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Cas Database

106-49-0

106-49-0

Identification

  • Product Name:p-Toluidine

  • CAS Number: 106-49-0

  • EINECS:203-403-1

  • Molecular Weight:107.155

  • Molecular Formula: C7H9N

  • HS Code:38220000

  • Mol File:106-49-0.mol

Synonyms:1-Amino-4-methylbenzene;4-Aminotoluene;4-Methyl-1-aminobenzene;4-Methylaniline;4-Methylbenzenamine;4-Methylphenylamine;4-Toluidine;4-Tolylamine;Benzenamine,4-methyl-;C.I. Azoic Coupling Component 107;Naphthol AS-KG;Naphtol AS-KG;Naphtol AS-KGLL;p-Aminotoluene;p-Methylaniline;p-Methylbenzenamine;p-Methylphenylamine;p-Tolylamine;DHET;Para Toluidine;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT,DangerousN

  • Hazard Codes: T:Toxic;

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH311 Toxic in contact with skin H319 Causes serious eye irritation H317 May cause an allergic skin reaction H331 Toxic if inhaled 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. Artificial respiration may be needed. Refer immediately for medical attention. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention. In case of eye contact Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention. If swallowed Rinse mouth. Refer immediately for medical attention. Absorption of toxic quantities by any route causes cyanosis (blue discoloration of lips, nails, skin); nausea, vomiting, and coma may follow. Repeated inhalation of low concentrations may cause pallor, low-grade secondary anemia, fatigability, and loss of appetite. Contact with eyes causes irritation. (USCG, 1999) 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 fine spray or fog to control fire by preventing its spread and absorbing some of its heat. Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Special Hazards of Combustion Products: Toxic and flammable vapors may form in fire. (USCG, 1999) 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. Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Approach release from upwind. Stop or control the leak, if this can be done without undue risk. Use water spray to cool and disperse vapors and protect personnel. Control runoff and isolate discharged material for proper disposal.

  • 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. Provision to contain effluent from fire extinguishing. Separated from strong oxidants, strong acids and food and feedstuffs. Well closed. Ventilation along the floor. Keep in the dark. Store in an area without drain or sewer access.Store in cool, dry, well-ventilated location. Store away from heat, oxidizers, and sunlight.

  • Exposure controls/personal protection:Occupational Exposure limit valuesNIOSH considers p-toluidine 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

Supplier and reference price

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  • Manufacture/Brand:AK Scientific
  • Product Description:4-Aminotoluene
  • Packaging:1g
  • Price:$ 14
  • Delivery:In stock
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  • Manufacture/Brand:AK Scientific
  • Product Description:4-Aminotoluene
  • Packaging:25g
  • Price:$ 37
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  • Manufacture/Brand:AK Scientific
  • Product Description:4-Aminotoluene
  • Packaging:100g
  • Price:$ 40
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:p-Toluidine, 99+%
  • Packaging:1000g
  • Price:$ 52.4
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:p-Toluidine, 99+%
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:p-Toluidine, 99+%
  • Packaging:5000g
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:PARA-TOLUIDINE 95.00%
  • Packaging:10G
  • Price:$ 1183.88
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:PARA-TOLUIDINE 95.00%
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  • Manufacture/Brand:Azepine
  • Product Description:p-Toluidine 98
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  • Manufacture/Brand:Azepine
  • Product Description:p-Toluidine 98
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Relevant articles and documentsAll total 612 Articles be found

Zeolite-Catalyzed Isomerization of Aromatic Amines to Methyl-Aza-Aromatics

Stamm, T.,Kouwenhoven, H. W.,Seebach, D.,Prins, R.

, p. 268 - 282 (1995)

The scope and mechanism of the isomerization of arylamines to methyl-substituted aromatic heterocycles have been studied.Aniline, toluidines, naphthylamines and m-phenylenediamine all reacted to the corresponding ortho-methyl-substituted aza-aromatiics when exposed to high NH3 pressure and elevated temperature in the presence of acid catalysts.Zeolites with a three-dimensional pore structure, especially H-ZSM-5, showed the best performance.Optimum reaction conditions are around 600 K and 10 MPa.Two mechanisms which had been proposed earlier for this apparent N-ortho C exchange reaction proved untenable.Neither incorporation of the N atom into the aromatic ring nor a mechanism based on an intramolecular Ritter reaction could explain the required high NH3 pressure or the product distribution.Two new mechanisms are proposed which can explain all observations.In both mechanisms, reaction starts with addition of NH3 to the arylamine, followed by ring opening.In one mechanism an alkyno-imine intermediate is formed; in the other mechanism an enamino-imine intermediate is formed through a reverse aldol reaction.In both cases ring closure and NH3 elimination lead to the required aromatic heterocycles.The high NH3 pressure is explained by the need to add NH3 to the aromatic ring, and the high temperature by the need to desorb NH3 from the acid sites.

Jacobson

, p. 13 (1909)

-

Campbell

, p. 4019 (1951)

-

Copper-catalysed reductive amination of nitriles and organic-group reductions using dimethylamine borane

Van Der Waals, Dominic,Pettman, Alan,Williams, Jonathan M. J.

, p. 51845 - 51849 (2014)

A heterogeneous copper catalyst, formed in situ, has been shown to dehydrocouple commercially available amine boranes whilst transferring hydrogen for the reduction of selected organic functional groups in an aqueous medium. The catalytic system has also been shown to promote the reductive amination of aryl nitriles. This journal is

Microbial deoxygenation of N-oxides with Baker's yeast-NaOH

Baik, Woonphil,Kim, Dong Ik,Koo, Sangho,Rhee, Jong Uk,Shin, Sung Hee,Kim, Byeong Hyo

, p. 845 - 848 (1997)

The microbial deoxygenation of a series of aromatic and heteroaromatic N-oxide compounds, including quinoline N-oxides, isoquinoline N-oxides, 2-aryl-2H-benzotriazole 1-oxides, benzo[c]cinnoline N-oxide and azoxybenzenes, has been performed with bakers'yeast-NaOH.

