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

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

Uses

Used in Pharmaceutical Industry:
Benzo[b]thiophene-3-boronic acid pinacol ester, 95% is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form carbon-carbon and carbon-heteroatom bonds through palladium-catalyzed coupling reactions. This allows for the creation of diverse molecular structures with potential therapeutic properties.
Used in Agrochemical Industry:
Benzo[b]thiophene-3-boronic acid pinacol ester, 95% is used as a building block in the development of agrochemicals, such as pesticides and herbicides, due to its reactivity in forming complex molecular structures with bioactive properties.
Used in Materials Science:
Benzo[b]thiophene-3-boronic acid pinacol ester, 95% is used as a precursor in the synthesis of advanced materials, including organic semiconductors, polymers, and sensors, leveraging its ability to form stable and functional molecular architectures.
Used in Research and Development:
Benzo[b]thiophene-3-boronic acid pinacol ester, 95% is used as a research chemical to explore new reaction pathways, develop novel synthetic methods, and investigate the properties of newly synthesized compounds in academic and industrial research settings. Its high purity ensures reliable and reproducible results in experiments.

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 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 761425-20-1 dimethyl-1-benzothiene-3-ylboronate 
• 73183-34-3 bis(pinacol)diborane 
• 95-15-8 Benzo[b]thiophene 
• 58981-23-0 3-butanoylbenzo[b]thiophene 

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.

Benzoic Acid-Promoted C2-H Borylation of Indoles with Pinacolborane

A benzoic acid-promoted C2-H borylation of indoles with pinacolborane to afford C2-borylated indoles is developed. Preliminary mechanistic studies indicate BH3-related borane species formed via the decomposition of pinacolborane to be the probable catalyst. This transformation provides a prompt route toward the synthesis of diverse C2-functionalized indoles.

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

Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions

Carbon-supported catalysts have been considered as macromolecular ligands which modulate the activity of the metallic catalytic center. Understanding the properties and the factors that control the interactions between the metal and support allows a fine tuning of the catalyzed processes. Although huge effort has been devoted to comprehending binding energies and charge transfer for single atom noble metals, the interaction of graphenic surfaces with cheap and versatile Cu(i) salts has been scarcely studied. A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed. We have also examined the effect of microwave (MW) radiation in the preparation of these type of materials using sustainable graphite nanoplatelets (GNP) as a support. A detailed analysis of all the possible species in solution revealed that the catalysis is mainly due to an interesting synergetic Cu2O/graphene performance, which has been corroborated by an extensive theoretical study. We demonstrated through DFT calculations at a high level of theory that graphene enhances the reactivity of the metal in Cu2O against the halide derivative favoring a radical departure from the halogen. Moreover, this material is able to stabilize radical intermediates providing unexpected pathways not observed using homogeneous Cu(i) catalysed reactions. Finally, we proved that other common carbon-based supports like carbon black, graphene oxide and reduced graphene oxide provided poorer results in the borylation process.

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.

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT COMPRISING THE SAME, AND ELECTRONIC DEVICE THEREOF

Disclosed are an organic electronic element comprising: a compound represented by chemical formula 1; a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, and an electronic device compri

C-H borylation by platinum catalysis

Herein, we describe the platinum-catalyzed borylation of aromatic C-H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)-H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C-H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C-H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C-H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C-H borylation process are described.

NOVEL ORGANIC ELECTROLUMINESCENCE COMPOUNDS AND ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE SAME

The present invention relates to a novel organic electroluminescent compound, and to an organic electroluminescent device comprising the same. The organic electroluminescent compound according to the present invention has higher light emitting efficiency compared with an existing organic electroluminescent compound. When being used in a light emitting layer of an organic EL device, the compound of the present invention excellently balances charge of holes and electrons in the light emitting layer, increases current/power efficiency of the device, and extends lifespan by reducing a driving voltage. The organic electroluminescent compound is represented by chemical formula 1.COPYRIGHT KIPO 2016

A I-shaped thiopheneglyoxylic bonzene compound and its preparation method

The invention relates to the technical field of organic semiconductor materials and in particular relates to an I-shaped benzothiophene compound and a preparation method thereof. The preparation method of the I-shaped benzothiophene compound comprises that firstly reaction is carried out on R substituted 3-bromobenzothiophene and an organic lithium reagent, so that benzothiophene lithium salt is generated, then isopropanol pinacol borate is added, a 1,2,4,5-tetra(benzothiophene) benzene compound is generated, and oxidization is carried out, thus the I-shaped benzothiophene compound is obtained. The I-shaped benzothiophene compound has the advantages that a production technology is simple, source of raw materials is wide, and semiconductor performance is good, so that the I-shaped benzothiophene compound has a broad application prospect.