476004-80-5

Usage

Uses

Used in Pharmaceutical Industry:
5-Methylthiophene-2-boronic acid pinacol ester, 95% is used as a reactant in the synthesis of N-(4-methylpyridin-2-yl)thiophene-2-carboxamide analog, which is a potential inhibitor of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). These enzymes play a crucial role in the regulation of neurotransmitter levels in the nervous system, and their inhibition can have therapeutic applications in various neurological disorders.
Used in Organic Chemistry:
5-Methylthiophene-2-boronic acid pinacol ester, 95% is used as a reactant in the palladium-catalyzed Suzuki coupling reaction for the preparation of heteroaryl derivatives. This reaction is a powerful tool in organic chemistry for the formation of carbon-carbon bonds, enabling the synthesis of a wide range of complex organic molecules with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.
Used in Materials Science:
5-Methylthiophene-2-boronic acid pinacol ester, 95% is used as a reactant in the preparation of organic recyclable mechanoluminescent luminogens via Wittig and Suzuki reactions. These luminogens exhibit unique properties, such as the ability to emit light upon mechanical stimulation, making them promising candidates for applications in smart materials, sensors, and optoelectronic devices.

InChI:InChI=1/C11H17BO2S/c1-8-6-7-9(15-8)12-13-10(2,3)11(4,5)14-12/h6-7H,1-5H3

Upstream product

• 554-14-3 2-Methylthiophene 
• 1196109-24-6 (dippe)Ir(Bpin)3 
• 17249-82-0 2-chloro-5-methylthiophene 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1257865-74-9 2-(5-methylthiophen-2-yl)benzo[d][1,3,2]dioxaborole 
• 765-58-2 2-bromo-5-methyl thiophene 
• 171364-78-6 (4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 162607-20-7 (5-methylthiophen-2-yl)boronic acid 

Downstream Products

• 1040281-90-0 2-methyl-5-(3-(trifluoromethyl)phenyl)thiophene 
• 85093-01-2 2-(4-methoxyphenyl)-5-methylthiophene 
• 85093-00-1 2-methyl-5-(4-methylphenyl)thiophene 
• 1108741-69-0 2-methyl-5-(o-methylphenyl)thiophene 
• 1172121-11-7 1-(4-(5-methylthiophen-2-yl)phenyl)ethan-1-one 
• 1392440-51-5 C₁₄H₁₆O₂S 
• 1172121-14-0 2-methyl-5-(4-nitrophenyl)-thiophene 
• 554-14-3 2-Methylthiophene 
• 162607-20-7 (5-methylthiophen-2-yl)boronic acid 
• 1089333-87-8 2-(4-fluorophenyl)-5-methylthiophene 
• 1382179-43-2 2-(2,6-dimethylphenyl)-5-methylthiophene 
• 214360-65-3 4-trifluoromethylphenylboronic acid pinacol ester 

Relevant academic research and scientific papers

Getting the sterics just right: A five-coordinate iridium trisboryl complex that reacts with C-H bonds at room temperature

Five-coordinate boryl complexes relevant to Ir mediated C-H borylations have been synthesized, providing a glimpse of the most fundamental step in the catalytic cycle for the first time.

Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives

Aryl boronic esters are bench-stable, platform building-blocks that can be accessed through metal-catalyzed aryl C(sp2)-H borylation reactions. C(sp2)-H bond functionalization reactions using rare- and precious-metal catalysts are well established, and while examples utilizing Earth-abundant alternatives have emerged, manganese catalysis remains lacking. The manganese-catalyzed C-H borylation of furan and thiophene derivatives is reported alongside an in situ activation method providing facile access to the active manganese hydride species. Mechanistic investigations showed that blue light irradiation directly affected catalysis by action at the metal center, that C(sp2)-H bond borylation occurs through a C-H metallation pathway, and that the reversible coordination of pinacolborane to the catalyst gave a manganese borohydride complex, which was as an off-cycle resting state.

