21700-74-3

Basic information

• Product Name: CHLOROPHENYLTRIETHOXYSILANE
• Synonyms: p-chlorophenyltriethoxysilane7%;p-chlorophenyltrimethoxysilane;Silane, (4-chlorophenyl)triethoxy-;(4-chlorophenyl)triethoxy-silan;(4-chlorophenyl)triethoxy-Silane;CHLOROPHENYLTRIETHOXYSILANE;Chlorophenyltriethoxysilane(mixed m.p isomers);1-CHLORO-4-TRIETHOXYSILYLBENZENE
• CAS NO: 21700-74-3
• Molecular Formula: C₁₂H₁₉ClO₃Si
• Molecular Weight: 274.82
• EINECS: 244-533-9
• Mol File: 21700-74-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 82-84 °C0.07 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.069 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0101mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• CAS DataBase Reference: CHLOROPHENYLTRIETHOXYSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOROPHENYLTRIETHOXYSILANE(21700-74-3)
• EPA Substance Registry System: CHLOROPHENYLTRIETHOXYSILANE(21700-74-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 21700-74-3(Hazardous Substances Data)

Usage

Description

CHLOROPHENYLTRIETHOXYSILANE is an organosilane compound characterized by its chlorophenyl group and three ethoxy groups attached to a central silicon atom. This unique structure endows it with versatile properties, making it a valuable component in various industrial applications.

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

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

Downstream Products

• 76666-25-6 1-(4-chloro-phenyl)-2,9,10-trioxa-6-aza-1-sila-bicyclo[4.3.3]dodecane 
• 29025-67-0 1-(4-chlorophenyl)silatrane 
• 13243-64-6 3-(4-chlorophenyl)-3-phenylpropanal 
• 19482-11-2 4-chloro-4'-methylbiphenyl 
• 1428770-71-1 tri(4-iodophenyl)(4-chlorophenyl)silane 
• 40832-73-3 N-(4-chlorophenyl)piperidine 
• 444144-86-9 1-(4-chlorophenyl)-2-nitro-1-phenylethane 
• 80565-30-6 4'-chlorobiphenyl-4-carbaldehyde 
• 5184-71-4 4-methylphenyl-4-chlorophenyl sulfone 
• 24382-97-6 1-(4-chlorophenyl)naphthalene 
• 49562-28-9 fenofibrate 
• 2069-48-9 4-chloro-4'-fluoro-benzophenone 
• 10547-60-1 4-chloro-4'-methoxybenzophenone 
• 134-85-0 4-chlorobenzophenone 

Relevant articles and documents

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.

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.

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.