69371-41-1

Upstream product

• 124-41-4 sodium methylate 
• 118-75-2 chloranil 
• 67-56-1 methanol 
• 135-77-3 1,2,4-trimethoxy-benzene 

Downstream Products

• 1416079-11-2 2,5-dichloro-6-methoxy-3-(4-amino-N-(5-methylisoxazol-3-yl)-benzene sulfonamide)cyclohexa-2,5-diene-1,4-dione 
• 1428747-96-9 C₁₀H₁₁N₃O₃S*C₁₀H₁₂O₆ 
• 1431139-93-3 [2,5-dichloro-3-(4-(hydroxydiphenylmethyl)piperidin-1-yl)-6-methoxycyclohexa-2,5-diene-1,4-dione] 
• 943843-71-8 C₁₃H₈Cl₂FNO₆S 
• 143800-60-6 2,5-Dichloro-3-methoxy-6-(1'-triphenylphosphoniocyclopentadien-3-yl)-p-benzoquinone 
• 877-13-4 5-hydroxyl-2,3,6-trichloro-1,4-benzoquinone 

Relevant academic research and scientific papers

Substituent effect on the electron acceptor property of 1,4-benzoquinone towards the formation of molecular complex with sulfamethoxazole

UV-Vis, 1H NMR, FT-IR, LC-MS and fluorescence spectral techniques were employed to investigate the mechanism of interaction of sulfamethoxazole with varying number of methoxy/chloro substituted 1,4-benzoquinones (MQ1-4) and to characterize the reaction products. The interactions of MQ1-4 with sulfamethoxazole (SULF) were found to proceed through the formation of a donor-acceptor complex, containing radical anion and its conversion to the product. Fluorescence quenching studies showed that the interaction between the donor and the acceptors are spontaneous. The results indicated that the progressive replacement of chlorine atom (-I effect) by methoxy group (+M effect) in the quinone decreased the electron acceptor property of the quinone. The results of the correlation of experimentally measured binding constants with electrochemical data and ab initio DFT calculations supported these observations.

Spectroscopic studies on the formation of molecular complexes of sulfamethoxazole with novel 2,3,5-trichloro-6-alkoxy-1,4-benzoquinones

UV-Vis, 1H NMR, FT-IR, LC-MS and fluorescence spectral techniques were employed to investigate the mechanism of interaction of sulfamethoxazole with alkoxy substituted 2,3,5-trichloro-1,4-benzoquinones and to characterize the reaction products. The interactions of these quinones with sulfamethoxazole (SULF) were found to proceed through the formation of donor-acceptor complex, containing radical anion and its conversion to the product. Fluorescence quenching studies indicated that the interaction between the donor and the acceptors are spontaneous. Correlation of association constants of the CT complexes with Taft's polar and steric constants indicated that polar factor plays a significant role in governing the reactivity. The results indicated that the electronic effects of the substituents play significant role in governing the reactivity of the quinones when compared to steric factor.

Spectral and theoretical studies on the molecular complexes of azacyclonol with new π-acceptors, alkoxysubstituted 1,4-benzoquinones

The molecular complexes of a series of new electron acceptors, 1,4-benzoquinones possessing variety of alkoxy substituents, with azacyclonol have been investigated using various spectral techniques such as UV-Vis, 1H NMR, FT-IR, fluorescence and LC-MS. The stoichiometry of the complexes was determined by Job's continuous variation method and was found to be 1:1, in all the cases. The results of equilibrium, and kinetic studies were well supported by ab initio DFT calculations. Correlation of formation constants of the complexes with Taft's polar and steric constants indicated that both these factors play significant role in governing the reactivity. Also, the results indicated that an increase in electron releasing property of the alkoxy group makes these acceptors increasingly weaker while an increase in steric property of the substituent decreased the formation constant.

Photoreactivity of some 2-alkoxy/phenoxy-3,5,6-tri-chloro/bromo-1,4-benzoquinones

We report the reaction between 2,3,5,6-tetrachloro/bromo-1,4-benzoquinones (5A/B) with deprotonated alkoholes/phenoles 7a-e to give yellow 2-alkoxy/phenoxy-3,5,6-trichloro/bromo-1,4-benzoquinones 9A/Ba-e. These reaction products are probably photodegraded yielding the corresponding 2-hydroxy-3,5,6-trichloro/bromo-1,4-benzoquinones 15A/B. The quinones 9A/B are not O-conjugated dehydrated, and the quinones 9Ba-e are not C-3-debrominated. These reactions are observed by photodegradation from 2-dialkylamino-3,5,6-trichloro/bromo-1,4-benzoquinones.

THE CRYSTAL STRUCTURE OF 2,5-DICHLORO-3-METHOXY-6-(1'-TRIPHENYLPHOSPHONIOCYCLOPENTADIEN-3-YL)-p-BENZOQUINONE

A single crystal X-ray diffraction study confirms that the reaction of triphenylphosphonio cyclopentadienide 1 with 3-methoxy-2,5,6-trichloro-p-benzoquinone 4 gives a product 5 with the cyclopentadiene ring substituted in position 3 and the chlorine atoms of the quinone ring replaced at positions 3 and 6.This data confirms the prediction of earlier multinuclear 2D nmr data on the reaction of 1 with chloranil. Key words: Triphenylphosphino cyclopentadienide; quinone derivative; X-ray crystallography; chloranil.

Reaction of p-chloranil with phenylethylamine derivatives in methanol

As p-chloranil reacts with phenylethylamine derivatives with methanol serving as a solvent, the first product is the radical anion of p-chloranil, which unexpectedly does not form a CT-complex, but 3,5,6-trichloro-2-methoxy-1,4-benzochinone as the main product.