77337-82-7

Usage

Chemical Properties

light brown crystalline powder

InChI:InChI=1/C7H6BrNO3/c1-12-7-4-5(9(10)11)2-3-6(7)8/h2-4H,1H3

Upstream product

• 97-52-9 2-methoxy-4-nitrophenylamine 
• 52427-05-1 2-bromo-5-nitrophenol 
• 74-88-4 methyl iodide 
• 554-84-7 meta-nitrophenol 
• 97-02-9 2,4-Dinitroanilin 
• 19164-31-9 5-bromo-4-methoxybenzo[c][1,2,5]oxadiazole 1-oxide 
• 89677-51-0 3-bromo-2-methoxy-6-nitro-aniline 
• 186581-53-3 diazomethane 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 113342-94-2 1-(2-methoxy-4-nitrophenyl)-2,5-dihydro-1H-pyrrole 
• 111795-95-0 (5-bromo-4-methoxy-2-nitrophenyl)acetonitrile 
• 113342-99-7 2-[(2-hydroxyethyl)(2-methoxy-4-nitrophenyl)amino]ethanol 
• 70995-08-3 Phenyl-(5-nitro-2-hydroxy-phenyl)-aether 
• 14064-93-8 1-methoxy-2-phenoxy-4-nitrobenzene 
• 71400-33-4 2,7-dinitrodibenzo-p-dioxin 
• 71400-34-5 2,8-dinitrodiphenylene dioxide 
• 60433-63-8 5-nitro-2-phenoxyphenol 
• 79807-67-3 2-(4-methylphenoxy)-4-nitrophenol 
• 79807-64-0 2-(4-methylphenoxy)-5-nitrophenol 
• 77896-09-4 2,4'-dihydroxy-4-nitrodiphenyl ether 
• 77896-08-3 2,4'-dihydroxy-5-nitrodiphenyl ether 
• 79807-63-9 1-methoxy-2-(4-methylphenoxy)-4-nitrobenzene 
• 79819-62-8 2-(2-bromo-5-nitrophenoxy)-5-nitrophenol 

Relevant academic research and scientific papers

Preparation method for 2,5-dibromophenol

The invention discloses an industrial preparation method for 2,5-dibromophenol. The industrial preparation method for the 2,5-dibromophenol comprises the following steps: using 2-amino-5-nitrobenzenemethyl ether as an initial raw material, and synthesizing the 2,5-dibromophenol through a four-step reaction of performing diazotization bromination, reduction, secondary diazotization bromination anddemethylation. The obtained 2,5-dibromophenol is a black solid, the purity is 97.5%, a raw material conversion rate in each step reaches 100% respectively, and a total yield of the whole process reaches 34%.

ARYL AMIDE KINASE INHIBITORS

The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

Development of 2-thioxoquinazoline-4-one derivatives as dual and selective inhibitors of dynamin-related protein 1 (Drp1) and puromycin-sensitive aminopeptidase (PSA)

An established inhibitor ot dynamin-related protein 1 (Drp1), 3-(2,4-dichloro-5-methoxyphenyl)- 2- thioxoquinazoline-4-one (mdivi-1), was recently reported also to show potent puromycin-sensitive aminopeptidase (PSA)-inhibitory activity. Herein, we report structural development of mdivi-1 derivatives and structure-activity relationship (SAR) analysis of the synthesized compounds, as well as the structurally related PSA-specific inhibitor 3-(2,6-diethylphenyl)quinazoline-2,4-dione (PAQ-22), with the aim of identifying key structural features for inhibitory activity in order to develop selective inhibitors of Drpl, which is a potential target for treatment of Huntington's disease. Among the synthesized compounds, 3-(4-chloro3methoxyphenyl)-2-thioxoquinazoline-4-one 10g) exhibited more potent Drpl-inhibitory activity than mdivi-1 with high selectivity for Drpl over PSA.

Halogenation and DNA cleavage via thermally stable arenediazonium camphorsulfonate salts

A series of stable arenediazonium camphorsulfonate salts (2a-2j) were synthesized by simple diazotization of several aromatic amines in the presence of sodium nitrite and camphorsulfonic acid. All the new arenediazonium camphorsulfonates, which were characterized by multinuclear (1H and 13C) NMR, IR, DSC, and X-ray diffraction analysis (2e and 2f) provide unambiguous proof for the molecular structures of 2e and 2f. The efficient application of these salts in halogenation reactions was studied in solvent and solvent-free conditions and the DNA cleavage activity was also assessed. These arenediazonium camphorsulfonate salts are noticed as efficient DNA cleaving agents.

