303006-89-5

Basic information

• Product Name: 2,2’-(2,5-Dimethyl-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• Synonyms: 2,2’-(2,5-Dimethyl-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane);2,5-Dimethyl-1,4-phenylenediboronic acid, pinacol ester
• CAS NO: 303006-89-5
• Molecular Formula: C₂₀H₃₂B₂O₄
• Molecular Weight: 358.091
• Mol File: 303006-89-5.mol

Chemical Properties

• Boiling Point: 454.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.02±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,2’-(2,5-Dimethyl-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2’-(2,5-Dimethyl-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)(303006-89-5)
• EPA Substance Registry System: 2,2’-(2,5-Dimethyl-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)(303006-89-5)

Safety Data

• Hazardous Substances Data: 303006-89-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,2’-(2,5-Dimethyl-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) is used as a reagent for cross-coupling, C-H activation, and carbon-carbon bond formation reactions. Its application in these processes is crucial for the creation of complex molecular structures that are often required in advanced organic chemistry and pharmaceutical research.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2,2’-(2,5-Dimethyl-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) is utilized as a key intermediate in the synthesis of potential drug candidates. Its ability to facilitate complex molecular constructions allows for the development of new and innovative therapeutic agents.
Used in Chemical Research:
2,2’-(2,5-Dimethyl-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) is employed as a research tool in academic and industrial laboratories. Its stability and compatibility with a broad range of reaction conditions make it an ideal candidate for exploring new chemical pathways and mechanisms, ultimately contributing to the advancement of chemical science.

Upstream product

• 106-42-3 para-xylene 
• 1074-24-4 2,5-dibromo-p-xylene 
• 73183-34-3 bis(pinacol)diborane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 1356822-77-9 2,2'-(2,5-bis(bromomethyl)-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 90085-60-2 2,5-dimethyl-1,4-benzenediboronic acid 

Relevant articles and documents

Synthesis of a double spiro-polyindenofluorene with a stable blue emission

(Chemical Equation Presented) A novel polyindenofluorene containing a double spiro-anthracene structure with solublizing alkyl groups was synthesized. Enhanced spectral stability of the polymer was investigated by heat treatment and photoirradiation in ai

High-performance stable n-type indenofluorenedione field-effect transistors

We developed high-performance stable n-type organic field-effect transistors (OFETs) using indenofluorenediones with different numbers of fluorine substituents (MonoF-IF-dione, DiF-IF-dione, and TriF-IF-dione). Top-contact OFETs were fabricated via the vacuum deposition of indenofluorenediones as the semiconducting channel material on polystyrene-treated SiO2/Si substrates. TriF-IF-dione FETs with Au source/drain contacts exhibited good device performances, with a field-effect mobility of 0.16 cm2/(V s), an on/off current ratio of 10 6, and a threshold voltage of 9.2 V. We found that the electrical stability for OFETs based on indenofluorenedione improved with the number of fluorine substituents, which was attributed to higher activation energies for charge trap creation. Moreover, the TriF-IF-dione FETs yielded excellent environmental stability properties, because the LUMO energy levels were relatively low, compared with those of the MonoF-IF-dione FETs.

Dimethyl modified terphenyl core based compounds as hosts of blue phosphorescent emitters

High triplet energy materials were derived from dimethyl modified terphenyl core structure in order to apply them as the host materials of blue-emitting phosphors. The dimethyl modification was effective to increase the triplet energy of the terphenyl and

Isoreticular Crystallization of Highly Porous Cubic Covalent Organic Cage Compounds**

Modular frameworks featuring well-defined pore structures in microscale domains establish tailor-made porous materials. For open molecular solids however, maintaining long-range order after desolvation is inherently challenging, since packing is usually governed by only a few supramolecular interactions. Here we report on two series of nanocubes obtained by co-condensation of two different hexahydroxy tribenzotriquinacenes (TBTQs) and benzene-1,4-diboronic acids (BDBAs) with varying linear alkyl chains in 2,5-position. n-Butyl groups at the apical position of the TBTQ vertices yielded soluble model compounds, which were analyzed by mass spectrometry and NMR spectroscopy. In contrast, methyl-substituted cages spontaneously crystallized as isostructural and highly porous solids with BET surface areas and pore volumes of up to 3426 m2 g?1 and 1.84 cm3 g?1. Single crystal X-ray diffraction and sorption measurements revealed an intricate cubic arrangement of alternating micro- and mesopores in the range of 0.97–2.2 nm that are fine-tuned by the alkyl substituents at the BDBA linker.

DIAMINE COMPOUND, POLYIMIDE PRECURSOR AND POLYIMIDE FILM PREPARED BY USING SAME

The present invention discloses a novel diamine having a structure including an intramolecular imide group while having an aromatic ring group with a rigid structure. In addition, and by comprising the novel diamine as a polymerization component, the present invention can provide a polyimide film having improved mechanical and thermal properties while maintaining optical properties of polyimide.

Boronate Ester-Capped Helicates

Triple-stranded helicates were obtained by metal-templated multicomponent reactions of bispyridyloxime ligands with arylboronic acids. The helicates feature two hexa-coordinated MII ions (M=Fe, Zn, or Mn), which are embedded in a macrobicyclic ligand framework, and two arylboronate ester capping groups. The latter can be used to introduce functional groups such as pyridines, aldehydes, nitriles, and carboxylic acids in apical position. The functionalized helicates have the potential to be used as nanoscale building blocks for more complex assemblies, as evidenced by the synthesis of a 3 nm-sized trianglimine.

Novel compound and organic light emitting device comprising the same

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Diverse Multi-Functionalized Oligoarenes and Heteroarenes for Porous Crystalline Materials

A modular synthesis of multi-functionalized biphenyl, terphenyl and higher linear oligophenylene dicarboxylic acids and pyridine-terminated oligoarenes by stepwise palladium–catalyzed borylation/Suzuki–Miyaura cross-coupling reactions is described. The presence of several distinct functional groups such as azide, hydroxy, and alkyne, as well as coordinative functional end groups (carboxylic acid or pyridine) combined in a single oligoarene molecular unit at strategic positions offer an advantageous dual-utility. First, these compounds can serve as useful molecular bricks (ditopic organic linkers) in the construction of complex porous crystalline materials. Second, after the assembly into the crystalline coordination networks, orthogonal functional sites within the linker-backbone offer tremendous potential from application perspectives as they can be modified by a wide range of post-synthetic modifications including azide–alkyne click chemistry. This allows further tailoring of the supramolecular assemblies to yield novel multifunctional materials.

Planarity of terphenyl rings possessing: O -carborane cages: Turning on intramolecular-charge-transfer-based emission

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CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

A condensed cyclic compound and an organic light-emitting device including the same, the condensed cyclic compound being represented by Formula 1: