130995-13-0

Usage

Chemical Properties

White solid

InChI:InChI=1/C9H12SSi/c1-11(2,3)7-5-9-4-6-10-8-9/h4,6,8H,1-3H3

Upstream product

• 3140-93-0 2,3-dibromothiophen 
• 1066-54-2 trimethylsilylacetylene 
• 10486-61-0 3-thienyl iodide 
• 872-31-1 3-Bromothiophene 
• 1003-09-4 2-bromothiophene 
• 67237-53-0 3-ethynylthiophene 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Downstream Products

• 67237-53-0 3-ethynylthiophene 
• 1309360-45-9 1-(2-methoxyphenyl)-3-thiophen-3-yl-prop-2-yn-1-ol 
• 1259446-07-5 4-[(2,5-dibromothiophen-3-yl)ethynyl]-N,N-dihexadecylaniline 
• 1438285-42-7 C₃₀H₃₈N₂SSi 
• 170859-75-3 3-(thiophen-3-yl)prop-2-yn-1-ol 
• 1468-83-3 1-(thiophen-3-yl)-ethanone 
• 1184872-81-8 3-(thiophen-3-yl)-1-o-tolylprop-2-yn-1-ol 
• 1184872-86-3 (Z)-2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)-3-(thiophen-3-yl)-1-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 
• 198489-54-2 6-Phenyl-5-trimethylsilanyl-6H-1-thia-6-arsa-pentalene 
• 198489-53-1 6-Phenyl-5-trimethylsilanyl-6H-1-thia-6-phospha-pentalene 

Relevant academic research and scientific papers

Insight into the Electronic State of 1-Phenylthienoborepin by Means of Nuclear Magnetic Resonance Spectroscopy

In order to obtain an insight into the electronic states in connection with the condensation modes of thiophene and borepin rings, we examined 1-phenylthienoborepin (2).While 1-phenylthienoborepin is a peripherally conjugated compound, 2 was shown to be an aromatic compound which maintains characteristics in conjugation of individual rings.

Synthesis of Graphene Nanoribbons by Ambient-Pressure Chemical Vapor Deposition and Device Integration

Graphene nanoribbons (GNRs), quasi-one-dimensional graphene strips, have shown great potential for nanoscale electronics, optoelectronics, and photonics. Atomically precise GNRs can be bottom-up synthesized by surface-assisted assembly of molecular building blocks under ultra-high-vacuum conditions. However, large-scale and efficient synthesis of such GNRs at low cost remains a significant challenge. Here we report an efficient bottom-up chemical vapor deposition (CVD) process for inexpensive and high-throughput growth of structurally defined GNRs with varying structures under ambient-pressure conditions. The high quality of our CVD-grown GNRs is validated by a combination of different spectroscopic and microscopic characterizations. Facile, large-area transfer of GNRs onto insulating substrates and subsequent device fabrication demonstrate their promising potential as semiconducting materials, exhibiting high current on/off ratios up to 6000 in field-effect transistor devices. This value is 3 orders of magnitude higher than values reported so far for other thin-film transistors of structurally defined GNRs. Notably, on-surface mass spectrometry analyses of polymer precursors provide unprecedented evidence for the chemical structures of the resulting GNRs, especially the heteroatom doping and heterojunctions. These results pave the way toward the scalable and controllable growth of GNRs for future applications.

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.

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

A redox-neutral Rh(iii)-catalyzed C-H annulation of indolyl oximes was developed. Relying on the use of various alkynyl silanes as the terminal alkyne surrogates, the reaction exhibited a reverse regioselectivity, thus giving an exclusive and easy way for the synthesis of a wide range of substituent free γ-carbolines at C3 position with high efficiency. Deuterium-labelling experiments and kinetic analysis have preliminarily shed light on the working mode of this catalytic system. This journal is

Palladium catalysed regio- and stereoselective synthesis of (E)-4-aryl-1,3-bis(trimethylsilyl)but-3-en-1-ynes

A practical and general synthetic approach to a series of 4-aryl-but-3-en-1-ynes is described. In the presence of palladium complexes a variety of aryl bromides (or iodides) undergo coupling with two equivalents of trimethylsilylacetylene with the formati

Intermolecular Desymmetrizing Gold-Catalyzed Yne–Yne Reaction of Push–Pull Diarylalkynes

Push–pull diaryl alkynes are dimerized in the presence of a cationic gold catalyst. The polarized structure of the applied starting materials enables the generation of a highly reactive vinyl cation intermediate in an intermolecular reaction. Trapping of the vinyl cation by a nucleophilic attack of the electron-poor aryl unit then leads to the selective formation of highly substituted naphthalenes in a single step and in complete atom economy.

Gold-Catalyzed Dimerization of Diarylalkynes: Direct Access to Azulenes

We have developed a simple gold-catalyzed procedure for the synthesis of substituted and modifiable azulenes. The azulenes are formed either by the dimerization of push–pull diarylalkynes bearing a fluorine atom in ortho or para position or by the dimeriz

Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of: O -methoxycarbonylphenylboronic acid with alkynes

Treatment of alkynes with o-methoxycarbonylphenylboronic acid in the presence of a cobalt catalyst resulted in the corresponding 2,3-disubstituted indenones in good yields. Excellent regioselectivities were observed, when silyl aryl alkynes were used. The intermediate 3-silyl-2-aryl-substituted indenones were converted to 2,3-diaryl indenones by a three-step protocol involving C-Si bromination and Suzuki-Miyaura coupling reaction.

Fluoroform-Derived CuCF3 for Trifluoromethylation of Terminal and TMS-Protected Alkynes

An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.