Intermetallic Nanocatalysts from Heterobimetallic Group 10-14 Pyridine-2-thiolate Precursors

Adamson, Marquix A. S.,Chen, Yunhua,Daniels, Carena L.,Dorn, Rick W.,Fan, Huajun,Knobeloch, Megan,Rossini, Aaron J.,Vela, Javier,Wu, Hao,Yox, Philip,Zhou, Guoquan

, (2020)

Intermetallic compounds are atomically ordered inorganic materials containing two or more transition metals and main-group elements in unique crystal structures. Intermetallics based on group 10 and group 14 metals have shown enhanced activity, selectivity, and durability in comparison to simple metals and alloys in many catalytic reactions. While high-temperature solid-state methods to prepare intermetallic compounds exist, softer synthetic methods can provide key advantages, such as enabling the preparation of metastable phases or of smaller particles with increased surface areas for catalysis. Here, we study a generalized family of heterobimetallic precursors to binary intermetallics, each containing a group 10 metal and a group 14 tetrel bonded together and supported by pincer-like pyridine-2-thiolate ligands. Upon thermal decomposition, these heterobimetallic complexes form 10-14 binary intermetallic nanocrystals. Experiments and density functional theory (DFT) computations help in better understanding the reactivity of these precursors toward the synthesis of specific intermetallic binary phases. Using Pd2Sn as an example, we demonstrate that nanoparticles made in this way can act as uniquely selective catalysts for the reduction of nitroarenes to azoxyarenes, which highlights the utility of the intermetallics made by our method. Employing heterobimetallic pincer complexes as precursors toward binary nanocrystals and other metal-rich intermetallics provides opportunities to explore the fundamental chemistry and applications of these materials.

Electrophilic amination of methylbenzenes with sodium azide in trifluoromethanesulfonic acid

Borodkin,Elanov,Shubin

, p. 934 - 935 (2009)

-

Carlin,Wich

, p. 4023,4025 (1958)

Simple and efficient reduction of aromatic nitro compounds using recyclable polymer-supported formate and magnesium

Abiraj, Keelara,Srinivasa, Gejjalagere R.,Gowda, D. Channe

, p. 149 - 151 (2005)

Aromatic nitro compounds were chemoselectively reduced to the corresponding amines using recyclable polymer-supported formate as a hydrogen donor in the presence of low-cost magnesium powder at room temperature. Use of the immobilized hydrogen donor affords the product amine in excellent yield (90-97%) without the need for any Chromatographic purification steps. This method was found to be highly facile with selectivity over several other functional groups, such as halogen, alkene, nitrile, carbonyl, ester, amide, methoxy, phenol, and hydroxyl groups. CSIRO 2005.

Process development of 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline dihydrochloride: A key intermediate for TAK-779, a small-molecule nonpeptide CCR5 antagonist

Hashimoto, Hideo,Ikemoto, Tomomi,Itoh, Tatsuya,Maruyama, Hideaki,Hanaoka, Tadashi,Wakimasu, Mitsuhiro,Mitsudera, Hiroyuki,Tomimatsu, Kiminori

, p. 70 - 73 (2002)

A new and efficient synthesis of 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline dihydrochloride, a key intermediate for the CCR5 antagonist TAK-779, is described. Reductive alkylation of methylamine with tetrahydro-4H-pyran-4-one followed by alkylation of N-methyl-N-(tetrahydropyran-4-yl)amine with 4-nitrobenzylbromide and reduction of N-(4-nitrobenzyl)-N-(tetrahydropyran-4-yl)amine results in a 78% isolated yield from the starting materials by a scalable method, using only commercially available reagents.

-

Keller,Smith

, p. 1122 (1944)

-

Rapid, efficient and selective reduction of aromatic nitro compounds with hydrazine hydrate in the presence of the plain and supported platinum nanoparticles as catalysts

Mehdizadeh, Soofia,Ahmadi, Seyed Javad,Sadjadi, Sodeh,Outokesh, Mohammad

, p. 1587 - 1592 (2014)

The current study aimed at application of the plain and supported platinum nanoparticles as a heterogenous catalyst for the reduction of aromatic nitro compounds. Monodispersed platinum nanoparticles were synthesized by reduction of H2PtCl6 by ethanol in the presence of polyvinyl pyrrolidone as a stabilizer, and then were immobilized on four types of zeolites. The obtained catalyst granules were characterized by X-ray diffractometry and transmission electron microscopy. The study then focused on elaboration of the catalytic activity of the nano catalysts under different operational conditions. It was found that reaction is adequately rapid at ambient temperature, and by utilizing a sufficient amount of catalyst, can be completed in nearly 30 min. Among the utilized zeolitic supports, zeolite 4A had the highest performance, but the mechanism of its synergetic effect on the activity of platinum nano catalyst was not found and requires more investigation.

-

Brown,Etzel,Henke

, p. 635 (1928)

-

Sodium dithionite reduction of nitroarenes using viologen as an electron phase-transfer catalyst

Park, Kwanghee Koh,Oh, Chang Hun,Joung, Won Kyou

, p. 7445 - 7446 (1993)

Various aromatic nitro compounds were reduced conveniently to the corresponding aniline derivatives with sodium dithionite using dioctyl viologen as an electron-transfer catalyst in dichloromethane- water two-phase system.

