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[ CAS No. 16858-01-8 ] {[proInfo.proName]}

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Chemical Structure| 16858-01-8
Chemical Structure| 16858-01-8
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Héctor Sánchez-Morán ; Joel L. Kaar ; Daniel K. Schwartz DOI:

Abstract: Recent advances have demonstrated the promise of complex multicomponent polymeric supports to enable supra-biological performance. However, the discovery of such supports has been limited by time-consuming, low-throughput synthesis and screening. Here, we describe a novel combinatorial and high-throughput platform that enables rapid screening of complex and heterogeneous copolymer brushes as immobilization supports, named combinatorial high-throughput support screening (CHESS). Using a 384-well plate format, we synthesized arrays of three-component polymer brushes in the microwells using photoactivated surface-initiated polymerization and immobilized in situ. The utility of CHESS to identify optimal immobilization supports under thermally and chemically denaturing conditions was demonstrated usingBacillus subtilisLipase A (LipA). The identification of supports with optimal compositions was validated by immobilizing LipA on polymer-brush-modified biocatalyst particles. We further demonstrated that CHESS could be used to predict the optimal composition of polymer brushes a priori for the previously unexplored , alkaline (AlkP). Our findings demonstrate that CHESS represents a predictable and reliable platform for dramatically accelerating the search of chemical compositions for immobilization supports and further facilitates the discovery of biocompatible and stabilizing materials.

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Coskun, Halil Ibrahim ; De Luca Bossa, Ferdinando ; Hu, Xiaolei , et al. DOI: PubMed ID:

Abstract: In atom transfer radical polymerization (ATRP), dormant alkyl halides are intermittently activated to form growing radicals in the presence of a CuI/L/X-CuII/L (activator/ deactivator) catalytic system. Recently developed very active copper complexes could decrease the catalyst concentration to ppm level. However, unavoidable radical termination results in irreversible oxidation of the activator to the deactivator species, leading to limited monomer conversions. Therefore, successful ATRP at a low catalyst loading requires continuous regeneration of the activators. Such a regenerative ATRP can be performed with various reducing agents under milder reaction conditions and with catalyst concentrations diminished in comparison to conventional ATRP. Photoinduced ATRP (PhotoATRP) is one of the most efficient methods of activator regeneration. It initially employed UV irradiation to reduce the air-stable excited X-CuII/L deactivators to the activators in the presence of sacrificial electron donors. Photocatalysts (PCs) can be excited after absorbing light at longer wavelengths and, due to their favorable redox potentials, can reduce X-CuII/L to CuI/L. Herein, we present the application of three commercially available xanthene dyes as ATRP PCs: (RB), (RD), and (RD-6G). Even at very low Cu catalyst concentrations (50 ppm), they successfully controlled PhotoATRP. Well-defined polymers with preserved livingness were prepared under green LED irradiation, with subppm concentrations ([PC] ≥ 10 ppb) of and or 5 ppm of . Interestingly, these PCs efficiently controlled ATRP at wavelengths longer than their absorption maxima but required higher loadings. Polymerizations proceeded with high initiation efficiencies, yielding polymers with narrow molecular weight distributions and high chain-end fidelity. UV?vis, fluorescence, and laser flash photolysis studies helped to elucidate the mechanism of the processes involved in the dual-catalytic systems, comprising parts per million of Cu complexes and parts per billion of PCs.

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Ting-Chih Lin ; Piotr Mocny ; Martin Cvek , et al. DOI:

