3989-13-7

Usage

Uses

Used in Organic Synthesis:
(3-Bromophenylethynyl)trimethylsilane is used as a synthetic intermediate for the preparation of various organic compounds. Its bromine atom can be replaced by other functional groups through palladium-catalyzed cross-coupling reactions, making it a versatile building block for the synthesis of complex organic molecules.
Used in the Preparation of 4-(3-Bromophenyl)-3-butyn-2-one:
(3-Bromophenylethynyl)trimethylsilane is specifically used in the preparation of 4-(3-bromophenyl)-3-butyn-2-one, a key intermediate in the synthesis of pharmaceuticals and agrochemicals. The ethynyl group in (3-bromophenylethynyl)trimethylsilane can be converted to a carbonyl group through a hydrolysis reaction, leading to the formation of the desired ketone.
Used in Materials Chemistry:
(3-Bromophenylethynyl)trimethylsilane can also be used in materials chemistry for the development of new materials with unique properties. Its bromine atom and ethynyl group can be utilized to create materials with tailored electronic, optical, or mechanical properties, making it a valuable component in the design and synthesis of advanced materials.

InChI:InChI=1/C11H13BrSi/c1-13(2,3)8-7-10-5-4-6-11(12)9-10/h4-6,9H,1-3H3

Upstream product

• 591-18-4 1-Bromo-3-iodobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 108-36-1 1,3-dibromobenzene 
• 583-53-9 2,3-dibromobenzene 
• 75-77-4 chloro-trimethyl-silane 
• 766-81-4 3-bromophenylacetylene 

Downstream Products

• 170474-61-0 2-<3-phenyl>ethynyl>silyl>-3-methylbutoxy>tetrahydro-2H-pyran 
• 296761-58-5 1-Triisopropylsilylethynyl-3-trimethylsilylethynylbenzene 
• 766-81-4 3-bromophenylacetylene 
• 405065-67-0 4-(3-bromophenyl)-3-butyn-2-one 
• 225797-90-0 1-ethynyl-3-[2-(triisopropylsilyl)ethynyl]benzene 
• 225797-88-6 5,5-Bis[3-(3-ethynyl-phenylethynyl)-5-hexyloxymethylphenyl]-[2,2']bipyridinyl 
• 296761-65-4 5,5-Bis[3-hexyloxymethyl-5-(3-triisopropylsilylethynylphenylethynyl)phenyl]-[2,2']bipyridinyl 
• 292868-56-5 C₂₂H₁₂Br₂ 
• 157326-11-9 3-trimethylsilyl-ethynylphenyldimethyl silane 
• 918487-34-0 2-fluoro-3-(3-((trimethylsilyl)ethynyl)phenyl)pyridine 
• 78629-74-0 Pt((CH₃)3SiC₂C₆H₄Br)(P(C₆H₅)3)2 
• 1061673-27-5 1-(3-t-butyldimethylsiloxymethylphenyl)-2-(3-trimethylsilylethynylphenyl)ethyne 
• 1239684-43-5 4-(1-tert-butyl-(2-methyl-1-(3'-(trimethylsilylethynyl)phenylpropyl)aminooxy)ethyl)benzyl 4-azidobenzoate 
• 1295508-42-7 4-(1-tert-butyl-(2-methyl-1-(3'-ethynylphenylpropyl)aminooxy)ethyl)benzyl 4-azidobenzoate 

Relevant academic research and scientific papers

Design and synthesis of 3′-(prop-2-yn-1-yloxy)-biphenyl substituted cyclic acylguanidine compounds as BACE1 inhibitors

Based on the lead compounds 1 and 2, a series of novel BACE1 inhibitors were designed and synthesized, among which compound 9h exhibited a 60 fold improvement in potency over the lead compound 1. This represents a good lead for the discovery of more promi

A threonine turnstile defines a dynamic amphiphilic binding motif in the AAA ATPase p97 allosteric binding site

