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Nitrosobenzene

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Nitrosobenzene is a chemical compound with the formula C6H5NO. It is a yellow crystalline solid used as a laboratory reagent and an intermediate in organic synthesis.

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Lab products found in correlation

Azobenzene, by Merck Group (4 mentions) Nitrobenzene, by Thermo Fisher Scientific (2 mentions) N methylaniline, by Merck Group (2 mentions) Hydrazobenzene, by Merck Group (2 mentions) Azoxybenzene, by Merck Group (2 mentions) Nitrobenzene, by Merck Group (2 mentions) Methylamine, by Merck Group (1 mentions) Hydrobromic acid, by Merck Group (1 mentions) Pbbr2, by Merck Group (1 mentions) 4 2 aminoethyl aniline, by Merck Group (1 mentions) Piperidine, by Merck Group (1 mentions) Cobalt 2 nitrate hexahydrate co no3 2 6h2o, by Merck Group (1 mentions) Sulfuric acid, by Avantor (1 mentions) Oleic acid, by Thermo Fisher Scientific (1 mentions) Carbon disulfide, by Merck Group (1 mentions) Tetradecane, by Merck Group (1 mentions) Hexamethyldisilazane, by Merck Group (1 mentions) 4 aminoacetophenone, by Merck Group (1 mentions) P toluidine, by Merck Group (1 mentions) 4 nitrobenzamide, by Merck Group (1 mentions)

6 protocols using nitrosobenzene

1

Synthesis of Organic Compounds

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Lead(II) bromide (PbBr2, Sigma-Aldrich, 99.9% purity), methylamine (CH3NH2·H2O, Sigma-Aldrich, 33 wt % in ethanol), 4-aminobenzylamine (C7H10N2, Sigma-Aldrich, 99% purity) 4-(2-aminoethyl)aniline (C8H12N2, Sigma-Aldrich, 97% purity), nitrosobenzene (C6H5NO, Sigma-Aldrich, 97% purity), 9-fluorenylmethoxycarbonyl chloride (C15H11ClO2, Fmoc-Cl, Carbolution, 98% purity), piperidine (C5H11N, Sigma-Aldrich, 99.5% purity), hydrobromic acid (48 wt % in H2O, Sigma-Aldrich), 4-(phenylazo)phenol (C12H10N2O, Sigma-Aldrich, 98% purity), 1,4-dibromobutane (C4H8Br2, Sigma-Aldrich, 99% purity), 1,12-dibromododecane (C12H24Br2, Sigma-Aldrich, 98% purity), phthalimide potassium salt (C8H4KNO2, abcr, 98% purity) and hydrazine monohydrate (N2H2·H2O, acros organics, 99% purity) were used without further purification.
Fillafer N., Seewald T., Schmidt-Mende L, & Polarz S. (2020). Interfacial charge transfer processes in 2D and 3D semiconducting hybrid perovskites: azobenzene as photoswitchable ligand. Beilstein Journal of Nanotechnology, 11, 466-479.
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2

Synthesis of Cobalt and Nickel Ferrite Catalysts

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The cobalt ferrite and nickel ferrite catalyst supports were synthetized from the following precursors: cobalt(II) nitrate hexahydrate, Co(NO3)2∙6H2O, MW: 291.03 g/mol (Sigma-Aldrich, Saint Louis, MO 63103, USA); nickel(II) nitrate hexahydrate, Ni(NO3)2∙6H2O, MW: 290.79 g/mol (Thermo Fisher GmbH, D-76870 Kandel, Germany); iron(III) nitrate nonahydrate, Fe(NO3)3∙9H2O (VWR International, Leuven, Belgium); ethylene glycol, HOCH2CH2OH, (VWR Int. Ltd., F-94126 Fontenay-sous-Bois, France); monoethanolamine, NH2CH2CH2OH (Merck KGaA, D-64271 Darmstadt, Germany); and sodium acetate, CH3COONa (ThermoFisher GmbH, D-76870 Kandel, Germany). Palladium(II) nitrate dihydrate, Pd(NO3)2·2H2O (Alfa Aesar Ltd., Ward Hill, MA 01835, USA) was used to deposit Pd onto the ferrite catalyst supports. Nitrogen (purity 4.0, Messer) and hydrogen (purity 4.0, Messer) were used during the experiments. Nitrobenzene (NB, Acros Organics, Morris Plains, NJ 07950, USA) was used as reactant during the catalytic hydrogenation tests. The analytical standards applied (azobenzene, nitrosobenzene, N-methylaniline) were purchased from Sigma-Aldrich Co. (St. Louis, MO 63118, USA).
Hajdu V., Prekob Á., Muránszky G., Kristály F., Daróczi L., Harasztosi L., Kaleta Z., Viskolcz B., Nagy M, & Vanyorek L. (2023). Amine Functionalization Leads to Enhanced Performance for Nickel- and Cobalt-Ferrite-Supported Palladium Catalysts in Nitrobenzene Hydrogenation. International Journal of Molecular Sciences, 24(17), 13347.
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3

Palladium-Catalyzed Carbon Foam Hydrogenation

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For the preparation of the carbon-based foam, 4-nitroaniline (Alfa Aesar GmbH, 76185 Karlsruhe, Germany) and sulfuric acid (95 wt%, VWR Intern. S.A.S, F-94126 Fontanay-sous-Bois, France) were used. Carbon dioxide was used to activate the prepared foam (Gourmet, Messer). Palladium(II) nitrate dihydrate (Pd(NO3)2*2H2O, Alfa Aesar Ltd., Ward Hill, 01835 MA, USA) was applied to deposit Pd onto the carbon foil support. Nitrogen (purity 4.0, Messer) and hydrogen (purity 4.0, Messer) were used during the experiments. Nitrobenzene (NB, Acros Organics, Fair Lawn, 07950 NJ, USA) was used as reactant during the catalytic hydrogenation tests. The applied analytical standards (azobenzene, nitrosobenzene, N-methylaniline) were purchased from Sigma-Aldrich Co. (St. Louis, 63118 MO, USA).
Prekob Á., Szamosvölgyi Á., Muránszky G., Lakatos J., Kónya Z., Fiser B., Viskolcz B, & Vanyorek L. (2022). Palladium Decorated N-Doped Carbon Foam as a Highly Active and Selective Catalyst for Nitrobenzene Hydrogenation. International Journal of Molecular Sciences, 23(12), 6423.
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4

Synthesis of Nitro-Containing Compounds

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Oleylamine (technical grade, 70%), tungsten(vi) chloride (WCl6, ≥99.9%, trace metal basis), hexamethyldisilazane (HMDS, reagent grade, ≥99%), carbon disulfide (CS2, ≥99.9%, anhydrous), tetrahydrofuran (THF, anhydrous, contains 250 ppm BHT as inhibitor, ≥99%), azobenzene (98%), 4-nitrobenzamide (98%), 4-nitrobenzenesulfonamide (97%), 4′-fluoro-3′-nitroacetophenone (97%), 3-nitrostyrene (96%), hydrazobenzene, 1-bromo-4-nitrobenzene (99%), ethyl 4-nitrocinnamate (predominately trans, 99%), 4′-aminoacetophenone (99%), 3-vinylaniline (contains KOH as inhibitor, 97%), 4-nitrothioanisole (96%), 1-chloro-4-nitrobenzene (99%), 1-iodo-4-nitrobenzene (98%), tetradecane (≥99%), nitrosobenzene (≥97%), 3-ethylaniline (98%), p-toluidine (99%), 4-(4-nitrobenzyl)pyridine (98%), 4-nitrobenzonitrile (97%), hydroxylamine hydrochloride (99%), azoxybenzene, and nitrobenzene (99%) were purchased from Sigma Aldrich. Oleic acid (technical grade, 90%) and 4-nitrobenzoic acid (99%) were purchased from Alfa Aesar. Methyl 4-nitrobenzoate (≥98.0%) and 4-nitrobenzaldehyde (≥98.0%) were purchased from TCI. 10% Pt on activated carbon powder was purchased from Premetek. Solvents, including hexane and isopropanol, were of analytical grade. All chemicals were used as received without further purification.
Sun Y., Darling A.J., Li Y., Fujisawa K., Holder C.F., Liu H., Janik M.J., Terrones M, & Schaak R.E. (2019). Defect-mediated selective hydrogenation of nitroarenes on nanostructured WS2 †Electronic supplementary information (ESI) available: Additional material characterization and DFT calculation data. See DOI: 10.1039/c9sc03337h. Chemical Science, 10(44), 10310-10317.
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5

Preparation of DMPO Spin Trap

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5,5-Dimethyl-1-pyrroline N-oxide (DMPO) was purchased from Cayman Chemical (Ann Arbor, MI, USA). All other chemicals, including nitrosobenzene, were purchased from Sigma Aldrich (St. Louis, MO, USA) at the highest available grade.
Davis I., Koto T, & Liu A. (2018). Radical Trapping Study of the Relaxation of bis-Fe(IV) MauG. Reactive oxygen species (Apex, N.C.), 5(13), 46-55.
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6

Chemical Synthesis of Nitro, Azo, and Halogenated Compounds

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Materials Nitrobenzene (99%), nitrosobenzene (97%), azoxybenzene, azobenzene (98%), hydrazobenzene, phenylhydroxylamine (97%), 4-chloroNitrobenzene (99%), 4chloroaniline (98%), 4-chlorobenzaldehyde (97%), 4-chlorobenzylalcohol (99%), 4-iodoNitrobenzene (98%), 4-iodoaniline (98%), 4-iodotoluene (99%), methanol (99.9%) and 1-butanol (99.7%) were all obtained from Sigma Aldrich. Potassium permanganate ($99%) was obtained from Fluka as was maleic acid ($98%). Metal precursors used were platinum nitrate (assay 15.14%) supplied by Johnson Matthey and palladium(II)nitrate hydrate procured from Sigma Aldrich. Research grade hydrogen was supplied by BOC. All chemicals were used as supplied.
McManus I.J., Daly H., Manyar H.G., Taylor S.F.R., Thompson J.M, & Hardacre C. (2016). Selective hydrogenation of halogenated arenes using porous manganese oxide (OMS-2) and platinum supported OMS-2 catalysts. Faraday discussions, 188.
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