107474-02-2

Usage

Uses

Used in the Semiconductor Industry:
Triisopropyl[(trimethylsilyl)ethynyl]silane is utilized as a precursor in the semiconductor industry for the synthesis of silicon-based materials. Its properties make it suitable for creating components and devices that are integral to the functioning of semiconductors.
Used in the Production of Functionalized Silicon Surfaces and Materials:
In the realm of material science, Triisopropyl[(trimethylsilyl)ethynyl]silane is employed as a precursor to produce functionalized silicon surfaces. This allows for the development of materials with tailored properties for specific applications, such as in coatings, adhesives, or sensors.
Used in Chemical Vapor Deposition Processes:
Triisopropyl[(trimethylsilyl)ethynyl]silane is used as a protective layer in chemical vapor deposition (CVD) processes. It plays a critical role in the synthesis of silicon-based thin films, which are essential in various electronic and optoelectronic applications due to their unique properties.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1066-54-2 trimethylsilylacetylene 
• 16029-98-4 trimethylsilyl iodide 
• 89343-06-6 tris-iso-propylsilyl acetylene 
• 13154-24-0 triisopropylsilyl chloride 

Downstream Products

• 1353273-75-2 C₂₁H₃₀OSi 
• 1353273-77-4 C₂₄H₃₈OSi₂ 
• 1353273-79-6 C₂₇H₄₄OSi₂ 
• 1353273-81-0 C₂₇H₃₄OSi 
• 263720-76-9 1-phenyl-3-(triisopropylsilyl)prop-2-yn-1-ol 
• 503595-76-4 3-(tri(isopropyl)silyl)-1-phenylprop-2-yn-1-one 

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.

Platinum-catalyzed domino reaction with benziodoxole reagents for accessing benzene-alkynylated Indoles

Indoles are omnipresent in natural products, bioactive molecules, and organic materials. Consequently, their synthesis or functionalization are important fields of research in organic chemistry. Most works focus on installation or modification of the pyrrole ring. To access benzene-ring-functionalized indoles with an unsubstituted pyrrole ring remains more challenging. Reported herein is a platinum-catalyzed cyclization/alkynylation domino process to selectively obtain C5- or C6-functionalized indoles starting from easily available pyrroles. The work combines, for the first time, a platinum catalyst with ethynylbenziodoxole hypervalent iodine reagents in a domino process for the synthesis of polyfunctionalized arene rings and gives access to important building blocks for the synthesis of bioactive compounds and organic materials.

C-Terminal Bioconjugation of Peptides through Photoredox Catalyzed Decarboxylative Alkynylation

We report the first decarboxylative alkynylation of the C-terminus of peptides starting from free carboxylic acids. The reaction is fast, metal-free, and proceeds cleanly to afford alkynylated peptides with a broad tolerance for the C-terminal amino acid. By the use of hypervalent iodine reagents, the introduction of a broad range of functional groups was successful. C-terminal selectivity was achieved by differentiation of the oxidation potentials of the carboxylic acids based on the use of fine-tuned organic dyes.

Regioselective: Ortho -functionalization of bromofluorenecarbaldehydes using TMPMgCl·LiCl

A highly regioselective functionalization of 7-bromofluorene-2-carbaldehydes, potent organic chromophores, in position C3 using a mild ortho-metallation strategy (DoM) with TMPMgCl·LiCl has been developed. This approach allows the preparation of highly functionalized fluorene derivatives by conversion of the in situ generated metalated species with various electrophiles giving a fast access to novel organic phosphorescent dyes.

Ethynylbenziodoxolones (EBX) as reagents for the ethynylation of stabilized enolates

Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scannin

Room-Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents

Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes fr

Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines

A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp2)-H functionalization of alkenes, offering 26 enynes in 62-92% yield with excellent functional group tolerance.

One-pot, three-component arylalkynyl sulfone synthesis

A one-pot three-component protocol for the preparation of arylsulfonyl alkynes through the reaction of ethynyl-benziodoxolone (EBX) reagents, DABSO (DABCO?·SO2), and either organomagnesium reagents or aryl iodides with a palladium catalyst is r

Intramolecular palladium-catalyzed alkene carboalkynylation

Abstract Carbocycles are essential building blocks for the synthesis of natural and synthetic bioactive compounds. Herein, we report the first example of palladium-catalyzed intramolecular carboalkynylation of non-activated olefins. Using activated carbon

“Doubly Orthogonal” Labeling of Peptides and Proteins

Herein, we report a cysteine bioconjugation methodology for the introduction of hypervalent iodine compounds onto biomolecules. Ethynylbenziodoxolones (EBXs) engage thiols in small organic molecules and cysteine-containing peptides and proteins in a fast and selective addition onto the alkynyl triple bond, resulting in stable vinylbenziodoxolone hypervalent iodine conjugates. The conjugation occurs at room temperature in an open flask under physiological conditions. The use of an azide-bearing EBX reagent enables a “doubly orthogonal” functionalization of the bioconjugate via strain-release-driven cycloaddition and Suzuki-Miyaura cross-coupling of the vinyl hypervalent iodine bond. We successfully applied the methodology on relevant and complex biomolecules, such as histone proteins. Through single-molecule experiments, we illustrated the potential of this doubly reactive bioconjugate by introducing a triplet-state quencher close to a fluorophore, which extended its lifetime by suppressing photobleaching. This work is therefore expected to find broad applications for peptide and protein functionalization. Understanding the molecular basis of life is essential in the search for new medicines. Chemical biology develops molecular tools for studying biological processes, setting the basis for new diagnostics and therapeutics, and relies heavily on the ability to selectively modify biomolecules. Two approaches have been especially fruitful: (1) selective modification of natural biomolecules and (2) selective reaction between non-natural functionalities in the presence of biomolecules (the so-called orthogonal bioconjugation). In our work, we contribute to both by transferring highly reactive hypervalent iodine reagents to cysteine residues in proteins and peptides. The obtained bioconjugates retain the reactive hypervalent bonds, which can be selectively functionalized via a metal-mediated reaction. Combined with a traditional azide tag, our approach allows a doubly orthogonal functionalization of biomolecules and is hence expected to be highly useful in chemical biology. Chemical biology develops molecular tools for studying biological processes, setting the basis for new diagnostics and therapeutics, and relies heavily on the ability to modify selectively biomolecules. In our work, we introduce hypervalent iodine bonds into peptides and proteins, via functionalization of cysteine, by using unique cyclic reagents developed in our group. The hypervalent bond can then be selectively modified in the presence of both natural and synthetic functional groups, opening new opportunities for applications in chemical biology.