942070-22-6

Basic information

• Product Name: 2-(2,5-Dibromo-3-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(2,5-Dibromo-3-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2,5-Dibromothiophene-3-boronic acid pinacol ester;2-(2,5-Dibromothiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;(2,5-DIBROMOTHIOPHEN-3-YL)BORONIC ACID PINACOL ESTER
• CAS NO: 942070-22-6
• Molecular Formula: C10H13BBr2O2S
• Molecular Weight: 368
• Mol File: 942070-22-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 72-73 °C
• Boiling Point: 371℃
• Flash Point: 178℃
• Appearance: /
• Density: 1.66
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2-(2,5-Dibromo-3-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,5-Dibromo-3-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(942070-22-6)
• EPA Substance Registry System: 2-(2,5-Dibromo-3-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(942070-22-6)

Safety Data

• Hazardous Substances Data: 942070-22-6(Hazardous Substances Data)

Usage

General Description

The chemical 2-(2,5-Dibromo-3-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, also known as DTB-TTDMS-borane, is a boron-based compound that is commonly used in organic synthesis as a boron reagent. It is a colorless liquid with a molecular formula of C10H13BBr2O2S and a molecular weight of 373.92 g/mol. DTB-TTDMS-borane is often utilized in the Suzuki-Miyaura cross-coupling reaction to form carbon-carbon bonds and in the functionalization of aromatic compounds. It is also used as a reagent for the stereospecific reduction of ketones to alcohols and in the protection of aldehydes and ketones. Additionally, this chemical has a wide range of applications in pharmaceutical and agrochemical industries.

Upstream product

• 128-08-5 N-Bromosuccinimide 
• 214360-70-0 4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane 
• 3141-27-3 2,5-dibromothiophen 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Relevant articles and documents

Metal-free halogenation of arylboronate with N-halosuccinimide

Efficient bromination and chlorination of aryl pinacol boronates were accomplished without the addition of metal reagent. The reaction proceeded efficiently with electron-rich arylboronates or heteroarylboronates in DMF or acetonitrile, to afford mono-, di-, or trihalogenated aryl pinacol boronates.

Gold(iii)-catalyzed halogenation of aromatic boronates with N -halosuccinimides

Aromatic boronates bearing halogen substituents in the aromatic ring can be synthesized by AuCl3-catalyzed halogenations with N-halosuccinimides.

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.