885692-91-1

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYLTHIOPHENE-2-BORONIC ACID PINACOL ESTER is used as a synthetic intermediate for the development of new pharmaceuticals. Its reactivity allows for the creation of a variety of drug candidates, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 3-METHYLTHIOPHENE-2-BORONIC ACID PINACOL ESTER is utilized as a key component in the synthesis of novel agrochemicals. Its role in organic reactions facilitates the production of innovative compounds designed to improve crop protection and yield.
Used in Materials Science:
3-METHYLTHIOPHENE-2-BORONIC ACID PINACOL ESTER is employed as a precursor in the development of new materials. Its potential to form complex organic molecules is harnessed to create advanced materials with specific properties for various applications in science and engineering.
Overall, 3-METHYLTHIOPHENE-2-BORONIC ACID PINACOL ESTER's applications are driven by its unique chemical properties and its capacity to undergo diverse organic reactions, making it an indispensable tool in the synthesis of a broad spectrum of organic compounds across different industries.

Upstream product

• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 14282-76-9 2-bromo-3-methylthiophene 
• 616-44-4 3-Methylthiophene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 22092-92-8 diisopropopylaminoborane 

Downstream Products

• 1447089-38-4 tris(4-(3-methylthiophene-2-yl)phenyl)amine 
• 951781-87-6 2-(4-fluorophenyl)-3-methylthiophene 
• 1332448-16-4 2,8-dimethyl-5-(3-(3-methylthiophen-2-yl)phenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 
• 1332449-11-2 2,8-dimethyl-5-(2-(3-methylthiophen-2-yl)phenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 
• 885692-92-2 1-Methyl-4-[3-(3-methyl-thiophen-2-yl)-4-nitro-phenyl]-piperazine 

Relevant academic research and scientific papers

Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand

The steric effects of substituents on five-membered rings are less pronounced than those on six-membered rings because of the difference in bond angles. Thus, the regioselectivities of reactions of five-membered heteroarenes that occur with selectivities dictated by steric effects, such as the borylation of C?H bonds, have been poor in many cases. We report that the silylation of five-membered-ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by the combination of [Ir(cod)(OMe)]2 (cod=1,5-cyclooctadiene) and a phenanthroline ligand or a new pyridyl-imidazoline ligand that further increases the regioselectivity. The silylation reactions with these catalysts produce high yields of heteroarylsilanes from functionalization at the most sterically accessible C?H bonds of these rings under conditions that the borylation of C?H bonds with previously reported catalysts formed mixtures of products or products that are unstable. The heteroarylsilane products undergo cross-coupling reactions and substitution reactions with ipso selectivity to generate heteroarenes that bear halogen, aryl, and perfluoroalkyl substituents.

Asymmetric supercapacitor devices based on dendritic conducting polymer and activated carbon

Dendritic conducting polymers(CPs) are a novel class of porous pseudocapacitive electrode materials assembled with the combination of highly reversible redox active triphenylamine(TPA) and thiophene, 3-methylthiophene, selenophene and thieno[3,2-b]thiophen moieties. Due to the unique combination of three dimensional conducting network, fast redox reversible reactions, porous morphology, high thermal and electrochemical stability have fetched these pseudocapacitive polymers to exhibit high specific capacitance and emerged as an ideal candidate for energy storage devices. The electrochemical performance of as-prepared polymers showed specific capacitance of 278, 257, 246 and 315 Fg?1 for poly tris[4-(2-thienyl)phenyl]amine (P1), poly tris(4-(3-methylthiophene-2-yl)phenyl)amine (P2), poly tris(4-(selenophen-2-yl)phenyl)amine (P3) and poly tris(4-thieno[3,2-b]thiophen-2-yl) phenyl)amine (P4) respectively with low internal resistance. An insertion of selenophene and thieno(3,2-b)thiophene linkers in TPA block showed enhanced electrochemical performance than the thiophene-TPA pair. Furthermore, asymmetric supercapacitors were assembled with the polymer as cathode and activated carbon as an anode and the detailed electrochemical characterizations has been investigated. This research may shed light on designing new redox active psuedocapacitors and other electrochemical devices.

Iridium/N-heterocyclic carbene-catalyzed C-H borylation of arenes by diisopropylaminoborane

Catalytic C-H borylation of arenes has been widely used in organic synthesis because it allows the introduction of a versatile boron functionality directly onto simple, unfunctionalized arenes. We report herein the use of diisopropylaminoborane as a boron source in C-H borylation of arenes. An iridium(I) complex with 1,3-dicyclohexylimidazol-2-ylidene is found to efficiently catalyze the borylation of arenes and heteroarenes. The resulting aminoborylated products can be converted to the corresponding boronic acid derivatives simply by treatment with suitable diols or diamines.

Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies

A transition-metal-free method has been developed for the boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with a silylborane in the presence of an alkali-metal alkoxide. The base-mediated boryl substitution of organohalides with a silylborane was recently reported to provide the corresponding borylated products in good to high yields, and exhibit good functional group compatibility and high tolerance to steric hindrance. In this study, the scope of this transformation has been extended significantly to include a wide variety of functionalized aryl-, heteroaryl- and alkenyl halides. In particular, the boryl substitution of (E)- and (Z)-alkenyl halides proceeded smoothly to afford the corresponding alkenyl boronates in good to high yields with retention of the configuration using modified reaction conditions. The results of the mechanistic studies suggest that this boryl substitution proceeds via a carbanion-mediated mechanism.

C-H bond activation/borylation of furans and thiophenes catalyzed by a half-sandwich iron N-heterocyclic carbene complex

A coordinatively unsaturated iron-methyl complex having an N-heterocyclic carbene ligand, [Cp*Fe-(LMe)Me] (1; Cp *=η5-C5Me5, L Me=1,3,4,5-tetramethyl-imidazol-2-ylidene), is synthesized from the reaction of [Cp*Fe(TMEDA)Cl] (TMEDA=N,N,N',N'- tetramethylethylenediamine) with methyllithium and LMe. Complex 1 is found to activate the C-H bonds of furan, thiophene, and benzene, giving rise to aryl complexes, [Cp*Fe(LMe)-(aryl)] (aryl=2-furyl (2), 2-thienyl (3), phenyl (4)). The C-H bond cleavage reactions are applied to the dehydrogenative coupling of furans or thiophenes with pinacolborane (HBpin) in the presence of tert-butylethylene and a catalytic amount of 1 (10 mol% to HBpin). The borylation of the furan/thiophene or 2-substituted furans/thiophenes occurs exclusively at the 2-or 5-positions, respectively, whereas that of 3-substituted furans/thiophenes takes place mainly at the 5-position and gives a mixture of regioisomers. Treatment of 2 with 2 equiv of HBpin results in the quantitative formation of 2-boryl-furan and the borohydride complex [Cp *Fe(LMe)(H2Bpin)] (5). Heating a solution of 5 in the presence of tert-butylethylene led to the formation of an alkyl complex [Cp*Fe-(LMe)CH2CH2tBu] (6), which was found to cleave the C-H bond of furan to produce 2. On the basis of these results, a possible catalytic cycle is proposed.

Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C-H functionalization

Iridium-catalyzed borylation has been applied to various substituted thiophenes to synthesize poly-functionalized thiophenes in good to excellent yields. Apart from common functionalities compatible with iridium-catalyzed borylations, additional functional group tolerance to acyl (COMe) and trimethylsilyl (TMS) groups was also observed. High regioselectivities were observed in borylation of 3- and 2,5-di-substituted thiophenes. Electrophilic aromatic C-H/C-Si bromination on thiophene boronate esters is shown to take place without breaking the C-B bond, and one-pot C-H borylation/Suzuki-Miyaura cross-coupling has been accomplished on 2- and 3-borylated thiophenes.

METHOD OF INHIBITING C-KIT KINASE

A method of reducing or inhibiting kinase activity of C-KIT in a cell or a subject, and the use of such compounds for preventing or treating in a subject a cell proliferative disorder and/or disorders related to C-KIT using a compound of the present invention: or a solvate, hydrate, tautomer or pharmaceutically acceptable salt thereof. The present invention is further directed to methods for treating conditions such as cancers and other cell proliferative disorders.

METHOD OF INHIBITING FLT3 KINASE

A method of reducing or inhibiting kinase activity of FLT3 in a cell or a subject, and the use of such compounds for preventing or treating in a subject a cell proliferative disorder and/or disorders related to FLT3 using a compound of the present invention (I), or a solvate, hydrate, tautomer or pharmaceutically acceptable salt thereof. The present invention is further directed to methods for treating conditions such as cancers and other cell proliferative disorders.

INHIBITORS OF C-FMS KINASE

The invention is directed to compounds of Formula (I): wherein A, X, R2 and W are set forth in the specification, as well as solvates, hydrates, tautomers and pharmaceutically acceptable salts thereof, that inhibit protein tyrosine kinases, especially c-fms kinase. Methods of treating autoimmune diseases; and diseases with an inflammatory component; treating metastasis from ovarian cancer, uterine cancer, breast cancer, colon cancer, stomach cancer, hairy cell leukemia and non-small lung carcinoma; and treating pain, including skeletal pain caused by tumor metastasis or osteoarthritis, or visceral, inflammatory, and neurogenic pain; as well as osteoporosis, Paget's disease, and other diseases in which bone resorption mediates morbidity including arthritis, prosthesis failure, osteolytic sarcoma, myeloma, and tumor metastasis to bone with the compounds of Formula (I), are also provided.

SYNERGISTIC MODULATION OF FLT3 KINASE USING A FLT3 INHIBITOR AND A FARNESYL TRANSFERASE INHIBITOR

The invention is directed to a method of inhibiting FLT3 tyrosine kinase activity or expression or reducing FLT3 kinase activity or expression in a cell or a subject comprising the administration of a farnesyl transferase inhibitor and a FLT3 kinase inhibitor selected from compounds of Formula I′: Included within the present invention is both prophylactic and therapeutic methods for treating a subject at risk of (or susceptible to) developing a cell proliferative disorder or a disorder related to FLT3.