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Cas Database

62-53-3

62-53-3

Identification

  • Product Name:Aniline

  • CAS Number: 62-53-3

  • EINECS:200-539-3

  • Molecular Weight:93.1283

  • Molecular Formula: C6H7N

  • HS Code:2921 41 00

  • Mol File:62-53-3.mol

Synonyms:Phenylamine;Arylamine;Aminophen;Benzene, amino;Kyanol;Anilinium nitrate;Phenyleneamine;Anyvim;Aniline and homologues;Aniline oil;Benzidam;Aniline, Reagent;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT, DangerousN, FlammableF

  • Hazard Codes:T,N,F

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH311 Toxic in contact with skin H318 Causes serious eye damage H317 May cause an allergic skin reaction H331 Toxic if inhaled H341 Suspected of causing genetic defects H351 Suspected of causing cancer H400 Very toxic to aquatic life

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Administration of oxygen may be needed. Refer immediately for medical attention. See Notes. In case of skin contact Administration of oxygen may be needed. Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention. See Notes. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Administration of oxygen may be needed. Rinse mouth. Do NOT induce vomiting. Rest. Refer immediately for medical attention. See Notes. It is classified as very toxic. Probable oral lethal dose in humans is 50-500 mg/kg for a 150 lb. person. Aniline poisoning is characterized by methemoglobin formation in the blood and resulting cyanosis or blue skin. The formation of methemoglobin interferes with the oxygen-carrying capacity of the blood. The approximate minimum lethal dose for a 150 lb. human is 10 grams. Serious poisoning may result from ingestion of 0.25 mL. People at special risk include individuals with glucose-6-phosphate-dehydrogenase deficiency and those with liver and kidney disorders, blood diseases, or a history of alcoholism. (EPA, 1998) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use alcohol foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. Fight fire from maximum distance. Dike fire control water for later disposal and do not scatter material. If a leak or spill has not ignited, use water spray to control vapors. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators recommended for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive-pressure mode. Combustion can produce toxic fumes including nitrogen oxides and carbon monoxide. Aniline vapor forms explosive mixtures with air. It is incompatible with strong oxidizers and strong acids and a number of other materials. Avoid heating. Hazardous polymerization may occur. Polymerizes to a resinous mass. (EPA, 1998) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Evacuate danger area! Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Wear breathing apparatus, eye protection, laboratory coat, and butyl rubber gloves. Cover the spill with a 1:1:1 mixture by weight of sodium carbonate or calcium carbonate, clay cat litter (bentonite), and sand. When the aniline has been absorbed, scoop the mixture into a plastic pail and add enough water to dissolve the sodium carbonate. Allow the solids to settle and decant the liquid to another container. Discard the solids with the normal refuse. To the liquidd, slowly (frothing will occur) add 6 M sulfuric acid to pH 2. Stir into the acidified solution sufficient solid potassium permanganate so that the liquid is purple (a drop of the liquid on filter paper will show a purple ring). Allow the mixture to stand at room temperature for 48 hours, and then neutralize with solid sodium carbonate (frothing will occur), or with a 10% aqueous solution of sodium hydroxide. Add solid sodium bisulfite until the solution is colorless. Decant the clear liquid into the drain and discard any brown solid with normal refuse.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants, strong acids and food and feedstuffs. Well closed. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.Aniline is slightly corrosive to some types of metal. So all amphoteric materials such as aluminum, copper, tin, zinc, and alloys containing one of these metals (brass, bronze) are not suitable for the handling of aniline, as they are corroded by it. For normal applications carbon steel or cast iron are appropriate materials for the aniline handling or storage. Only if discoloration must be kept to minimum, aniline should be stored and transported in stainless steel equipment with proper nitrogen blanketing.

  • Exposure controls/personal protection:Occupational Exposure limit valuesNIOSH considers aniline to be a potential occupational carcinogen.NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration.Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Aniline
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Aniline >98.0%(GC)(T)
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Relevant articles and documentsAll total 1669 Articles be found

Magnetic Field Effects on and Mechanism of Photoredox Reaction of Aromatic Nitro Group

Mutai, Kiyoshi,Nakagaki, Ryoichi,Tukada, Hideyuki

, p. 920 - 926 (1993)

Photoredox reaction mechanism of a homologous series p-O2NC6H4O(CH2)nNHPh (1) in acetonitrile and benzene is studied.The major products are p-ONC6H4O(CH2)n-1CHO (3) and aniline derived from intramolecular reaction, but the presence of minor amounts of intermolecular reaction products, p-O2NC6H4O(CH2)n-1CHO (4) and p-ONC6H4O(CH2)nNHPh (5) is confirmed in the reaction mixture.In the presence of an external magnetic field, the yield of 3 is suppressed and those of 4 and 5 are correspondingly increased, while the rates of the disappearance of 1 and of the formation of aniline remain unchanged, suggesting the presence of biradical recombination process accompanied by intersystem crossing in a rate-determining step.On the basis of these observations, two reaction schemes are proposed.The magnetic field effects provide strong evidence for the presence of a transient species with (nitro)N(OH)-O-CHN group generally supposed for nitro oxygen transfer process in this type photoreaction.

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Portsmouth,Beal

, p. 451,453-456 (1971)

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Structure and Catalytic Activity of Cr-Doped BaTiO3 Nanocatalysts Synthesized by Conventional Oxalate and Microwave Assisted Hydrothermal Methods

Srilakshmi, Chilukoti,Saraf, Rohit,Prashanth,Rao, G. Mohan,Shivakumara

, p. 4795 - 4805 (2016)

