4-Aminophenylboronic acid pinacol ester | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaboran-2yl)aniline | Organoboron

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Synonyms: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaboran-2yl)aniline

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Quality Control of 4-Aminophenylboronic acid pinacol ester Purity: 98% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Citations Show More

Fundamental Understanding of Palladium-Based Catalysts: From Pyrene-Based COFs to Size-Controlled Bimetallic Nanostructures

Saha, Hridita Purba ;

Abstract: The catalytic properties of single atoms (SAs) have attracted growing attention due to their unique electronic characteristics and their ability to maximize atomic efficiency compared to nanoparticles. As particle size decreases, the coordination environment around the metal atoms becomes increasingly unsaturated, which raises the surface free energy and enhances the reactivity of the metal species toward supports and adsorbates—this underpins the well-known size effects in metal nanocatalysts. In the extreme case of single-atom catalysts (SACs), the combination of highly active valence electrons, quantum confinement effects, and discrete energy levels leads to maximized surface free energy and distinct chemical behavior. Covalent organic frameworks (COFs), a class of porous and crystalline materials composed of light elements (H, B, C, N, and O), are attractive supports for SACs due to their designable periodic structures and stable covalent bonding. These frameworks offer uniform and tunable binding sites ideal for anchoring metal atoms. Therefore, Single metal atoms anchored on COFs offer a powerful platform for tailoring active sites, enabling the optimization of catalytic activity, selectivity, and stability, with promising potential for use in a wide range of industrial chemical processes. Ethylene hydrogenation has long been used as a model reaction in heterogeneous catalysis to better understand the mechanism of selective acetylene hydrogenation over metal catalysts. Improving selectivity often depends on how strongly the reactants adsorb onto the metal surface. When ethylene binds more weakly to the active sites, selectivity improves—an insight that has led to growing interest in designing catalysts with isolated single metal atoms. Pd single-atom catalysts are highly valued for their activity in ethylene and acetylene hydrogenation under ambient conditions. In this work, we employed PdCl₂-functionalized, pyrene-based COFs that provide uniform binding sites ideal for stabilizing isolated palladium atoms. In this study, we used X-ray photoelectron spectroscopy (XPS) and diffuse reflectance infrared Fourier transform spectroscopy (DRIFTS) with CO as a probe molecule along with catalytic performance evaluation through ethylene hydrogenation kinetics. However, the pyrene-based COF inherently incorporates palladium impurities during synthesis, and the observed catalytic activity of pristine COF can vary significantly depending on the level of these residual Pd species. This makes it difficult to distinguish between the intrinsic activity of the pristine COF and that of atomically dispersed Pd. To reduce these impurities, we implemented two monomer purification methods prior to COF synthesis: triphenylphosphine (PPh₃) treatment and acid column purification. These approaches lowered the Pd content from 0.35% to 0.23% and 0.04%, respectively. PPh₃ purification was not optimal, as it introduced structural defects in the COF, leading to higher catalytic activity compared to the non-purified COF. Conversely, acid column purification preserved the Pd and N coordination environment, revealing distinct activity differences between the 4% Pd-loaded sample and the pristine COF. Notably, even at a reduced 1% Pd loading—critical for stability under reaction conditions—a significantly higher activity than that of the pristine COF was observed. This work highlights the critical role of purification and its underlying mechanisms in shaping the coordination environment and structural integrity of COFs, which in turn significantly impacts their catalytic activity and selectivity in ethylene and acetylene hydrogenation. Bimetallic catalysts often outperform their monometallic counterparts and are widely used in essential chemical transformations such as selective hydrogenation, reforming, coupling, and oxidation. Among them, PdAu alloy catalysts have garnered particular interest due to their ability to undergo dynamic surface restructuring, which plays a critical role in tuning catalytic activity and selectivity. The extent of this restructuring is influenced by factors such as the Pd-to-Au ratio, nanoparticle size, and the nature of adsorbates under reaction conditions. This study investigates how surface structures in Au, Pd, and PdAu nanoparticles evolve with variations in composition, particle size, and temperature. Results show that larger and samller nanoparticles tend to form Au rich surface. Notably, increasing the temperature from cryogenic levels induces Pd migration from the core to the surface, facilitating the formation of Pd trimers. These structural changes are reversible, with Pd atoms re-segregating back into the bulk upon cooling, highlighting the temperature-sensitive and reversible nature of surface restructuring in PdAu catalysts.

