171364-86-6

Basic information

• Product Name: Benzo[b]thiophene-3-boronic acid pinacol ester, 95%
• Synonyms: 2-Benzo[b]thiophen-3-yl-4,4,5,5-tetramethyl- [1,3,2]dioxaborolane;2-(1-benzothiophen-3-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• CAS NO: 171364-86-6
• Molecular Formula: C₁₄H₁₇BO₂S
• Molecular Weight: 278.17486
• Mol File: 171364-86-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 377.7±15.0 °C(Predicted)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Benzo[b]thiophene-3-boronic acid pinacol ester, 95%(CAS DataBase Reference)
• NIST Chemistry Reference: Benzo[b]thiophene-3-boronic acid pinacol ester, 95%(171364-86-6)
• EPA Substance Registry System: Benzo[b]thiophene-3-boronic acid pinacol ester, 95%(171364-86-6)

Safety Data

• Hazardous Substances Data: 171364-86-6(Hazardous Substances Data)

Usage

General Description

Benzo[b]thiophene-3-boronic acid pinacol ester, 95% is a chemical compound with a purity of 95%. It is a boronic acid ester derived from benzo[b]thiophene, a heterocyclic compound containing a benzene ring fused to a thiophene ring. The pinacol ester group is a common protecting group in organic synthesis, which can be removed under mild conditions. Benzo[b]thiophene-3-boronic acid pinacol ester, 95% is commonly used in organic synthesis and medicinal chemistry as a versatile building block for the synthesis of pharmaceuticals, agrochemicals, and materials. Its high purity makes it suitable for a wide range of applications in research and industry.

Upstream product

• 7342-82-7 3-Bromothianaphthene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 73183-34-3 bis(pinacol)diborane 
• 58981-23-0 3-butanoylbenzo[b]thiophene 
• 95-15-8 Benzo[b]thiophene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 761425-20-1 dimethyl-1-benzothiene-3-ylboronate 

Downstream Products

• 1135148-67-2 C₂₆H₁₇NOS₃ 
• 1174298-62-4 4,5-di(benzo[b]thiophen-3-yl)-2-phenylthiazole 
• 1403580-37-9 4-(benzo[b]thiophen-3-yl)-5-(2-ethoxybenzo[b]thiophen-3-yl)-2-phenylthiazole 

Relevant articles and documents

Iridium(III) complexes adopting thienylpyridine derivatives for yellow-to-deep red OLEDs with low efficiency roll-off

By introduction of trifluoromethyl and phenyl groups to 2-(2-thienyl)pyridine (thp), four new phosphorescent bis-cyclometalated iridium(III) complexes, (thp)2Ir(tpip), (cf3thp)2Ir(tpip), (cf3btp)2Ir(tpip) and (3-cf3btp)2Ir(tpip) (cf3thp = 2-(thiophen-2-yl)-4-(trifluoromethyl)pyridine, cf3btp = 2-(benzo[b]thiophen-2-yl)-4- (trifluoromethyl)pyridine, 3-cf3btp = 2-(benzo[b]thiophen-3-yl)-4-(trifluoromethyl)pyridine, tpip = tetraphenylimidodiphosphinate), were synthesized and fully characterized. The density functional theory and time-dependent DFT calculations show that the frontier orbitals are mainly localized in the Ir(III) ion and the cyclometalated ligands. Thus, the photophysical properties were dominated by the cyclometalated C∧N ligand, attributed to 3MLCT and 3ILCT transition. These Ir(III) complexes emit in the yellow-to-deep red region with photoluminescence quantum yields in the range 40.5–86.4% in CH2Cl2 solutions at 298 K. The organic light-emitting diodes (OLEDs) using (thp)2Ir(tpip), (cf3thp)2Ir(tpip) and (cf3btp)2Ir(tpip) as yellow, orange and deep red emitters display good electroluminescent performance with low efficiency roll-off. Notably, the device based on (cf3thp)2Ir(tpip) possesses very high EL efficiencies with the maximum luminance efficiency and external quantum efficiency (EQE) of 53.9 cd A?1 and 17.9%, respectively. Furthermore, the EQE for this complex could be still retained as 15.4% at a luminance of 1000 cd m?2.

Anthracene-containing dimer skeleton ligand and preparation method thereof, and application in metal catalytic reaction

The invention provides an anthracene dimer derivative phosphine-containing ligand as shown in the following formula I, wherein the anthracene dimer derivative phosphine-containing ligand can be used for a series of transition metal catalyzed coupling reac

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.