In the present study synthesis of BaTi1-xCrxO3 nanocatalysts (x = 0.0 ≤ x ≤ 0.05) by conventional oxalate and microwave assisted hydrothermal synthesis methods was carried out to investigate the effect of synthesis methods on the physicochemical and catalytic properties of nanocatalysts. These catalysts were thoroughly characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), N2 physisortion, and total acidity by pyridine adsorption method. Their catalytic performance was evaluated for the reduction of nitrobenzene using hydrazine hydrate as the hydrogen source. Structural parameters refined by Rietveld analysis using XRD powder data indicate that BaTi1-xCrxO3 conventional catalysts were crystallized in the tetragonal BaTiO3 structure with space group P4mm, and microwave catalysts crystallized in pure cubic BaTiO3 structure with space group Pm3μm. TEM analysis of the catalysts reveal spherical morphology of the particles, and these are uniformly dispersed in microwave catalysts whereas agglomeration of the particles was observed in conventional catalysts. Particle size of the microwave catalysts is found to be 20-35 nm compared to conventional catalysts (30-48 nm). XPS studies reveal that Cr is present in the 3+ and 6+ mixed valence state in all the catalysts. Microwave synthesized catalysts showed a 4-10-fold increase in surface area and pore volume compared to conventional catalysts. Acidity of the BaTiO3 catalysts improved with Cr dopant in the catalysts, and this could be due to an increase in the number of Lewis acid sites with an increase in Cr content of all the catalysts. Catalytic reduction of nitrobenzene to aniline studies reveals that BaTiO3 synthesized by microwave is very active and showed 99.3% nitrobenzene conversion with 98.2% aniline yield. The presence of Cr in the catalysts facilitates a faster reduction reaction in all the catalysts, and its effect is particularly notable in conventional synthesized catalysts.

-

Wibaut

, p. 545 (1917)

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Pd nanoparticles immobilized on halloysite decorated with a cyclodextrin modified melamine-based polymer: a promising heterogeneous catalyst for hydrogenation of nitroarenes

Sadjadi, Samahe,Akbari, Maryam,Monflier, Eric,Heravi, Majid M.,Leger, Bastien

, p. 15733 - 15742 (2018)

For the first time, a hybrid system composed of halloysite (Hal) and a cyclodextrin modified melamine-based polymer is developed and employed for immobilization of Pd(0) nanoparticles. The resulting catalytic hybrid system, Pd@HTMC, was then applied as a

Mesoporous silica supported cobalt catalysts for gas phase hydrogenation of nitrobenzene: role of pore structure on stable catalytic performance

Kondeboina, Murali,Enumula, Siva Sankar,Gurram, Venkata Ramesh Babu,Yadagiri, Jyothi,Burri, David Raju,Kamaraju, Seetha Rama Rao

, p. 15714 - 15725 (2018)

Highly dispersed cobalt nanoparticles were prepared over mesoporous silica with different pore structures (2D-hexagonal COK-12 and 3D-cubic SBA-16). These catalysts were evaluated for gas phase hydrogenation of nitrobenzene to aniline at atmospheric H2 pressure. A combination of catalytic activity and characterization results were assessed to establish the role of the support pore structure on hydrogenation activity. XRD, N2-physisorption, SEM and TEM analysis confirmed the presence of mesoporous structures in the supported cobalt catalysts. H2-TPR, H2-pulse chemisorption and TEM studies demonstrated higher dispersion of cobalt nanoparticles in Co/SBA-16 than in the Co/COK-12 catalyst. During the time-on-stream study the Co/SBA-16 catalyst experienced a gradual deactivation whereas the Co/COK-12 catalyst exhibited constant catalytic performance with respect to the hydrogenation of nitrobenzene. The interconnected cage type pores in Co/SBA-16 catalyst allowed the product molecules to participate in further reactions. This resulted in the formation of condensed products and coke deposition. The Co/SBA-16 catalyst was rapidly deactivated due to pore blocking through coke deposition. N2-Physisorption, TGA, H2-TPR and CHNS elemental analysis of spent catalysts confirmed the severe coke deposition in the Co/SBA-16 catalyst compared to the Co/COK-12 catalyst.

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Nicol

, p. 211 (1882)

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Well-dispersed bimetallic nanoparticles confined in mesoporous metal oxides and their optimized catalytic activity for nitrobenzene hydrogenation

Liu, Juanjuan,Zou, Shihui,Xiao, Liping,Fan, Jie

, p. 441 - 446 (2014)

Well-dispersed bimetallic nanoparticles (BMNPs = PtPd/AuPd/AuPt) confined in mesoporous metal oxides (MMOs = TiO2/Al2O 3/SiO2/ZrO2) are synthesized by a general and mild one-step sol-gel strategy. Thi

Palladium nanoparticles supported on silicate-based nanohybrid material: highly active and eco-friendly catalyst for reduction of nitrobenzene at ambient conditions

Ebadati, Esmat,Aghabarari, Behzad,Bagheri, Mozhgan,Khanlarkhani, Ali,Martinez Huerta, Maria Victoria

, p. 569 - 578 (2021)

In this study, spent bleaching earth (SBE), a hazardous industrial waste was used as raw material to synthesis carbon/silicate nanohybrid material (CSNH) as support for mono and bimetallic palladium and nickel nanoparticles. The synthesized catalysts were

Efficient reduction catalysis of viologen-bound iron porphyrin and its application to six-electron reduction of nitrobenzene to aniline

Sakaki, Shigcyoshi,Koga, Hiroaki,Tao, Kou-Ichiro,Yamashita, Takafumi,Iwashita, Tetsuro,Hamada, Taisuke

, p. 1015 - 1017 (2000)

A newly synthesized methylviologen-bound iron porphyrin chloro(5-{4-[3-(1′-methyl-4,4′-bipyridinium)ethylcarboxyamidyl] phenyl}-10,15,20-triphenylporphyrin)iron dichloride, efficiently catalyzes six-electron reduction of nitrobenzene to aniline, a model reaction of NO2- conversion to NH4+ by nitrite reductase. The Royal Society of Chemistry 2000.

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Masilamani et al.

, p. 3687,3688, 3691 (1976)

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Kuhn, L. P.,Corwin, A. H.

, p. 3370 - 3375 (1948)

A Modification of the Sheverdina-Kocheshkov Amination: The Use of Methoxyamine-Methyllithium as a Convenient Synthetic Equivalent for NH2+

Beak, Peter,Kokko, Bruce J.

, p. 2822 - 2823 (1982)

Direct stoichiometric amination of organolithiums can be achieved in high yields by methoxyamine and methyllithium in hexane-ether.The synthetic advantages of this approach are noted.

