the early 1980s, quickly becoming a staple in synthetic organic chemistry.

Tert-butyldimethylsilyl chloride is primarily used to protect alcohols, phenols, and amines in reactions where selective protection is required. The silyl group formed is relatively inert to a wide range of reagents, allowing for the execution of various synthetic steps without interfering with the protected functional group. The TBDMS group can be removed easily under mildly acidic conditions, making it ideal for use in multistep syntheses where selective deprotection is necessary.

In addition to its use as a protecting group, tert-butyldimethylsilyl chloride has found applications in other areas of organic chemistry. It is frequently used in the preparation of nucleophilic reagents and in the synthesis of complex natural products. The compound has also been explored in materials science, where its properties are utilized to modify surfaces and create new materials with tailored chemical reactivity.

In summary, tert-butyldimethylsilyl chloride is a versatile reagent in organic synthesis, widely used for the protection of functional groups in multi-step synthetic pathways. Its stability, ease of use, and selective deprotection make it a valuable tool in the synthesis of complex molecules across a variety of fields.