97308-62-8

Usage

Uses

Used in Organic Synthesis:
2-[(TRIMETHYLSILYL)ETHYNYL]BENZONITRILE is used as a building block in organic synthesis for the preparation of various pharmaceuticals and agrochemicals. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of a wide range of organic compounds.
Used in Electronics Industry:
In the electronics industry, 2-[(TRIMETHYLSILYL)ETHYNYL]BENZONITRILE is utilized in the production of organic light-emitting diodes (OLEDs) and organic photovoltaic devices. Its properties contribute to the performance and efficiency of these devices, making it an essential component in their manufacturing process.
Used in the Synthesis of Organic Materials and Polymers:
2-[(TRIMETHYLSILYL)ETHYNYL]BENZONITRILE is a key component in the synthesis of various organic materials and polymers. Its presence in these materials can enhance their properties, such as stability, reactivity, and other characteristics, making it a crucial ingredient in the development of new materials for various applications.

InChI:InChI=1/C12H13NSi/c1-14(2,3)9-8-11-6-4-5-7-12(11)10-13/h4-7H,1-3H3

Upstream product

• 2042-37-7 o-cyanobromobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 557-21-1 dicyanozinc 
• 137648-47-6 1-iodo-2-ethynylbenzene 
• 4387-36-4 2-iodobenzonitrile 
• 615-42-9 1,2-Diiodobenzene 

Downstream Products

• 97308-60-6 2-(β-ethoxyethenyl)benzonitrile 
• 40888-26-4 2-ethynylbenzonitrile 
• 244158-07-4 2-(3(Z)-dodecen-1,5-diynyl)benzonitrile 
• 244158-06-3 2-(3(Z)-undecen-1,5-diynyl)benzonitrile 
• 491-30-5 1-isoquinolone 
• 97308-61-7 2-(β-ethoxyethenyl)benzamide 
• 3032-92-6 4-cyanophenylacetylene 
• 38379-21-4 (2-ethynylphenyl)methanamine 
• 121668-44-8 2-(2-benzofuranyl)-benzonitrile 
• 1557159-30-4 1-((2-cyanophenyl)ethynyl)-1,2-benziodoxol-3(1H)-one 
• 1557159-50-8 2-((2,3-dihydro-1H-inden-2-yl)ethynyl)benzonitrile 

Relevant academic research and scientific papers

Tertiary amines acting as Alkyl radical equivalents enabled by a P/N heteroleptic Cu(I) photosensitizer

An unprecedented exploration of tertiary amines as alkyl radical equivalents for cross-coupling with aromatic alkynes to access allylarenes has been achieved by a P/N heteroleptic Cu(I)based photosensitizer under photoredox catalysis conditions. Mechanist

Synthesis of N-Heteroaromatic Compounds through Cyclocarbonylative Sonogashira Reactions

A protocol based on cyclocarbonylative Sonogashira reactions has been developed for the synthesis of nitrogen-containing heterocycles. The process is carried out under CO pressure, in the presence of a small amount of PdCl2(PPh3)sub

Gold-Catalyzed Cycloisomerization/1,5-H Migration/Diels-Alder Reaction Cascade: Synthesis of Complex Nitrogen-Containing Heterocycles

An unprecedented gold-catalyzed cycloisomerization/1,5-H migration/Diels-Alder reaction cascade has been developed that enables the rapid construction of complex nitrogen polycyclic compounds. This one-pot, three-step cascade reaction offers good yields o

Visible-light-induced chemoselective deboronative alkynylation under biomolecule-compatible conditions

Here, we report a visible-light-induced deboronative alkynylation reaction, which is redox-neutral and works with primary, secondary and tertiary alkyl trifluoroborates or boronic acids to generate aryl, alkyl and silyl substituted alkynes. This reaction is highly chemoselective and performs well on substrates containing alkenes, alkynes, aldehydes, ketones, esters, nitriles, azides, aryl halides, alkyl halides, alcohols, and indoles, with no detectable occurrence of side reactions. The mechanism of this novel C(sp3)-C(sp) bond coupling reaction was investigated by luminescence quenching, radical trapping, on-off light, and 13C-isotopic-labeling experiments. This reaction can be performed in neutral aqueous conditions, and it is compatible with amino acids, nucleosides, oligosaccharides, nucleic acids, proteins, and cell lysates.