Transition Metal Catalyzed Reduction of Azidoarenes to Aminoarenes with Carbon Monoxide-Water System

Shim, Sang Chul,Choi, Kui Nam,Yeo, Young Kuk

, p. 1149 - 1150 (1986)

Azidoarenes were readily transformed to aminoarenes in good yields under mild conditions with carbon monoxide and water in the presence of a catalytic amount of rhodium(III) complex, which is more catalytically active than rhodium(I) or palladium(II) complexes.

Pd immobilized on polymeric network containing imidazolium salt, cyclodextrin and carbon nanotubes: Efficient and recyclable catalyst for the hydrogenation of nitroarenes in aqueous media

Sadjadi, Samahe,Koohestani, Fatemeh

, (2020)

A novel polymeric network benefiting from the chemistry of imidazolium salt (IL), cyclodextrin (CD) and carbon nanotube (CNT) is fabricated through a multi-step process, in which silica coated CNTs were vinyl functionalized and polymerized with poly (ethy

Decolorization of azo dye Orange G by aluminum powder enhanced by ultrasonic irradiation

Cai, Mei Qiang,Wei, Xiao Qin,Song, Zhi Jun,Jin, Mi Cong

, p. 167 - 173 (2015)

In this work, the decolorization of azo dye Orange G (OG) in aqueous solution by aluminum powder enhanced by ultrasonic irradiation (AlP-UI) was investigated. The effects of various operating operational parameters such as the initial pH, initial OG conce

Synthesis of PVP-stabilized Pt/Ru colloidal nanoparticles by ethanol reduction and their catalytic properties for selective hydrogenation of ortho-chloronitrobenzene

Liu, Manhong,Zhang, Jin,Liu, Jinqiang,Yu, William W.

, p. 1 - 7 (2011)

Stable poly(N-vinyl-2-pyrrolidone)-stabilized Pt/Ru colloidal nanoparticles (PVP-Pt/Ru) were prepared via ethanol reduction of H2PtCl 66H2O and RuCl3nH2O. The average diameters of the nanoparticles with different molar ratio of Pt/Ru were in a range of 2.1-2.8 nm with narrow size distributions. X-ray photoelectron spectroscopy verified that both Pt and Ru were in the metallic state and Ru was rich on the surface. These nanoparticles were employed to selectively hydrogenate ortho-chloronitrobenzene at 298 K and 0.1 MPa hydrogen pressure. They showed high activity [TOF was in the range of 0.8-5.3 × 10 -2 molo-CNB/(molM,surface atom) s] and high selectivity (93-99%) to ortho-chloroaniline (o-CAN) for the reaction, which were composition-dependent. The selectivity to o-CAN monotonously increased, but the activity of the catalyst decreased with the increasing proportion of Ru in Pt/Ru colloidal catalysts. PVP-1Pt/4Ru nanoparticles exhibited the highest selectivity of 99.0% to o-CAN at a complete conversion.

Direct amination of benzene to aniline with H2O2 and NH3·H2O over Cu/SiO2 catalyst

Yu, Tianhua,Yang, Ruiguang,Xia, Sheng,Li, Guiying,Hu, Changwei

, p. 3159 - 3167 (2014)

The direct amination of benzene to aniline with H2O2 and NH3·H2O was studied using a series of Cu/SiO2 catalysts with mesoporous structures under mild conditions, and an acceptable yield (5.4%) and selectivity (74.0%) to aniline was obtained. Ultraviolet-visible diffuse reflectance spectroscopy, Fourier transform infrared spectroscopy and X-ray photoelectron spectroscopy demonstrated that some of the Cu atoms were incorporated into the mesoporous silica network forming Cu-O-Si species, which enabled the selective activation of the N-H bond of NH 3. The medium-strong acid sites were beneficial for the amination reaction. The concentration of the reactants was found to be another critical factor for aniline formation. The amination of the aromatic ring of substituted benzenes was also investigated under the optimized conditions. the Partner Organisations 2014.

Thermolysis of azobenzene

Budyka, M. F.,Kantor, M. M.

, p. 1495 - 1497 (1993)

Thermolysis of azobenzene in a melt and in solution results in the formation of aniline.The possible directions of the reaction are considered.Comparison of the enthalpies of the reaction proves that the cleavage of a ?-bond in the N=N group to form a biradical intermediate is thermodynamically more favorable than that of a C-N ?-bond.

Multicomponent Strategy for the Preparation of Pyrrolo[1,2-a]pyrimidine Derivatives under Catalyst-Free and Microwave Irradiation Conditions

Xun, Zhan,Feng, Xian,Wang, Jianjun,Shi, Daqing,Huang, Zhibin

, p. 696 - 702 (2016)

A simple and efficient one-pot procedure has been developed for the construction of pyrrolo[1,2-a]pyrimidines via the three-component domino reaction of 5-aminopyrazoles, acetylenedicarboxylates and malononitrile under catalyst-free, microwave irradiation conditions. The key step in this transformation is the N N bond cleavage reaction of the 5-aminopyrazole substrate, which has been reported in this context for the first time in this study. The advantages of this protocol include readily available starting materials, short reaction times and good regioselectivity.

Photochemical locking and unlocking of an acyl nitroso dienophile in the Diels-Alder reaction

Schultz, Kevin P.,Spivey, David W.,Loya, E. Kirkbride,Kellon, Jaclyn E.,Taylor, Lisa M.,McConville, Marie R.

, p. 1296 - 1299 (2016)

Photochromic Diels-Alder cycloadducts consisting of acyl nitroso dienophiles, which are known nitroxyl (HNO) donors, and dithienyldienes are presented. The dithienylethene-type photochromic cycloadducts were found to exhibit reversible electrocyclic ring closing and ring opening reactions to 'lock' or 'unlock' the retro Diels-Alder reaction, respectively. The release of an acyl nitroso dienophile via a retro Diels-Alder reaction at 92 °C was shown to occur only from the open or 'unlocked' form of a photochromic dithienylcyclopentene and not from the closed or 'locked' isomer.

Square Wave Voltammetry for Two-Step Surface Reductions

O'Dea, John J.,Osteryoung, Janet G.