Mild and general procedure for Pd/C-catalyzed hydrodechlorination of aromatic chlorides

Sajiki, Hironao,Kume, Akira,Hattori, Kazuyuki,Hirota, Kosaku

, p. 7247 - 7250 (2002)

A mild and efficient one-pot hydrodechlorination using a Pd/C-Et3N system proceeds at room temperature, which is general for the dechlorination of a variety of aromatic chlorides.

GRAPHITE CATAlYZED REDUCTION OF AROMATIC AND ALIPHATIC NITRO COMPOUNDS WITH HYDRAZINE HYDRATE

Han, Byung Hee,Shin, Dae Hyun,Cho, Sung Yun

, p. 6233 - 6234 (1985)

Aromatic and aliphatic nitro compounds were readily reduced to amino compounds in excellant yields with graphite and hydrazine hydrate.

Metal-assisted lossen rearrangement

Jasikova, Lucie,Hanikyrova, Eva,Skriba, Anton,Jasik, Juraj,Roithova, Jana

, p. 2829 - 2836 (2012)

A new reaction mechanism for the Lossen rearrangement of hydroxamic acids catalyzed by basic salts is presented. It is shown that the rearrangement proceeds in metal complexes of deprotonated hydroxamic acids. The deprotonation can occur either at the oxygen atom (observed for the zinc complexes) or at the nitrogen atom (observed for the potassium complexes). Both anionic forms are characterized by infrared multiphoton dissociation spectroscopy. The rearrangements proceed from the reactive N-deprotonated metal hydroxamates and lead to metal carbamates. The mechanism is elucidated by computational chemistry, mass-spectrometric studies, and preparative experiments.

-

Kovacic,Bennett

, p. 221,224 (1961)

-

Rearrangement of N-Methylaniline over H-ZSM-5, H-Theta-1, and H-Y Zeolites

Mordi, Raphael C.,Dwyer, John,Fields, Roy

, p. 627 - 630 (1993)

-

-

Ogata et al.

, p. 2399 (1979)

-

Nickel oxide nanoparticles grafted on reduced graphene oxide (rGO/NiO) as efficient photocatalyst for reduction of nitroaromatics under visible light irradiation

Al-Nafiey, Amer,Kumar, Anurag,Kumar, Malika,Addad, Ahmed,Sieber, Brigitte,Szunerits, Sabine,Boukherroub, Rabah,Jain, Suman L.

, p. 198 - 207 (2017)

Nickel oxide nanoparticles were grafted on reduced graphene oxide via simultaneous reduction of graphene oxide and nickel salt in a single step reaction. The synthesized material (rGO/NiO) was found to be efficient visible light active photocatalyst for the reduction of nitroaromatic derivatives to their corresponding amino compounds. Hydrazine monohydrate provided necessary protons and electrons for the targeted reaction. After completion of the reaction, the photocatalyst could readily be recovered by simple external magnet and could be reused for six runs without any significant loss of its activity. More importantly, the photocatalyst did not show any leaching during the reaction as confirmed by ICP-AES analysis of the recovered catalyst.

One-Pot Synthesis of Secondary Amines from Nitroarenes and Aldehydes on Supported Copper Catalysts in a Flow Reactor: The Effect of the Support

Artyukha,Nuzhdin,Bukhtiyarova,Derevyannikova,Gerasimov, E. Yu.,Gladkii, A. Yu.,Bukhtiyarov

, p. 593 - 600 (2018)

The effect of the support on the properties of copper catalysts supported on γ-Al2O3, SiO2, and TiO2–SiO2 with a ~5 wt % Cu content was studied in the one-pot synthesis of N-heptyl-p-toluidine from p-nitrotoluene and n-heptanal. The catalysts were characterized by elemental analysis, X-ray diffraction analysis, transmission electron microscopy, temperature-programmed reduction, and low-temperature nitrogen adsorption. The reaction was carried out in a flow reactor with the use of molecular hydrogen as a reducing agent. It was established that the nature of the support exerts a profound effect on the yield of the target secondary amine; in this case, 5%Cu/Al2O3 was found the most active catalyst. A combination of high catalyst activity in the hydrogenation of a nitro group to an amino group with the presence of acid sites, which facilitate imine formation as a result of the interaction of n-heptanal with p-toluidine, on the catalyst surface is necessary for reaching the greatest yield of N-heptyl-p-toluidine. The study of reaction mechanism on the 5%Cu/Al2O3 catalyst showed that p-nitrotoluene inhibits the hydrogenation of n-heptanal, and aldehyde hydrogenation into alcohol begins only after the conversion of the major portion of p-nitrotoluene as a result of the selective adsorption of the nitroarene under the conditions of the simultaneous presence of p-nitrotoluene and n-heptanal in the reaction mixture.

Photocatalytic formation of a carbamate through ethanol-assisted carbonylation of p-nitrotoluene

Maldotti, Andrea,Amadelli, Rossano,Samiolo, Luca,Molinari, Alessandra,Penoni, Andrea,Tollari, Stefano,Cenini, Sergio

, p. 1749 - 1751 (2005)

The nitroarene p-nitrotoluene is converted with a selectivity higher than 85% to the corresponding carbamate at room temperature and atmospheric pressure, using photoexcited particles of TiO2 as catalyst and EtOH as carbonylating species. The Royal Society of Chemistry 2005.

