23030-65-1

Usage

Uses

Used in Organic Chemistry:
2-Bromo-5-methoxycyclohexa-2,5-diene-1,4-dione is used as a key intermediate for the synthesis of various organic compounds, leveraging its reactive functional groups to facilitate a range of chemical reactions and the formation of new compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Bromo-5-methoxycyclohexa-2,5-diene-1,4-dione serves as a valuable precursor in the development of new drugs. Its unique structure and reactivity contribute to the creation of pharmaceuticals with potential therapeutic applications.
Used in Materials Science:
2-Bromo-5-methoxycyclohexa-2,5-diene-1,4-dione is employed as a component in the production of advanced materials, where its chemical properties can be harnessed to enhance material performance or introduce new functionalities.
Used in Research and Development:
Due to its potential for modification and the versatility of its structure, 2-Bromo-5-methoxycyclohexa-2,5-diene-1,4-dione is utilized in ongoing research and development efforts to explore new applications and improve existing ones across multiple chemical and scientific disciplines.

Upstream product

• 52783-67-2 2-bromo-4-hydroxy-5-methoxybenzyl alcohol 
• 154377-22-7 5-bromo-2,4-dimethoxyphenol 
• 37895-73-1 1,2-dibromo-4,5-dimethoxybenzene 
• 174769-28-9 2-bromo-5-methoxy-1,4-dihydroxybenzene 
• 130333-46-9 5-bromo-2, 4-dimethoxybenzaldehyde 
• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 20129-11-7 1-bromo-2,4,5-trimethoxybenzene 
• 60632-40-8 6-bromovanillin 

Downstream Products

• 99853-31-3 1,4-diacetoxy-2-bromo-5-methoxy-benzene 
• 84568-11-6 2-Bromo-5-methoxy-3-((E)-penta-2,4-dienyl)-[1,4]benzoquinone 
• 154377-23-8 2-methoxy-5-<(phenylmethyl)amino>cyclohexa-2,5-diene-1,4-dione 
• 23149-38-4 1,3,4-triacetoxy-2-bromo-5-methoxybenzene 
• 154377-14-7 2-amino-5-methoxycyclohexa-2,5-diene-1,4-dione 
• 84568-17-2 2-Amino-5-methoxy-3-((E)-penta-2,4-dienyl)-[1,4]benzoquinone 
• 109035-03-2 2-Azido-5-methoxy-3-((E)-penta-2,4-dienyl)-[1,4]benzoquinone 
• 23030-67-3 1,2,5-triacetoxy-3-methoxy-benzene 
• 1189760-41-5 C₁₆H₁₆O₅ 
• 1189760-40-4 C₁₆H₁₄O₆ 
• 1352089-64-5 C₁₅H₁₄O₆ 
• 1352089-65-6 C₁₄H₁₁ClO₅ 
• 1352089-59-8 C₁₄H₁₀O₅ 
• 1352089-60-1 C₁₅H₁₂O₆ 

Relevant academic research and scientific papers

ONO-pincer ruthenium complex-bound norvaline for efficient catalytic oxidation of methoxybenzenes with hydrogen peroxide

The enhanced catalytic activity of ruthenium complex-bound norvaline Boc-l-[Ru]Nva-OMe 1, in which the ONO-pincer ruthenium complex Ru(pydc)(terpy) 2 is tethered to the α-side chain of norvaline, has been demonstrated for the oxidation of methoxybenzenes to p-benzoquinones with a wide scope of substrates and unique chemoselectivity.

Synthesis of indolequinones from bromoquinones and enamines mediated by Cu(OAc)2H2O

A Cu(II)-mediated synthesis of indolequinones from the corresponding bromoquinones and enamines is reported. The key oxidative cyclization proceeds in good yield for a broad range of substrates and can be performed on a multigram scale, allowing access to biologically interesting structures.

Total synthesis of graphislactones A, C, D, and H, of ulocladol, and of the originally proposed and revised structures of graphislactones e and F

Graphislactones A-H and the structurally related ulocladol are highly oxygenated resorcylic lactones produced by lichens and fungi. We present total syntheses of graphislactones A, C-F, H and of ulocladol. Graphislactones E, F, and H were synthesized for the first time. The spectra of graphislactones E and F synthesized as the originally proposed structures were not in agreement with published data. Consequently, revised structures for these compounds are proposed, whose correctness is unambiguously proven by total synthesis and comparison of the spectroscopic data. Key steps in all syntheses are Suzuki couplings for the construction of the central biaryl bond and Dakin reactions to supply further hydroxy groups required in these highly oxygenated substrates. Graphislactones A, C, and H, acylated graphislac- tone D and ulocladol were prepared in 8-11 steps with 7-20% yield starting with purchasable compounds, where the longest linear sequence consists of 5-9 steps. The syntheses are thus significantly shorter than the previously published syntheses of graphislactones A-D and of ulocladol. Graphis- lactones E and F were synthesized in 8 steps, where the longest linear sequences consist of 6 and 5 steps, respectively. They were isolated as the respective acetylated compounds with 25 and 10% yield.