Purchased from AmBeed: 214360-73-3 ; 14221-01-3 ; 128-63-2

PROTACs Targeting MLKL Protect Cells from Necroptosis

Rathje, Oliver H. ; Perryman, Lara ; Payne, Richard J. ; Hamprecht, Dieter W. ;

DOI: 10.1021/acs.jmedchem.3c00665 PubMed ID: 37535857 JMC,2023,66(16):11216-11236.

Abstract: Mixed Lineage Kinase domain-Like pseudokinase (MLKL) is implicated in a broad range of diseases due to its role as the ultimate effector of necroptosis and has therefore emerged as an attractive drug target. Here, we describe the development of PROteolysis TArgeting Chimeras (PROTACs) as a novel approach to knock down MLKL through chem. means. A series of candidate degraders were synthesized from a high-affinity pyrazole carboxamide-based MLKL ligand leading to the identification of a PROTAC mol. that effectively degraded MLKL and completely abrogated cell death in a TSZ model of necroptosis. By leveraging the innate ability of these PROTACs to degrade MLKL in a dose-dependent manner, the quant. relationship between MLKL levels and necroptosis was interrogated. This work demonstrates the feasibility of targeting MLKL using a PROTAC approach and provides a powerful tool to further our understanding of the role of MLKL within the necroptotic pathway.

Purchased from AmBeed: 30100-16-4 ; 4530-20-5 ; 1703808-53-0 ; 2840-26-8 ; 234081-98-2 ; 108466-89-3 ; 1005342-46-0 ; 154775-43-6 ; 214360-73-3 ; 31108-57-3 ; 57294-38-9 ; 234081-98-2 ; 73183-34-3 ; 462100-06-7 ; 187389-52-2 ; 191732-72-6 ; 173405-78-2 ; 154590-35-9 ; 6404-29-1 ; 1807518-63-3 ; 62595-74-8 ; 77383-17-6 ; 1310949-97-3 ; 138563-69-6 ; 138563-68-5 ; 2704620-74-4 ; 2284453-73-0 ; 191732-72-6 ; 181073-79-0

Tailoring porous organic polymers with enhanced capacity, thermal stability and surface area for perfluorooctane sulfonic acid (PFOS) elimination from water environment

Elboughdiri, Noureddine ; Amari, Abdelfattah ; Harharah, Hamed N. ; Al-Ansari, Nadhir ; Sammen, Saad Sh. ;

DOI: 10.1007/s13201-023-02014-0 Appl. Water Sci.,2023,13(11):211.

Abstract: Perfluorooctane sulfonic acid (PFOS), a perfluoroalkyl substance, has engendered alarm over its presence in water sources due to its intrinsic toxicity. Hence, there is a pressing need to identify efficacious adsorbents capable of removing PFAS derivatives from water. To achieve this, batch adsorption studies under various circumstances were employed to tune amorphous polymer networks regarding their morphol. configuration, heat durability, surface area and capacity to adsorb PFOS in water. A facile, one-pot nucleophilic substitution reaction was employed to synthesize amorphous polymer networks using triazine derivatives as building units for monomers. Notably, POP-3 exhibited a superlative adsorption capacity, with a removal efficiency of 97.8%, compared to 90.3% for POP-7. POP-7 exhibited a higher sp. surface area (SBET) of 232 m2 g-1 compared to POP-3 with a surface area of 5.2 m2 g-1. Addnl., the study emphasizes the importance of electrostatic forces in PFOS adsorption, with pH being a significant element, as seen by changes in the PFOS sorption process by both polymeric networks under neutral, basic and acidic environments. The optimal pH value for the PFOS removal process using both polymers was found to be 4. Also, POP-7 exhibited a better thermal stability performance (300°C) compared to POP-3 (190°C). Finally, these findings indicate the ease with which amorphous polymeric frameworks may be synthesized as robust and effective adsorbents for the elimination of PFOS from waterbodies.

Keywords: Adsorption ; PFOS removal ; Polymer networks ; Water treatment

Purchased from AmBeed: 6710-92-5 ; 214360-73-3

Triazine- and Heptazine-Based Porous Organic Polymer Networks for the Efficient Removal of Perfluorooctanoic Acid

Abdullatif, Dana ; Khosropour, Ahmadreza ; Khojastegi, Anahita ; Mosleh, Imann ; Khazdooz, Leila ; Zarei, Amin , et al.

DOI: 10.1021/acsapm.2c01580 ACS Appl. Polym. Mater.,2022,5(1):412-419.