Abstract: Poly(vinylidene fluoride) (PVDF) is commonly used in membranes, lithium-ion battery binders, and coatings due to its thermal and chemical robustness. Nevertheless, PVDF-based copolymers can broaden the application scope and performance capabilities of pristine PVDF. PVDF has been modified via grafting-from reactions. However, grafting density and graft length, two important properties of graft copolymers, cannot be accurately determined. Herein, we used grafting-onto thiol-ene reactions as a method to modify PVDF. The molar mass of pre-synthesized, thiol-terminated polymers were accurately determined, and grafting densities were calculated. Unsaturated sites were generated through dehydrofluorination and dehydrochlorination in PVDF and P(VDF-co-chlorotrifluoroethylene) (PVDF-CTFE). Various conditions were studied, including the molar mass and chemical structure of grafts, the degree of thiol substitution, and thiol-ene reaction mechanisms. Base-catalyzed Michael addition with secondary thiols performed best, with the highest grafting density calculated to be about 4 chains per PVDF chain. Despite the low grafting density, changes in material properties between the product and starting materials were observed, validating this controlled method for PVDF modification.

Keywords: poly(vinylidene fluoride) ; Controlled radical polymerization ; Thiol-eneGrafting-onto

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Bisirri, Evan A. ; Wright, Thaiesha A. ; Schwartz, Daniel K. , et al. DOI: PubMed ID:

Abstract: Protein-polymer conjugation provides an opportune means to adjust the local environment of proteins and enhance protein stability, performance, and solubility Although much attention has been focused on tuning protein-polymer interactions, the properties of polymer-modified proteins may also be altered by polymer-polymer interactions. Herein, we sought to better understand the influence of polymer-polymer interactions on Candida rugosa lipase, which was modified with random co-polymers composed of sulfobetaine methacrylate (SBMA) and poly(ethylene glycol) methacrylate (PEGMA). Our findings suggest that there is an apparent activity-stability tradeoff as a function of polymer composition Specifically, as the ratio of SBMA to PEGMA increased, lipase stability was enhanced, whereas activity decreased. By tuning the monomer ratio, we showed that lipase productivity could be optimized. These findings are discussed in the context of complex enzyme-polymer and polymer-polymer interactions and ultimately may enable more informed conjugate designs and improved enzyme productivity in industrial biotransformations under harsh or extreme conditions.

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Kapil, Kriti ; Xu, Shirley ; Lee, Inseon , et al. DOI: PubMed ID:

Abstract: Infectious diseases caused by pathogens are a health burden, but traditional pathogen identification methods are complex and time-consuming. In this work, we have developed well-defined, multifunctional copolymers with rhodamine B dye synthesized by atom transfer radical polymerization (ATRP) using fully oxygen-tolerant photoredox/copper dual catalysis. ATRP enabled the efficient synthesis of copolymers with multiple fluorescent dyes from a biotin-functionalized initiator. Biotinylated dye copolymers were conjugated to antibody (Ab) or cell-wall binding domain (CBD), resulting in a highly fluorescent polymeric dye-binder complex. We showed that the unique combination of multifunctional polymeric dyes and strain-specific Ab or CBD exhibited both enhanced fluorescence and target selectivity for bioimaging of Staphylococcus?aureus by flow cytometry and confocal microscopy. The ATRP-derived polymeric dyes have the potential as biosensors for the detection of target DNA, protein, or bacteria, as well as bioimaging.

Keywords: pathogen identification ; bioimaging ; fluorescence ; copolymer ; ATRP ; flow cytometry ; confocal imaging

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Jazani, Arman Moini ; Schild, Dirk J. ; Sobieski, Julian , et al. DOI: PubMed ID:

Abstract: Atom transfer radical polymerization (ATRP) of oligo(ethylene oxide) monomethyl ether methacrylate (OEOMA500) in H2O is enabled using CuBr2 with tris(2-pyridylmethyl)amine (TPMA) as a ligand under blue or green-light irradiation without requiring any addnl. reagent, such as a photo-reductant, or the need for prior deoxygenation. Polymers with low dispersity (D = 1.18-1.25) are synthesized at high conversion (>95%) using TPMA from 3 different suppliers, while no polymerization occurred with TPMA synthesized and purified in the laboratory Based on spectroscopic studies, probably TPMA impurities (i.e., imine and nitrone dipyridine), which absorb blue and green light, can act as photosensitive co-catalyst(s) in a light region where neither pure TPMA nor [(TPMA)CuBr]+ absorbs light.

