3989-14-8

Usage

Uses

Used in Organic Synthesis:
(4-Methoxyphenylethynyl)trimethylsilane is used as a building block for the synthesis of various functionalized silicon-containing molecules, contributing to the development of novel compounds with potential applications in different fields.
Used in Biologically Active Compounds Synthesis:
In the pharmaceutical industry, (4-Methoxyphenylethynyl)trimethylsilane serves as a key intermediate in the synthesis of biologically active compounds, facilitating the discovery and production of new drugs with therapeutic potential.
Used in Material Science Research:
(4-Methoxyphenylethynyl)trimethylsilane is utilized in material science for surface modification, allowing for the enhancement of material properties such as biocompatibility, stability, and reactivity.
Used in Silicon-Based Polymers Production:
(4-METHOXYPHENYLETHYNYL)TRIMETHYLSILANE& is employed in the production of silicon-based polymers, which have applications in various industries, including electronics, automotive, and aerospace, due to their unique properties like thermal stability and resistance to environmental degradation.
Used as a Reagent in Coupling Reactions:
In organic chemistry, (4-Methoxyphenylethynyl)trimethylsilane is used as a reagent in coupling reactions, particularly in cross-coupling processes, to form new chemical bonds and create complex molecular structures. This application is crucial for advancing the field of organic synthesis and developing new chemical entities.

InChI:InChI=1/C12H16OSi/c1-13-12-7-5-11(6-8-12)9-10-14(2,3)4/h5-8H,1-4H3

Upstream product

• 696-62-8 para-iodoanisole 
• 78389-87-4 ((trimethylsilyl)ethynyl)zinc(II) chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1066-54-2 trimethylsilylacetylene 
• 105497-65-2 2-exo-cyano-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl acetate 
• 1068-69-5 Tris(trimethylsilyl)methane 
• 874-90-8 4-methoxybenzonitrile 
• 66107-29-7 4-methoxyphenyl triflate 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 768-60-5 4-methoxyphenylacetylen 
• 16029-98-4 trimethylsilyl iodide 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 623-12-1 4-chloromethoxybenzene 

Downstream Products

• 13623-25-1 6-methoxy-2,3-dihydro-1H-inden-1-one 
• 110598-38-4 2,2-bis(4-methoxyphenyl)-1-trimethylsilylethylene 
• 75-77-4 chloro-trimethyl-silane 
• 81787-69-1 5-(2'-acetoxyphenyl) 1-(4'-methoxyphenyl)-pent-1-yn-4-enone 
• 101653-71-8 (E)-β-iodo-β-(trimethylsilyl)-p-methoxystyrene 
• 768-60-5 4-methoxyphenylacetylen 
• 81787-68-0 5-(3',4'-dimethoxyphenyl)-1-(4'-methoxyphenyl)-pent-1-yn-4-enone 
• 56982-37-7 4-[(4-methoxyphenyl)ethynyl]benzonitrile 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 23429-36-9 1-methoxy-4-(phenylbuta-1,3-diynyl)benzene 
• 22779-05-1 1,4-bis(4-methoxyphenyl)-1,3-butadiyne 
• 119327-32-1 (Z)-trimethyl<2-(4-methoxyphenyl)ethenyl>silane 
• 7380-78-1 4-(phenylethynyl)anisole 
• 123770-67-2 1-(4-((4-methoxyphenyl)ethynyl)phenyl)ethanone 

Relevant academic research and scientific papers

Alkynylborinates in organoborane conversions

10-Methoxy-9-oxa-10-bora[3.3.2]decane (1), easily prepared from the oxidation of B-MeO-9-BBN with trimethylamine N-oxide (TMANO), is readily converted to alkynylborinate complexes (2) with its reaction with representative lithium acetylides. These complexes serve as efficient alkynylating agents in the Suzuki-Miyaura coupling and their demethoxylation furnishes stable alkynylboranes (3) which also provide a convenient new entry to cis-vinylboranes (5).

29Si and 13C NMR Spectra of Alkenyl- and Alkynyl-trimethylsilanes

29Si and 13C chemical shifts in substituted alkenyl-and alkynyl-trimethylsilanes have been recorded and assigned.The 13C NMR study of R-alkynyltrimethylsilanes gave new evidence for p?-d? bonding or an equivalent interaction between the bonded carbon and

Synthesis of diphenylacetylenes containing donor and acceptor substituents with 4′-formyl-4-methoxydiphenylacetylene as an example

A method for the synthesis of diphenylacetylenes containing donor and acceptor groups in aryl substituents was proposed. 4′-Formyl-4- methoxydiphenylacetylene was synthesized as an example.

Regulation of peptide-π-peptide nanostructure bundling: the impact of ‘cruciform’ π-electron segments

The self-assembly and photophysical properties of peptide-π-peptide molecules with ‘cruciform’ presentation of the π-electron core were studied. Derivatives of 1,4-bis(phenylethynyl)benzene were incorporated into a peptide backbone via the alkynylation of

Remote substituent control of the regioselectivity of the aryl- and vinylpalladation of 7-oxabicyclo[2.2.1]heptenes

Pd-catalyzed arylations of 2-exo-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-endo-yl acetate and 7-oxabicyclo[2.2.1]hept-5-en-2-one are regio- and stereoselective giving products of H2 (HCOOH) and Me3SiC ≡ CH coupling in which the aryl grou

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines

Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

Atom-Economical Thiocyanation-Amination of Alkynes with N-Thiocyanato-Dibenzenesulfonimide

A highly regioselective protocol for intermolecular thiocyanation-amination of alkynes by N-thiocyano-dibenzenesulfonimide (NTSI) as the SCN and nitrogen sources has been developed. A C-S bond and C-N bond are simultaneously constructed in only one step. The reaction under simple mild conditions features a broad substrate scope, atom economy, high yields (up to 94%), and excellent functional group tolerance.

Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes

Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.