393857-27-7

Basic information

• Product Name: (4-ETHYLPHENYLETHYNYL)TRIMETHYLSILANE
• Synonyms: Silane,[(4-ethylphenyl)ethynyl]trimethyl- (9CI);4-Ethyl-1-trimethylsilylethynylbenzene
• CAS NO: 393857-27-7
• Molecular Formula: C6H4CH2CH3C≡CSi(CH3)3
• Molecular Weight: 202.37
• Product Categories: Alkynes;Internal;Organic Building Blocks;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 393857-27-7.mol

Chemical Properties

• Boiling Point: 72 °C0.1 mm Hg(lit.)
• Flash Point: 228 °F
• Appearance: /
• Density: 0.881 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0589mmHg at 25°C
• Refractive Index: n20/D 1.5270(lit.)
• CAS DataBase Reference: (4-ETHYLPHENYLETHYNYL)TRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-ETHYLPHENYLETHYNYL)TRIMETHYLSILANE(393857-27-7)
• EPA Substance Registry System: (4-ETHYLPHENYLETHYNYL)TRIMETHYLSILANE(393857-27-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 393857-27-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(4-Ethylphenylethynyl)trimethylsilane is used as a synthetic intermediate for the production of various organic compounds. Its capacity to transfer the ethynyl group to a wide range of organic substrates makes it a crucial component in this application, enhancing the synthesis process and expanding the possibilities for creating diverse organic molecules.
Used in Organometallic Chemistry:
In the field of organometallic chemistry, (4-Ethylphenylethynyl)trimethylsilane serves as a ligand, particularly in the synthesis of transition metal complexes. Its role in this application is vital for the formation and stabilization of these complexes, which are essential in various chemical reactions and industrial processes.
Used in the Production of Functional Materials:
(4-Ethylphenylethynyl)trimethylsilane is utilized as a building block in the creation of functional materials. Its unique properties and reactivity contribute to the development of materials with specific characteristics and applications, such as in electronics, coatings, and other advanced technologies.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, (4-Ethylphenylethynyl)trimethylsilane is employed as a key component in the synthesis of various drugs and pharmaceutical compounds. Its versatility and reactivity make it an invaluable asset in the development of new medications and therapies, potentially leading to breakthroughs in the treatment of various diseases and conditions.

InChI:InChI=1/C13H18Si/c1-5-12-6-8-13(9-7-12)10-11-14(2,3)4/h6-9H,5H2,1-4H3

Upstream product

• 135005-24-2 [(4-ethenylphenyl)ethynyl]trimethylsilane 
• 1585-07-5 1-bromo-4-ethylbenzene 
• 1066-54-2 trimethylsilylacetylene 
• 25309-64-2 4-ethyl-1-iodobenzene 

Downstream Products

• 29778-20-9 1-ethyl-4-(phenylethynyl)benzene 
• 937-30-4 4-ethylacetophenone 
• 40307-11-7 1-ethyl-4-ethynylbenzene 

Relevant articles and documents

Microwave-assisted copper- and palladium-catalyzed sonogashira-type coupling of aryl bromides and iodides with trimethylsilylacetylene

An efficient and rapid method was developed for the synthesis of 1-aryl-2-(trimethylsilyl)acetylene. Copper and palladium-catalyzed sonogashira-type coupling of trimethylsilylacetylene and aryl bromides or iodides in the presence of triethylamine as base

Tandem catalytic C(sp3)-H amination/sila-sonogashira-hagihara coupling reactions with iodine reagents

A new tandem C-N and C-C bond-forming reaction has been achieved through RhII/Pd0 catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations. I(003) is a double agent: A tandem C-N and C-C bond-forming reaction has been achieved through RhII/Pd0 catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process affords complex building blocks with high yields, and demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations.

One-pot synthesis of 1,3-enynes with a CF3 group on the terminal sp2 carbon by an oxidative Sonogashira cross-coupling reaction

Oxidative Sonogashira cross-coupling reactions of (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane with arylacetylene were achieved using silver fluoride and a palladium catalyst, to afford high yields of various 1,3-enynes with a CF3 group on the terminal sp2 carbon. Silver fluoride promoted C-Si bond dissociation and oxidation of palladium, enabling catalytic use of palladium.

Reactivity switch enabled by counterion: Highly chemoselective dimerization and hydration of terminal alkynes

A counterion-controlled reactivity tuning in Pd-catalyzed highly chemoselective and regioselective dimerization and hydration of terminal alkynes is reported. The use of acetate as counterion favors the formation of an alkenyl alkynyl palladium intermediate which forms hitherto less reported 1,3-diaryl-substituted conjugated enynes after reductive elimination. Using chloride, which is a better leaving group, leads to anion exchange on the alkenylpalladium intermediate with hydroxide which after reductive elimination and tautomerization delivered the hydration products.

Synthesis of oxygen- and sulfur-bridged dirhodium complexes and their use as catalysts in the chemoselective hydrogenation of alkenes

Oxygen-bridged and sulfur-bridged rhodium homobimetallic complexes were synthesized as air-stable crystals by using 2,6-bis(phosphanylmethyl)phenolate and -thiophenolate as the ligands, respectively. The oxygen-bridged dirhodium complex has a symmetrical structure where the carbon atom at the ipso position, oxygen, and two rhodium atoms are located in the same plane. It is thermally stable compared to the sulfur-bridged dirhodium complex and shows catalytic activity for hydrogenation of alkenes with high chemoselectivity.

Access to flavones via a microwave-assisted, one-pot sonogashira- carbonylation-annulation reaction

Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6- phosphaadamantane are shown to be effective catalytic systems facilitating the sequential application of a microwave-assisted Sonogashira and carbonylative annulation reaction for the preparation of substituted flavones.

Linear free-energy correlation analysis of the electronic effects of the substituents in the Sonogashira coupling reaction

Relative rate constants (krel) for the Sonogashira coupling were determined in competitive reactions between iodobenzene and a series of para- and meta-substituted iodobenzenes and compared to the charge on iodine and the z-component of the qua

Palladium-catalyzed carbon-carbon coupling reactions using aryl Grignards

Coupling reactions using Pd(PPh3)4 were investigated with a number of electron donating and electron withdrawing substituents. High yields were obtained with both types of substituents. In competitive reactions the electron-withdrawi