171364-80-0

Usage

Uses

Used in Chemical Synthesis:
Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is used as a synthetic intermediate for the preparation of 2-aryl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes. These compounds are synthesized through palladium-catalyzed coupling reactions, which are widely employed in the formation of carbon-carbon and carbon-heteroatom bonds in organic chemistry. The use of Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate in such reactions allows for the creation of a diverse range of molecules with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is used as a key building block for the development of novel drug candidates. The ability to form 2-aryl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes through palladium-catalyzed coupling reactions enables the synthesis of complex molecular structures with potential therapeutic properties. These molecules may be further optimized and tested for their efficacy in treating various diseases and medical conditions.
Used in Materials Science:
Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate also finds application in the field of materials science, where it can be used to synthesize new materials with unique properties. The resulting 2-aryl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes can be incorporated into the design of advanced materials, such as polymers, coatings, and composites, with potential applications in various industries, including electronics, automotive, and aerospace.

InChI:InChI=1/C14H21BO5/c1-13(2,17)14(3,4)20-15(18)11-8-6-10(7-9-11)12(16)19-5/h6-9,17-18H,1-5H3

Upstream product

• 17763-67-6 Phenyl triflate 
• 17763-71-2 4-carbomethoxyphenyl triflate 
• 73183-34-3 bis(pinacol)diborane 
• 17640-15-2 methyl cyanoformate 
• 106-37-6 1.4-dibromobenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 6018-41-3 methyl coumalate 
• 347389-74-6 2-ethynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 59776-81-7 methyl 2-pyrone-4-carboxylate 
• 51901-85-0 bromocatecholborane 
• 7440-66-6 zinc 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 22821-70-1 methyl 4-(methanesulfonyl)benzoate 
• 437764-07-3 methyl 4-((2R)-2-{[(tert-butoxycarbonyl)amino]methyl}-3,4-dihydro-2H-chromen-6-yl)-benzoate 
• 473596-87-1 4-methoxycarbonyl-2-methylbenzeneboronic acid pinacol ester 
• 276694-16-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide 
• 1046491-61-5 methyl 2',5'-bis[(E)-1,2-difluoro-2-(4-octyloxyphenyl)vinyl]-4'-methoxybiphenyl-4-carboxylate 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 1198278-09-9 methyl 4-(3-formyl-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzoate 
• 20442-96-0 methyl 4-azidobenzoate 
• 1234215-38-3 methyl 4-(5-((tert-butyldimethylsilyl)oxy)pent-1-en-3-yl)benzoate 
• 1234215-40-7 methyl 4-(6-chlorohex-1-en-3-yl)benzoate 
• 1234215-43-0 methyl 4-(7-azidohept-1-en-3-yl)benzoate 
• 1234215-41-8 methyl 4-(7-cyanohept-1-en-3-yl)benzoate 
• 1234215-45-2 methyl 4-(2-methylenecyclopentyl)benzoate 
• 592528-46-6 3-(4-methyloxycarbonylphenyl)-1-phenylpropene 

Relevant academic research and scientific papers

Functionalized heterocycle-appended porphyrins: Catalysis matters

The scope and limitations of the condensation of labile 2,3-diaminoporphyrin derivatives with aromatic aldehydes to provide functionalized imidazole- and pyrazine-appended porphyrins were investigated in detail. The presence of an acidic catalyst in the reaction was found to be a tool that allows the reaction path to be switched. The influence of the electronic origin of the substituents in the carbonyl components of the condensation on the yields and selectivity of the reaction was revealed. Metal-promoted cross-coupling transformations were found to be convenient for the further targeted construction of functional derivatives based on the prepared bromo-substituted pyrazinoporphyrins. Overall, these strategies provide a versatile technique for the elaboration of a variety of functionalized heterocycle-appended porphyrins for further application in the development of hybrid materials. This journal is

Sandmeyer-type reaction to pinacol arylboronates in water phase: A green borylation process

Copper(I)-catalyzed cross-coupling reactions of aryl diazonium salts with bis(pinacolato)diboron can proceed smoothly in the water phase at room temperature to give the corresponding arylboronate esters in good to high yields. The Sandmeyer-type borylation not only provides direct access to arylboronates bearing halo and acidic substituents, but also achieves a green borylation process. Georg Thieme Verlag Stuttgart · New York.