Beard,Hodgson

, p. 4 (1944)

Nanocrystalline Pt-CeO2 as an efficient catalyst for a room temperature selective reduction of nitroarenes

Shukla, Astha,Singha, Rajib Kumar,Sasaki, Takehiko,Bal, Rajaram

, p. 785 - 790 (2015)

We have developed a new synthesis strategy to prepare Pt nanoparticles with size between 2 and 5 nm supported on CeO2 nanoparticles with size between 30 and 60 nm by the hydrothermal method in the presence of the surfactant cetyltrimethyl ammonium bromide (CTAB) and a polymer (PVP). It was found that the catalyst is highly active for the chemoselective hydrogenation of nitro compounds in aqueous medium in the presence of molecular hydrogen at room temperature (25 °C). The catalyst was characterized by XRD, ICP-AES, XPS, BET-surface area measurements, SEM, TEM and EXAFS. Different reaction parameters like reaction time, catalyst ratio, Pt loading etc. were studied in detail. The investigation revealed that the site of Pt plays a crucial role in the activity by favouring the reduction of nitro-compounds. The catalyst shows >99.9% conversion of nitro-compounds with 99% selectivity of amino compounds. The reusability of the catalyst was tested by conducting the experiment with the same catalyst and it was found that the catalyst does not change its activity and selectivity even after five reuses. This journal is

Mesoporous Au-TiO2 nanoparticle assemblies as efficient catalysts for the chemoselective reduction of nitro compounds

Tamiolakis, Ioannis,Fountoulaki, Stella,Vordos, Nikolaos,Lykakis, Ioannis N.,Armatas, Gerasimos S.

, p. 14311 - 14319 (2013)

In this article, we demonstrate novel mesoporous Au-loaded TiO2 nanoparticle assemblies (Au-MTA) as high-effective catalysts for the selective transformation of nitroaromatics into the corresponding aryl amine products. These materials feature

SYNTHESIS OF METHYL-N-ARYLCARBAMATES BY THE CARBONYLATION OF AZOXY, AZO, AND NITRO COMPOUNDS

Manov-Yuvenskii, V. I.,Petrovskii, K. B.,Lapidus, A. L.

, p. 543 - 545 (1984)

-

Nitroarene reduction using Raney nickel alloy with ammonium chloride in water

Bhaumik, Kankan,Akamanchi

, p. 197 - 198 (2003)

Aromatic nitroarenes are reduced in high yields using a user-friendly combination of Raney nickel alloy and ammonium chloride in water at 80-90°C.

-

Gilman,Sternbach

, p. 465 (1971)

-

Selective Synthesis of Primary Anilines from NH3 and Cyclohexanones by Utilizing Preferential Adsorption of Styrene on the Pd Nanoparticle Surface

Koizumi, Yu,Jin, Xiongjie,Yatabe, Takafumi,Miyazaki, Ray,Hasegawa, Jun-ya,Nozaki, Kyoko,Mizuno, Noritaka,Yamaguchi, Kazuya

, p. 10893 - 10897 (2019)

Dehydrogenative aromatization is one of the attractive alternative methods for directly synthesizing primary anilines from NH3 and cyclohexanones. However, the selective synthesis of primary anilines is quite difficult because the desired primary aniline products and the cyclohexanone substrates readily undergo condensation affording the corresponding imines (i.e., N-cyclohexylidene-anilines), followed by hydrogenation to produce N-cyclohexylanilines as the major products. In this study, primary anilines were selectively synthesized in the presence of supported Pd nanoparticle catalysts (e.g., Pd/HAP, HAP=hydroxyapatite, Ca10(PO4)6(OH)2) by utilizing competitive adsorption unique to heterogeneous catalysis; in other words, when styrene was used as a hydrogen acceptor, which preferentially adsorbs on the Pd nanoparticle surface in the presence of N-cyclohexylidene-anilines, various structurally diverse primary anilines were selectively synthesized from readily accessible NH3 and cyclohexanones. The Pd/HAP catalyst was reused several times though its catalytic performance gradually declined.

Magnetically Recyclable Metal–Organic Framework@Fe3O4 Composite-Catalyzed Facile Reduction of Nitroarene Compounds in Aqueous Medium

Yang, Sen,Zhang, Zhi-Hui,Chen, Qun,He, Ming-Yang,Wang, Liang

, (2018)

A kind of Metal–organic framework (MOF) composite namely Cu-BTC@Fe3O4 (BTC?=?1,3,5-benzenetricarboxylate) was prepared and showed good catalytic activity toward the reduction of nitroarenes. This reaction proceeded smoothly under mild reaction conditions in aqueous medium using sodium borohydride as the reduction agent, affording the corresponding anilines in good to excellent yields. In addition, the catalyst could be easily recovered with an external permanent magnet and be reused for successive six runs with slight decrease in its activity.

Negishi-type coupling of bromoarenes with dimethylzinc

Herbert, John M.

, p. 817 - 819 (2004)

Treatment of bromoarenes with dimethylzinc in the presence of a palladium catalyst provides a high-yielding route to methylarenes. The process accommodates a wide range of aromatic substituents and, in the majority of cases, is free of side reactions.

-

Albisetti et al.

, p. 1489,1492 (1959)

-

SELECTIVE AND SEQUENTIAL REDUCTION OF NITROAROATICS BY MONTMORILLONITESILYLAMINEPALLADIUM(II) COMPLEX

Mukkanti, K.,Rao, Y. V. Subba,Choudary, B. M.

, p. 251 - 252 (1989)

Nitroaromatics are sequently and selectively hydrogenated in quantitative yields at room temperature and atmospheric pressure by interlamellarmontmorillonitepalladium(II) complex, a heterogenised homogenous catalyst.

