1040281-97-7

Basic information

• Product Name: 3-Chlorothiophene-2-boronic acid pinacol ester
• Synonyms: 3-Chlorothiophene-2-boronic acid pinacol ester;2-(3-Chlorothiophen-2-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• CAS NO: 1040281-97-7
• Molecular Formula: C10H14BClO2S
• Molecular Weight: 262.56124
• Mol File: 1040281-97-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 318.3 °C at 760 mmHg
• Flash Point: 146.3 °C
• Appearance: /
• Density: 1.18 g/cm³
• Vapor Pressure: 0.000681mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Chlorothiophene-2-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chlorothiophene-2-boronic acid pinacol ester(1040281-97-7)
• EPA Substance Registry System: 3-Chlorothiophene-2-boronic acid pinacol ester(1040281-97-7)

Safety Data

• Hazardous Substances Data: 1040281-97-7(Hazardous Substances Data)

Usage

General Description

3-Chlorothiophene-2-boronic acid pinacol ester is a chemical compound that belongs to the class of boronic acid pinacol esters. It is primarily used in organic synthesis as a reagent for the Suzuki reaction, which is a widely-used carbon-carbon bond forming reaction in organic chemistry. 3-Chlorothiophene-2-boronic acid pinacol ester is important because it can be used to introduce the 3-chlorothiophene group into organic molecules, making it a valuable building block for the synthesis of pharmaceuticals, agrochemicals, and materials with specific electronic and optical properties. Additionally, its pinacol ester form provides stability and ease of handling in the laboratory, making it a versatile and useful reagent for chemical synthesis.

InChI:InChI=1/C10H14BClO2S/c1-9(2)10(3,4)14-11(13-9)8-7(12)5-6-15-8/h5-6H,1-4H3

Upstream product

• 17249-80-8 3-chlorothiophene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 

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.

Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C-H functionalization

Iridium-catalyzed borylation has been applied to various substituted thiophenes to synthesize poly-functionalized thiophenes in good to excellent yields. Apart from common functionalities compatible with iridium-catalyzed borylations, additional functional group tolerance to acyl (COMe) and trimethylsilyl (TMS) groups was also observed. High regioselectivities were observed in borylation of 3- and 2,5-di-substituted thiophenes. Electrophilic aromatic C-H/C-Si bromination on thiophene boronate esters is shown to take place without breaking the C-B bond, and one-pot C-H borylation/Suzuki-Miyaura cross-coupling has been accomplished on 2- and 3-borylated thiophenes.