942070-06-6

Basic information

• Product Name: 4-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER
• Synonyms: 4-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER;4-BROMOTHIOPHEN-2-BORONIC ACID PINACOL ESTER;2-(4-BroMothiophen-2-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• CAS NO: 942070-06-6
• Molecular Formula: C₁₀H₁₄BBrO₂S
• Molecular Weight: 289
• Mol File: 942070-06-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER(942070-06-6)
• EPA Substance Registry System: 4-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER(942070-06-6)

Safety Data

• Hazardous Substances Data: 942070-06-6(Hazardous Substances Data)

Usage

General Description

4-Bromothiophene-2-boronic acid pinacol ester is a chemical compound that falls under the category of organoboronic acids and esters. It is used primarily in scientific research, specifically in the field of organic synthesis. With a molecular formula of C12H14BBrO2S, this compound exhibits characteristics typical of boronic esters like stability and reactivity. 4-Bromothiophene-2-boronic acid pinacol ester is involved in various chemical reactions, including Suzuki-Miyaura cross-coupling reactions helpful in the creation of complex organic compounds. It requires careful handling due to its potentially hazardous nature.

Upstream product

• 872-31-1 3-Bromothiophene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 

Relevant articles and documents

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

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.