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

Uses

5-Methylthiophene-2-boronic acid pinacol ester can be used as a reactant: In the palladium-catalyzed Suzuki coupling reaction for the preparation of heteroaryl derivatives. To synthesize N-(4-methylpyridin-2-yl)thiophene-2-carboxamide analog as potential inhibitor of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). To prepare organic recyclable mechanoluminescent luminogen via Wittig and Suzuki reactions.

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 
• 765-58-2 2-bromo-5-methyl thiophene 
• 17249-82-0 2-chloro-5-methylthiophene 
• 1257865-74-9 2-(5-methylthiophen-2-yl)benzo[d][1,3,2]dioxaborole 
• 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 

Downstream Products

• 1040281-90-0 2-methyl-5-(3-(trifluoromethyl)phenyl)thiophene 
• 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 
• 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 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.

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.

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.