Highly Stable Zr(IV)-Based Metal-Organic Frameworks for the Detection and Removal of Antibiotics and Organic Explosives in Water

Antibiotics and organic explosives are among the main organic pollutants in wastewater; their detection and removal are quite important but challenging. As a new class of porous materials, metal-organic frameworks (MOFs) are considered as a promising platform for the sensing and adsorption applications. In this work, guided by a topological design approach, two stable isostructural Zr(IV)-based MOFs, Zr6O4(OH)8(H2O)4(CTTA)8/3 (BUT-12, H3CTTA = 5′-(4-carboxyphenyl)-2′,4′,6′-trimethyl-[1,1′:3′,1″-terphenyl]-4,4″-dicarboxylic acid) and Zr6O4(OH)8(H2O)4(TTNA)8/3 (BUT-13, H3TTNA = 6,6′,6″-(2,4,6-trimethylbenzene-1,3,5-triyl)tris(2-naphthoic acid)) with the the-a topological structure constructed by D4h 8-connected Zr6 clusters and D3h 3-connected linkers were designed and synthesized. The two MOFs are highly porous with the Brunauer-Emmett-Teller surface area of 3387 and 3948 m2 g-1, respectively. Particularly, BUT-13 features one of the most porous water-stable MOFs reported so far. Interestingly, these MOFs represent excellent fluorescent properties, which can be efficiently quenched by trace amounts of nitrofurazone (NZF) and nitrofurantoin (NFT) antibiotics as well as 2,4,6-trinitrophenol (TNP) and 4-nitrophenol (4-NP) organic explosives in water solution. They are responsive to NZF and TNP at parts per billion (ppb) levels, which are among the best performing luminescent MOF-based sensing materials. Simultaneously, both MOFs also display high adsorption abilities toward these organic molecules. It was demonstrated that the adsorption plays an important role in the preconcentration of analytes, which can further increase the fluorescent quenching efficiency. These results indicate that BUT-12 and -13 are favorable materials for the simultaneous selective detection and removal of specific antibiotics and organic explosives from water, being potentially useful in monitoring water quality and treating wastewater.

Effects of main chain and acceptor content on phase behaviors of hydrogen-bonded main-chain/side-chain combined liquid crystalline polymers

Main-chain/side-chain combined liquid crystalline polymers (MCSCLCPs) are usually difficult to synthesize and their degrees of polymerization are relatively low, which bring difficulties in studying their structure-property relationships. In order to solve this problem, we prepared a new series of MCSCLCPs containing mesogen-jacketed liquid crystalline polymer (MJLCP) main chains via hydrogen-bonding (H-B). A pyridine derivative with a triphenylene (Tp) unit is the H-B acceptor. In addition to the temperature dependence, the phase behavior of the resulting complex is strongly influenced by the content of the H-B acceptor and the rigidity of the side-chain core of the MJLCP. The resulting complexes exhibit different phase structures: (1) a columnar nematic phase or a smectic A (SmA) phase formed by the supramolecular MJLCP chain as a whole; (2) hierarchical nanostructures including a hexagonal columnar phase or a SmA phase of the whole polymer chain plus a discotic nematic phase associated with the Tp moieties.

Synthesis, structures and luminescent properties of two coordination polymers based on 5-(4-carboxyphenyl)-2, 6-pyridinedicarboxylic acid

Two coordination polymers, Zn7O(cpda)3(OH) 3 (1) and [Tb(H2cpda)(Hcpda)(H2O)] ·(H2O) (2) (H3cpda = 5-(4-carboxyphenyl)-2, 6-pyridinedicarboxylic acid), were synthesized and chara

Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Potential Foldamers Based on an ortho-Terphenyl Amino Acid

We describe the synthesis and characterization of a new class of oligomers built from a terphenyl-based amino acid. These oligomeric amides are of interest because the adoption of specific conformations could potentially be driven by the coordinated formation of inter-residue hydrogen bonds and aromatic interactions. Although high-resolution structural data have proven inaccessible, circular dichroism and nuclear magnetic resonance studies suggest that the new oligomers fold concomitantly with discrete self-association in chloroform.

Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates

Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.

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.