519054-55-8

Basic information

• Product Name: 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-BENZOFURAN
• Synonyms: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran;Benzofuran-5-boronic acid pinacol ester;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan;2-(Benzofuran-5-yl);5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-BENZOFURAN;2-(benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Benzo[b]furan-5-boronic acid, pinacol ester;2-dioxaborolan-2-yl)-1-benzofuran
• CAS NO: 519054-55-8
• Molecular Formula: C₁₄H₁₇BO₃
• Molecular Weight: 244.09
• Mol File: 519054-55-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 72 °C
• Boiling Point: 340°C at 760 mmHg
• Flash Point: 159.4°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 0.000174mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-BENZOFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-BENZOFURAN(519054-55-8)
• EPA Substance Registry System: 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-BENZOFURAN(519054-55-8)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 519054-55-8(Hazardous Substances Data)

Usage

General Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran is a chemical compound that belongs to the class of benzofuran derivatives. It is characterized by the presence of a benzofuran group connected to a 1,3,2-dioxaborolane ring. 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-BENZOFURAN is often used in organic synthesis as a versatile reagent for the installation of boron-containing groups. It is also utilized in the development of pharmaceuticals and other advanced materials due to its unique structural and chemical properties. Additionally, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran has potential applications in the field of organic electronics and optoelectronics, making it a valuable molecule for scientific research and industrial applications.

InChI:InChI=1/C14H17BO3/c1-13(2)14(3,4)18-15(17-13)11-5-6-12-10(9-11)7-8-16-12/h5-9H,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 331834-13-0 2,3-dihydro-1-benzofuran-5-ylboronic acid 
• 73183-34-3 bis(pinacol)diborane 
• 23145-07-5 5-bromobenzofuran 

Downstream Products

• 1426095-56-8 N-[4-(1-benzofuran-5-yl)-2-fluorophenyl]-2-[(3S)-1-cyclopropylcarbonyl-3-pyrrolidinyl]-N-methylacetamide 
• 1426095-50-2 N-[4-(1-benzofuran-5-yl)phenyl]-2-[(3S)-1-cyclopropylcarbonyl-3-pyrrolidinyl]-N-methylacetamide 
• 1426095-40-0 4-(1-benzofuran-5-yl)-N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-N-(phenylmethyl)benzamide 
• 1332332-79-2 4-[4-(1-benzofuran-5-yl)-2-chloro-6-fluorophenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1332332-66-7 4-[4-(1-benzofuran-5-yl)phenyl]-5-{[(3R)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1332331-78-8 4-[4-(1-benzofuran-5-yl)phenyl]-5-{[1-(cyclopropylcarbonyl)-3-azetidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1332331-68-6 4-[4-(1-benzofuran-5-yl)-2,5-difluorophenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1332331-67-5 4-[4-(1-benzofuran-5-yl)-2-hydroxyphenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1332331-65-3 4-[4-(1-benzofuran-5-yl)-3-(methyloxy)phenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1332331-58-4 4-[4-(1-benzofuran-5-yl)-2,6-difluorophenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1332333-36-4 1,1-dimethylethyl(3S)-3-({4-[4-(1-benzofuran-5-yl)phenyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxylate 
• 1332331-48-2 4-[4-(1-benzofuran-5-yl)-2-methylphenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1332331-40-4 4-[4-(1-benzofuran-5-yl)-2-fluorophenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1366766-53-1 5-[4-(1-benzofuran-5-yl)phenyl]-1-{[(3R)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-1H-tetrazol 

Relevant articles and documents

Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds

Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.

Transformations of Aryl Ketones via Ligand-Promoted C?C Bond Activation

The coupling of aromatic electrophiles (aryl halides, aryl ethers, aryl acids, aryl nitriles etc.) with nucleophiles is a core methodology for the synthesis of aryl compounds. Transformations of aryl ketones in an analogous manner via carbon–carbon bond activation could greatly expand the toolbox for the synthesis of aryl compounds due to the abundance of aryl ketones. An exploratory study of this approach is typically based on carbon–carbon cleavage triggered by ring-strain release and chelation assistance, and the products are also limited to a specific structural motif. Here we report a ligand-promoted β-carbon elimination strategy to activate the carbon–carbon bonds, which results in a range of transformations of aryl ketones, leading to useful aryl borates, and also to biaryls, aryl nitriles, and aryl alkenes. The use of a pyridine-oxazoline ligand is crucial for this catalytic transformation. A gram-scale borylation reaction of an aryl ketone via a simple one-pot operation is reported. The potential utility of this strategy is also demonstrated by the late-stage diversification of drug molecules probenecid, adapalene, and desoxyestrone, the fragrance tonalid as well as the natural product apocynin.

ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME

The present invention relates to an indole-based compound with excellent hole injection and hole transport ability; and to an organic electroluminescent device which includes the compound in one or more layers and thus has increased light emitting efficiency, needs lower driving voltages, and has an extended life span. According to the present invention, the electroluminescent device includes: (i) a positive electrode; (ii) a negative electrode; and (iii) one or more organic layers interposed between the positive electrode and the negative electrode.