99770-93-1

Basic information

• Product Name: 1,4-Benzenediboronic acid bis(pinacol) ester
• Synonyms: 1 4-BENZENEDIBORONIC ACID DIPINACOL EST%;1,4-Benzenediboronic acid bis(pinacol) ester, 97%;Benzene-1,4-diboronic acid, pinacol diester;1,4-Phenylenediboronic acid, pinacol diester;1,4-phenyldiboronic acid, bis(pinacol) ester;1,4-Benzenediboronic acid dipinacol ester, 1,4-Bis(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene;1,4-Phenylenediboronic acid, pinacol di96%;1,4-Phenylenediboronic acid, pinacol ester
• CAS NO: 99770-93-1
• Molecular Formula: C₁₈H₂₈B₂O₄
• Molecular Weight: 330.04
• Product Categories: blocks;BoronicAcids
• Mol File: 99770-93-1.mol
• Article Data: 81

Chemical Properties

• Melting Point: 241-245 °C
• Boiling Point: 416.3°Cat760mmHg
• Flash Point: 205.6°C
• Appearance: /
• Density: 1.03g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• CAS DataBase Reference: 1,4-Benzenediboronic acid bis(pinacol) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Benzenediboronic acid bis(pinacol) ester(99770-93-1)
• EPA Substance Registry System: 1,4-Benzenediboronic acid bis(pinacol) ester(99770-93-1)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• Hazardous Substances Data: 99770-93-1(Hazardous Substances Data)

Usage

Description

1,4-Benzenediboronic acid bis(pinacol) ester is an organic compound that serves as a versatile reagent in various chemical reactions and applications. It is characterized by its ability to form stable boron-carbon bonds, making it a valuable intermediate in the synthesis of complex organic molecules and materials.

Uses

Used in Chemical Synthesis:
1,4-Benzenediboronic acid bis(pinacol) ester is used as a reagent for Suzuki-Miyaura cross-coupling reactions and polymerizations. It facilitates the formation of carbon-carbon bonds, enabling the synthesis of a wide range of organic compounds and polymers with potential applications in various industries.
Used in Solar Energy Industry:
1,4-Benzenediboronic acid bis(pinacol) ester is used as a reagent in the preparation of efficient solar cell photoelectric polymers. Its incorporation into these materials enhances their light absorption and charge transport properties, leading to improved solar cell performance and energy conversion efficiency.
Used in Electronics Industry:
1,4-Benzenediboronic acid bis(pinacol) ester is used as a component in the development of field-effect transistors and photovoltaic cells. Its electronic properties and compatibility with other materials make it suitable for use in these devices, contributing to their performance and efficiency.
Used in Optoelectronics Industry:
1,4-Benzenediboronic acid bis(pinacol) ester is used as a precursor for the synthesis of fluorescent compounds and materials, such as blue OLED devices, blue polymeric light-emitting diodes, and white LEDs. Its ability to emit light upon excitation makes it a valuable component in the development of advanced optoelectronic devices with improved brightness, color quality, and energy efficiency.

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 71-43-2 benzene 
• 589-87-7 1,4-bromoiodobenzene 
• 106-39-8 bromochlorobenzene 
• 106-46-7 para-dichlorobenzene 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 73183-34-3 bis(pinacol)diborane 
• 73852-88-7 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 106-37-6 1.4-dibromobenzene 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 624-38-4 para-diiodobenzene 
• 214360-58-4 2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 68716-49-4 p-bromophenylboronic acid pinacol ester 

Downstream Products

• 164173-99-3 1,4-bis(2',2,6',6-tetracarboxy-1,4':4,4-pyridyl)benzene 
• 1314299-16-5 4(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl azide 
• 1217269-85-6 [8]cyclo-para-phenylene 
• 845870-55-5 N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine 

Relevant articles and documents

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Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides

Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN?-*, which can be used to activate reductively recalcitrant aryl chlorides (Ered ≈ -1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.