Novel and efficient synthesis of p-quinones in water via oxidative demethylation of phenol ethers using hypervalent iodine(III) reagents

A new method for preparing p-quinone derivatives from phenol ether derivatives in water using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) was developed. The present reaction proceeds in good to excellent yields under mild reaction conditions. This oxidation is expected to be environmentally benign since it uses recyclable poly-bis(trifluoroacetoxyiodo)styrene (PBTIS) in water.

Analogs of 3-hydroxy-1H-1-benzazepine-2,5-dione: Structure-activity relationship at N-methyl-D-aspartate receptor glycine sites

A series of aromatic and azepine ring-modified analogs of 3-hydroxy-1H- 1-benzazepine-2,5-dione (HBAD) were synthesized and evaluated as antagonists at NMDA receptor glycine sites. Aromatic ring-modified HBADs were generally prepared via a Schmidt reaction with substituted 2-methoxynaphthalene-1,4- diones followed by demethylation. Electrophilic aromatic substitution of benzazepine 3-methyl ethers gave 7-substituted analogs. The preparation of multiply substituted 2-methoxynaphthalene-1,4-diones was effected via Diels- Alder methodology utilizing substituted butadienes with 2- methoxybenzoquinones followed by aromatization. Structural modifications, such as elimination of the aromatic ring, removal of the 3-hydroxyl group, and transfer of the hydroxyl group from C-3 to C-4, were also studied. An initial evaluation of NMDA antagonism was performed using a [3H]MK801 binding assay. HBADs demonstrating NMDA antagonist activity as indicated by inhibition of [3H]MK801 binding were further evaluated employing a [3H]- 5,7-dichlorokynurenic acid (DCKA) glycine site binding assay. Selected HBADs were characterized for functional antagonism of NMDA and AMPA receptors using electrophysiological assays in Xenopus oocytes and cultured rat cortical neurons. Antagonist potency of HBADs showed good correlation between the different assay systems. HBADs substituted at the 8-position possessed the highest potency with the 8-methyl (5), 8-chloro (6), and 8-bromo (7) analogs being the most active. For HBAD 6, the IC50 in [3H]-DCKA binding assays was 0.013 μM and the K(b) values for antagonism of NMDA receptors in oocytes (NR1a/2C) and cortical neurons were 0.026 and 0.048 μM, respectively. HBADs also antagonized AMPA-preferring non-NMDA receptors expressed in oocytes but at a lower potency than corresponding inhibition of NMDA receptors. HBADs demonstrating a high potency for NMDA glycine sites showed the highest steady-state selectivity index relative to AMPA receptors. Substitution at the 6-, 7-, and 9-positions generally reduced or eliminated glycine site affinity. Moving the hydroxyl group from C-3 to C-4 reduced receptor affinity, and potency was eliminated by the removal of the aromatic ring or the hydroxyl group. These data indicate that the HBAD series has specific structural requirements for high receptor affinity. With the exception of substitution at C-8, modified HBADs generally have a lower affinity at NMDA receptor glycine sites than the parent compound 3. Mouse maximum electroshock-induced seizure studies show that the three HBADs selected for testing have in vivo potency with the 6,8-dimethyl analog (52) being the most potent (ED50 = 3.9 mg/kg, iv).

AZEPINE SYNTHESIS VIA A DIELS-ALDER REACTION

Disclosed are methods of preparing azepines by a multistep synthesis including a Diels-Alder reaction. Also disclosed are methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, inducing anesthesia and treating or preventing opiate tolerance are disclosed by administering to an animal in need of such treatment an azepine which has high binding to the NMDA glycine site.

THE ESR SPECTRA, STRUCTURE, AND REACTIVITY OF AROMATIC RADICAL-CATIONS IN SUPERACIDS

The oxidation of aromatic compounds by lead dioxide in superacids based on fluorosulfonic acid at -75 deg C takes place by a one-electron mechanism and leads in many cases to relatively stable radical-cations.The ESR spectra, the isotropic hyperfine coupling constants, data on the reactivity of the radical-cations, and the structures of the final products from their transformations under "long-life" conditions are presented.

A NOVEL DEGRADATIVE STRATEGY FOR THE SYNTHESIS OF p-QUINONES.

p-Hydroxybenzylalcohols undergo Fremy's salt promoted degradative oxidation to give the corresponding p-benzoquinones.A novel strategy for the synthesis of p-benzoquinones based on the regioselective metalation of 2-methoxy-4-methoxymethyl phenols is presented.