4186-14-5

Basic information

• Product Name: Silane, trimethyl[(4-methylphenyl)ethynyl]-
• CAS NO: 4186-14-5
• Molecular Formula: C12H16Si
• Molecular Weight: 188.345
• Mol File: 4186-14-5.mol

Chemical Properties

• CAS DataBase Reference: Silane, trimethyl[(4-methylphenyl)ethynyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, trimethyl[(4-methylphenyl)ethynyl]-(4186-14-5)
• EPA Substance Registry System: Silane, trimethyl[(4-methylphenyl)ethynyl]-(4186-14-5)

Safety Data

• Hazardous Substances Data: 4186-14-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Silane, trimethyl[(4-methylphenyl)ethynyl]is used as a starting material for the synthesis of organic and organometallic compounds. Its unique structure allows for the creation of a wide range of compounds with diverse applications.
Used in Semiconductor Industry:
In the semiconductor industry, Silane, trimethyl[(4-methylphenyl)ethynyl]is utilized in the production of specialty materials. Its properties make it suitable for use in the development of advanced semiconductor devices and technologies.
Used in Production of Specialty Materials:
Silane, trimethyl[(4-methylphenyl)ethynyl]is employed in the production of specialty materials due to its unique chemical properties. These materials can be used in various applications, including coatings, adhesives, and other industrial products.
Used as a Reagent in Chemical Reactions:
Due to its versatile nature, Silane, trimethyl[(4-methylphenyl)ethynyl]is used as a reagent in various chemical reactions. Its ability to participate in a range of reactions makes it a valuable tool for researchers and chemists in different scientific fields.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 73839-44-8 (Z)-1-[2-bromovinyl]-4-methylbenzene 
• 624-31-7 4-tolyl iodide 
• 78389-87-4 ((trimethylsilyl)ethynyl)zinc(II) chloride 
• 123725-21-3 2,2,6,6-Tetramethyl-4,8-bis(4-methylphenyl)-3,7-bis(trimethylsilyl)-1,5-dioxa-2,6-disila-3,7-cyclooctadiene 
• 106-38-7 para-bromotoluene 
• 1066-54-2 trimethylsilylacetylene 
• 4526-06-1 trimethylsilyl-1,3-butadiyne 
• 78-80-8 2-methylbut-1-en-3-yne 
• 250643-77-7 tris(2-(trimethylsilyl)ethynyl)indium 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 766-97-2 4-n-methylphenylacetylene 
• 54655-07-1 lithium trimethylsilylacetylenide 
• 1866-39-3 trans-p-methylcinnamic acid 

Downstream Products

• 101653-72-9 (E)-β-iodo-Sb-(trimethylsilyl)-p-methylstyrene 
• 766-97-2 4-n-methylphenylacetylene 
• 3287-02-3 4-(phenylethynyl)toluene 
• 2789-88-0 1,2-bis(4-methylphenyl)acetylene 
• 7370-24-3 (E)-2-(4-methylstyryl)pyridine 
• 852657-84-2 1-benzyl-4-p-tolyl-1H-[1,2,3]triazole 
• 1209467-43-5 (S,E)-trimethyl-[1-(4-methylbenzylidene)-2-phenylbut-3-enyl]silane 
• 1217677-74-1 (4-(4-tolyl)but-1-en-3-yne-1,1,2-triyl)tribenzene 
• 14939-05-0 1-phenyl-3-(4-methylphenyl)prop-2-yn-1-one 
• 68809-45-0 5-(4-methylphenyl)-1-phenyl-1H-1,2,3-triazole 
• 75990-62-4 methyl (2Z,4E)-5-((p-methyl)phenyl)penta-2,4-dienoate 
• 92356-72-4 methyl (2E,4E)-5-((p-methyl)phenyl)penta-2,4-dienoate 
• 1434153-12-4 4-phenoxy-1-(p-tolyl)-3H-pyrrolo[3,2,1-de]acridin-3-one 
• 1434153-13-5 8-methyl-4-phenoxy-1-(p-tolyl)-3H-pyrrolo[3,2,1-de]acridin-3-one 

Relevant articles and documents

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines

Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Metal scavenging and catalysis by periodic mesoporous organosilicas with 2,2′-bipyridine metal chelating ligands

A periodic mesoporous organosilica containing 2,2′-bipyridine (BPy-PMO) was assessed as a metal scavenger and heterogeneous catalyst. The functionalized PMO was synthesized based on a modified version of a previously reported procedure and showed a large

Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block

A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.

Catalytic Decarboxylation of Silyl Alkynoates to Alkynylsilanes

Herein, we describe a decarboxylative approach to the preparation of alkynylsilanes. Treatment of a silyl alkynoate in N,N-dimethylformamide (DMF) at 80 °C in the presence of catalytic amounts of CuCl and PCy3 produced the corresponding alkynylsilane in excellent yield. The copper-catalyzed decarboxylation proceeded smoothly with low catalyst loadings (0.5 mol % of CuCl and 1.0 mol % of PCy3) under mild reaction conditions and is easily scalable to gram quantities.

Photochemical Functionalization of Heterocycles with EBX Reagents: C?H Alkynylation versus Deconstructive Ring Cleavage**

The development of novel methodologies for the functionalization of saturated heterocycles is highly desirable. Herein, we report a cheap and efficient photochemical method for the C?H functionalization of saturated O-heterocycles, as well as the deconstructive ring-cleavage of S-heterocycles, employing hypervalent iodine alkynylation reagents (ethynylbenziodoxolones, EBX). This photochemical alkynylation is performed utilizing phenylglyoxylic acid as the photoinitiator, leading to the corresponding products in good to high yields, under household fluorescent light bulb irradiation. When O-heterocycles were employed, the expected α-C?H alkynylation took place. In contrast, oxidative ring-opening to form a thioalkyne and an aldehyde was observed with S-heterocycles. Preliminary mechanistic experiments are presented to give first insights into this puzzling divergent reactivity.

Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

γ-Carboline synthesis enabled by Rh(iii)-catalysed regioselective C-H annulation

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