Keywords: ATRP ; green light ; oxygen tolerance ; water

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Thevenin, Lucas ; Fliedel, Christophe ; Fantin, Marco , et al. DOI: PubMed ID:

Abstract: Cyanoisopropyl radicals, generated thermally by the decomposition of azobis(isobutyronitrile) (AIBN), participate in reductive radical termination (RRT) under the combined effect of copper(I) complexes and proton donors (water, methanol, triethylammonium salts) in acetonitrile or benzene. The investigated copper complexes were formed in situ from [CuI(MeCN)4]+BF4- in CD3CN or CuIBr in C6D6 using tris[2-(dimethylamino)ethyl]amine (Me6TREN), tris(2-pyridylmethyl)amine (TPMA), and 2,2'-bipyridine (BIPY) ligands. Upon keeping all other conditions constants, the impact of RRT is much greater for the Me6TREN and TPMA systems than for the BIPY system. RRT scales with the proton donor acidity (Et3NH+ ? H2O > CH3OH), it is reduced by deuteration (H2O > D2O and CH3OH > CD3OD), and it is more efficient in C6D6 than in CD3CN. The collective evidence gathered in this study excludes the intervention of an outer-sphere proton-coupled electron transfer (OS-PCET), while an inner-sphere PCET (IS-PCET) cannot be excluded for coordinating proton donors (water and methanol). On the other hand, the strong impact of RRT for the noncoordinating Et3NH+ in CD3CN results from the formation of an intermediate CuI-radical adduct, suggested by DFT calculations to involve binding via the N atom to yield keteniminato [L/Cu-N:C:CMe2]+ derivatives with only partial spin delocalization onto the Cu atom.

Keywords: Copper ; Coupled Proton-Electron Transfer ; Protonolysis ; Organocopper(II) complexes ; Radical

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Product Details of [ 16858-01-8 ]

CAS No. :16858-01-8 MDL No. :MFCD14708176
Formula : C18H18N4 Boiling Point : No data available
Linear Structure Formula :N(CH2(C5H4N))3 InChI Key :VGUWFGWZSVLROP-UHFFFAOYSA-N
M.W : 290.36 Pubchem ID :379259
Synonyms :

Calculated chemistry of [ 16858-01-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.17
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 86.28
TPSA : 41.91 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 1.64
Log Po/w (WLOGP) : 2.62
Log Po/w (MLOGP) : 1.04
Log Po/w (SILICOS-IT) : 3.16
Consensus Log Po/w : 2.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.88
Solubility : 0.38 mg/ml ; 0.00131 mol/l
Class : Soluble
Log S (Ali) : -2.13
Solubility : 2.14 mg/ml ; 0.00736 mol/l
Class : Soluble
Log S (SILICOS-IT) : -6.86
Solubility : 0.0000403 mg/ml ; 0.000000139 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.99

Safety of [ 16858-01-8 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16858-01-8 ]

* 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 [ 16858-01-8 ]

[ 16858-01-8 ] Synthesis Path-Downstream   1~1

  • 1
  • cobalt(II) tetrafluoroborate hydrate [ No CAS ]
  • [ 4877-80-9 ]
  • [ 16858-01-8 ]
  • C72H60Co3N12O6(4+)*4BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% A solution of Co(BF4)2H2O (102.4 mg, 0.3 mmol) in dry methanol (10 mL) was added to a solution of tris(2-pyridylmethyl)amine (87.6 mg, 0.3 mmol). The resulting solution was stirred for 1 hr, and then 30 mL of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong> (H6L, 32.5 mg, 0.1 mmol) dissolved in methanol containing triethylamine was added dropwise. The resulting solution was stirred for 1 hr. Diethylether was added to the solution slowly to obtain the complex. This solution was cooled to -5 °C and over the period of 10 days a deep green microcrystals of [Co3(tpa)3(L)](BF4)4 separated from the solution in 69percent (119.3 mg) yield.
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