69371-41-1

Basic information

• Product Name: 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trichloro-6-methoxy-
• CAS NO: 69371-41-1
• Molecular Formula: C7H3Cl3O3
• Molecular Weight: 241.458
• Mol File: 69371-41-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trichloro-6-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trichloro-6-methoxy-(69371-41-1)
• EPA Substance Registry System: 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trichloro-6-methoxy-(69371-41-1)

Safety Data

• Hazardous Substances Data: 69371-41-1(Hazardous Substances Data)

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 articles and documents

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.

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.

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.