1310384-98-5

Basic information

• Product Name: 3-Methoxythiophene-2-boronic acid pinacol ester
• Synonyms: 3-Methoxythiophene-2-boronic acid pinacol ester;4,4,5,5-Tetramethyl-2-(3-methoxy-2-thienyl)-1,3,2-dioxaborolane
• CAS NO: 1310384-98-5
• Molecular Formula: C11H17BO3S
• Molecular Weight: 240.12688
• Mol File: 1310384-98-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 124-128°C
• Boiling Point: 333.1±27.0 °C(Predicted)
• Appearance: /
• Density: 1.10±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3-Methoxythiophene-2-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxythiophene-2-boronic acid pinacol ester(1310384-98-5)
• EPA Substance Registry System: 3-Methoxythiophene-2-boronic acid pinacol ester(1310384-98-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1310384-98-5(Hazardous Substances Data)

Usage

Description

3-Methoxythiophene-2-boronic acid pinacol ester is an organic compound that serves as a versatile intermediate in the synthesis of various complex organic molecules, particularly in the fields of pharmaceuticals, materials science, and organic chemistry.

Uses

Used in Organic Synthesis:
3-Methoxythiophene-2-boronic acid pinacol ester is used as an intermediate for the synthesis of benzothiadiazole derivatives, which are valuable building blocks in the preparation of organic semiconductors. These semiconductors are essential components in the development of electronic devices such as solar cells, light-emitting diodes (LEDs), and field-effect transistors (FETs).
Used in Luminescent Materials:
3-Methoxythiophene-2-boronic acid pinacol ester is used as a starting material in the synthesis of imidazo[1,2-a]pyridine derivatives. These derivatives exhibit bright excited-state intramolecular proton transfer (ESIPT) luminescence property in the solid-state, making them promising candidates for applications in the development of advanced optical materials and sensors.
Used in Polycyclic Aromatic Compounds:
3-Methoxythiophene-2-boronic acid pinacol ester is also used as a starting material in the preparation of polycyclic aromatic triptycenes. These complex molecular structures are of interest in the field of materials science due to their unique electronic, optical, and structural properties, which can be exploited in the design of novel materials with tailored properties for various applications.

Upstream product

• 17573-92-1 3-methoxy-thiophene 
• 73183-34-3 bis(pinacol)diborane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand

The steric effects of substituents on five-membered rings are less pronounced than those on six-membered rings because of the difference in bond angles. Thus, the regioselectivities of reactions of five-membered heteroarenes that occur with selectivities dictated by steric effects, such as the borylation of C?H bonds, have been poor in many cases. We report that the silylation of five-membered-ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by the combination of [Ir(cod)(OMe)]2 (cod=1,5-cyclooctadiene) and a phenanthroline ligand or a new pyridyl-imidazoline ligand that further increases the regioselectivity. The silylation reactions with these catalysts produce high yields of heteroarylsilanes from functionalization at the most sterically accessible C?H bonds of these rings under conditions that the borylation of C?H bonds with previously reported catalysts formed mixtures of products or products that are unstable. The heteroarylsilane products undergo cross-coupling reactions and substitution reactions with ipso selectivity to generate heteroarenes that bear halogen, aryl, and perfluoroalkyl substituents.

CONDENSED POLYCYCLIC COMPOUND

PROBLEM TO BE SOLVED: To provide a compound usable preferably as a material for an organic semiconductor or an organic electroluminescent element. SOLUTION: There is provided a compound having a structure obtained by condensing a plurality of rings. The compound is, for example, a compound formed by condensing two 5-membered rings on the right and left sides respectively around a center 6-membered ring, as shown in figure (9). SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT