1040281-83-1

Usage

Uses

Used in Pharmaceutical Industry:
5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde is used as a key intermediate in the synthesis of pharmaceutical compounds for its ability to facilitate the formation of complex molecular structures through carbon-carbon bond formation. Its unique boron-containing substituent and carbaldehyde group make it a valuable building block for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde serves as a precursor for the synthesis of novel agrochemicals, including pesticides and herbicides. Its reactivity allows for the creation of molecules with targeted biological activity, potentially leading to more effective and environmentally friendly products.
Used in Materials Science:
5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde is utilized as a component in the development of advanced materials with specific properties. Its incorporation into polymers and other materials can enhance their performance, such as conductivity, stability, or responsiveness to environmental stimuli, making it suitable for applications in electronics, sensors, and other high-tech industries.
Overall, the diverse applications of 5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde stem from its unique structural features and reactivity, positioning it as a promising compound for innovation in various scientific and industrial domains.

Upstream product

• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 58268-08-9 2-(2-thienyl)-1,3-dioxolane 

Downstream Products

• 1404193-12-9 C₅₉H₇₅N₃O₅S₃ 
• 1404193-14-1 C₆₅H₇₉N₃O₅S₃ 
• 1404193-16-3 C₆₂H₇₆N₄O₆S₃ 
• 1404193-18-5 C₆₈H₈₀N₄O₆S₃ 
• 1172120-75-0 5-(5'-(5''-(diphenylamino)thiophen-2''-yl)thiophen-2'-yl)-thiophene-2-carbaldehyde 

Relevant academic research and scientific papers

Highly Lewis Acidic Arylboronate Esters Capable of Colorimetric Turn-On Response

A series of boronate-π-acceptor compounds containing different types of π bridges (1,4-phenylen or thien-2,5-diyl or furan-2,5-diyl) that link the switchable boronate ester group with the efficient TCF acceptor group (TCF=2-dicyanomethylen-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran) has been synthesized. A TCF chromophore of this type undergoes transition to a donor-π-acceptor compound upon coordination of Lewis bases at the Lewis acidic boron center, which is accompanied by an enhanced intramolecular charge-transfer interaction. The Lewis acid character has been investigated by spectroscopic measurements (UV/Vis, NMR spectroscopies) as well as DFT and ab initio-based calculations. It is shown that the TCF acceptor group and thiophene or furan π-bridges directly bound to the boron atom cooperatively increase the Lewis acidity. UV/Vis titration experiments confirm fluoride binding constants in the range of up to 108 M-1 in CH2Cl2. In addition to the strong boron fluoride binding motif, Lewis interactions also occur with weaker Lewis bases, such as pyridine or aliphatic alcohols. The unique combination of chromophoric and Lewis acidic properties is responsible for the intense colorimetric turn-on response detectable after complex formation. Push me, pull you: The interplay between the strongly electron-withdrawing TCF acceptor group (TCF=2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran) and the electron-rich heterocyclic π-bridges thiophene and furan dramatically increases the Lewis acidity of new donor-π-acceptor-type arylboronate esters and enables a colorimetric turn-on response induced by the interaction with fluoride ions and weaker Lewis bases, such as pyridine.

Macrocyclic triphenylamine based organic dyes for efficient dye-sensitized solar cells

A novel class of organic D-π-A dyes employing macrocyclic triphenylamine dimer as electron donor was designed and synthesized for dye-sensitized solar cells. The prepared compounds showed high chemical and elelctrochemical stabilities as well as good long-wave absorption. Photovoltaic devices based on these dyes showed high open circuit voltage (higher than that of N3) and achieved a solar energy to electricity conversion efficiency of 6.31%. All the performances indicate the dyes containing macrocyclic triphenylamine dimer is a good candidate for dyes sensitized solar cells.

Design, synthesis and biological evaluation of substituted 2-(thiophen-2-yl)-1,3,5-triazine derivatives as potential dual PI3Kα/mTOR inhibitors

The phosphoinositide 3-kinase (PI3K) and mammalian target of rapamycin (mTOR) have been regarded as promising targets for the treatment of cancer. Herein, we synthesized a new series of substituted 2-(thiophen-2-yl)-1,3,5-triazine derivatives as novel PI3

Aerobic Visible-Light-Driven Borylation of Heteroarenes in a Gel Nanoreactor

Heteroarene boronate esters constitute valuable intermediates in modern organic synthesis. As building blocks, they can be further applied to the synthesis of new materials, since they can be easily transformed into any other functional group. Efforts toward novel and efficient strategies for their preparation are clearly desirable. Here, we have achieved the borylation of commercially available heteroarene halides under very mild conditions in an easy-to-use gel nanoreactor. Its use of visible light as the energy source at room temperature in photocatalyst-free and aerobic conditions makes this protocol very attractive. The gel network provides an adequate stabilizing microenvironment to support wide substrate scope, including furan, thiophene, selenophene, and pyrrole boronate esters.

Rapid Access to Borylated Thiophenes Enabled by Visible Light

Boron-containing thiophenes are important entities in organic/medicinal chemistry as well as in material science. In this Letter, a novel, straightforward, and fast procedure for their production employing visible light as an energy source at room temperature and ambient pressure is reported. All substrates are commercially available, and the process does not require the use of any external photocatalyst.

Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction

Macrocyclization of linear peptide precursors using the Petasis borono-Mannich reaction affords a diverse range of macrocycles with an endocyclic amine. Analysis of the corresponding macrocyclic structures underscores that the hydrogen bond between an endocyclic amine and the adjacent amide NH is a powerful control element for conformationally homogenous peptide macrocycles.

The structure of the aryl-containing five-membered heterocyclic connected triazine compound and its preparation method and application

The invention discloses a structure of the aryl-containing five-membered heterocyclic connected triazine compound and its preparation method. The invention containing aryl structure of five-membered heterocyclic connected to the triazine compound, and its pharmaceutically acceptable salt, hydrate or solvate thereof as an active ingredient, with a pharmaceutically acceptable carrier or excipient mixed preparation composition in, and prepared into a clinically acceptable dosage form. The compounds of the invention in preparing and treating and/or preventing proliferative disorders application of the medicament, for treating and/or preventing cancer of application of the medicament, for treating and/or preventing breast cancer, colon cancer and non-small cell lung cancer in the application.

Elucidating the structure-property relationships of donor-π-acceptor dyes for dye-sensitized solar cells (DSSCs) through rapid library synthesis by a one-pot procedure

The creation of organic dyes with excellent high power conversion efficiency (PCE) is important for the further improvement of dye-sensitized solar cells. We wish to describe the rapid synthesis of a 112-membered donor-π-acceptor dye library by a one-pot procedure, evaluation of PCEs, and elucidation of structure-property relationships. No obvious correlations between ε, and the η were observed, whereas the HOMO and LUMO levels of the dyes were critical for η. The dyes with a more positive EHOMO, and with an ELUMOsc, and it was the most important parameter for a high η. The above criteria of EHOMO and E LUMO should be useful for creating high PCE dyes; nevertheless, that was not sufficient for identifying the best combination of donor, π, and acceptor blocks. Combinatorial synthesis and evaluation was important for identifying the best dye. Combinatorial chemistry: A 112-membered donor-π-acceptor dye library was rapidly constructed by a one-pot, three-component coupling procedure (see scheme, SM=Suzuki-Miyaura). The evaluation of absorption spectroscopic and electrochemical measurements of all synthesized dyes, and cell performances of the selected 54 dyes were performed. The dyes with a more positive EHOMO, and with an E LUMO-0.80 V, exerted higher power conversion efficiencies.