20307-43-1

Basic information

• Product Name: 2-(4-Chlorophenyl)cyclohexa-2,5-diene-1,4-dione
• Synonyms: 2-(4-Chlorophenyl)cyclohexa-2,5-diene-1,4-dione
• CAS NO: 20307-43-1
• Molecular Formula: C₁₂H₇ClO₂
• Molecular Weight: 218.63578
• Mol File: 20307-43-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 152.1 °C
• Appearance: /
• Density: 1.365 g/cm³
• Vapor Pressure: 2.28E-05mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 2-(4-Chlorophenyl)cyclohexa-2,5-diene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Chlorophenyl)cyclohexa-2,5-diene-1,4-dione(20307-43-1)
• EPA Substance Registry System: 2-(4-Chlorophenyl)cyclohexa-2,5-diene-1,4-dione(20307-43-1)

Safety Data

• Hazardous Substances Data: 20307-43-1(Hazardous Substances Data)

Usage

General Description

2-(4-Chlorophenyl)cyclohexa-2,5-diene-1,4-dione is a chemical compound with the molecular formula C12H7ClO2. It is a yellow crystalline solid that is often used in the synthesis of pharmaceuticals and dyes. The compound is classified as a cyclohexane derivative and contains a cyclohexadienedione functional group. It is important to note that this compound is not considered stable and may be hazardous if mishandled or improperly stored. Additionally, it should be used and handled by qualified individuals in a controlled laboratory setting with appropriate protective equipment.

InChI:InChI=1/C12H7ClO2/c13-9-3-1-8(2-4-9)11-7-10(14)5-6-12(11)15/h1-7H

Upstream product

• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 106-51-4 p-benzoquinone 
• 75-30-9 2-iodo-propane 
• 123-31-9 hydroquinone 

Downstream Products

• 381241-02-7 7-(4-chlorophenyl)-5-hydroxy-1,3-benzoxathiole-2-thione 
• 70881-41-3 C₁₂H₁₀ClO₂ 
• 10551-37-8 2-(4'-chlorophenyl)-1,4-hydroquinone 

Relevant articles and documents

Reduction of Arenediazonium Salts by Hydroquinone. Kinetics and Mechanism for the Electron-Transfer Step

Arenediazonium tetrafluoroborate salts undergo facile electron transfer reaction with hydroquinone in aqueous phosphate-buffered solutions containing the hydrogen donor solvent acetonitrile.Reaction rates are the first-order in hydroquinone and arenediazonium ion concentrations, and they exhibit inverse first order dependence on the hydrogen ion concentration over the pH range of 1.0-9.5.Benzoquinone and arene are the principial products, but arylation of acetonitrile and benzoquinone are competitive in a reaction process that exhibits a 2:1 stoichiometric relationship between the arenediazonium ion salt and hydroquinone.Rate constants for reduction of substituted benzediazonium ions by the monoanion of hydroquinone correlate with ? constants yielding a ρ value of 3.5.Reactions performed in deuterium oxide show kinetic isotope effects that reflect the solvent isotope effect on the acidity constant for hydroquinone, and levels of isotope incorporation by deuterium abstraction from deuterium oxide and/or acetonitrile-d3 demonstrate that neither water nor hydroquinone are hydrogen atom donors to intermediate aryl radicals.Reduction of arenediazonium ions involves a rate-limiting single electron transfer from the monoanion of hydroquinone followed by a rapid single electron transfer from the semiquinone intermediate to the diazonium ion.Application of Marcus theory provides calculated rate constants for electron transfer from the hydroquinone monoanion to arenediazonium ions.These rate constants, together with the absence of evidence for a diazo ether intermediate and rate constants for diazotate formation, suggest that electron transfer occurs by an outer-sphere mechanism.

Photochemical Dediazoniation of Arene Diazonium Salts Catalyzed by Quinones

The rate constants of the hydrogen abstraction of triplet-excited p-benzoquinone (BQ), duroquinone (DQ), p-chlorophenyl-p-benzoquinone (PQ) and 2,5-di(p-chlorophenyl)-p-benzoquinone (P2Q) from n-heptane and acetonitrile are determined by laser flash photolysis as well as the rate constants for the reactions with oxygen. The semiquinones formed are in equilibrium with their respective semiquinone anions; at pH 3 and pH 7, respectively, it was possible in acetonitrile/water solution to determine separately the rate constants for their disproportionation affording quinones and hydroquinones and the rate constants for electron transfer to p-chlorbenzene diazonium tetrafluoroborate.It comes out that the electron transfer to the diazonium compound only competes favorably with the disproportionation in the case of the semiquinone anions.