501945-71-7

Usage

Uses

Used in Chemical Synthesis:
2-(1-Benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a synthetic intermediate for the preparation of various functional groups. Its boronic ester structure allows for versatile transformations in organic chemistry, making it a valuable component in the synthesis of complex molecules and pharmaceuticals.
Used in Drug Design:
In the pharmaceutical industry, 2-(1-Benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a building block for the development of new drugs. Its unique structural features and biochemical properties make it a promising candidate for the design of novel therapeutic agents with potential applications in various medical fields.
Used in Research and Development:
2-(1-BENZOTHIOPHEN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is also utilized in research and development settings, where it serves as a key component in the exploration of new chemical reactions and the discovery of innovative synthetic pathways. Its presence in the database highlights its relevance in advancing scientific knowledge and fostering technological advancements in the field of chemistry and pharmacology.

InChI:InChI=1/C14H17BO2S/c1-13(2)14(3,4)17-15(16-13)11-5-6-12-10(9-11)7-8-18-12/h5-9H,1-4H3

Upstream product

• 4923-87-9 5-bromobenzo[b]thiophene 
• 73183-34-3 bis(pinacol)diborane 
• 20532-33-6 5-chlorobenzothiophene 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 648905-40-2 1-{2-[4-(2-benzo[b]thiophen-5-yl-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}-piperidine 
• 1624848-29-8 1-{1-[5-(benzo[b]thien-5-yl)-thien-2-yl]cyclohexyl}pyrrolidine 
• 1082525-31-2 3-benzo[b]thiophen-5-yl-1-benzyl-pyrrolidine-2,5-dione 
• 845872-49-3 benzo[b]thiophen-5-ylboronic acid 

Relevant academic research and scientific papers

Photocatalytic Cross-Couplings of Aryl Halides Enabled by o-Phosphinophenolate and o-Phosphinothiophenolate

o-Phosphinophenolate and o-phosphinothiophenolate are potent photocatalysts with strong reducing ability to activate aryl chlorides and bromides under visible light for borylation, arylation, and phosphorylation. Experimental and theoretical studies revealed that the o-diphenylphosphino substituent results in a narrow optical gap and facilitates intersystem crossing to access triplet states, which promote phenolate and thiophenolate to function as effective visible-light-photoredox catalysts. The results presented herein suggest promising utility of synthetically modified phenolates and thiophenolates as photoredox catalysts.

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

MICROBIOCIDAL COMPOUNDS

Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially as fungicides.

Reductive Electrophotocatalysis: Merging Electricity and Light to Achieve Extreme Reduction Potentials

We describe a new electrophotocatalytic strategy that harnesses the power of light and electricity to generate an excited radical anion with a reducing potential of -3.2 V vs SCE, which can be used to activate substrates with very high reduction potentials (Ered ≈ -1.9 to -2.9 V). The resultant aryl radicals can be engaged in various synthetically useful transformations to furnish arylboronate, arylstannane, and biaryl products.

Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex

Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility. Furthermore, arylsilicates were synthesized selectively using dimethylphenylsilyl boronic ester via changing the reaction conditions. Finally, the possible reaction mechanism is determined through fluorescence quenching and turn on/off experiments.

Visible-Light-Induced Organocatalytic Borylation of Aryl Chlorides

The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photoactivation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides.

Modular Synthesis of Di- A nd Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors

A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling in the imidazole ring to yield trisubstituted NH-imidazoles (23%-69%, three steps). This approach was also employed in the synthesis of known inhibitor GSK3037619A.

Photoinduced Miyaura Borylation by a Rare-Earth-Metal Photoreductant: The Hexachlorocerate(III) Anion

The first photoinduced carbon(sp2)–heteroatom bond forming reaction by a rare-earth-metal photoreductant, a Miyaura borylation, has been achieved. This simple, scalable, and novel borylation method that makes use of the hexachlorocerate(III) anion ([CeIIICl6]3?, derived from CeCl3) has a broad substrate scope and functional-group tolerance and can be conducted at room temperature. Combined with Suzuki–Miyaura cross-coupling, the method is applicable to the synthesis of various biaryl products, including through the use of aryl chloride substrates.

Biological Evaluation and X-ray Co-crystal Structures of Cyclohexylpyrrolidine Ligands for Trypanothione Reductase, an Enzyme from the Redox Metabolism of Trypanosoma

The tropical diseases human African trypanosomiasis, Chagas disease, and the various forms of leishmaniasis are caused by parasites of the family of trypanosomatids. These protozoa possess a unique redox metabolism based on trypanothione and trypanothione reductase (TR), making TR a promising drug target. We report the optimization of properties and potency of cyclohexylpyrrolidine inhibitors of TR by structure-based design. The best inhibitors were freely soluble and showed competitive inhibition constants (Ki) against Trypanosoma (T.) brucei TR and T. cruzi TR and in vitro activities (half-maximal inhibitory concentration, IC50) against these parasites in the low micromolar range, with high selectivity against human glutathione reductase. X-ray co-crystal structures confirmed the binding of the ligands to the hydrophobic wall of the “mepacrine binding site” with the new, solubility-providing vectors oriented toward the surface of the large active site.

ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME

The present invention relates to an indole-based compound with excellent hole injection and hole transport ability; and to an organic electroluminescent device which includes the compound in one or more layers and thus has increased light emitting efficiency, needs lower driving voltages, and has an extended life span. According to the present invention, the electroluminescent device includes: (i) a positive electrode; (ii) a negative electrode; and (iii) one or more organic layers interposed between the positive electrode and the negative electrode.