1079-21-6

Usage

Uses

Used in Organic Synthesis:
PHENYLHYDROQUINONE is used as a synthetic intermediate for [application reason] in the chemical industry. Its chemical properties make it a valuable compound for creating various organic compounds and materials.

Safety Profile

Poison by intraperitoneal andintravenous routes. Mutation data reported. When heatedto decomposition it emits acrid smoke and irritatingfumes.

InChI:InChI=1/C12H10O2/c13-10-6-7-12(14)11(8-10)9-4-2-1-3-5-9/h1-8,13-14H

Upstream product

• 64-17-5 ethanol 
• 42860-77-5 4-hydroxy-4-phenyl-cyclohexa-2,5-dienone 
• 127-09-3 sodium acetate 
• 107449-13-8 O-(2-biphenylyl)hydroxylamine 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 363-03-1 2-phenyl-1,4-benzoquinone 
• 917-54-4 methyllithium 
• 25939-01-9 p-toluoyl chloride phenylhydrazone 
• 36590-52-0 N-phenyl-p-chlorobenzohydrazonoyl chloride 
• 831-82-3 4-Phenoxyphenol 
• 67-56-1 methanol 
• 92-52-4 biphenyl 
• 108-95-2 phenol 
• 4197-75-5 cyclohexyl-1,4-benzenediol 

Downstream Products

• 79520-76-6 5-[5-(4-Methoxycarbonyl-4-methyl-pentyloxy)-biphenyl-2-yloxy]-2,2-dimethyl-pentanoic acid methyl ester 
• 363-03-1 2-phenyl-1,4-benzoquinone 
• 79520-77-7 5,5'-[(1,1'-biphenyl)-2,5-diylbis(oxy)]bis[2,2-dimethylvaleric] acid 
• 7403-36-3 2,3,5-trichloro-6-phenyl-[1,4]-benzoquinone 
• 1267658-48-9 C₁₈⁽¹¹⁾CH₂₁NO₃ 
• 1267658-49-0 [carbonyl-11C]-N-cyclohexyl-5-hydroxy[1,1'-biphenyl]-3-ylcarbamic acid ester 
• 1267658-61-6 5-hydroxy-(1,1′-biphenyl)-2-yl N-cyclohexylcarbamate 
• 1267658-60-5 1,1'-biphenyl-2,5-diyl bis(cyclohexylcarbamate) 
• 1351158-86-5 2,3-bis(2-hydroxy-4-methyl-6-oxocyclohex-1-enyl)-5-phenylcyclohexa-2,5-diene-1,4-dione 
• 1351158-87-6 2,3-bis(4-hydroxy-2-oxo-2H-chromen-3-yl)-5-phenylcyclohexa-2,5-diene-1,4-dione 
• 1351158-85-4 2,3-bis(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-5-phenylcyclohexa-2,5-diene-1,4-dione 
• 1375353-19-7 2,5-bis([3,4,5-tris(benzyloxy)benzoyl]oxy)-1,1'-biphenyl 
• 1416734-99-0 C₂₀H₁₅ClO₃ 
• 14672-90-3 6-(benzyloxy)-(1,1′-biphenyl)-3-ol 

Related news

Genotoxic effects of the o-phenylphenol metabolites PHENYLHYDROQUINONE (cas 1079-21-6) and phenylbenzoquinone in V79 cells08/11/2019

o-Phenylphenol (OPP) and its sodium salt, sodium o-phenylphenate are broad spectrum fungicides and disinfectants with widespread usage. Both chemicals have been reported to induce cancer in the kidney and urinary bladder of Fischer 344 rats. Recently it has been proposed that the metabolic activ...detailed

Relevant academic research and scientific papers

Synthesis of hydroxybiphenyls

Cyclohexylphenols were converted into hydroxybiphenyls via dehydration over large-scale palladium catalysts. The process involves slow reaction of the substrate with active centers of the catalyst with subsequent fast product formation and hydrogen desorption.

Simple, mild, and efficient method for the reduction of 1,4-benzoquinones to hydroquinones by the action of NaN3

A simple, mild, and efficient method is presented for the reduction of 1,4-benzoquinones to hydroquinones by the action of NaN3 under neutral conditions in the presence of water. Copyright Taylor & Francis Group, LLC.

Metabolic activation of o-phenylphenol to a major cytotoxic metabolite, phenylhydroquinone: Role of human CYP1A2 and rat CYP2C11/CYP2E1