The turnstile motion of two neighboring threonines sets up a dynamic side chain interplay that can accommodate both polar and apolar ligands in a small molecule allosteric protein binding site. A computational model based on SAR data and both X-ray and cr

(3-(1H-1,2,3-triazole)phenyl)phosphoric acid derivative as well as preparation method and application thereof

The invention relates to the technical field of medicinal chemistry, and discloses a (3-(1H-1,2,3-triazole)phenyl)phosphoric acid derivative derivative as shown in a formula X which is described in the specification. The derivative has good and broad-spec

COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY APPARATUS

The present invention relates to a compound for an organic optoelectronic device represented by chemical formula 1, an organic optoelectronic device employing the same and a display device apparatus. The details of chemical formula 1 are as defined in the specification.

Catalytic Activation of Trimethylsilylacetylenes: A One-Pot Route to Unsymmetrical Acetylenes and Heterocycles

For the synthesis of unsymmetrical acetylenes, a Sonogashira coupling-deprotection-Sonogashira coupling reaction sequence is often used. Removal of protecting groups requires harsh conditions or an excess of difficult to handle and expensive reagents. Herein, we disclose a novel catalytic method for the selective deprotection of trimethylsilylacetylenes in Sonogashira reaction. The reagent hexafluorosilicic acid, an inexpensive nontoxic compound, was used to promote the selective desilylation. This method enables the efficient synthesis of unsymmetric acetylenes with other silylated functional groups present. Further possibilities of the method were explored by synthesis of heterocycles.

Enantioselective synthesis of β-fluoro-β-aryl-α-aminopentenamides by organocatalytic [2,3]-sigmatropic rearrangement

The tetramisole-promoted catalytic enantioselective [2,3]-sigmatropic rearrangement of quaternary ammonium salts bearing a (Z)-3-fluoro-3-arylprop-2-ene group generates, after addition of benzylamine, a range of β-fluoro-β-aryl-α-aminopentenamides containing a stereogenic tertiary fluorine substituent. Cyclic and acyclic nitrogen substituents as well as various aromatic substituents are tolerated, giving the β-fluoro-β-aryl-α-aminopentenamide products in up to 76% yield, 96:4 dr, and 98:2 er.

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.

Formal anti-markovnikov hydroamination of terminal aryl alkynes with pinacolborane and hydroxylamines via Zr/Cu sequential catalysis

We have explored a novel dry plasma process for the fabrication of electrodes on Nafion surfaces. Nanosized pillar structures were prepared through argon ion (Ar+) plasma treatment. The shear strengths of Au electrodes on plasma-treated Nafion surfaces were investigated. We found that the maximum shear strength (1.08 MPa) of Au-Nafion was observed under the optimal conditions (8 min, 100 W, 5 Pa, Ar+). Finally, we successfully prepared strongly bonded Au electrodes on Nafion through plasma surface treatment without using a wet plating process.

Regioselective preferential nucleophilic addition of N-heterocycles onto haloarylalkynes over N-arylation of aryl halides

The study of preferential addition of heterocyclic amines onto halo-substituted arylalkynes over N-arylation under various catalytic conditions is described. The present work supports and confirms the mechanistic pathway of our recent work on the tandem synthesis of indolo- and pyrrolo-[2,1-a] isoquinolines via hydroamination followed by oxidative addition and not vice versa.

Regioselective solvent-dependent benzannulation of conjugated enynes

The transformation of enynes under cobalt-catalysis leads to symmetrical benzannulation products in dichloromethane. In tetrahydrofuran the cobalt-catalysed reactions afforded the unprecedented unsymmetrical benzannulation products in moderate to good yields and good regioselectivities. In addition, cyclotrimerisation of the alkyne subunit can be realised when electron-deficient enynes are applied in the cobalt-catalysed transformations to generate 1,2,4-trivinylbenzene derivatives using tetrahydrofuran as solvent.