Zinc catalysed electrophilic C-H borylation of heteroarenes

Cationic zinc Lewis acids catalyse the C-H borylation of heteroarenes using pinacol borane (HBPin) or catechol borane (HBCat). An electrophile derived from [IDippZnEt][B(C6F5)4] (IDipp = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) combined withN,N-dimethyl-p-toluidine (DMT) proved the most active in terms of C-H borylation scope and yield. Using this combination weakly activated heteroarenes, such as thiophene, were amenable to catalytic C-H borylation using HBCat. Competition reactions show these IDipp-zinc cations are highly oxophilic but less hydridophilic (relative to B(C6F5)3), and that borylation proceedsviaactivation of the hydroborane (and not the heteroarene) by a zinc electrophile. Based on DFT calculations this activation is proposed to proceed by coordination of a hydroborane oxygen to the zinc centre to generate a boron electrophile that effects C-H borylation. Thus, Lewis acid binding to oxygen sites of hydroboranes represents an under-developed route to access reactive borenium-type electrophiles for C-H borylation.

Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates

Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.

Method for efficiently catalyzing selective boronation reaction of five-membered heterocycle

The invention relates to a method for efficiently catalyzing a selective boronation reaction of a five-membered heterocycle. A heterocyclic borate product can be smoothly prepared through convenientlycatalyzing a selective boronation reaction of furan and thiophene derivatives and a cheap and easily available organic boron reagent under a mild condition by a cheap ruthenium metal complex taken asa catalyst. Compared with a reported method, the method of the invention has the obvious advantages of specific reaction selectivity, low catalyst dosage, convenience in operation, no need of addinga reaction solvent and the like, and an efficient and high-selectivity reaction strategy is provided for laboratory preparation or industrial production of the heterocyclic borate product.

Iron-catalysed C(sp2)-H borylation enabled by carboxylate activation

Arene C(sp2)-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. Applying an in situ catalyst activation method using air-stable and easily handed reagents, the iron-catalysed C(sp2)-H borylation reactions of furans and thiophenes under blue light irradiation have been developed. Key reaction intermediates have been prepared and characterised, and suggest two mechanistic pathways are in action involving both C-H metallation and the formation of an iron boryl species.

Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation

A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain via the Ullmann or the Suzuki coupling protocols. Finally, we have shown a one-pot sequence describing C-H borylation/Cu-catalyzed homocoupling/Pd-catalyzed Suzuki coupling to obtain π-extended arene frameworks.

Isodesmic C-H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis

The potential advantages of using arylboronic esters as boron sources in C-H borylation are discussed. The concept is showcased using commercially available 2-mercaptopyridine as a metal-free catalyst for the transfer borylation of heteroarenes using arylboronates as borylation agents. The catalysis shows a unique functional group tolerance among C-H borylation reactions, tolerating notably terminal alkene and alkyne functional groups. The mechanistic investigation is also described.

Electrophilic borylation of terminal alkenes with BBr3/2,6-disubstituted pyridines

A variety of terminal alkenes, as well as heteroaromatic compounds, are borylated by the combined use of BBr3/2,6-dichloropyridine (B3) or BBr3/2,6-lutidine (B5). α,α-Diarylalkenes prefer the former reagent combination, while other alkenes prefer the latter. Mechanistic considerations strongly suggest that the former and latter reactions proceed through electrophilic substitution reactions with BBr3 and [BBr2·B5]+BBr4-, respectively.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF

The present invention relates to a compound for an organic electronic element including a benzo fluorine compound and a derivative thereof, an organic electronic element utilizing the same, and an electronic device thereof. According to the present invention, the light emitting efficiency, the color purity, and the lifetime of the organic electronic element can be improved. [Reference numerals] (401) Substrate;(402) Anode;(404) Hole transport layer;(405) Light emitting layer;(406) Electron transport layer;(408) Cathode