1. The in vitro metabolic activation of o-phenylphenol has been evaluated as yielding a toxic metabolite, 2,5-dihydroxybiphenyl (phenylhydroquinone), by p-hydroxylation in liver microsomes of rat and human. The involvement of rat CYP2C11, CYP2E1 and human CYP1A2 in the p-hydroxylation of o-phenylphenol is suggested. 2. 2,3- and phenylhydroquinone, which induced DNA single-strand scission in the presence of 1 μM CuCl2, were the most cytotoxic chemicals examined to cultured mammalian cell lines among o-phenylphenol, m-phenylphenol, p-phenylphenol, 2,2'-, 4,4'-, 2,3- and phenylhydroquinone. 3. Rat and human liver microsomes catalysed the formation of phenylhydroquinone, but not 2,3-dihydroxybiphenyl, using o-phenylphenol as a substrate. A higher rate of metabolic activation of o-phenylphenol was observed with livers of the male than the female rats by 5.6- and 2.6-fold respectively. 4. Inhibitory antibodies against the male-specific CYP2C11 inhibited hepatic o-phenylphenol p-hydroxylation in the male F344 and Sprague-Dawley rat by > 70 %. Liver microsomes from the isoniazid-treated rats produced 1.8- and 3-fold induction of o-phenylphenol p-hydroxylation and chlorzoxazone 6-hydroxylation (a CYP2E1-dependent activity) respectively. 5. Human CYP1A2, expressed by baculovirus-mediated cDNA expression systems, exhibited a remarkably higher capacity for o-phenylphenol p-hydroxylation at concentrations of 5 (> 5-fold), 50 (> 2-fold) and 500 μM (> 2-fold) than CYP2A, CYP2B, CYP2Cs, CYP2D6, CYP2E1 and CYP3A4 on the basis of pmol P450. 6. Among various CYP inhibitors tested here, 7,8-benzoflavone and furafylline, typical human CYP1A2 inhibitors, inhibited the microsomal p-hydroxylation of o-phenylphenol in human livers most potently by 70 and 50 % respectively. 7. The results thus indicate the involvement of rat CYP2C11/CYP2E1 and human CYP1A2 in the hepatic p-hydroxylation of o-phenylphenol.

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

A dinuclear iron(II) complex bearing multidentate pyridinyl ligand: Synthesis, characterization and its catalysis on the hydroxylation of aromatic compounds

A dinuclear iron(II) complex Fe2L2(μ2-Cl)2Cl2 (L = N,N-bis(pyridin-2-ylmethyl)prop-2-yn-1-amine) was prepared and fully characterized by UV–Vis spectroscopy, elemental analysis, electrochemical analysis and X-ray single crystal diffraction analysis. The catalytic activity of the complex was assessed for the hydroxylation of aromatic compounds by using aqueous H2O2 as an oxidant in acetonitrile. The catalytic system was applicable in a wide range of substrates including aromatic compounds with both electron-donating and electron-withdrawing substituents and showed moderate to good catalytic activity and selectivity in the oxidation reactions. Particularly, in the case of benzene the selectivity of phenol achieve to 74% with the reaction conversion of 24.8%.

Oxidative coupling and hydroxylation of phenol over transition metal and acidic zeolites: Insights into catalyst function

Reaction of phenol with hydrogen peroxide over H-MFI, Fe-MFI, H-BEA, Fe-BEA and TS-1 zeolite catalysts was investigated. Over H-BEA, biphenyl product was observed. It is suggested, that the larger pore size of H-BEA facilitates coupling of two phenol molecules. Two distinct reaction mechanisms are proposed for acid and redox catalysts.

Reversible formation of aryloxenium ions from the corresponding quinols under acidic conditions

Quinols, 1, are products of the hydration of O-aryloxenium ions, 2, and N-arylnitrenium ions, 3, and they are being investigated for medical uses. Under acidic conditions (pH 1-3) kinetics and products of Br- trapping demonstrate that 1a, 4-phenyl-4-hydroxy-2,5-cyclohexadienone, and 1b, 4-p-tolyl-4-hydroxy-2,5-cyclohexadienone, generate the corresponding oxenium ions 2a and 2b, respectively, as steady-state intermediates. Formation and trapping of the oxenium ions occurs in competition with the acid catalyzed dienone-phenol rearrangement. Because oxenium ion formation is reversible, the ion can only be detected by trapping with a nucleophile. Br- is an efficient trap under acidic conditions because, unlike N3 -, it is not protonated under those conditions. Attempts to detect the oxenium ions 2a and 2b at pH 4.6 and 7.1 with N3- were unsuccessful indicating that oxenium ion formation only occurs under acidic conditions. The oxenium ion 2c could not be detected under acidic conditions from the quinol 1c, 4-(benzothiazol-2-yl)-4-hydroxy-2,5-cyclohexadienone, by Br- trapping methods, even though this ion can be detected during hydrolysis of the corresponding ester, 4c. Although the benzothiazol-2-yl group is a resonance electron donor that is capable of stabilizing an O-aryloxenium ion, it is also a strong inductive electron withdrawing group that hinders the formation of 2c from 1c by decreasing the extent of protonation of 1c to generate 1cH+ and by destabilizing the transition state for ionization of 1cH+. Generation of an oxenium ion from the corresponding quinol is feasible under acidic conditions as long as the 4-substituent of the quinol is both a resonance and inductive electron donor. Copyright

A direct approach to 5-hydroxybenzofurans via a platinum-catalyzed domino rearrangement/5-endo-dig cyclization reaction of quinols

(Chemical Equation Presented) A highly efficient and atom-economical construction of 2-substituted 5-hydroxybenzofurans was accomplished by employing a platinum-catalyzed domino dienone-phenol rearrangement/5-endo-dig cyclization reaction of quinols beari

One step hair coloring compositions using salts

A hair coloring composition comprising the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an amino phenol, a naphthol, a polyhydric phenol, a catechol and mixtures thereof; wherein the composition comprising one or more oxidative hair coloring agents further comprises al least one water soluble carbonate releasing salts; and optionally a water soluble ammonium salt, is described.

Transition metal complexes as dye forming catalysts in hair coloring compositions

A hair coloring composition comprising a first composition which comprises: (a) a dye forming transition metal salt or complex; which is first applied to the hair; and a second composition which comprises the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an aminophenol, a polyhydric phenol a catechol and mixtures thereof.