21700-74-3

Usage

Uses

Used in Photovoltaic Devices:
CHLOROPHENYLTRIETHOXYSILANE is used as a connecting agent for facilitating the bond between dipolar mixed monolayers and zinc oxide, which is crucial for the efficient functioning of photovoltaic devices.
Used in Chemical Synthesis:
CHLOROPHENYLTRIETHOXYSILANE serves as a substrate in the Ni-catalyzed decarboxylative coupling with alkynyl carboxylic acids, yielding substituted diarylalkynes. These compounds are essential in the development of advanced materials and pharmaceuticals.
Used in Hiyama Cross-Coupling Reactions:
In the field of organic chemistry, CHLOROPHENYLTRIETHOXYSILANE is utilized as a substrate in Hiyama cross-coupling reactions with 3-iodoazetidines, leading to the formation of substituted 3-arylazetidines. These products are valuable intermediates in the synthesis of complex organic molecules.
Used in Sensor Applications:
CHLOROPHENYLTRIETHOXYSILANE acts as an intermediate in the synthesis of tripod-shaped oligo(p-phenylene)s, which are employed in the surface immobilization of gold and CdS quantum dots. This application is particularly relevant in the development of highly sensitive and selective sensors for various analytical purposes.

InChI:InChI=1/2C12H19ClO3Si/c1-4-14-17(15-5-2,16-6-3)12-9-7-11(13)8-10-12;1-4-14-17(15-5-2,16-6-3)12-9-7-8-11(13)10-12/h2*7-10H,4-6H2,1-3H3

Upstream product

• 106-39-8 bromochlorobenzene 
• 78-10-4 tetraethoxy orthosilicate 
• 998-30-1 Triethoxysilane 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 106-46-7 para-dichlorobenzene 
• 64-17-5 ethanol 
• 637-87-6 1-Chloro-4-iodobenzene 

Downstream Products

• 76666-25-6 1-(4-chloro-phenyl)-2,9,10-trioxa-6-aza-1-sila-bicyclo[4.3.3]dodecane 
• 13243-64-6 3-(4-chlorophenyl)-3-phenylpropanal 
• 19482-11-2 4-chloro-4'-methylbiphenyl 
• 2051-62-9 4'-biphenyl chloride 
• 1186241-73-5 N-(3-(4-chlorophenyl)-2H-chromen-4-yl)acetamide 
• 1193875-24-9 (E)-4-(4-chlorophenyl)but-2-en-1-ol 
• 98011-68-8 (Z)-4-(4-chlorophenyl)but-2-en-1-ol 
• 1428770-71-1 tri(4-iodophenyl)(4-chlorophenyl)silane 
• 623-03-0 4-Cyanochlorobenzene 
• 2050-68-2 4,4'-dichlorobiphenyl 
• 153850-83-0 4'-chlorobiphenyl-2-carboxaldehyde 
• 15729-63-2 S-(n-butyl) 4-chlorobenzothioate 
• 2373-43-5 diethyl (4-chlorophenyl)phosphonate 
• 24382-97-6 1-(4-chlorophenyl)naphthalene 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed Direct C-H Arylation of Various Acyclic Enamides with Arylsilanes

The stereoselective β-C(sp2)-H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by the gram-scale synthesis and further elaboration of the product. In addition, Rh(III)-catalyzed C-H activation is considered to be the critical step in the reaction mechanism.

Synthesis of azobenzene substituted tripod-shaped bi(p-phenylene)s. Adsorption on gold and CdS quantum-dots surfaces

We report here the synthesis of several tripod-shaped oligo(p-phenylene)s with legs composed of two phenylene units. Each leg is end-capped with a thioacetate group for adhesion to metallic surfaces. An azobenzene chromophore group is present on the functional arm of the tripod. The key step in the synthesis is the Pd-catalyzed Suzuki cross-coupling reaction of the silicon derivative core molecule with substituted phenyl moieties and azobenzene derivatives. Gold surfaces prepared by thermal evaporation and CdS quantum-dots surfaces were covered by the tripod-shaped molecules. Modified surfaces were characterized by atomic force microscopy (AFM), fluorescence, and Kelvin Probe analyses.

Advances in siloxane-based coupling reactions: Application of palladium-mediated allyl-aryl coupling to the synthesis of pancratistatin derivatives. The formal total synthesis of (±)-7-deoxypancratistatin

Palladium-mediated coupling of an allylic carbonate and an aryl siloxane has been applied to the formal total synthesis of 7-deoxypancratistatin and pancratistatin analogues. The key coupling reaction involved the use of a novel palladium olefin complex resulting in regio- and stereoselective arylation yielding a tetracyclic A-C ring intermediate. The observed regioselectivity of the coupling reaction was consistent with a model in which an unsymmetrical p-allyl palladium complex was formed. Coupling of a variety of substituted phenyl siloxane derivatives was achieved using the new Pd(0) system to provide access to novel pancratistatin derivatives.

Synthesis of aryltriethoxysilanes via rhodium(I)-catalyzed cross-coupling of aryl electrophiles with triethoxysilane

The general and efficient silylation of aryl halides has been developed utilizing triethoxysilane and a rhodium catalyst. The substrate scope is broad and includes ortho-, meta-, and para-substituted electron-rich and -deficient aryl iodides. In addition, the silylation of aryl bromides and fluoroalkanesulfonates proceeded in the presence of tetra-n-butylammonium iodide.

Palladium-catalyzed cross-coupling reaction of aryltriethoxysilanes with aryl bromides under basic aqueous conditions

Aryltriethoxysilanes were cross-coupled with aryl bromides in high yield in the presence of a palladium catalyst and aqueous sodium hydroxide.

Improved synthesis of aryltriethoxysilanes via palladium(O)-catalyzed silylation of aryl iodides and bromides with triethoxysilane

The scope of the palladium-catalyzed silylation of aryl halides with triethoxysilane has been expanded to include aryl bromides. A more general Pd(0) catalyst/ligand system has been developed that activates bromides and iodides: palladium(O) dibenzylideneacetone (Pd(dba)2) is activated with 2-(di-tert-butylphosphino)biphenyl (Buchwald's ligand) (1:2 mol ratio of Pd/phosphine). Electronrich para- and meta-substituted aryl halides (including unprotected aniline and phenol derivatives) undergo silylation to form the corresponding aryltriethoxysilane in fair to excellent yield; however, ortho-substituted aryl halides failed to be silylated.