Abstract: The presence of perfluorooctanoic acid, a perfluoralkyl substance, in water sources has raised health concerns due to its toxicity. Finding effective adsorbents is essential to ensure healthy sources of water for consumption. In this study, a heptazine-based polymer network (Py-HPOP) was synthesized using a one-pot nucleophilic substitution of 2,5,8-trichloro-s-heptazine (TCH) with 4,4′,4′′,4′′′-(pyrene-1,3,6,8-tetrayl) tetraaniline (Py-TA). For comparison, a triazine-based polymeric network (Py-TPOP) was also prepared using 2,4,6-trichloro-1,3,5-triazine under similar conditions. Both polymers were used to treat aqueous solutions containing 1 mg/L PFOA. Py-TPOP exhibited superior adsorption capacity (98.4% PFOA removal) relative to Py-HPOP (80.8% PFOA removal) despite Py-HPOP′s higher Brunauer-Emmett-Teller (BET) surface area SBET at 205 m2 g-1. The effect of electrostatic interactions was also observed as a critical factor for PFOA adsorption as demonstrated by the change in PFOA adsorption by both polymers under basic, neutral, and acidic conditions. This investigation illustrates a facile synthesis of amorphous covalent frameworks as strong, competitive adsorbents for PFOA removal from water.

Keywords: perfluoroalkyl substance ; perfluorooctanoic acid ; triazine ; heptazine ; porous organic polymer

Purchased from AmBeed: 214360-73-3

Product Details of 4-Aminophenylboronic acid pinacol ester

CAS No. :	214360-73-3
Formula :	C₁₂H₁₈BNO₂
M.W :	219.09
SMILES Code :	C1=C(C=CC(=C1)N)B2OC(C(O2)(C)C)(C)C
Synonyms :	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaboran-2yl)aniline
MDL No. :	MFCD02093721
InChI Key :	ZANPJXNYBVVNSD-UHFFFAOYSA-N
Pubchem ID :	2734620

Safety of 4-Aminophenylboronic acid pinacol ester

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 4-Aminophenylboronic acid pinacol ester

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 214360-73-3 ]

[ 214360-73-3 ] Synthesis Path-Downstream 1~30

1
[ 108-24-7 ]
[ 214360-73-3 ]
[ 214360-60-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	In dichloromethane; at 20℃; for 10h;	To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3.0 g, 13.7 mmol) in DCM (70mL), was added acetic anhydride (7.0 g, 68.5 mmol). The reaction mixture was stirred at RT for 10 h. It was then concentrated under reduced pressure and the resulting residue was purified by flash column chromatography over silica gel (PE/EA 1:1, v/v) to give N-(4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl) acetamide as a yellow solid (3.1 g, 87%). LC-MS (ESI): m/z (M+1)+ = 262.31.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 4780 - 4783.
[2]Patent: WO2019/213570,2019,A1 .Location in patent: Paragraph 0331; 0677-0679.
[3]Journal of the American Chemical Society,2005,vol. 127,p. 13094 - 13095.

2
[ 799293-73-5 ]
[ 214360-73-3 ]
[ 799293-74-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80.0℃; for 14.0h;	The mixture of 4-amino-3-bromo-furo [3,2-c] pyridine (7) (63 mg, 0. 29MOL), 4- (4,4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline (84 mg, 0.38 MMOL), Pd (PPH3) 4 (34 mg, 0.029 MMOL) and sodium carbonate (0.74 ml, 1.5 MMOL) in 3 ml of DME was stirred for 14 hours at 80C. The solvent was removed, and the resultant residue was purified by chromatography on a silica gel column gel to afford the titled compound (55 mg) 1 H NMR (400MHZ, DMSO-d6) ppm 7.82 (d, J = 6. 1 Hz, 1H), 7.77 (s, 1H), 7.15 (d, J = 8.3 Hz, 2H), 6.89 (d, J = 5.8 Hz, 1H), 6.69 (d, J = 8. 3 Hz, 2H), 5.49 (s, 2H), 5.32 (s, 2H). MS: m/z 226 (M+H) +

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 250 - 254.
[2]Patent: WO2004/100947,2004,A2 .Location in patent: Page 22.

3
[ 180995-12-4 ]
[ 621-29-4 ]
[ 214360-73-3 ]
N-[4-(3-amino-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl]-N'-(3-methylphenyl)urea [ No CAS ]
N-[4-(3-amino-1H-pyrazolo[4,3-c]pyridin-4-yl)phenyl]-N'-(3-methylphenyl)urea [ No CAS ]