On the mechanism of the initiation reaction in Grubbs-Hoveyda complexes

Grubbs-Hoveyda-type complexes with variable 4-R (complexes 1: 4-R = NEt2, OiPr, H, F, NO2) and 5-R substituents (complexes 2: 5-R = NEt2, OiPr, Me, F, NO2) at the 2-isopropoxy benzylidene ether ligand and with variable 4-R substituents (complexes 3: 4-R = H, NO2) at the 2-methoxy benzylidene ether ligand were synthesized and the respective Ru(II/III) redox potentials (ranging from ΔE = +0.46 to +1.04 V), and UV-vis spectra recorded. The initiation kinetics of complexes 1-3 with the olefins diethyl diallyl malonate (DEDAM), butyl vinyl ether (BuVE), 1-hexene, styrene, and 3,3-dimethylbut-1-ene were investigated using UV-vis spectroscopy. Electron-withdrawing groups at the benzylidene ether ligands were found to increase the initiation rates, while electron-donating groups lead to slower precatalyst activation; accordingly with DEDAM, the complex 1(NO 2) initiates almost 100 times faster than 1(NEt2). The 4-R substituents (para to the benzylidene carbon) were found to have a stronger influence on physical and kinetic properties of complexes 1 and 2 than that of 5-R groups para to the ether oxygen. The DEDAM-induced initiation reactions of complexes 1 and 2 are classified as two-step reactions with an element of reversibility. The hyperbolic fit of the kobs vs [DEDAM] plots is interpreted according to a dissociative mechanism (D). Kinetic studies employing BuVE showed that the initiation reactions simultaneously follow two different mechanistic pathways, since the kobs vs [olefin] plots are best fitted to kobs = kD·k4/k -D·[olefin]/(1 + k4/k-D·[olefin]) + kI·[olefin]. The kI·[olefin] term dominates the initiation behavior of the sterically less demanding complexes 3 and was shown to correspond to an interchange mechanism with associative mode of activation (Ia), leading to very fast precatalyst activation at high olefin concentrations. Equilibrium and rate constants for the reactions of complexes 1-3 with the bulky PCy3 were determined. In general, sterically demanding olefins (DEDAM, styrene) and Grubbs-Hoveyda type complexes 1 and 2 preferentially initiate according to the dissociative pathway; for the less bulky olefins (BuVE, 1-hexene) and complexes 1 and 2 both D and I a are important. Activation parameters for BuVE reactions and complexes 1(NEt2), 1(H), and 1(NO2) were determined, and ΔS? was found to be negative (ΔS ? = -113 to -167 J·K-1·mol -1) providing additional support for the Ia catalyst activation.

Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts

Arenediazonium tosylate salts have been successfully employed as a new and efficient reagent in halogenation reactions. A novel and economic protocol has been developed for the bromination and chlorination of various anilines using arenediazonium tosylate salts. A wide variety of reaction conditions were studied in acetonitrile at either room temperature or 60 °C in the presence or absence of catalyst with good to excellent yields. A surprising result showed the formation of acetanilides as a major product of aniline and methyl-substituted aniline halogenations in high yields.

An expeditious and environmentally benign preparation of aryl halides from aryl amines by solvent-free grinding

An efficient solvent-free methodology for conversion of various aryl amines into bromides and chlorides via arenediazonium tosylate salts under grinding conditions is disclosed. This new methodology not only avoids the use of strong acids and expensive reagents for diazotization-halogenation reactions, but also decreases the amount of organic waste from the reaction process.

Reactions of Organic Anions, 147.- Simple and General Synthesis of Hydroxy- and Methoxyindoles via Vicarious Nucleophilic Substitution of Hydrogen

A simple synthesis of 4-, 5-, 6-, and 7-hydroxy- and -methoxyindoles via cyanoalkylation of O-protected nitrophenols by vicarious nucleophilic substitution of hydrogen, followed by catalytic hydrogenation of the (2-nitroaryl)acetonitriles obtained is described.

The Smiles Rearrangement of 2-Aryloxy-5-nitrophenoxides. Attempted Routes to Benzoxirens and Tribenzotrioxonins

Formation of dibenzo-p-dioxins by the pyrolysis of 2-halogenophenoxides does not appear to involve intermediate benzoxirens.Thermal self-condensation to potassium 2-bromo-5-nitrophenoxide (1b) gave a mixture of 2,7- and 2,8-dinitrobenzo-p-dioxins (6d) and (6e).The mechanism of formation of the 2,8-isomer (6e) is shown to involve Smiles rearrangement of potassium 2-(2-bromo-5-nitrophenoxy)-5-nitrophenoxide (9a).Further examples of Smiles rearrangements of 2-aryloxy-5-nitrophenoxides and an attempted synthesis of the tribenzotrioxonin derivatives (16) are described.