Pd Nanoparticles Assembled on Metalporphyrin-Based Microporous Organic Polymer as Efficient Catalyst for Tandem Dehydrogenation of Ammonia Borane and Hydrogenation of Nitro Compounds

Zou, Zhijuan,Jiang, Yaya,Song, Kunpeng

, p. 1277 - 1286 (2020)

Abstract: Metalporphyrin-based porous polymers supporting high dispersed Pd nanoparticle (NP) catalysts (HUST-1-Pd) were prepared with a novel solvent-knitting hyper-crosslinked polymer method using 5-, 10-, 15-, and 20-tetraphenylporphyrin (TPP) as building blocks. The N2 sorption isotherms of the catalysts show that the HUST-1-Pd possesses many ultra-micropores and continuous mesopores. The NPs are assembled on tetraphenylporphyrin structures and show Pd-N4 composition-dependent catalysis for methanolysis of ammonia borane (AB) and hydrogenation of aromatic nitro compounds to primary amines in methanol solutions at room temperature. The nano-palladium reduced by NaBH4 has efficient catalytic activity for AB methanolysis. A variety of R-NO2 derivatives were reduced selectively into R-NH2 via palladium catalyzed tandem reactions with 5–30?min of reaction time with conversion yields reaching up to 90%. The derivatives also give excellent recycling performance (more than 10 times). Furthermore, the turnover frequency (TOF) can reach 87,209?h?1. The HUST-1-Pd compounds represent a unique metal catalyst for hydrogenation reactions in a green environment without using pure hydrogen. Graphic Abstract: A monodisperse Pd NPs embed in porphyrin-based microporous organic polymer was reported to catalyse the tandem dehydrogenation of ammonia borane and hydrogenation of R-NO2 to R-NH2 at room temperature. The catalyst is efficient and reusable in an environment-friendly process with short reaction times and high yields.[Figure not available: see fulltext.]

Carbonylation of nitro and azo compounds in the presence of iron carbonyl catalysts

Lapidus,Pelrovskii,Manov-Yuvenskii,Zelinsky

, p. 2331 - 2334 (1996)

The reactions of nitro and azo compounds with carbon monoxide were studied in the presence of iron carbonyl catalysts. It was shown that these catalytic systems differ substantially from Pd- and Rh-containing catalysts. In the case of the iron catalysts, the products of coupling of molecules are formed as intermediates and azo compounds are the final reaction products. The reactions involving the palladium and rhodium catalysts proceed without the intermediate formation of the coupling products and lead to isocyanates or carbamates. When combined using PdCh and Fe(CO)5/Al2Oj, the catalysts inhibit each other, especially in the presence of pyridine.

One-pot tandem catalysis over Pd@MIL-101: boosting the efficiency of nitro compound hydrogenation by coupling with ammonia borane dehydrogenation

Yang, Qihao,Chen, Yu-Zhen,Wang, Zhiyong U.,Xu, Qiang,Jiang, Hai-Long

, p. 10419 - 10422 (2015)

The hydrogenation efficiency of nitro compounds was found to be greatly boosted by coupling with dehydrogenation of ammonia borane. The Pd@MIL-101 with tiny Pd NPs is exceptionally efficient and recyclable in the tandem reactions and diverse nitro compounds can be selectively reduced to the corresponding amines in 1.5-5 min with quantitative yields.

Effect of pressure on the reaction between 3-methyl-1-p-tolyl-triazene and benzoic acid; a kinetic study

Laila, Abdulhameed,Isaacs, Neil S.

, p. 691 - 694 (1996)

Rates of reaction between 3-methyl- 1p-tolytriazene and benzoic acid were measured with variation of pressure in chloroform and acetonitrile. Activation volumes were found to be -15 and -4 cm3 mol-1, respectively. The reaction mechanism is discussed in the context of these values. Johann Ambrosius Barth 1996.

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

Pantaine, Lo?c,Humblot, Vincent,Coeffard, Vincent,Vallée, Anne

, p. 648 - 658 (2017)

Aniline-terminated self-assembled monolayers (SAMs) on gold surfaces have successfully reacted with ArSO2NHOSO2Ar (Ar = 4-MeC6H4 or 4-FC6H4) resulting in monolayers with sulfamide moieties

Palladium-catalyzed reduction of nitroaromatic compounds to the corresponding anilines

Mirza-Aghayan, Maryam,Boukherroub, Rabah,Rahimifard, Mahshid,Bolourtchian, Mohammad

, p. 477 - 480 (2010)

Reduction of a variety of nitroaromaticcompoundswith triethylsilane in thepresence of catalytic amounts ofpalladium chloride in ethanol resulted in the formation of the corresponding anilines in excellent yields. Copyright

-

Micewicz

, (1928)

-

Promoting effect of na2SeO3 on the activity of MoO3 catalyst for nitroarenes reduction to amines with sodium borohydride

Yanada, Kazuo,Yanada, Reiko,Meguri, Haruo

, p. 1463 - 1464 (1992)

Sodium selenite enhances the catalytic activity of molybdenum(VI) oxide during the reduction of nitroarenes (XC6H4NO2, X = 4-CN, 4-CO2Et, H, 4-Cl, 2-Me, 3-Me, 4-Me, 4-OMe) with sodium borohydride to arenamines (86-98 % yields) under mild conditions. X= 4-CN, 4-CO2Et, H, 4-Cl, 2-Me, 3-Me, 4-Me, 4-OMe in 86-98 % yields.

Transition metal imide/organic imine metathesis reactions: Unexpected observations

McInnes, Jacqueline M.,Mountford, Philip

, p. 1669 - 1670 (1998)

Mixtures of [Ti(NBut)Cl2(py)3] 1 and PhC(NAr)H (Ar = C6H3Me2-2,6 or C6H4Me-4) gave quantitative conversion to [Ti(NAr)Cl2(py)3] and PhC(NBut)H, the products of Ti=N-But/C=NAr transition metal imide/organic imine metathesis; examination of the kinetics for Ar = C6H4Me-4 showed that the rate limiting step for this process is zero order in [1], demonstrating that these reactions do not involve metal imide particiption in the rate limiting step.

