227936-62-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
(3-Chlorophenylethynyl)trimethylsilane is used as a reagent in the synthesis of pharmaceuticals and agrochemicals for its ability to readily react with nucleophiles, facilitating the creation of complex organic molecules that can exhibit biological activity.
Used in Silicone Resin and Polymer Preparation:
In the field of materials science, (3-Chlorophenylethynyl)trimethylsilane serves as a crosslinking agent in the preparation of silicone resins and polymers, enhancing their properties and performance in various applications.
Used in Materials Science:
(3-CHLOROPHENYLETHYNYL)TRIMETHYLSILAN& is also utilized in materials science, where it is studied for potential applications that can leverage its unique chemical properties to develop innovative materials with specific characteristics.
Used as a Building Block in Chemical Structure Development:
Furthermore, (3-Chlorophenylethynyl)trimethylsilane is recognized as a building block in the development of new chemical structures, allowing chemists to explore novel molecular architectures with potential applications in various industries.

InChI:InChI=1/C11H13ClSi/c1-13(2,3)8-7-10-5-4-6-11(12)9-10/h4-6,9H,1-3H3

Upstream product

• 625-99-0 3-iodochlorobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 75-77-4 chloro-trimethyl-silane 
• 766-83-6 m-chlorophenylacetylene 

Downstream Products

• 1184872-84-1 (Z)-3-(3-chlorophenyl)-2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)-1-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 
• 1184872-74-9 3-(3-chlorophenyl)-1-cyclohexylprop-2-yn-1-ol 
• 766-84-7 3-chloro-benzonitrile 
• 1459714-42-1 5-(3-chlorophenyl)-3-methylenepent-4-yn-1-ol 
• 80221-18-7 1,4-bis(3-chlorophenyl)buta-1,3-diyne 
• 1354640-26-8 2,5-bis(3-chlorophenyl)thiophene 
• 1279694-62-0 4,6-di(3-chlorophenyl)-[1,2]-oxathiine 2,2-dioxide 
• 1279694-90-4 4,6-di(3-chlorophenyl)-3-(phenylethynyl)-1,2-oxathiine 2,2-dioxide 
• 1279694-76-6 3-bromo-4,6-di(3-chlorophenyl)-[1,2]-oxathiine 2,2-dioxide 

Relevant academic research and scientific papers

Synthesis, Characterization of Spirocyclic λ3-Iodanes and Their Application to Prepare 4,1-Benzoxazepine-2,5-diones and 1,3-Diynes

Herein, a [3+2] cycloaddition of aza-oxyallylic cations with ethynylbenziodoxolones for synthesis of new λ3-iodanes containing spirocyclic 4-oxazolidinone has been developed. This cyclic λ3-iodanes display stability in air and excellent solubility in organic solvent. Using them as substrate, both the 4,1-benzoxazepine-2,5-diones and symmetrical 1,3-diynes derivatives were afforded in high yield under copper(I)-catalyzed conditions.

Asymmetric Hydrosilylation of β-Silyl Styrenes Catalyzed by a Chiral Palladium Complex

A palladium complex coordinated with a chiral SIPHOS ligand was evaluated as an efficient catalyst for asymmetric hydrosilylation of β-silyl styrenes with trichlorosilane and 23 1,2-bis(silyl) chiral compounds were produced. Good to excellent enantioselec

Sustainable Ligand-Free Heterogeneous Palladium-Catalyzed Sonogashira Cross-Coupling Reaction in Deep Eutectic Solvents

The commercially available and cheap Pd/C was found to promote Sonogashira couplings in the environmentally friendly choline chloride/glycerol eutectic mixture in the absence of external ligands. Under heterogeneous conditions, (hetero)aryl iodides were successfully coupled with both aromatic and aliphatic alkynes in yields ranging from 50 to 99 % within 3 h at 60 °C. The aforementioned catalytic system proved to be effective also towards electron-rich iodides, which are notoriously known to be poorly reactive in Pd-catalyzed Sonogashira coupling reactions. The eutectic mixture and the catalyst could easily and successfully be recycled up to four times with an E-factor as low as 24.4.

γ-Carboline synthesis enabled by Rh(iii)-catalysed regioselective C-H annulation

A redox-neutral Rh(iii)-catalyzed C-H annulation of indolyl oximes was developed. Relying on the use of various alkynyl silanes as the terminal alkyne surrogates, the reaction exhibited a reverse regioselectivity, thus giving an exclusive and easy way for the synthesis of a wide range of substituent free γ-carbolines at C3 position with high efficiency. Deuterium-labelling experiments and kinetic analysis have preliminarily shed light on the working mode of this catalytic system. This journal is

Iridium-Catalyzed Asymmetric Transfer Hydrogenation of Alkynyl Ketones Using Sodium Formate and Ethanol as Hydrogen Sources

A green and efficient iridium-catalyzed asymmetric transfer hydrogenation of alkynyl ketones to chiral propargylic alcohols has been developed. By using sodium formate and ethanol as hydrogen sources, a series of alkynyl ketones were hydrogenated by chira

Microwave-assisted copper- and palladium-catalyzed sonogashira-type coupling of aryl bromides and iodides with trimethylsilylacetylene

An efficient and rapid method was developed for the synthesis of 1-aryl-2-(trimethylsilyl)acetylene. Copper and palladium-catalyzed sonogashira-type coupling of trimethylsilylacetylene and aryl bromides or iodides in the presence of triethylamine as base

Cleavage of the Carbon–Carbon Triple Bonds of Arylacetylenes for the Synthesis of Arylnitriles without a Metal Catalyst

Cleavage of the carbon–carbon triple bonds of alkynes was achieved, which led to the synthesis of arylnitriles under transition-metal-free conditions. A vast range of terminal alkyne substrates underwent this reaction to provide the corresponding nitriles in moderate to good yields with good functional group tolerance.

Visible-Light-Promoted Vinylation of Tetrahydrofuran with Alkynes through Direct C-H Bond Functionalization

(Chemical Equation Presented) Mild and direct C-H bond functionalizations and vinylations of tetrahydrofuran with alkynes have been accomplished through visible light photocatalysis, yielding a range of vinyl tetrahydrofurans under the synergistic actions of organic dye-type photocatalyst eosin Y, tert-butyl hydroperoxide (t-BuOOH), and a 45 W household lightbulb. A significant kinetic isotope effect (KIE) was recorded, which helps shed light on the mechanistic course.

Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds

1,3-Dienic δ-sultones 4,6-diaryl-[1,2]oxathiine 2,2-dioxides were synthesized via a one-step reaction of arylalkynes with dioxane sulfotrioxide. The reactivity of various alkynes in this reaction was investigated. The resulting sultones were brominated with Br2 or N-bromosuccinimide regioselectively to sulfur and subsequently coupled with phenylacetylene using Sonogashira conditions.

Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira-Glaser cyclization sequence

Based upon a consecutive one-pot Sonogashira-Glaser coupling-cyclization sequence a variety of 2,5-di(hetero)arylthiophenes were synthesized in moderate to good yields. A single Pd/Cu-catalyst system, without further catalyst addition, and easily available, stable starting materials were used, resulting in a concise and highly efficient route for the synthesis of the title compounds. This novel pseudo five-component synthesis starting from iodo(hetero)arenes is particularly suitable as a direct access to well-defined thiophene oligomers, which are of peculiar interest in materials science.