15394-91-9

Usage

Physical state

Yellow solid

Use

Intermediate in the synthesis of pharmaceuticals and dyes

Chemical structure

Cyclohexadienedione (quinone)

Reactivity

Capable of participating in various chemical reactions due to the presence of the nitro group on the phenyl ring

Toxicity

Toxic

Hazards

Can cause skin and eye irritation upon contact

InChI:InChI=1/C12H7NO4/c14-10-5-6-12(15)11(7-10)8-1-3-9(4-2-8)13(16)17/h1-7H

Upstream product

• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 106-51-4 p-benzoquinone 
• 75-30-9 2-iodo-propane 
• 123-31-9 hydroquinone 
• 75-05-8 acetonitrile 

Downstream Products

• 54717-54-3 2-(4-nitrophenyl)-1,4-naphthoquinone 
• 131148-49-7 3-Nitro-7-(4-nitro-phenyl)-benzofuran-5-ol 
• 127245-04-9 2-(4-morpholino)-2-benzyl-2,3-dihydro-4-(p-nitrophenyl)-5-hydroxybenzofuran 
• 365217-34-1 6,7-dimethyl-2-(4-nitro-phenyl)-5,8-dihydro-naphthalene-1,4-diol 
• 365217-36-3 6,7-dimethyl-2-(4-nitro-phenyl)-[1,4]naphthoquinone 
• 127245-02-7 2-benzyl-4-(p-nitrophenyl)-5-hydroxybenzofuran 

Relevant academic research and scientific papers

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.