476004-80-5

Basic information

• Product Name: 5-Methylthiophene-2-boronic acid pinacol ester, 95%
• Synonyms: 5-Methylthiophene-2-boronic acid pinacol ester, 95%;4,4,5,5-TetraMethyl-2-(5-Methylthiophen-2-yl)-1,3,2-dioxaborolane;5-Methylthiophene-2-boronic acid pinacol ester 95%;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen (5-methylthiophen-2-yl)boronate;5-Methylthiophen-2-boronic acid pinacol ester;4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)
• CAS NO: 476004-80-5
• Molecular Formula: C₁₁H₁₇BO₂S
• Molecular Weight: 224.13
• Mol File: 476004-80-5.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 308.2°Cat760mmHg
• Flash Point: 105 °C
• Appearance: /
• Density: 0.937
• Vapor Pressure: 0.00125mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-Methylthiophene-2-boronic acid pinacol ester, 95%(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methylthiophene-2-boronic acid pinacol ester, 95%(476004-80-5)
• EPA Substance Registry System: 5-Methylthiophene-2-boronic acid pinacol ester, 95%(476004-80-5)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 37
• WGK Germany: 2
• Hazardous Substances Data: 476004-80-5(Hazardous Substances Data)

Usage

Description

5-Methylthiophene-2-boronic acid pinacol ester, 95% is an organic compound that serves as a versatile reactant in various chemical reactions, particularly in the synthesis of heteroaryl derivatives and organic recyclable mechanoluminescent luminogens.

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

Downstream Products

• 1040281-90-0 2-methyl-5-(3-(trifluoromethyl)phenyl)thiophene 
• 1207328-88-8 3-benzyl-1,3,4-trimethyl-6-[1-[2-(5-methylthiophen-2-yl)pyridin-3-yl]meth-(Z)-ylidene]piperazine-2,5-dione 
• 1239277-80-5 4-(4-methoxyphenyl)-7-(5-methylthiophen-2-yl)-2,1,3-benzothiadiazole 
• 1332448-91-5 2,8-dimethyl-5-(2-(5-methylthiophen-2-yl)phenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 
• 1332448-58-4 2,8-dimethyl-5-(3-(5-methylthiophen-2-yl)phenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b] indole 
• 1357566-23-4 tris(4-(5-methylthiophen-2-yl)phenyl)amine 
• 1380855-79-7 3-(4-butoxyphenyl)-3-(4-methoxyphenyl)-5,7-difluoro-11-(5-methylthiophen-2-yl)-13,13-dimethyl-3H,13H-indeno[2',1':3,4]naphtho[1,2-b]pyran 
• 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 

Relevant articles and documents

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.

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.

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.