930303-82-5

Usage

General Description

(5-methylthiophen-3-yl)boronic acid is a chemical compound with a boronic acid functional group attached to a thiophene ring. (5-methylthiophen-3-yl)boronic acid is commonly used in the field of organic chemistry as a building block for the synthesis of various pharmaceuticals, agrochemicals, and materials. It is often utilized in Suzuki-Miyaura cross-coupling reactions, where it serves as a key component in the formation of carbon-carbon bonds. The presence of the methyl group on the thiophene ring gives the compound certain electronic and steric properties that make it suitable for a wide range of synthetic applications. Additionally, the boronic acid functionality allows for selective reactions with other functional groups, making it a valuable tool in the development of new chemical entities.

Upstream product

• 29421-92-9 4-bromo-2-methylthiophene 
• 688-74-4 boric acid tributyl ester 
• 13675-18-8 tetrahydroxydiboron 

Downstream Products

• 38418-27-8 5,5′-dimethyl-3,3′-bithiophene 

Relevant academic research and scientific papers

Development of Red-Shifted and Fluorogenic Nucleoside and Oligonucleotide Diarylethene Photoswitches

The reversible modulation of fluorescence signals by light is of high interest for applications in super-resolution microscopy, especially on the DNA level. In this article we describe the systematic variation of the core structure in nucleoside-based diarylethenes (DAEs), in order to generate intrinsically fluorescent photochromes. The introduction of aromatic bridging units resulted in a bathochromic shift of the visible absorption maximum of the closed-ring form, but caused reduced thermal stability and switching efficiency. The replacement of the thiophene aryl unit by thiazol improved the thermal stability, whereas the introduction of a benzothiophene unit led to inherent and modulatable turn-off fluorescence. This feature was further optimized by introducing a fluorescent indole nucleobase into the DAE core, resulting in an effective photoswitch with a fluorescence quantum yield of 0.0166 and a fluorescence turn-off factor of 3.2. The site-specific incorporation into an oligonucleotide resulted in fluorescence-switchable DNA with high cyclization quantum yields and switching efficiency, which may facilitate future applications.

Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts

We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.

SYNTHESIS OF CYCLOPENTADIENEDITHIOPHENE DERIVATIVES

A process for preparing cyclopentadiene derivatives having formula (I) wherein T1 is selected from the group consisting of oxygen (O), or sulphur (S); R1, R2, R3 an d R4, are hydrogen atoms, or hydrocarbon radicals; comprising the following steps: a) reacting a compound of formula (II) with a compound of formula (III) in the presence of a palladium or nickel based catalyst and a base; b) contacting the obtained compound with a carbonylating system; and c) treating the product obtained in step b) with a reducing agent.