338998-93-9

Basic information

• Product Name: 2-Methylfurane-5-boronic acid pinacol ester
• Synonyms: 2-Methylfurane-5-boronic acid pinacol ester;5-Methyl-2-furanboronic acid pinacol ester;5-Methylfuran-2-boronic acid p;5-Methylfuran-2-boronic acid pinacol ester 95%;5-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)furan, 2-(5-Methylfur-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 338998-93-9
• Molecular Formula: C₁₁H₁₇BO₃
• Molecular Weight: 208.06
• Mol File: 338998-93-9.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 277.794 °C at 760 mmHg
• Flash Point: 121.806 °C
• Appearance: /
• Density: 1.023 g/mL at 25 °C
• Vapor Pressure: 0.00748mmHg at 25°C
• Refractive Index: n20/D1.476
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Methylfurane-5-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylfurane-5-boronic acid pinacol ester(338998-93-9)
• EPA Substance Registry System: 2-Methylfurane-5-boronic acid pinacol ester(338998-93-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 338998-93-9(Hazardous Substances Data)

Usage

Description

2-Methylfurane-5-boronic acid pinacol ester is an organic compound that serves as a versatile reagent in the field of organic chemistry. It is characterized by the presence of a boronic acid group attached to a furan ring, with a methyl group at the 2-position and a pinacol ester group at the 5-position. This unique structure allows it to participate in various chemical reactions, making it a valuable synthetic intermediate.

Uses

Used in Organic Synthesis:
2-Methylfurane-5-boronic acid pinacol ester is used as a reagent for the borylation of furans, pyrroles, and other organic reactions. Its boronic acid functionality enables it to undergo Suzuki-Miyaura cross-coupling reactions, which are widely used in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Methylfurane-5-boronic acid pinacol ester is used as a key intermediate in the synthesis of various biologically active compounds. Its ability to form stable boron-containing intermediates makes it a valuable building block for the development of new drugs with potential applications in the treatment of various diseases.
Used in Material Science:
2-Methylfurane-5-boronic acid pinacol ester is also utilized in the field of material science, where it is employed in the synthesis of novel materials with unique properties. Its incorporation into polymers and other materials can lead to the development of advanced materials with improved mechanical, thermal, and electrical properties.

InChI:InChI=1/C11H17BO3/c1-8-6-7-9(13-8)12-14-10(2,3)11(4,5)15-12/h6-7H,1-5H3

Upstream product

• 534-22-5 2-methylfuran 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 680192-98-7 deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 557087-01-1 2-dimethylamino-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 953391-62-3 3-fluoro-4-(5-methyl-2-furanyl)-N-[2-(methyloxy)-5-nitrophenyl]benzenesulfonamide 
• 953391-81-6 1,1-dimethylethyl ((1S)-2-{[3-({[2-chloro-4-(5-methyl-2-furanyl)phenyl]sulfonyl}amino)-4-(methyloxy)phenyl]amino}-1-methyl-2-oxoethyl)methylcarbamate 
• 953391-94-1 N-[5-amino-2-(methyloxy)phenyl]-2-chloro-4-(5-methyl-2-furanyl)benzenesulfonamide 
• 953391-97-4 N-[5-({[3-fluoro-4-(5-methyl-2-furanyl)phenyl]sulfonyl}amino)-2-(methyloxy)phenyl]acetamide 
• 953392-01-3 3-fluoro-4-(5-methyl-2-furanyl)-N-(3-nitrophenyl)benzenesulfonamide 
• 953392-06-8 N-(5-amino-2-chlorophenyl)-3-fluoro-4-(5-methyl-2-furanyl)benzenesulfonamide 
• 953392-10-4 1,1-dimethylethyl (2-{[4-fluoro-3-({[3-fluoro-4-(5-methyl-2-furanyl)phenyl]sulfonyl}amino)phenyl]amino}-1,1-dimethyl-2-oxoethyl)carbamate 
• 953392-25-1 N₁-[3-({[2-chloro-4-(5-methyl-2-furanyl)phenyl]sulfonyl}amino)-4-(methyloxy)phenyl]-2-methylalaninamide hydrochloride 
• 952289-48-4 C₂₃H₂₇FN₄O₄S 
• 952289-53-1 C₂₃H₂₈N₄O₄S 
• 952289-55-3 C₂₃H₂₇FN₄O₄S 
• 1132936-08-3 N-(6-(5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxy-3-(5-methylfuran-2-yl)phenyl)naphthalen-2-yl)methanesulfonamide 
• 534-22-5 2-methylfuran 
• 62306-79-0 5-methylfuran-2-boronic acid 

Relevant articles and documents

C-H Borylation Catalysis of Heteroaromatics by a Rhenium Boryl Polyhydride

Transition metal complexes bearing metal-boron bonds are of particular relevance to catalytic C-H borylation reactions, with iridium polyboryl and polyhydrido-boryl complexes the current benchmark catalysts for these transformations. Herein, we demonstrate that polyhydride boryl phosphine rhenium complexes are accessible and catalyze the C-H borylation of heteroaromatic substrates. Reaction of [K(DME)(18-c-6)][ReH4(Bpin)(ν2-HBpin)(κ2-H2Bpin)] 1 with 1,3-bis(diphenylphosphino)propane (dppp) produced [K(18-c-6)][ReH4(ν2-HBpin)(dppp)] 2 through substitution of two equivalents of HBpin, and protonation of 2 formed the neutral complex [ReH6(Bpin)(dppp)] 3. Combined X-ray crystallographic and DFT studies show that 2 is best described as a σ-borane complex, whereas 3 is a boryl complex. Significantly, the boryl complex 3 acted as a catalyst for the C(sp2)-H borylation of a variety of heteroarenes (14 examples including furan, thiophene, pyrrole and indole derivatives) and displayed similar reactivity to the iridium analogues.

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.

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.