33729-92-9

Basic information

• Product Name: tert-Butyldiphenylsilane
• Synonyms: tert-Butyldiphenylsilane;tert-Butyldiphenylsilane
• CAS NO: 33729-92-9
• Molecular Formula: C₁₆H₂₀Si
• Molecular Weight: 240
• Mol File: 33729-92-9.mol

Chemical Properties

• Boiling Point: 309℃
• Flash Point: 137℃
• Appearance: /
• Refractive Index: 1.5570-1.5610
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: tert-Butyldiphenylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyldiphenylsilane(33729-92-9)
• EPA Substance Registry System: tert-Butyldiphenylsilane(33729-92-9)

Safety Data

• Hazardous Substances Data: 33729-92-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Tert-butyldiphenylsilane is used as a reagent in organic synthesis for its ability to facilitate the formation of silicon-containing compounds, which are valuable in the development of new materials and pharmaceuticals.
Used in Silicon-Containing Polymers:
In the polymer industry, tert-butyldiphenylsilane is used as a precursor for the synthesis of silicon-containing polymers, which exhibit unique properties such as thermal stability and resistance to environmental degradation.
Used as a Protective Group in Organic Chemistry Reactions:
Tert-butyldiphenylsilane serves as a protective group in organic chemistry reactions, allowing chemists to temporarily block certain functional groups during the synthesis process, ensuring selective reactions and facilitating the synthesis of complex organic molecules.
Used as a Source of tert-Butyl Groups:
In organic synthesis, tert-butyldiphenylsilane is used as a source of tert-butyl groups, which are commonly employed as protecting groups for alcohols and carboxylic acids, as well as in the formation of stable carbocations in various reactions.
Used in the Preparation of Silicon-Based Materials:
Tert-butyldiphenylsilane is utilized as a precursor for the preparation of silicon-based materials, which have applications in various fields, including electronics, optoelectronics, and materials science, due to their unique properties such as high thermal stability and electrical conductivity.

Upstream product

• 136985-00-7 benzyl 2-C-(1-butynyl)-2-deoxy-4-O-(tert-butyldiphenylsilyl)-α-L-arabinopyranoside 
• 136985-01-8 benzyl 2-C-butyl-2-deoxy-4-O-(tert-butyldiphenylsilyl)-α-L-arabinopyranoside 
• 136984-99-1 benzyl 2,3-anhydro-4-O-(tert-butyldiphenylsilyl)-α-L-ribopyranoside 
• 136985-02-9 (2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,5-di-hydroxy-4-(tert-butyldiphenylsiloxy)-pentane 
• 789-25-3 HSiPh₃ 
• 775-12-2 diphenylsilane 
• 594-19-4 tert.-butyl lithium 
• 6843-66-9 dimethoxy(diphenyl)silane 
• 677-22-5 tert-butylmagnesium chloride 
• 136985-03-0 (2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3-hydroxy-5-(methanesulfonyloxy)-4-(tert-butyldiphenylsiloxy)-pentane 
• 6157-41-1 sodium bis(benzene-1,2-diolatophenyl)silicate 
• 127808-34-8 Diphenylsilyltrifluormethansulfonat 

Downstream Products

• 1354714-74-1 (3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldiphenylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopentafuran-2-one 

Relevant articles and documents

Sila-metalation route to hydrido(trialkylsilyl)silyllithiums

The proton abstraction (sila-metalation) of trialkylsilyl-substituted dihydridosilanes with t-BuLi or LDA in THF was found to be a convenient route to the corresponding silyllithiums (RR′SiHLi; 1a, R, R′ = t-BuMe2Si; 1b, R, R′ = Me3S

A Catalytic SEAr Approach to Dibenzosiloles Functionalized at Both Benzene Cores

A general procedure for the catalytic preparation of dibenzosiloles functionalized at one or both benzene rings starting from readily available ortho-silylated biphenyls is reported. This method provides rapid access to silole building blocks substituted with chlorine atoms at both phenylene groups, thereby allowing catalytic access to directly polymerizable dibenzosiloles. Moreover, it is shown that, despite the involvement of highly electrophilic intermediates, a considerable range of Lewis-basic, for example, oxygen- and nitrogen-containing, functional groups is tolerated. The mechanism of this intramolecular electrophilic aromatic substitution (SEAr) proceeds through a sulfur-stabilized silicon cation, generated catalytically from the hydrosilane precursor.

Intramolecular termination of radical-polar crossover reactions

Cyclic ethers result from intramolecular trapping of cations formed through the radical-polar crossover process.

Preparation of New Monomeric, Oligomeric, and Polymeric Silyl Triflates

The highly reactive silyl triflates R3SiOSO2CF3 are valuable reagents in organosilicon chemistry.New triflate derivatives of mono- and oligosilanes have been prepared by substitution of phenyl groups or hydrogen atoms for the trifluoromethanesulfonyl group.The presence of the electron-withdrawing triflate group leads to a strong deactivation of the other substituents at the silicon atom, and the displacement of a second phenyl group at the same silicon atom is much slower than the first step.For this reason in the case of phenylated oligosilanes stepwisemonosubstitution of the silicon atoms has been found.Other new oligomeric silyl triflates are obtained by reaction of silanediyl(triyl) bis(tris)(trifluoromethanesulfonates) with lithium derivatives of organosilicon compounds.Finally, the cleavage of silicon - phenyl bonds of poly by CF3SO3H leads to triflate derivatives of polysilanes. Key Words: Silyl triflates / Organosilanes

Organoaluminium induced ring-opening of epoxypyranosides. V. Formal total synthesis of antimycin A3 and synthesis of (+)-blastmycinone

Epoxide ring-opening of the benzyl 2,3-anhydro-α-L-ribopyranoside 6 with lithium butynyl(trimethyl)aluminate followed by functional group interconversions gave the dihydroxy thioacetal 11, which was regio-selectively acylated with an L-threonine derivativ

STEREO-CONTROLLED SYNTHESIS OF ERYTHRONOLIDES A AND B FROM 1,6-ANHYDRO-β-D-GLUCOPYRANOSE (LEVOGLUCOSAN). SKELETON ASSEMBLY IN (C9 - C13) + (C7 - C8) + (C1 - C6) SEQUENCE

Stereospecific syntheses of erythronolides A and B have been accomplished starting from 1,6-anhydro-β-D-glucopyranose (levoglucosan) in a uniform synthetic sequence.

Reactivity of Hypervalent Species: Reactions of Anionic Penta-Coordinated Silicon Complexes towards Nucleophiles

The reactivity of anionic penta-coordinated silicon complexes 4-O)2>-Na+ 1 with nucleophilic reagents has been studied. 1 can be reduced to organosilanes RSiH3 by metallic hydrides.Reactions with an excess of Grignard or organolithium reagents (R'MgX or R'Li) gave tetraorganosilanes RSiR'3.When only two molar equivalents of Grignard reagents (R'MgX) or lithium reagents (R'Li) are added to complexs 1 functional silanes RR'2SiX can be prepared.