77123-58-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(TRIMETHYLSILYL)ETHYNYLBENZALDEHYDE is used as a synthetic intermediate for the development of pharmaceutical compounds. Its reactivity and the ability to undergo various chemical reactions make it a valuable component in the synthesis of new drugs and medicinal agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(TRIMETHYLSILYL)ETHYNYLBENZALDEHYDE is utilized as a precursor in the synthesis of agrochemicals. Its functional groups and synthetic flexibility are harnessed to create compounds that can be used in the development of pesticides, herbicides, and other agricultural chemicals.
Used in Materials Science:
2-(TRIMETHYLSILYL)ETHYNYLBENZALDEHYDE is employed as a key component in the creation of advanced materials in materials science. Its unique structure and the capacity for diverse chemical transformations enable its use in the fabrication of new materials with specific properties for various applications, such as in electronics, coatings, or composites.

InChI:InChI=1/C12H14OSi/c1-14(2,3)9-8-11-6-4-5-7-12(11)10-13/h4-7,10H,1-3H3

Upstream product

• 229027-92-3 {2-[2-(trimethylsilyl)ethynyl]phenyl}methanol 
• 26260-02-6 2-iodobenzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 5159-41-1 2-iodobenzyl alcohol 
• 171261-70-4 2-iodo-N,N-diisopropyl-4-methylbenzamide 
• 118-48-9 isatoic anhydride 
• 133776-41-7 anthranilic acid N-methoxy-N-methylamide 
• 529-23-7 o-aminobenzaldehyde 
• 24599-57-3 1,3-cyclohexadiene monoxide 
• 68-12-2 N,N-dimethyl-formamide 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 38846-64-9 2-ethynylbenzaldehyde 
• 106824-51-5 2-Trimethylsilanylethynyl-benzaldehyde oxime 
• 160087-20-7 4-Methyl-1-(2-trimethylsilanylethynyl-phenyl)-pent-4-en-2-yn-1-ol 
• 166757-18-2 2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene 
• 229027-92-3 {2-[2-(trimethylsilyl)ethynyl]phenyl}methanol 
• 328086-31-3 3-o-tolyl-1-{2-[(trimethylsilyl)ethynyl]phenyl}prop-2-yn-1-ol 
• 328086-30-2 3-phenyl-1-{2-[(trimethylsilyl)ethynyl]phenyl}prop-2-yn-1-ol 
• 119-65-3 isoquinoline 
• 349150-35-2 1-(2-trimethylsilylethynylphenyl)but-3-en-1-ol 
• 798553-38-5 Trimethyl-[2-((E)-2-phenyl-propenyl)-phenylethynyl]-silane 
• 871795-57-2 1-(2-trimethylsilanylethynyl-phenyl)-hex-2-yn-1-ol 

Relevant academic research and scientific papers

Palladium-Catalyzed Aminomethylation and Cyclization of Enynol to O-Heterocycle Confined 1,3-Dienes

The rational tuning of the electrophilicity of the allylpalladium intermediates enables the regioselectively intramolecular 1,2-addition of enynol in the presence of aminal. This aminomethylation and cyclization reaction via C-N bond activation and intramolecular nucleophilic addition provides a rare example for the synthesis of O-containing heterocycle-confined 1,3-dienes, which is of synthetic potential for further derivatization. The method possesses broad substrate generality as well as functional group compatibility and efficiently affords a wide range of desired products with 5-, 6-, and 8-membered O-containing heterocycles with various functional groups.

Palladium-Catalyzed Aminomethylative Oppolzer-Type Cyclization of Enynes: Access to Aminomethylated Benzofulvenes

A novel palladium-catalyzed Oppolzer-type cyclization reaction aided by the aminomethyl cyclopalladated complex has been developed, which provides rapid access to functionalized benzofulvenes with excellent stereoselectivity. The corresponding products can undergo Diels–Alder reaction with maleimides, providing a series of complex polycyclic compounds with excellent regio- and stereoselectivities.

