196212-27-8

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Phenyldiboronic acid, bis(pinacol) ester is utilized as a synthetic intermediate for the development of pharmaceutical compounds. Its ability to form carbon-carbon bonds and participate in cross-coupling reactions is instrumental in constructing complex molecular structures that can exhibit therapeutic properties.
Used in Materials Science:
In the realm of materials science, 1,3-phenyldiboronic acid, bis(pinacol) ester is employed as a component in the synthesis of advanced materials. Its reactivity and structural versatility contribute to the creation of new materials with unique properties for various applications.
Used in Agricultural Chemistry:
1,3-Phenyldiboronic acid, bis(pinacol) ester is used as a chemical intermediate in the development of agrochemicals. Its role in organic synthesis aids in the production of compounds that can be used in pest control, crop protection, and other agricultural applications, enhancing crop yields and quality.

InChI:InChI=1/C18H28B2O4/c1-15(2)16(3,4)22-19(21-15)13-10-9-11-14(12-13)20-23-17(5,6)18(7,8)24-20/h9-12H,1-8H3

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 71-43-2 benzene 
• 108-36-1 1,3-dibromobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 626-39-1 1,3,5-trisbromobenzene 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 195062-59-0 2-methylphenylboronic acid pinacol ester 
• 372-18-9 1,3-Difluorobenzene 
• 541-73-1 1,3-Dichlorobenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 372-38-3 1,3,5-trifluorobenzene 
• 626-00-6 1,3-Diiodobenzene 

Downstream Products

• 1067236-01-4 ((C₄(CH₃CH₂)2NH)2HC₃HO₂BF₂)2 
• 1067235-98-6 ((C₄(CH₃CH₂)2NH)2HC₃HO₂BF₂)2C₆H₄ 
• 1180668-40-9 C₆₈H₇₂N₆O₁₀ 
• 1269695-72-8 C₉₄H₁₀₆B₄F₈N₈O₈ 
• 916985-28-9 C₂₀H₁₆N₂O₂ 
• 949097-24-9 C₁₄H₁₄N₄ 
• 1369963-51-8 1,3-bis(4-amino-2-pyridyl)benzene 
• 1369963-50-7 C₂₀H₁₈N₄O₂ 
• 1369963-53-0 C₂₈H₃₄N₄O₂ 
• 1334124-89-8 tOXD-mTP 
• 1334124-94-5 tpOXD-mTP 
• 1423631-52-0 1,3-bis(6-{2,5-bis[2-(tert-butyldimethylsilanyloxy)ethyl]-4-pyridin-2-ylphenyl}pyridin-3-yl)benzene 
• 1255519-88-0 2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 95962-62-2 3,3''-dibromo-1,1':3',1''-terphenyl 

Relevant academic research and scientific papers

Self-complementary and narcissistic self-sorting of bis-acridinium tweezers

A molecular tweezer incorporating two acridinium moieties linked by a 1,3-dipyridylbenzene spacer was synthesized in three steps. The formation of its self-complementary dimer in water was demonstrated as a result of π-π stacking and hydrophobic interacti

A Molybdenum(0) Isocyanide Analogue of Ru(2,2′-Bipyridine)32+: A Strong Reductant for Photoredox Catalysis

We report the first homoleptic Mo0complex with bidentate isocyanide ligands, which exhibits metal-to-ligand charge transfer (3MLCT) luminescence with quantum yields and lifetimes similar to Ru(bpy)32+(bpy=2,2′-b

A chemically-responsive bis-acridinium receptor

A dicationic receptor based on two acridinium moieties linked by a triphenylene spacer was studied in solution and in the solid state. Recognition moieties, namely acridiniums, were exploited to evidence a host-guest response of the receptor with electron rich guests. Upon addition of methoxide anions, the formation of the bis-acridane form of the receptor was observed. The chemical responsiveness of the receptor to these anions inhibits its recognition properties towards π-donor guests. In addition, the reversibility of the chemical response was demonstrated under acidic conditions.

Synthesis, Structures, and Assembly of Geodesic Phenine Frameworks with Isoreticular Networks of [ n]Cyclo- para-phenylenes

A series of macrocycles were designed by rendering geodesic phenine frameworks in isoreticular networks of [n]cyclo-para-phenylenes. Large, nanometer-sized molecules exceeding molecular weights of 2000 Da were synthesized by five-step transformations incl

Regioselective aromatic borylation in an inert solvent.

[reaction: see text]. A protocol for performing Rh catalyzed aromatic borylations in cyclohexane has been devised. Borylation at the 5-position of several 1,3-substituted aromatic species ranging from electron-rich (1,3-(NMe(2))(2)C(6)H(4)) to electron-deficient (1,3-(CF(3))(2)C(6)H(4)) yields the corresponding aryl boronate esters. Veratrole was selectively borylated at the 4-position, thus extending regioselectivity to 1,2-substituted benzenes. Selective borylation at the 3-position of an N-protected pyrrole has also been demonstrated, providing a valuable reagent for cross-coupling reactions in a single step.

Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices

Two types of helically chiral compounds bearing one and two boron atoms were synthesized by a modular approach. Formation of the helical scaffolds was executed by the introduction of boron to flexible biaryl and triaryl derived from small achiral building blocks. All-ortho-fused azabora[7]helicenes feature exceptional configurational stability, blue or green fluorescence with quantum yields (Φfl) of 18–24 % in solution, green or yellow solid-state emission (Φfl up to 23 %), and strong chiroptical response with large dissymmetry factors of up to 1.12×10?2. Azabora[9]helicenes consisting of angularly and linearly fused rings are blue emitters exhibiting Φfl of up to 47 % in CH2Cl2 and 25 % in the solid state. As revealed by the DFT calculations, their P–M interconversion pathway is more complex than that of H1. Single-crystal X-ray analysis shows clear differences in the packing arrangement of methyl and phenyl derivatives. These molecules are proposed as primary structures of extended helices.

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.

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

Probing Peripheral H-Bonding Functionalities in BN-Doped Polycyclic Aromatic Hydrocarbons

The replacement of carbon atoms at the zigzag periphery of a benzo[fg]tetracenyl derivative with an NBN atomic triad allows the formation of heteroatom-doped polycyclic aromatic hydrocarbon (PAH) isosteres, which expose BN mimics of the amidic NH function

Concentration-dependent circularly polarized luminescence of chiral cyclometalated platinum(II) complexes for electroluminescence

Circularly polarized organic light-emitting diodes (CP-OLEDs) have been attracting increasing attention due to the direct generation of CP light, and they show the improved image contrast and luminous efficiency in OLEDs displays. In this work, a pair of chiral Pt(II) complexes with methylbenzylisocyanide and 1,3-bis(2-pyridyl)benzene as a tridentate N∧C∧N ligand were synthesized. Both of them exhibited bright green emission in dilute acetonitrile solution, while strong orange emission in high concentration of acetonitrile solution. However, when the complexes were doped into polymethyl methacrylate, the green emission originated from intrinsic single molecule can be changed to the red emission from excimer by adjusting the doping ratios. More importantly, the amplification of CPL signal can be achieved compared with the solution state. Furthermore, the monochrome devices were fabricated by utilizing these two enantiomers as emitters.