2404-87-7

Usage

Uses

Conducting polymer precursor.

Synthesis Reference(s)

The Journal of Organic Chemistry, 33, p. 2902, 1968 DOI: 10.1021/jo01271a064

InChI:InChI=1/C10H8S/c1-2-4-9(5-3-1)10-6-7-11-8-10/h1-8H

Upstream product

• 188290-36-0 thiophene 
• 938-81-8 N-nitrosoacetanilide 
• 127-66-2 2-Phenyl-3-butyn-2-ol 
• 99059-46-8 2,3-dihydro-4-phenylthiophene 
• 767-99-7 2-phenylbut-2-ene 
• 2227-79-4 benzenecarbothioamide 
• 872-31-1 3-Bromothiophene 
• 108-86-1 bromobenzene 
• 35717-22-7 2-chloro-3-phenylthiophene 
• 35717-21-6 2-chloro-4-phenylthiophene 
• 21676-88-0 4-phenyl-2-thiophenecarboxylic acid 
• 6007-83-6 2,3-thiophenedicarboxylic acid anhydride 
• 71-43-2 benzene 
• 53283-28-6 phenyl-succinic acid ; disodium-compound 

Downstream Products

• 18132-94-0 2-nitro-3-phenyl-thiophene 
• 18132-95-1 2-nitro-4-phenyl-thiophene 
• 35717-22-7 2-chloro-3-phenylthiophene 
• 35717-21-6 2-chloro-4-phenylthiophene 
• 10341-87-4 2-bromo-3-phenylthiophene 
• 97272-02-1 5-phenyl-2-thiophenesulphonyl chloride 
• 19698-46-5 2,5-Dibromo-3-phenylthiophene 
• 10353-18-1 2-bromo-4-phenyl thiophene 
• 20851-07-4 2,3,5-triphenylthiophene 
• 23062-41-1 3-bromo-4-phenylthiophene 
• 500772-24-7 3-phenyl-4-[(4-phenylthien-3-yl)thio]thiophene 
• 500772-25-8 3,5-diphenyldithieno[3,2-b:2',3'-d]thiophene 
• 500772-26-9 3,5-diphenyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide 
• 500772-27-0 2-bromo-3,5-diphenyl-dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide 

Relevant academic research and scientific papers

Suzuki-Miyaura coupling under air in water promoted by polymer supported palladium nanoparticles

Suzuki couplings of aryl bromides were efficiently performed by a polymer supported palladium catalyst under air in water at 100°C without additives. In the case of activated aryl chlorides the reactions proceeded smoothly in the presence of a suitable phase transfer agent. The catalyst was active and recyclable for at least five times. Atomic absorption analyses revealed that the metal content in the polymeric support did not significantly decrease with the cycles while inductively coupled plasma analyses revealed that the palladium amount both in the mother liquors and in the organic products after reactions was lower than 500 ppb. The activity of the mother liquors has been investigated in detail. A transmission electron microscopy study of the supported catalyst before, during and after duty is also described.

Substituent effects on indirect carbon-carbon couplings, J(CC), in substituted thiophenes, pyrroles, and furans studied by experiment and theory

An excellent linear correlation is found between a large set of experimental spin-spin carbon-carbon coupling constants, J(CC), in thiophene, pyrrole, and furan systems and the corresponding B3PW91/6-311++G(2d,p)//B3PW91/ 6-311++G(2d,p) calculated estimates. The correlation does not differ significantly from the simplest relationship possible, J(CC)exp. = J(CC)calcd., within a small and random spread of about 1 Hz. There are 285 experimental values considered, and 202 out of these are new and come from the present work. The character of the correlation indicates that rovibronic effects on aromatic J(CC)'s, and those of nuclear motions on aromatic J(CC)'s are practically negligible. All of this is in a perfect agreement with our recent extensive studies on aromatic J(CC)'s in pyridine and benzene ring systems. As has been shown by computations, not only large one-bond couplings but also almost all long-range ones occurring between the carbons of the heteroaromatic rings are, with a few exceptions, positive. Significant substituent effects experimentally observed in the one-bond as well as long-range couplings are very accurately reproduced by the computation. The experimental coupling magnitudes vary from ca. 1 to 98 Hz. The J(CC)'s computed for the model variously substituted trimethylsilyl and fluoro derivatives, which are not easily accessible experimentally, span a range of about 130 Hz, from ca. -2 in up to ca. +125 Hz. Copyright

Structure and Internal Rotation in 3-Phenylthiophene Using NMR Spectra of Liquid-Crystalline Solutions

The NMR spectra of 3-phenylthiophene as solute in liquid-crystal solvents were analyzed and the direct couplings constants, Dij obtained were used to test different models of the potential energy function V(φ) for intramolecular rotation of the phenyl and thiophene units.The data are consistent with a V(φ) having a minimum at about 24 deg.The LCNMR technique is highly discriminant among different models of V(φ) provided that enough Dij couplings are available.Ab initio calculations are also reported.

Fabrication of hollow palladium spheres and their successful application to the recyclable heterogeneous catalyst for suzuki coupling reactions

Novel palladium hollow spheres were synthesized using silica spheres as a template, and they were successfully applied as recyclable heterogeneous catalysts for Suzuki cross coupling reactions. Copyright

A C3v-symmetric triphosphine ligand derived from trindane skeleton: synthesis, inclusion of C60, and catalytic activity of its Pd complex

With the aim to design a multidentate C3v-symmetric trindane-based trisphosphine ligand 3 for Suzuki-Miyaura cross-coupling of 3-bromothiophene with phenylboronic acid, we observed the ability of this ligand to form an inclusion complex with buckyball C60. Along with its catalytic activity, the pyramidal inversion at phosphorous atoms of 3 and the formation of 3@C60 were investigated by 1H NMR, 31P{1H} NMR and DFT methods.

Electrochemical Preparation of Highly Anode-active Poly(3-phenylthiophene)

The electrochemical preparation of poly(3-phenylthiophene) is described; when doped with cations as well as anions, it exhibits interesting spectroscopic properties.

Organocatalytic synthesis of (Het)biaryl scaffoldsviaphotoinduced intra/intermolecular C(sp2)-H arylation by 2-pyridone derivatives

A uniqueN,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcasedviathe construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.

2-Phosphinoimidazole Ligands: N-H NHC or P-N Coordination Complexes in Palladium-Catalyzed Suzuki-Miyaura Reactions of Aryl Chlorides

We report the synthesis of two palladium 2-(dialkylphosphino)imidazole complexes and demonstrate their activity as catalysts for Suzuki-Miyaura reactions with (hetero)aryl chlorides at room temperature. Our mechanistic studies demonstrate that these palladium complexes exist as an equilibrium mixture between the P-N coordinated and N-H NHC forms of ligand. Our studies suggest that the N-H NHC form may be important for high catalytic activity in Suzuki-Miyaura reactions with aryl chlorides. These reactions proceed at or near room temperature in good to excellent yields. Heteroaryl chlorides are also reactive at lower catalyst loadings.

Lipids as versatile solvents for chemical synthesis

Development of safe, renewable, cheap and versatile solvents is a longstanding challenge in chemistry. We show here that vegetable oils and related systems can become prominent solvents for organic synthesis. Suzuki-Miyaura, Hiyama, Stille, Sonogashira and Heck cross-couplings proceed with quantitative yields in a range of vegetable oils, fish oil, butter and waxes used as solvents. Appropriate methodologies for high-throughput screening and sustainable isolation techniques applicable for vegetable oils and related lipids are presented.

Redox-Divergent Construction of (Dihydro)thiophenes with DMSO

Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.