31465-40-4

Upstream product

• 99-54-7 3,4-dichloronitrobenzene 
• 150-76-5 4-methoxy-phenol 
• 350-30-1 3-chloro-4-fluoronitrobenzene 

Downstream Products

• 1433608-38-8 2,6-dibromo-4-[2-chloro-4-(diethylamino)phenoxy]phenol 
• 1433608-56-0 2,6-dibromo-4-[5-bromo-2-chloro-4-(dibenzylamino)phenoxy]phenol 
• 31465-41-5 3-chloro-4-(4-methoxyphenoxy)aniline 
• 1433607-64-7 3-chloro-4-(4-methoxyphenoxy)-N,N-dimethylbenzenamine 

Relevant academic research and scientific papers

Design and Performance Validation of a Conductively Heated Sealed-Vessel Reactor for Organic Synthesis

A newly designed robust and safe laboratory scale reactor for syntheses under sealed-vessel conditions at 250 °C maximum temperature and 20 bar maximum pressure is presented. The reactor employs conductive heating of a sealed glass vessel via a stainless steel heating jacket and implements both online temperature and pressure monitoring in addition to magnetic stirring. Reactions are performed in 10 mL borosilicate vials that are sealed with a silicone cap and Teflon septum and allow syntheses to be performed on a 2-6 mL scale. This conductively heated reactor is compared to a standard single-mode sealed-vessel microwave instrument with respect to heating and cooling performance, stirring efficiency, and temperature and pressure control. Importantly, comparison of the reaction outcome for a number of different synthetic transformations performed side by side in the new device and a standard microwave reactor suggest that results obtained using microwave conditions can be readily mimicked in the operationally much simpler and smaller conventionally heated device.

Structural Development of Salicylanilide-Based SPAK Inhibitors as Candidate Antihypertensive Agents

Hypertension is an important target for drug discovery. We have focused on the with-no-lysine kinase (WNK)-oxidative stress-responsive 1 (OSR1) and STE20/SPS1-related proline-alanine-rich protein kinase (SPAK)-NaCl cotransporter (NCC) signal cascade as a potential target, and we previously developed a screening system for inhibitors of WNK-OSR1/SPAK-NCC signaling. Herein we used this system to examine the structure-activity relationship (SAR) of salicylanilide derivatives as SPAK kinase inhibitors. Structural design and development based on our previous hit compound, aryloxybenzanilide derivative 2, and the veterinary anthelmintic closantel (3) led to the discovery of compound 10 a as a potent SPAK inhibitor with reduced toxicity. Compound 10 a decreased the phosphorylation level of NCC in mouse kidney in vivo, and appears to be a promising lead compound for a new class of antihypertensive drugs.

Structural development of N-(4-phenoxyphenyl)benzamide derivatives as novel SPAK inhibitors blocking WNK kinase signaling

We report here structural development of N-(4-phenoxyphenyl)benzamide derivatives as novel SPAK (STE20/SPS1-related proline/alanine-rich kinase) inhibitors. Abnormal activation of the signal cascade of with-no-lysine kinase (WNK) with OSR1 (oxidative stress-responsive kinase 1)/SPAK and NCC (NaCl cotransporter) results in characteristic salt-sensitive hypertension, and therefore inhibitors of the WNK-OSR1/SPAK-NCC cascade are candidates for antihypertensive drugs. Based on the structure of lead compound 2, we examined the SAR of N-(4-phenoxyphenyl)benzamide derivatives, and developed compound 20l as a potent SPAK inhibitor. Compounds 20l is a promising candidate for a new class of antihypertensive drugs.

Design and evaluation of improved magnetic stir bars for single-mode microwave reactors

Magnetic stirring in sealed cylindrical vessels designed for use in single-mode microwave instruments is typically less than optimal, and is not comparable to the efficient agitation that can be generally obtained in a round-bottomed flask fitted with a suitable magnetic stir bar or using overhead mechanical stirring systems. A new "vertical blade" stir bar design that improves the stirring performance in the very narrow, flow-constricting microwave vessels has been developed and evaluated for several different transformations where stirring and efficient agitation are known to be of importance. The better performance of these novel stirrers compared to the traditional cylindrical stir bar design is not only due to the geometry of the stirrer but also to the utilization of a magnetic material with a stronger magnetic transmission force (Sm2Co17) compared to standard ferrite or AlNiCo alloys. For all three tested cases involving solid/liquid, liquid/liquid and highly viscous reaction systems, the new vertical blade stirrers showed a distinctively improved performance resulting in higher conversions and/or product yields.

Simulating microwave chemistry in a resistance-heated autoclave made of semiconducting silicon carbide ceramic

"Microwave chemistry" without microwaves: A resistance-heated SiC autoclave can effectively mimic the sealed-vessel capabilities, rapid heating and cooling profiles, and excellent process-control features that are inherent to modern microwave reactors. Applied to synthetic chemistry, the ready-to-assemble small device provides identical results as can be obtained in a (costly) microwave system (see figure). Copyright

Study on the structure-activity relations of brominated hydroxy diphenyl ethers derivatives with anilines

In order to study the influence of anilines on antibacterial activity, eight novel brominated hydroxy diphenyl ethers derivatives were designed and synthesized. The antibacterial activities of the new compounds were tested via agar-well diffusion method in vitro under different concentrations. The results showed the derivatives had antibacterial activities at the concentration 50 μg/mL against Staphylococcus aureus SC and Staphylococcus aureus ATCC26112.

Synthesis of functionalized dioxa-aza[7]helicenes using palladium catalyzed arylations

Despite the recent reports on transition-metal catalyzed cycloisomerization strategies toward helicenes, the amount of palladium catalyzed routes remains rather scarce. Within this letter the successful preparation and characterization of novel dioxa-aza[

Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated SNAr reaction

Whilst microwave heating has been widely demonstrated as a synthetically useful tool for rapid reaction screening, a microwaveabsorbing solvent is often required in order to achieve efficient reactant heating. In comparison, microreactors can be readily h

Scale-up of microwave-assisted reactions in a multimode bench-top reactor

An evaluation of a new bench-top microwave batch reactor that uses a single 1 L reaction vessel is presented. Several microwave-assisted organic reactions have been scaled-up, including Newman Kwart and Diels-Alder reactions, Pd-catalyzed cross-couplings, heterocycle synthesis, aromatic substitution, and a Knoevenagel condensation. A range of different solvents (high and low microwave absorbing), varying reaction times (4 s up to 2 h), and temperatures (120-250 °C) have been explored in these investigations. For all studied transformations, it was possible to perform a direct scale-up (up to 720 mL reaction volume) without changing the previously optimized reaction conditions achieved in a laboratory-scale single-mode microwave instrument (2-20 mL processing volume), obtaining similar isolated product yields. A scalability up to 360-fold, when moving from 3 mmol up to 1.08 mol, was demonstrated, and isolated product yields up to 300 g (2.5 mol scale) in a single run could be accomplished, providing the potential for a kilogram output per day for specific transformations by performing multiple sequential runs.

The application of stop-flow microwave technology to scaling-out S NAr reactions using a soluble organic base

A model SNAr reaction which gives a range of substituted diaryl ethers has been re-developed to function with the soluble organic base DBU in the place of insoluble potassium carbonate. Manufacture of these diaryl ethers has then been achieved by scaling-out in an automated stop-flow microwave reactor to give productivities of >0.5 kg per day. Analogous reaction partners have also been scaled up in this reactor to extend the scope of the study. Brief comparison in a scale-up batch microwave reactor is also made. Lastly, continuous 24 h processing is reported in this small microwave stop-flow reactor, which requires no manual intervention once started.