, p. 650 - 658 (1997)

Strongly adsorbed species on an electrode surface are used to create a stable, redox-modified surface. Square wave voltammetry is then used to degrade the surface electrochemically, as evidenced by the resulting voltammetric response. This process can be mathematically modeled as a quasi-reversible surface reaction coupled with a first-order irreversible surface reaction of the product. This is the simplest possible model that can explain a two-step surface reduction. Exemplary calculations for square wave voltammetry show a wide variety of peak shapes depending on rate constants and square wave amplitude. The reduction of Dimethyl Yellow (4-(dimethylamino)azobenzene) adsorbed on mercury is accurately described by this model. Characteristic parameters of the overall surface process are obtained from voltammograms by using the two-step model with nonlinear least-squares analysis (COOL). For Dimethyl Yellow in Britton - Robinson buffer (pH 6.00) at a surface concentration of 17.3 pmol cm-2, these parameters are as follows: standard potential, E10 = -0.397 ± 0.001 V vs SCE; transfer coefficient for the first step, α1 = 0.43 ± 0.02; rate constant for the first step, k10 = 103 ± 8 s-1; transfer coefficient for the second step, α2 = 0.11 ± 0.04; and rate constant for the second step, k20 (referenced to E10) = 11.1 ± 1.7 s-1. Uncertainties are 95% confidence intervals derived from a pool of 11 voltammograms collected at different square wave amplitudes (ESW = 0-100 mV).

Oxidation-reduction conversions of derivatives of 1,4-dihydropyridine and 4H-pyran on interaction of alicyclic 1,5-diketones with 4-aminoazobenzene

Maslov,Akimova,Kaminski

, p. 417 - 421 (2002)

The interaction of 2,2′-methylenedicyclohexanone and 2,2′-methylenedicyclopentanone with 4-aminoazobenzene in acetic acid leads to reduction of the azo group of 1,4-dihydropyridine and 4H-pyran derivatives formed as intermediates. The reduction products were isolated as the corresponding pyridinium salts.

Visible light photocatalytic synthesis of aniline with an Au/LaTiO3 nanocomposites

Mkhalid

, p. 298 - 302 (2015)

An ultrasonic method was used to prepare LaTiO3 nanoparticles and a photo-assisted deposition method was used to loading gold into surface of LaTiO3. The samples obtained were characterized using a photoluminescence emission spectra,

Methylene blue sensitized photodechlorination of isomeric mono- and dichloroanilines via molecular complex formation mechanism

Pande,Dwivedi

, p. 1086 - 1093 (2011)

The photosensitized dechlorination of isomeric mono- and dichloroanilines has been studied using methylene blue as photosensitizer in alkaline medium. The dechlorination products have been identified and formation of molecular complex between aniline and methylene blue has been observed. The effects of the pH, concentration of the sensitizer, concentration of the substrate, the intensity of the light and the temperature on the rate of the reaction have been studied. The quantum efficiency of the photodechlorination has been evaluated. The mechanism of the photodechlorination has been suggested.

Determination of the Carbamate Herbicide Propham by Synchronous Derivative Spectrofluorometry following Fluorescamine Fluorogenic Labeling

Sanchez, F.Garcia,Blanco, C.Cruces

, p. 73 - 76 (1986)

Three methods for the determination of propham by fluorogenic labeling with fluorescamine and synchronous derivative spectrofluorometry are described and discussed.The herbicide is hydrolyzed in 1 M NaOH at 100 deg C for 40 min, and the liberated aniline reacts instantaneously wih fluorescamine in an aqueous buffer solution (pH 4.0).Reaction rates, fluorescence phenomena, and synchronous derivative parameters are investigated.To enhance sensitivity, the analysis of the fluorescamine derivative is used following extraction in ethyl acetate.Linear analytical curves are obtained between 24 and 2000 ng/mL.The minimum detectable quantity is estimated to be 7.2 ng/mL.Wellwater samples containing low concentrations of carbamate are also analyzed.

Trimethylsilyl Azide/Triflic Acid, a Highly Efficient Electrophilic Aromatic Amination Reagent

Olah, George A.,Ernst, Thomas D.

, p. 1203 - 1204 (1989)

-

-

Fields et al.

, p. 2435 (1952)

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Features of the phenylhydroxylamine catalytic hydrogenation in water solutions of 2-propanole on skeletal nickel

Budanov,Lefedova,Ulitin,Kha, Nguen Tkhi Tkhu

, p. 1901 - 1904 (2010)

The kinetics of phenylhydroxylamine hydrogenation reaction on skeletal nickel catalyst in 2-propanole aqueous solutions was studied. It was shown that the value of phenylhydroxylamine and aniline adsorption increases with an increase in the molar fraction of water in the binary solvent 2-propanole-water. It was found experimentally that the hydrogenation reaction is of the first order with phenylhydroxilamine and of the zero order with hydrogen. It is noted that the amount of hydrogen absorbed in the reduction of phenylxydroxylamine in the initial phase of the reaction is considerably lower than the stehiometry of the reaction would indicate. The reasons for the effect of solvent on the features of phenylhydroxilamine hydrogenation are discussed.

Synergetic effects of graphene-CoPc/silk fibroin three-dimensional porous composites as catalysts for acid red G degradation

Ma, Hui,Zhang, Huanxia,Tong, Mingqiong,Cao, Jianda,Wu, Wen

, p. 24751 - 24759 (2019)

The disposal of dye wastewater is one of the hotspots of scientific research. Upon combining the ability of graphene to accelerate the hydroxyl radical generation with the Fenton system, it has shown a faster degradation rate and can be recycled, showing greater degradation efficiency than the traditional dye treatment method. Herein, a catalytic system based on the regenerated silk fibroin (SF) gel integrated with cobalt tetraaminophthalocyanine (CoTAPc)-grafted-reduced graphene oxide (RGO) sheets were fabricated, and its catalytic activity was assessed via the degradation of acid red G (ARG) at varying catalyst and H2O2 dosages, pH values, and temperatures. The results revealed that the three-dimensional (3D) porous RGO-CoTAPc/SF gel exhibited a much stronger catalytic behavior than the other arbitrary components due to its high surface area and synergetic hydroxyl radical generation efficiency, with the dye removal ratio by RGO-CoTAPc/SF being higher in an acidic medium than in an alkaline medium. It also increases with the increase in temperature and RGO-CoTAPc/SF and H2O2 dosages. Further, the catalytic oxidation process of ARG was determined, and the possible degradation mechanism of ARG has been discussed. Our results suggest that the composite materials with high catalytic activity can provide a reference for future Fenton-like catalytic systems.

Vilsmeier-Haack reagent-promoted formyloxylation of α-chloro-N-arylacetamides by formamide

Huang, Jiann-Jyh,Lu, Shi-Han,Chung, Yu Hsuan,Wong, Fung Fuh

, p. 35934 - 35939 (2015)

In this study, a Vilsmeier-Haack reagent-promoted formyloxylation of α-chloro-N-arylacetamides by formamide was developed. The reaction successfully provided the desired α-formyloxy-N-arylacetamides 4 and 7a-n in moderate to excellent yields (70-96%) by use of 3.0 equivalents of PBr3 at 80-90 °C and was applicable to substrates bearing electron-donating or withdrawing groups at the aryl moiety. For α-chloro-N-(naphthalenyl)acetamide (8a), α-chloro-N-(quinolin-8-yl)acetamide (8b), and α-chloro-N-(thiazol-2-yl)acetamide (8c) possessing the α-chloro group, the reaction also provided the desired formyloxylated products 9a-c in 70-87% yields. A plausible mechanism was proposed through the activation of α-chloroacetamide by the Vilsmeier-Haack reagent to account for the new transformation.

Preparation of NiO Nanocatalyst Supported on MWCNTs and Its Application in Reduction of Nitrobenzene to Aniline in Liquid Phase

Hashemi, Majid,Khodaei, Mohammad Mehdi,Teymouri, Mohammad,Rashidi, Alimorad,Mohammadi, Hadi

, p. 959 - 967 (2016)

In this research NiO nanoparticles supported on multiwalled carbon nanotubes (MWCNTs) and activated carbon were prepared and applied as nanocatalyst in hydrogenation of nitrobenzene (NB) to aniline (AN). The nanocatalysts were prepared via homogenous depo

o-Phenylenediamine from sulfur, ammonia, and cyclohexane

Weigert

, p. 1936 - 1937 (1981)

-

Preparation, structural characterization of a novel egg-shell palladium sulfide catalyst and its application in selective reductive alkylation reaction

Zhang, Qun Feng,Wu, Jia Chun,Su, Chang,Feng, Feng,Ding, Qiao Ling,Yuan, Zhao Lian,Wang, Hong,Ma, Lei,Lu, Chun Shan,Li, Xiao Nian

, p. 1111 - 1114,4 (2012)

A novel egg-shell Pd-S catalyst with palladium metal as the core and a membrane of palladium sulfide as the surface has been prepared by sulphidizing Pd/C with H2S. This catalyst is effective for the reductive alkylation of p-amino diphenylamine (PADPA) and methylisobutyl ketone (MIBK) to afford N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenedianine (DBPPD) with conversion up to 99.42% and selectivity to 97.46%. Comparing with the other common palladium sulfide catalysts, the membrane of palladium sulfide on the surface and the core of palladium metal cause the Pd on the surface of the new catalyst in a lower sulfur coordination, which improves its activity. Our result indicates that this new egg-shell Pd-S/C is an efficient hydrogenation catalyst.

METAL-ASSISTED REACTIONS. PART 24: THE IMPORTANCE OF SOLVENTS IN LIQUID-PHASE HETEROGENEOUS CATALYTIC TRANSFER REDUCTION

Brigast, Amadeu F.,Johnstone, Robert A. W.

, p. 7735 - 7746 (1992)

In liquid-phase catalytic transfer reduction in which a hydrogen donor is used to effect hydrogenation of a substrate, reaction often proceeds sluggishly in single phase solvents but goes rapidly in biphasic solvent systems in which the catalyst usually resides in one or other of the phases.Depending on the nature of the substrate and donor, an excess of either can lead to the catalyst surface becoming saturated with one component, thereby preventing reaction.It is shown that the biphasic solvent system is, in practice, a simple means of controlling access to the catalyst by either the substrate or donor such that both are present on the surface in comparable amounts, leading to optimum or near optimum reaction rates.

Preparation and reactivity of UV light-reduced Pd/α-Fe2O3 catalyst towards the hydrogenation of o-chloronitrobenzene

Jiang, Weidong,Xu, Bin,Xiang, Zhen,Liu, Xiaoqiang,Liu, Fuan

, p. 65 - 72 (2016)

A type of Pd/α-Fe2O3 catalyst was synthesized by a convenient UV light-induced reduction in the presence of Fe3+ ions. The synthesized Pd/α-Fe2O3 particles were characterized by X-ray diffraction (XRD), low-resolution transmission electron microscopy (TEM), high-resolution transmission electron microscopy (HR-TEM), X-ray photoelectron spectrum (XPS), atomic force microscope (AFM), scan electron microscopy with energy dispersion spectra (SEM-EDS), FT-IR and BET. Related characterizations confirm that UV light-induced reduction is a feasible, simply and environment-friendly method for the preparation of supported catalysts containing active metal. Furthermore, hydrogenation of o-chloronitrobenzene (o-CNB) to o-chloroaniline (o-CAN) by the selected Pd(0.5%)/α-Fe2O3 was investigated systematically. The α-Fe2O3-supported Pd catalyst was found to exhibit good catalytic activity and selectivity for the o-CNB reduction under mild conditions. The hydrogenation of o-CNB over the resulting Pd-based catalyst gave a 100% o-CNB conversion and 91.4% selectivity of o-CAN under the reaction conditions of 50 °C, 2 h, 1 MPa hydrogen pressure, no-CNB/nPd = 6000:1. Moreover, the resulting Pd-based catalyst remained higher hydrogenation reactivity after three runs even if a sharply decrease in activity was observed at the fourth run. The obtained results reveal the as-prepared Pd/α-Fe2O3 is an efficient catalyst for the hydrogenation of o-CNB even at a high level of substrate concentration.

NN bond cleavage of azobenzene: Via photocatalytic hydrogenation with Dy-doped Zn(O,S): The progress from hydrogen evolution to green chemical conversion

Abdullah, Hairus,Kuo, Dong-Hau,Gultom, Noto Susanto

, p. 2651 - 2663 (2019)

Hydrogen-evolved Dy-doped Zn(O,S) photocatalysts with different amounts of Dy precursor have been synthesized, characterized and further utilized for hydrogenation reactions. The Dy catalysts are first examined using electrochemical impedance spectroscopy, photo responsivity, and the hydrogen evolution reaction. Dy-doped Zn(O,S) with 10% Dy precursor shows the best photocatalyst performance with the highest H2 production rate of 8.160 mmol g-1 h-1. This catalyst is chosen for conducting the hydrogenation reaction. It is our intention to confirm the correlation between the photocatalytic H2 production rate and the hydrogenation reactions of 4-nitrophenol to 4-aminophenol and azobenzene to aniline, which is a step further in the hydrogenation reaction to challenge the NN bond cleavage of azobenzene. A 100% photo conversion of 60 ppm azobenzene to aniline in 6 h was confirmed under a low-power UV light illumination in a 10% ethanol solution. Kinetic steps and kinetic mechanisms are proposed, which involve the important reaction steps of solvation, adsorption, pinning, and surface hydrogenation reaction operating together.

Hill, A. E.,Macey, R.

, p. 1132 - 1150 (1924)

7-Bromo-5-phenyl-1,2-dihydro-3H-1,3,5-benztriazepin-2-one

Vlasiuk,Pavlovsky,Andronati,Gdaniec,Simonov

, p. 1077 - 1085 (2000)

7-Bromo-5-phenyl-1,2-dihydro-3H-1,4-benztriazepin-2-one was obtained by thermolysis of the syn-4-phenylsemicarbazone of 2-aminobenzophenone. Its molecular and crystal structure were established by X-ray crystallography. The nature of the hydrogen bonds be

Direct amination of benzene to aniline by reactive distillation method over copper doped hierarchical TS-1 catalyst

Yu, Tianhua,Zhang, Qian,Xia, Sheng,Li, Guiying,Hu, Changwei

, p. 639 - 647 (2014)

We report an effective method for the direct amination of benzene to aniline where aqueous ammonia was employed as aminating agent with hydrogen peroxide as oxidant and copper doped hierarchical TS-1 as catalyst, using a reactive distillation reactor under mild conditions. A desirable aniline yield (12.4%) with excellent selectivity (84.7%) was obtained under optimized conditions. A probable catalytic pathway of benzene ammoxidation to aniline over hierarchical TS-1 or metal doped hierarchical TS-1 was proposed.

Study of dehalogenation of halogenoanilines using Raney Al-Ni alloy in aqueous medium at room temperature

Weidlich, Tomas,Krejcova, Anna,Prokes, Lubomir

, p. 1015 - 1020 (2010)

Dehalogenation of halogenated anilines by action of powdered aluminium-nickel alloy in aqueous alkaline solution at room temperature has been studied. The reaction course was monitored by means of1H nuclear magnetic resonance (NMR) spectroscopy. The rates of dehalogenation of 4-bromo-, 4-chloro-, 4-fluoro-and 3-chloroaniline were compared under conditions of minimum necessary excess of Al-Ni alloy as reducing agent in edetane buffer medium at pH 10.9. The dehalogenation rates of halogenated anilines decreased in the following order: 3-chloroaniline > 4-bromoaniline ≥ 4-chloroaniline >4-fluoroaniline. On the basis of the results obtained in buffers, the dehalogenation method of aqueous solutions of halogenoanilines was verified using NaOH as the base. Springer-Verlag 2010.

Synthesis, characterization and catalytic activity of copper incorporated and immobilized mesoporous MCM-41 in the single step amination of benzene

Parida,Rath, Dharitri,Dash

, p. 85 - 93 (2010)

The paper reports the synthesis, surface and textural characterization of copper and amine modified MCM-41 and its application for the single step amination of benzene to aniline at 70 °C. Varying the amount of Cu different Cu/amine modified MCM-41 samples was synthesized by co-condensation and impregnation method. The samples were characterized by nitrogen adsorption-desorption, X-ray powder diffraction, Fourier-transform infrared spectroscopy (FT-IR), 29Si magic-angle spinning (MAS) and 13C Nuclear Magnetic Resonance (NMR) and UV-vis diffuse reflectance spectroscopy (UV-vis DRS). X-ray diffraction patterns indicate that the modified materials retain the standard MCM-41 structure. FT-IR and DRS results indicated that Cu and amino groups are incorporated into the Si-O framework and frame wall respectively. NMR showed higher degree of condensation of materials in framework position. Cu-amine-MCM-41 samples showed significant catalytic activity for single step amination of benzene in acetic acid-water medium under mild reaction conditions using hydroxylamine as aminating agent. The Cu-amine-MCM-41 (Si/Cu = 20) showed highest benzene conversion (72.2%) and 100% selectivity for aniline.

Synthesis of palladium nanoparticles over graphite oxide and carbon nanotubes by reduction in ethylene glycol and their catalytic performance on the chemoselective hydrogenation of para-chloronitrobenzene

Dongil,Pastor-Pérez,Fierro,Escalona,Sepúlveda-Escribano

, p. 89 - 97 (2016)

Pd nanoparticles have been synthesized over carbon nanotubes (CNT) and graphite oxide (GO) by reduction with ethylene glycol and by conventional impregnation method. The catalysts were tested on the chemoselective hydrogenation of p-chloronitrobenzene and the effect of the synthesis method and surface chemistry on their catalytic performance was evaluated. The catalysts were characterized by N2 adsorption/desorption isotherms at 77 K, TEM, powder X-ray diffraction, thermogravimetry, infrared and X-ray photoelectron spectroscopy and ICP-OES. It was observed that the synthesis of Pd nanoparticles employing ethylene glycol resulted in metallic palladium particles of smaller size compared to those prepared by the impregnation method and similar for both supports. The presence of oxygen groups on the support surface favored the activity and diminished the selectivity. It seems that ethylene glycol reacted with the surface groups of GO, this favoring the selectivity. The activity was higher over the CNT-based catalysts and both catalysts prepared by reduction in ethylene glycol were quite stable upon recycling.

Physicochemical properties of 4,5-(aryl,alkyl)-3-substituted 2-aminothiophenes sulfonyl derivatives

Chekanova,Manylova,Pavlov,Vasyanin,Shurov,Maiorova

, (2017)

Physicochemical properties of 4,5-(aryl, alkyl)-3-substituted 2-sulfonylaminothiophenes have been studied. The effect of the nature of the substituents in the thiophene ring on acid-base properties, solubility, and chemical stability was investigated.

-

Cann et al.

, p. 3969 (1978)

-

Reactivity of phenyl N-phenylcarbamates in the alkaline hydrolysis reaction

Nalbantova, Didi,Cheshmedzhieva, Diana,Hadjieva, Boriana,Ilieva, Sonia,Galabov, Boris

, p. 1166 - 1171 (2011)

In the present study, we explore the application of several theoretically estimated indices that characterize the reactivity of a series of phenyl N-phenylcarbamates in the alkaline hydrolysis reaction. The rate constants (at 25°C) for the hydrolysis of several derivatives were spectrophotometrically determined. The obtained kinetic data in this study, combined with literature data for other derivatives, were then correlated with theoretically estimated reactivity indices: Hirshfeld and NBO atomic charges, the Parr electrophilicity index (ω), and the electrostatic potential at the carbon and oxygen atoms of the reaction centre (VC, VO). The predictive ability of these quantities is discussed in a comparative context. Copyright

Functionalization of a plasmonic Au/TiO2 photocatalyst with an Ag co-catalyst for quantitative reduction of nitrobenzene to aniline in 2-propanol suspensions under irradiation of visible light

Tanaka, Atsuhiro,Nishino, Yuri,Sakaguchi, Satoshi,Yoshikawa, Takayuki,Imamura, Kazuya,Hashimoto, Keiji,Kominami, Hiroshi

, p. 2551 - 2553 (2013)

A functionalized plasmonic Au/TiO2 photocatalyst with an Ag co-catalyst was successfully prepared by the combination of two types of photodeposition methods, and it quantitatively converted nitrobenzene and 2-propanol to aniline and acetone under irradiation of visible light.

-

Aono

, p. 169,172 (1930)

-

Kinetics of the hydrogenation of a mixture of nitrobenzene and azoxybenzene on skeletal nickel in an aqueous solution of propan-2-ol

Merkin,Latypova,Kha, Nguen Tkhi Tkhu,Lefedova

, p. 1772 - 1775 (2015)

The sequence of the reduction of nitro and azoxy groups in the combined hydrogenation of nitrobenzene and azoxybenzene on skeletal nickel in an aqueous azeotropic solution of propan-2-ol is considered. The time dependences of the rates and concentrations of the initial compound and reaction product for the hydrogenation of individual compounds (nitrobenzene and azoxybenzene) in the solvent of the indicated composition are discussed for comparative analysis. In all cases, the reactions proceed selectively to aniline without accumulating side products. The reduction of the nitro and azoxy groups involves hydrogen bound by the active sites of the catalyst surface. The competitive character of adsorption between the initial compounds and formed aniline is observed. Nitrobenzene is characterized by the highest adsorbability, whereas azoxybenzene and aniline are less adsorbable.

REACTION OF TETRACYANOCOBALTATE(I) WITH ARYL HALIDES. FORMATION OF ?-ARYLPENTACYANOCOBALTATES AND CYANATION TO ARYL CYANIDES

Funabiki, Takuzo,Nakamura, Hitoshi,Yoshida, Satohiro

, p. 95 - 100 (1983)

Tetracyanocobaltate(I), which is formed in strongly alkaline solutions of cyanocobaltate under H2 at Cn:Co 5;1, reacts readily with aryl halides to form ?-arylpentacyanocobaltates(III). 1H and 13C NMR spectra of these new and fairly stable complexes have been determined.In the reactions of some aryl halides, aryl cyanides as well as hydrogenolysis products are formed, and α-bromonaphthalene reacts selectively to give the highest yield of the nitrile.The reactions are explained by a mechanism involving an electron-transfer process.

Palladated composite of Cu-BDC MOF and perlite as an efficient catalyst for hydrogenation of nitroarenes

Koohestani, Fatemeh,Sadjadi, Samahe

, (2021/11/04)

A novel composite of metal-organic framework and perlite is prepared through hydrothermal treatment of terephthalic acid and Cu(NO3)2·3H2O in the presence of perlite. The resulting composite was then utilized as a support for the immobilization of Pd nanoparticles. The obtained compound was characterized via XRD, TGA, ICP, FTIR, TEM, FE-SEM/EDS and elemental mapping analysis and applied as a catalyst for the hydrogenation of nitroarenes under mild reaction condition. The results approved that the catalyst could efficiently promote hydrogenation of various nitroarenes with different electronic densities and steric properties. Moreover, the catalyst showed high selectivity towards hydrogenation of nitro groups. Hot filtration test affirmed heterogeneous nature of catalysis. Furthermore, the present catalytic composite was highly recyclable with low Pd leaching. A comparative study also approved superior activity of the composite compared to palladated perlite and metal-organic framework.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter

supporting information, p. 133 - 146 (2021/11/04)

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions

Nannapaneni, Madhavi,Pendem, Venkata Bhavanarushi,Tamminana, Ramana

, (2022/01/12)

The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized reaction conditions to provide their respective target products in good to excellent yields. Furthermore, we have confirmed that no other by-products could be identified during our experimental reaction process. Graphical abstract: Iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology.[Figure not available: see fulltext.].

