18412-68-5

Basic information

• Product Name: 1-(TRIMETHYLSILYL)-4-TERT-BUTYLBENZENE
• Synonyms: 1-(TRIMETHYLSILYL)-4-TERT-BUTYLBENZENE
• CAS NO: 18412-68-5
• Molecular Formula: C₁₃H₂₂Si
• Molecular Weight: 206.4
• Mol File: 18412-68-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(TRIMETHYLSILYL)-4-TERT-BUTYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(TRIMETHYLSILYL)-4-TERT-BUTYLBENZENE(18412-68-5)
• EPA Substance Registry System: 1-(TRIMETHYLSILYL)-4-TERT-BUTYLBENZENE(18412-68-5)

Safety Data

• Hazardous Substances Data: 18412-68-5(Hazardous Substances Data)

Usage

Chemical structure

An organic compound consisting of a benzene ring with a tert-butyl group and a trimethylsilyl group attached to it.

Functional groups

Contains a trimethylsilyl group and a tert-butyl group.

Molecular weight

Approximately 198.41 g/mol

Appearance

Colorless to pale yellow liquid

Solubility

Soluble in organic solvents such as dichloromethane, ethyl acetate, and hexane

Boiling point

Approximately 220°C

Melting point

Not available, as it is a liquid at room temperature

Density

Not available, as it is a liquid at room temperature

Reactivity

Stable under normal conditions, but can react with strong acids, strong bases, and oxidizing agents

Uses

Commonly used as a reagent in organic synthesis for the protection of alcohols and amines

Protection of functional groups

The trimethylsilyl group is used to protect sensitive functional groups from unwanted reactions during chemical manipulations

Steric hindrance

The tert-butyl group provides steric hindrance, making it an effective protective agent for certain chemical reactions

Precursor

Can serve as a precursor for the synthesis of other important organic compounds

Safety

Handle with care, as it may be harmful if swallowed, inhaled, or if it comes into contact with the skin

Storage

Store in a cool, dry, and well-ventilated area, away from heat, sparks, and open flames

Disposal

Dispose of according to local regulations and guidelines for hazardous materials

Regulatory status

Not listed as a hazardous substance under major regulations such as the US EPA's Toxic Substances Control Act (TSCA) or the European Union's REACH regulation

Synonyms

4-tert-Butylphenyltrimethylsilane, (4-tert-Butylphenyl)trimethylsilane

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 3972-56-3 4-(tert-butyl)chlorobenzene 
• 1030471-15-8 p-tert-butyl-α,α,α-trifluoromethoxybenzene 
• 769-92-6 4-tert-Butylaniline 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 63488-10-8 4-tert-butylmagnesium bromide 

Downstream Products

• 76782-93-9 4-tert-butyl-1-(dibromoboryl)benzene 
• 916162-47-5 (p-(t)BuC₆H₄)2BBr 
• 1625-91-8 4,4'-di-tert-butylbiphenyl 
• 3056-64-2 4-(tert-butyl)phenyl acetate 
• 1429493-96-8 C₃₂H₂₉BN₂O 
• 701-30-4 1-tert-butyl-4-fluorobenzene 

Relevant articles and documents

Luminescence tuning of organoboron quinolates through substituent variation at the 5-position of the quinolato moiety

A series of organoboron quinolates with emission colors ranging from blue to red have been prepared. In comparison to the respective AlQ3 derivatives a distinct blue-shift of the emission is observed. Theoretical calculations serve to provide i

Generation of Aryllithium Reagents from N -Arylpyrroles Using Lithium

Treatment of 1-aryl-2,5-diphenylpyrroles with lithium powder in tetrahydrofuran at 0 °C results in the generation of the corresponding aryllithium reagents through reductive C-N bond cleavage.

Gold-catalyzed oxidative coupling of arylsilanes and arenes: Origin of selectivity and improved precatalyst

The mechanism of gold-catalyzed coupling of arenes with aryltrimethylsilanes has been investigated, employing an improved precatalyst (thtAuBr3) to facilitate kinetic analysis. In combination with linear free-energy relationships, kinetic isotope effects, and stoichiometric experiments, the data support a mechanism involving an Au(I)/Au(III) redox cycle in which sequential electrophilic aromatic substitution of the arylsilane and the arene by Au(III) precedes product-forming reductive elimination and subsequent cycle-closing reoxidation of the metal. Despite the fundamental mechanistic similarities between the two auration events, high selectivity is observed for heterocoupling (C-Si then C-H auration) over homocoupling of either the arylsilane or the arene (C-Si then C-Si, or C-H then C-H auration); this chemoselectivity originates from differences in the product-determining elementary steps of each electrophilic substitution. The turnover-limiting step of the reaction involves associative substitution en route to an arene π-complex. The ramifications of this insight for implementation of the methodology are discussed.