One-Pot Synthesis of Heterobimetallic Metal–Organic Frameworks (MOFs) for Multifunctional Catalysis

Iqbal, Bushra,Saleem, Murtaza,Arshad, Salman Noshear,Rashid, Jamshaid,Hussain, Naveed,Zaheer, Muhammad

, p. 10490 - 10498 (2019)

A one-pot synthesis of bimetallic metal–organic frameworks (Co/Fe-MOFs) was achieved by treating stoichiometric amounts of Fe and Co salts with 2-aminoterephthalic acid (NH2-BDC). Monometallic Fe (catalyst A) and Co (catalyst F) were also prepared along with mixed-metal Fe/Co catalysts (B–E) by changing the Fe/Co ratio. For mixed-metal catalysts (B–E) SEM energy-dispersive X-ray (EDX) analysis confirmed the incorporation of both Fe and Co in the catalysts. However, a spindle-shaped morphology, typically known for the Fe-MIL-88B structure and confirmed by PXRD analysis, was only observed for catalysts A–D. To test the catalytic potential of mixed-metal MOFs, reduction of nitroarenes was selected as a benchmark reaction. Incorporation of Co enhanced the activity of the catalysts compared with the parent NH2-BDC-Fe catalyst. These MOFs were also tested as electrocatalysts for the oxygen evolution reaction (OER) and the best activity was exhibited by mixed-metal Fe/Co-MOF (Fe/Co batch ratio=1). The catalyst provided a current density of 10 mA cm?2 at 410 mV overpotential, which is comparable to the benchmark OER catalyst (i.e., RuO2). Moreover, it showed long-term stability in 1 m KOH. In a third catalytic test, dehydrogenation of sodium borohydride showed high activity (turnover frequency=87 min?1) and hydrogen generation rate (67 L min?1 g?1 catalyst). This is the first example of the synthesis of bimetallic MOFs as multifunctional catalysts particularly for catalytic reduction of nitroarenes and dehydrogenation reactions.

PROTONATION OF REAGENTS AND ACID-BASE CATALYSIS IN ACYLATION

Kalnin'sh, K. K.

, p. 822 - 828 (1992)

The kinetic characteristics of the model reaction of electron transfer and the reaction of acylation of aromatic amines by aromatic acid anhydrides were investigated as a function of the concentration of acid catalyst and a correlation was established between the type of this function and the characteristics of protonation of the amines.The rate constants of the catalytic and noncatalytic flows of the forward and reverse reactions in the phthalic anhydride-p-toluidine system were determined as a function of the molarity and proton-acceptor properties of the solvent.The mechanism of acid-base catalysis was examined as a sequence of proton and electron transfer processes. Keywords: catalysis, kinetics, protonation.

Dinuclear Palladium(II) Complexes Containing Anilide Anions as Bridging Ligands

Okeya, Seichi,Yoshimatsu, Hisako,Nakamura, Yukio,Kawaguchi, Shinichi

, p. 483 - 491 (1982)

The reactions of with aniline and its derivatives (L) in benzene at room temperature afforded 3)L>, (hfac), and (hfac)2 depending on the reactants mole ratio.On the other hand, the reactions of various complexes with L in refluxing benzene (in most cases) gave rise to the anilide-bridged dinuclear complexes 2, which in turn reacted with primary amines and pyridine (L') to produce 2(β-dik)2.

Iodide Reduction of Sulfilimines. 2. Evidence for Concurrent Stepwise and Concerted Mechanisms for the Decomposition of Sulfurane Intermediates

Young, Paul R.,Huang, H. C.

, p. 1805 - 1809 (1987)

The iodide reduction of N-(substituted ethyl or phenyl)-S,S-dimethylsulfilimmonium salts (aqueous solution, 25 deg C, μ = 1.0 with KCl) is first order in proton activity and iodide concentration in the pH range 0.5-5.The solvent deuterium isotope effects for the reduction reaction vary in the range kH/kD = 0.26-0.48 as the nitrogen substituent is changed from ethyl- to trifluoroethylamine.Electron-withdrawing groups in the leaving group decrease the rate of the reaction and give βl.g. values of ca. 0.7 for cyanoethyl- and trifluoroethylamine leaving groups and ca. 0.1 for the more basic ethylamine derivatives; a βl.g. of 0.58 is observed for aniline derivatives.General acid catalysis is observed in the reduction of the acidic ethylamine and aniline derivatives with Broensted α values of 0.59 and 0.39 for cyanoethyl- and trifluoroethylamine leaving groups, respectively; for anilines, the Broensted α values decreased from 0.67 to 0.50 as the leaving group is changed from 4-methyl- to 3-nitroaniline.The value of βl.g. decreases with decreasing strength of the catalyzing acid and the term pxy = (δβl.g./δpKaHA) = (δα/δKal.g.) ca. -0.06 to -0.1.The solvent deuterium isotope effect on the general catalyzed reduction reaction increases with increasing acid strength; for the cyanoethylamine derivative, kBH/kBD = 1.47-2.32 for acetic and chloroacetic acids, respectively.A mechanism is suggested involving concurrent stepwise and concerted mechanisms for the reduction reaction; the mechanism observed seems to depend on the nature of the catalyzing acid.

