171364-84-4

Basic information

• Product Name: 4,4,5,5-Tetramethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborolane
• Synonyms: 4,4,5,5-Tetramethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborolane
• CAS NO: 171364-84-4
• Molecular Formula: C15H23BO2
• Molecular Weight: 246.16
• Mol File: 171364-84-4.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 335.9±41.0 °C(Predicted)
• Appearance: /
• Density: 0.97±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4,4,5,5-Tetramethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5-Tetramethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborolane(171364-84-4)
• EPA Substance Registry System: 4,4,5,5-Tetramethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborolane(171364-84-4)

Safety Data

• Hazardous Substances Data: 171364-84-4(Hazardous Substances Data)

Usage

General Description

4,4,5,5-Tetramethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborolane is a chemical compound with the molecular formula C15H23BO2. It is a boron-containing compound that is used in organic synthesis, particularly in the field of cross-coupling reactions. 4,4,5,5-Tetramethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborolane has a boron atom attached to a dioxaborolane ring and a 2,4,6-trimethylphenyl group. It is commonly used as a reagent in Suzuki-Miyaura cross-coupling reactions, which are important in the synthesis of various organic compounds. Additionally, it has been studied for its potential application in materials science, particularly in the development of organic light-emitting diodes and other optoelectronic devices.

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Relevant articles and documents

Dibenzo[a,e]pentalenes with Low-Lying LUMO Energy Levels as Potential n-Type Materials

Ambipolar organic semiconductors are of high interest for organic field-effect transistors. For n-type conduction, low LUMO energies are required. Dibenzo[a,e]pentalenes (DBPs) are promising compounds; however, few derivatives exist with energetically low-lying LUMO levels. Here, we present DBP derivatives with LUMO energies down to -3.73 eV and small bandgaps down to 1.63 eV determined through cyclic voltammetry, UV/vis absorption spectroscopy, and TDDFT calculations. Single-crystal X-ray diffraction analysis revealed a 1D π-stacking mode. The addition of arylalkynyl substituents at the five-membered rings in a facile and versatile synthetic route allowed for tuning of the band gaps and LUMO energies. The synthetic route can easily be modified to access a variety of DBP derivatives. The LUMO energies of the DBP derivatives presented herein make them attractive for an application in n-type or ambipolar field-effect transistors.

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis

Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.

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.