Simultaneous synthesis of aniline and γ-butyrolactone from nitrobenzene and 1,4-butanediol over Cu-CoOx-MgO catalyst via catalytic hydrogen transfer process: Effect of calcination temperature

Kannapu, Hari Prasad Reddy,Park, Young-Kwon,Vaddeboina, Veeralakshmi

, (2022/01/26)

This study examined a hydrogen transfer reaction from 1,4-butanediol to nitrobenzene for γ-butyrolactone and aniline simultaneously over Cu-CoOx-MgO catalysts. The catalyst was developed by co-precipitation followed by metal hydroxycarbonate mixing and calcination at three different temperatures (500, 700, and 900 °C). The hydrogenation of nitrobenzene to aniline and the dehydrogenation of 1,4-butanediol to γ-butyrolactone was accomplished in a gas-phase fixed-bed continuous reactor system at 250 °C. The catalyst Cu-CoOx-MgO-500 calcined at 500 °C showed outstanding performance because of the higher copper dispersion and negligible spinel species (CuCo2O4 /MgCo2O4) compared to the other two catalysts. The order of activity decreased with increasing calcination temperature from 500° to 900°C. The activity trend followed the order, Cu-CoOx-MgO-500 > Cu-CoOx-MgO-700 > Cu-CoOx-MgO-900. The effect of calcination on the catalytic properties was analyzed by atomic absorption spectroscopy elemental analysis, Brunauer-Emmett-Teller surface area, N2O pulse chemisorption, temperature-programmed reduction-H2, X-ray diffraction, and X-ray photoelectron spectroscopy. The results showed that Cu-CoO-MgO-500 exhibited more active copper sites (Cu0/Cu+1) and optimal metal-support interactions that decrease the reduction temperature of copper. On the other hand, Cu-Co and Mg-Co spinel (CuCo2O4/MgCo2O4) content, which adversely affects the catalyst activity, increased with increasing calcination temperature. In summary, simultaneous hydrogenation and dehydrogenation reactions via hydrogen transfer reactions have potential commercial applications.

2-(4-Nitrophenyl)-1H-indolyl-3-methyl Chromophore: A Versatile Photocage that Responds to Visible-light One-photon and Near-infrared-light Two-photon Excitations

Abe, Manabu,Guo, Runzhao,Hamao, Kozue,Lin, Qianghua,Takagi, Ryukichi

supporting information, p. 153 - 156 (2022/02/14)

Due to cell damage caused by UV light, photoremovable protecting groups (PPGs) that are removed using visible or near-infrared light are attracting attention. A 2-(4-nitrophenyl)- 1H-indolyl-3-methyl chromophore (NPIM) was synthesized as a novel PPG. Various compounds were caged using this PPG and uncaged using visible or near-infrared light. Low cytotoxicity of NPIM indicates that it may be applied in physiological studies.

Process route upstream and downstream products

Process route

p-nitrophenylbenzotriazene
13113-75-2

p-nitrophenylbenzotriazene

Benzenesulfinic acid
618-41-7

Benzenesulfinic acid

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

aniline
62-53-3

aniline

phenylazo phenyl sulfone
14922-16-8

phenylazo phenyl sulfone

Conditions
Conditions Yield
methanol
67-56-1

methanol

4-nitrophenyl N-phenylbenzimidate
87775-62-0

4-nitrophenyl N-phenylbenzimidate

aniline
62-53-3

aniline

orthobenzoic acid trimethyl ester
707-07-3

orthobenzoic acid trimethyl ester

Conditions
Conditions Yield
With hydrogenchloride; at 25 ℃; Product distribution; Rate constant; Mechanism;
<i>N</i>-pyrrol-2-ylmethylene-aniline
4089-09-2

N-pyrrol-2-ylmethylene-aniline

2-pyrrole aldehyde
1003-29-8,254729-95-8

2-pyrrole aldehyde

aniline
62-53-3

aniline

Conditions
Conditions Yield
With hydrogenchloride; In methanol; water; at 25 ℃; Rate constant; Mechanism; pH=0.65-13.5, buffers, aq.NaOH;
ethyl 2-(N-phenylamino)-1-cyclopentene-1-carboxylate
52909-66-7

ethyl 2-(N-phenylamino)-1-cyclopentene-1-carboxylate

2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

aniline
62-53-3

aniline

Conditions
Conditions Yield
With water; at 25 ℃; Rate constant; Mechanism; presence and absence of various enzyme systems; pH range: 1-9;
N-(2,4-Dinitro-phenyl)-N'-phenyl-acetamidine
128915-26-4

N-(2,4-Dinitro-phenyl)-N'-phenyl-acetamidine

2,4-dinitroacetanilide
610-53-7

2,4-dinitroacetanilide

aniline
62-53-3

aniline

Conditions
Conditions Yield
With acetic acid; In water; at 25 ℃; Rate constant;
4-nitrophenyl N-phenylbenzimidate
87775-62-0

4-nitrophenyl N-phenylbenzimidate

N-phenyl benzoyl amide
93-98-1,5705-51-1

N-phenyl benzoyl amide

p-nitrophenylbenzoate
959-22-8

p-nitrophenylbenzoate

aniline
62-53-3

aniline

Conditions
Conditions Yield
With water; In tetrahydrofuran; at 25 ℃; Product distribution; Rate constant; var. acid concentration, var. solvents;
cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

aniline
62-53-3

aniline

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

cyclohexanol
108-93-0

cyclohexanol

Conditions
Conditions Yield
With ammonia; palladium on activated charcoal; at 250 ℃; for 3h; Product distribution;
68 % Chromat.
18 % Chromat.
3.8 % Chromat.
0.7 % Chromat.
cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexanone N-cyclohexylimine
10468-40-3

cyclohexanone N-cyclohexylimine

diphenylamine
122-39-4

diphenylamine

aniline
62-53-3

aniline

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
chromium; silica gel; nickel; copper; sodium sulfate; at 390 ℃; Product distribution; Mechanism; other volume flow rate;
40.0 % Chromat.
16.5 % Chromat.
5.0 % Chromat.
18.0 % Chromat.
C<sub>17</sub>H<sub>18</sub>N<sub>2</sub>
54683-47-5

C17H18N2

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

8-methylquinoline
611-32-5

8-methylquinoline

aniline
62-53-3

aniline

<i>o</i>-toluidine
95-53-4

o-toluidine

Conditions
Conditions Yield
at 850 ℃; for 3h; under 0.003 Torr; Further byproducts given;
1-(benzyloxy)-1H-benzo[d][1,2,3]triazole
68930-15-4

1-(benzyloxy)-1H-benzo[d][1,2,3]triazole

1,2,3-Benzotriazole
95-14-7,27556-51-0

1,2,3-Benzotriazole

cyclohexylcyclohexane
92-51-3

cyclohexylcyclohexane

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

Azobenzene
1227476-15-4

Azobenzene

Conditions
Conditions Yield
for 8h; Product distribution; Irradiation;
14%
10%
4%
9%
53%
23%

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