Gold Catalysis Meets Materials Science – A New Approach to π-Extended Indolocarbazoles

Herein we describe a modular, convergent synthesis of substituted benzo[a]benzo[6,7]-indolo[2,3-h]carbazoles (BBICZs) using a bidirectional gold-catalyzed cyclization reaction as a key step. A building block strategy enabled the easy variation of substituents at different positions of the core structure and a general analysis of substitution effects on the materials properties of the target compounds. All BBICZs were fully characterized and their optical and electronic properties were studied experimentally as well as by computational methods. Organic thin-film transistors based on eight selected derivatives were fabricated by vacuum deposition and charge-carrier mobilities up to 1 cm2/Vs were measured. (Figure presented.).

ION CHANNEL ANTAGONISTS/BLOCKERS AND USES THEREOF

Provided are ion channel antagonists/blockers and uses thereof. Specifically, it provides the compounds of formula (I) or pharmaceutically acceptable salts, stereoisomers, solvates or prodrugs, preparation method therefor and application thereof. Definition of each group in the formula can be found in the specification for details. Provided is also pharmaceutical composition useful for treatment of heart disease and other ion channel related diseases.

Enzyme-like Supramolecular Iridium Catalysis Enabling C?H Bond Borylation of Pyridines with meta-Selectivity

The use of secondary interactions between substrates and catalysts is a promising strategy to discover selective transition metal catalysts for atom-economy C?H bond functionalization. The most powerful catalysts are found via trial-and-error screening due to the low association constants between the substrate and the catalyst in which small stereo-electronic modifications within them can lead to very different reactivities. To circumvent these limitations and to increase the level of reactivity prediction in these important reactions, we report herein a supramolecular catalyst harnessing Zn???N interactions that binds to pyridine-like substrates as tight as it can be found in some enzymes. The distance and spatial geometry between the active site and the substrate binding site is ideal to target unprecedented meta-selective iridium-catalyzed C?H bond borylations with enzymatic Michaelis–Menten kinetics, besides unique substrate selectivity and dormant reactivity patterns.

Palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination: Access to functionalized naphthalenes

A palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination of enyne-tethered allylic alcohols with aminals is described. Under the reaction conditions, the cationic vinyl allylpalladium species undergoes selective migratory insertion of alkenes rather than reductive elimination with nucleophiles. This strategy provides an efficient and unique approach to the construction of functionalized naphthalenes, which are important building blocks in synthetic organic chemistry. Mechanistic studies have revealed that the selective sequential migratory insertion of enyne and alkene is crucial for the cyclization.

Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives

An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups.

Polarization Effect on Regioselectivity of Pd-Catalyzed Cyclization of 2-Alkynylbenzaldehydes

We report a study on the relationship between the polarization of C≡C bond in a series of 2-alkynylbenzaldehydes and the regioselectivity of their Pd-catalyzed annulation reactions. The electrophilic and nucleophilic character of the triple bond carbon atoms was examined using 13C and HMBC NMR experiments. The direction of polarization is determined only by the formyl group and its position on an aromatic ring. On the other hand, the strength of the polarization expressed through chemical shift difference Δδ of acetylenic carbon atoms is a result of electron-withdrawing or electron-donating ability of the other substituent. Out of two possible regioisomers, the Pd-catalyzed cyclization reactions of 2-alkynylbenzaldehydes that were studied predominantly afforded 1H-isochromenes suggesting that the polarization of a triple bond is one of the contributing factors in the regioselectivity of this process.

Palladium-Catalyzed Synthesis of 6H-Dibenzo[c,h]chromenes and 5,6-Dihydrobenzo[c]phenanthridines: Application to the Synthesis of Dibenzo[c,h]chromene-6-ones, Benzo[c]phenanthridines, and Arnottin I

6H-Dibenzo[c,h]chromenes and 5,6-dihydrobenzo[c]phenanthridines have been synthesized via Palladium (II)-catalyzed domino reactions of acetylenic substrates involving intramolecular trans-oxo/amino palladation onto the triple bond followed by nucleophilic

Lewis Acid-Catalyzed Intramolecular [3 + 2] Cross-Cycloaddition of Donor- Acceptor Epoxides with Alkenes for Construction of Oxa-[n.2.1] Skeletons

The first LA-catalyzed [3 + 2]IMCC of GDA-epoxides with carbon-carbon double bonds has been developed. This provides an efficient and general strategy for construction of bridged oxa-[n.2.1] skeletons. A novel SN-like mechanism through a carbon-carbon bond cleavage of epoxide ring has been proposed.