Catalytic Deoxygenation of Nitroarenes Mediated by High-Valent Molybdenum(VI)-NHC Complexes

Liu, Shenyu,Amaro-Estrada, Jorge Ivan,Baltrun, Marc,Douair, Iskander,Schoch, Roland,Maron, Laurent,Hohloch, Stephan

, p. 107 - 118 (2021)

The high-valent molybdenum(VI) N-heterocyclic carbene complexes, (NHC)MoO2 (1) and (NHC)MoO(NtBu) (2) (NHC = 1,3-bis(3,5-di-tert-butyl-2-phenolato)-benzimidazol-2-ylidene), are investigated toward their catalytic potential in the deoxygenation of nitroarenes. Using pinacol as the sacrificial and green reductant, both complexes are shown to be very active (pre)catalysts for this transformation allowing a reduction of the catalyst loading down to 0.25 mol %. Mechanistic investigations show μ-oxo bridged molybdenum(V) complexes [(NHC)MoO]2O (4) and [(NHC)Mo(NtBu)]2O (5) as well as zwitterionic pinacolate benzimidazolium complex 6, with a doubly protonated NHC ligand, to be potentially active species in the catalytic cycle. Both 4 and 5 can be prepared independently by the deoxygenation of 1 and 2 using triethyl phosphine (PEt3) or triphenyl phosphine (PPh3) and were shown to exhibit an unusual multireferenced ground state with a very small singlet-triplet gap at room temperature. Computational studies show that the spin state plays an unneglectable role in the catalytic process, efficiently lowering the reaction barrier of the deoxygenation step. Mechanistic details, putting special emphasis on the fate of the catalyst will be presented and potential routes how nitroarene reduction is facilitated are evaluated.

Recyclable aluminium oxy-hydroxide supported Pd nanoparticles for selective hydrogenation of nitro compounds via sodium borohydride hydrolysis

G?ksu, Haydar

, p. 8498 - 8504 (2015)

The reduction of aromatic/aliphatic nitro compounds to primary amines with high yields was easily realized by transfer hydrogenation comprising commercially available aluminium oxy-hydroxide-supported Pd nanoparticles (0.5 wt% Pd, Pd/AlO(OH)) as catalysts and NaBH4 as the hydrogen reservoir at room temperature in a water/methanol mixture (v/v = 7/3). The presented catalytic methodology is highly efficient for the reduction of various nitro compounds as well as reusable. A variety of R-NO2 derivatives were tested by performing the Pd/AlO(OH) catalysed reduction reaction and all the nitro compounds were selectively reduced to their corresponding primary amines in reaction times ranging from 0.75 to 13 min with yields reaching up to 99%. This process can be assessed as an eco-friendly method involving both reusable catalysts (Pd/AlO(OH) NPs) and hydrogen sources (NaBH4).

Studies on the Mechanism of Transfer Hydrogenation of Nitroarenes by Formate Salts Catalyzed by Pd/C

Wiener, Harold,Blum, Jochanan,Sasson, Yoel

, p. 4481 - 4486 (1991)

The hydrogenation of nitroarenes to aminoarenes using formate salts as hydrogen donors and Pd/C as catalyst in a liquid/liquid/solid system was found to be a true hydrogen transfer process.The mechanism of the reaction comprises successive adsorption of a

Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efficient and Recyclable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction and Nitroarene Reduction in Water

Dong, Zhenhua,Pan, Hongguo,Gao, Pengwei,Xiao, Yongmei,Fan, Lulu,Chen, Jing,Wang, Wentao

, p. 299 - 306 (2021/05/10)

An efficient and recyclable Pd nano-catalyst was developed via immobilization of Pd nanoparticles on polyimide linked covalent organic frameworks (PCOFs) that was facilely prepared through condensation of melamine and 3,3′,4,4′-biphenyltetracarboxylic dianhydride. The Pd nanoparticles (Pd NPs) catalyst was thoroughly characterized by FT-IR, XRD, SEM, TEM. Furthermore, the catalytic activity of Pd NPs catalyst was evaluated by Suzuki–Miyaura coupling reaction and nitroarene reduction in water, respectively. The excellent yields of corresponding products revealing revealed that the Pd NPs catalyst could be applied as an efficient and reusable heterogeneous catalyst for above two reactions. Graphical Abstract: [Figure not available: see fulltext.]

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

-

Paragraph 0111-0119, (2021/05/29)

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

METHOD FOR PRODUCING AMINO AROMATIC COMPOUND

-

Paragraph 0040-0045, (2021/03/03)

To provide a novel method for producing an amino aromatic compound.SOLUTION: A method for producing a compound (B) having at least one amino group on an aromatic ring, includes at least a step in which a compound (A) at least having an aromatic ring and one group represented by -CR=CH2 [R is a hydrogen atom or a C1-3 alkyl group] on the aromatic ring is reacted with sodium azide in the presence of acid.SELECTED DRAWING: None

Generation of a Sulfinamide Species from Facile N-O Bond Cleavage of Nitrosobenzene by a Thiolate-Bridged Diiron Complex

Chen, Yifeng,Qu, Jingping,Wang, Baomin,Xu, Sunlin,Yang, Dawei,Ye, Shengfa

supporting information, p. 17374 - 17387 (2021/10/25)

The activation of nitrosobenzene promoted by transition-metal complexes has gained considerable interest due to its significance for understanding biological processes and catalytic C-N bond formation processes. Despite intensive studies in the past decades, there are only limited cases where electron-rich metal centers were commonly employed to achieve the N-O or C-N bond cleavage of the coordinated nitrosobenzene. In this regard, it is significant and challenging to construct a suitable functional system for examining its unique reactivity toward reductive activation of nitrosoarene. Herein, we present a {Fe2S2} functional platform that can activate nitrosobenzene via an unprecedented iron-directed thiolate insertion into the N-O bond to selectively generate a well-defined diiron benzenesulfinamide complex. Furthermore, computational studies support a proposal that in this concerted four-electron reduction process of nitrosobenzene the iron center serves as an important electron shuttle. Notably, compared to the intact bridging nitrosoarene ligand, the benzenesulfinamide moiety has priority to convert into aniline in the presence of separate or combined protons and reductants, which may imply the formation of the sulfinamide species accelerates reduction process of nitrosoarene. The reaction pattern presented here represents a novel activation mode of nitrosobenzene realized by a thiolate-bridged diiron complex.

Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex

Ioannou, Dimitris I.,Gioftsidou, Dimitra K.,Tsina, Vasiliki E.,Kallitsakis, Michael G.,Hatzidimitriou, Antonios G.,Terzidis, Michael A.,Angaridis, Panagiotis A.,Lykakis, Ioannis N.

supporting information, p. 2895 - 2906 (2021/02/27)

We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.

Process route upstream and downstream products

Process route

N-((1H-pyrrol-2-yl)methylene)-4-methylbenzenamine
14479-37-9

N-((1H-pyrrol-2-yl)methylene)-4-methylbenzenamine

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

2-pyrrole aldehyde

Conditions
Conditions Yield
With hydrogenchloride; In methanol; water; at 25 ℃; Rate constant; Mechanism; pH=0.65-13.5, buffers, aq.NaOH;
N-(2,4-Dinitro-phenyl)-N'-p-tolyl-acetamidine
128915-25-3

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

2,4-dinitroacetanilide
610-53-7

2,4-dinitroacetanilide

Conditions
Conditions Yield
With acetic acid; In water; at 25 ℃; Rate constant;
trimethylsilyl-N-p-tolyl carbamate
73120-08-8

trimethylsilyl-N-p-tolyl carbamate

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

isopropoxytrimethylsilane
1825-64-5

isopropoxytrimethylsilane

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

Conditions
Conditions Yield
With lithium chloride; Kinetics; Thermodynamic data; Product distribution; ΔH excit;
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

N-p-Tolyl-N'-α-naphthyl thiourea
81286-46-6

N-p-Tolyl-N'-α-naphthyl thiourea

1-amino-naphthalene
134-32-7

1-amino-naphthalene

1-isothiocyanatonaphthalene
551-06-4

1-isothiocyanatonaphthalene

1-isothiocyanato-4-methylbenzene
622-59-3

1-isothiocyanato-4-methylbenzene

Conditions
Conditions Yield
at 150 ℃;
1-<i>p</i>-toluidino-cyclohexanecarboxylic acid
99216-79-2

1-p-toluidino-cyclohexanecarboxylic acid

cyclohexene-1-carboxylic acid
636-82-8

cyclohexene-1-carboxylic acid

Conditions
Conditions Yield
bei der Destillation;
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

benzyl-p-methylphenyltriazene
17683-09-9

benzyl-p-methylphenyltriazene

p-cresol
106-44-5

p-cresol

benzyl chloride
100-44-7

benzyl chloride

benzylamine
100-46-9

benzylamine

Conditions
Conditions Yield
Produkt 5: Stickstoff;
N-(4-methylphenyl)benzamide
582-78-5

N-(4-methylphenyl)benzamide

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With [fac-8-(2-diphenylphosphinoethyl)aminotrihydroquinoline]RuH(η1-BH4)(CO); hydrogen; In isopropyl alcohol; at 120 ℃; for 24h; under 37503.8 Torr; Autoclave;
95 %Chromat.
93 %Chromat.
With Ag/γ-Al2O3 (2.5 mol%); potassium tert-butylate; hydrogen; In 1,4-dioxane; at 150 ℃; for 72h; under 37503.8 Torr; chemoselective reaction; Green chemistry;
99 %Spectr.
99 %Spectr.
With potassium tert-butylate; hydrogen; [Ru(PtBuNNHBn)H(CO)Cl]; In tetrahydrofuran; at 19 - 24 ℃; for 68h; under 7500.75 Torr;
97 %Chromat.
98 %Chromat.
3-methyl-1-p-tolyltriazene
20667-76-9,20667-77-0,21124-13-0

3-methyl-1-p-tolyltriazene

m-hydroxyphenylacetic acid
621-37-4

m-hydroxyphenylacetic acid

3-hydroxy-benzeneacetic acid, methyl ester
42058-59-3

3-hydroxy-benzeneacetic acid, methyl ester

Conditions
Conditions Yield
In acetone; at 25 ℃; Rate constant;
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

1,2-bis(4-methylphenyl)diazene oxide
955-98-6,21650-69-1,71297-92-2

1,2-bis(4-methylphenyl)diazene oxide

Conditions
Conditions Yield
With [(5-phenyl-2,8-di-2-pyridinylanthyridine)Ru26-C6H6)2Cl2](PF6)2; hydrazine; In ethanol; at 80 ℃; for 10h;
52 %Spectr.
9 %Spectr.
35 %Spectr.
With methyldiazene; In acetonitrile; at 28 ℃; for 1h; Irradiation; Inert atmosphere;
71 %Spectr.
18 %Spectr.
11 %Spectr.
With methyldiazene; In methanol; at 28 ℃; for 1h; Solvent; Irradiation; Inert atmosphere;
62 %Spectr.
18 %Spectr.
15 %Spectr.
With [Co(κS,N-4-(trifluoromethyl)pyrimidine-2-thiolate)3]; methylhydrazine; In ethanol; at 70 ℃; for 5h; Reagent/catalyst; Temperature; Solvent; Catalytic behavior; Sealed tube;
13 %Spectr.
58 %Spectr.
8 %Spectr.
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

Conditions
Conditions Yield
With [Pd2(2,7-bis(2-pyridinyl)-1,8-naphthyridine)(μ-OH)(CF3CO2)2](CF3CO2); hydrogen; In methanol; at 25 ℃; for 6h; under 760.051 Torr;
17%
8%
In ethanol; water; at 25 ℃; Rate constant; Mechanism; Product distribution; polarographic reduction; potential-dependent rate constants kf,h, αna; pH = 1.81-11.00;
With hydrazine hydrate; In chloroform; for 1.25h; Overall yield = 87 %; Overall yield = 35.4 mg; chemoselective reaction;

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