Synthesis of spiroaminals and spiroketals with bimetallic relay catalysis

A novel tandem metal relay catalytic system was developed by combining gold-catalyzed cycloisomerization with an early transition-metal-catalyzed inverse-electron-demand hetero-Diels-Alder (IED-HDA) reaction. Various biologically important spiroaminals an

Formation of indoles, dihydroisoquinolines, and dihydroquinolines by ruthenium-catalyzed heterocyclizations

Indoles, dihydroisoquinolines, and dihydroquinolines were efficiently prepared by ruthenium-catalyzed heterocyclizations of aromatic homo- and bis-homopropargyl amines/amides in the presence of an amine/ammonium base-acid pair. These regioselective 5-endo and 6-endo cyclizations most probably occur by nucleophilic trapping of key ruthenium-vinylidene intermediates. Georg Thieme Verlag Stuttgart · New York.

Metal-free oxidative trifluoromethylthiolation of terminal alkynes with CF3SiMe3 and elemental sulfur

A metal-free oxidative trifluoromethyl-thiolation of terminal alkynes using readily available CF3SiMe3 and elemental sulfur at room temperature has been developed. This reaction provides an efficient and convenient method for the preparation of alkynyl trifluoromethyl sulfides bearing a wide range of functional groups. Preliminary investigation revealed that elemental sulfur instead of air acted as the oxidant.

Ruthenium-catalyzed cycloisomerization of aromatic homo- and bis-homopropargylic amines/amides: Formation of indoles, dihydroisoquinolines and dihydroquinolines

Ruthenium-catalyzed cycloisomerizations of aromatic homo- and bis-homopropargylic amines/amides efficiently afford indoles, dihydroisoquinolines and dihydroquinolines. These processes were regioselective (5- and 6-endo cyclizations) on using key Ru vinylidene intermediates. The presence of an amine/ammonium base-acid pair increased the rate of cyclization and facilitated the catalytic turnover. Copyright

Copper-catalyzed cross-coupling of alkyl and aryl grignard reagents with alkynyl halides

(Chemical Equation Presented) Good old copperl A new general procedure to couple aliphatic and aromatic Grignard reagents with alkynyl halides under copper catalysis is described (see scheme; NMP=N-methylpyrrolidinone). The reaction is chemoselective and allows preparation of a vast array of simple and functionalized internal alkynes in high yields.

Block modification of rod-shaped π conjugated carbon frameworks with donor and acceptor groups toward highly fluorescent molecules: Synthesis and emission characteristics

To create organic molecules that are highly fluorescent at a longer wavelength region, we investigated the synthesis (using Pd-catalyzed cross-coupling) and photophysical properties (Φ f, λ em, τ , λ abs, and ε ) of the following π conjugated molecular rods consisting of p-phenyleneethynylene units modified by donor (OMe) and/or acceptor (CN) groups: (1) side-donor modification systems (SD systems), (2) side-acceptor modification systems (SA systems), and (3) systems consisting of a donor block and an acceptor block (BL systems). As a consequence, very high Φ f values (>0.95) were obtained for BL systems. Bathochromic shifts of λ em for the same π conjugation length were largest for BL systems. Thus we succeeded in creating highly efficient light emitters at a longer wavelength region by block modification (e.g., Φ f = 0.97, λ em = 464 nm for BL-9). Considerably intense solid emission (Φ f ～ 0.5) at a longer wavelength region (500- 560 nm) was also found for BL systems. It has been found that BL-6 and BL-8 exhibit interesting two photon absorption characteristics. This journal is The Royal Society of Chemistry.