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

Uses

(4-Chlorophenyl)triethoxysilane can be used:To facilitate the connection between dipolar mixed monolayers and?zinc oxide in photovoltaic devices.As a substrate in the Ni-catalyzed decarboxylative coupling with alkynyl carboxylic acids to yield substituted diarylalkynes.As a substrate in the Hiyama cross-coupling reactions with 3-iodoazetidines to yield substituted 3-arylazetidines.As an intermediate in the synthesis of tripod-shaped oligo(p-phenylene)s, which are used in the surface immobilization of gold and CdS quantum dots for sensor applications.

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

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

Downstream Products

• 76666-25-6 1-(4-chloro-phenyl)-2,9,10-trioxa-6-aza-1-sila-bicyclo[4.3.3]dodecane 
• 80565-30-6 4'-chlorobiphenyl-4-carbaldehyde 
• 444144-86-9 1-(4-chlorophenyl)-2-nitro-1-phenylethane 
• 19482-11-2 4-chloro-4'-methylbiphenyl 
• 2051-62-9 4'-biphenyl chloride 
• 1428770-71-1 tri(4-iodophenyl)(4-chlorophenyl)silane 
• 153850-83-0 4'-chlorobiphenyl-2-carboxaldehyde 
• 15729-63-2 S-(n-butyl) 4-chlorobenzothioate 
• 42175-12-2 butyl (E)-4-chlorocinnamate 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 1193875-24-9 (E)-4-(4-chlorophenyl)but-2-en-1-ol 
• 98011-68-8 (Z)-4-(4-chlorophenyl)but-2-en-1-ol 
• 1186241-73-5 N-(3-(4-chlorophenyl)-2H-chromen-4-yl)acetamide 
• 5002-07-3 4'-(4-chlorophenyl)acetophenone 

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.