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Cas Database




  • Product Name:Acetophenone

  • CAS Number: 98-86-2

  • EINECS:202-708-7

  • Molecular Weight:120.151

  • Molecular Formula: C8H8O

  • HS Code:2914.30 Oral rat LD50: 815 mg/kg

  • Mol File:98-86-2.mol

Synonyms:FEMA No. 2009;RCRA waste number U004;Ketone, methyl phenyl;Ketone, methyl phenyl-;1/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H;Ethanone,1-phenyl-;Benzoyl methide;FEMA Number 2009;Acetylbenzol;Hypnone;Hypnon;Acetofenon [Czech];Benzoylmethide;Acetophenon;Phenyl methyl ketone;Acetylbenzene;Benzene, acetyl-;1-Phenyl-1-ethanone;1-Phenylethanone;USAF EK-496;Methyl phenyl ketone;RCRA waste no. U004;Acteophone;Acetophenone , 98%;Acetophenone PG , 99%;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,ToxicT,FlammableF

  • Hazard Codes: Xn:Harmful;

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. 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 Rinse mouth. Refer for medical attention . No toxicity expected from inhalation or ingestion except slight narcotic effect. Liquid can cause eye and skin irritation on contact. (USCG, 1999) Call for medical aid. ... Remove contaminated clothing and shoes. Flush affected areas with plenty of water. IF IN EYES, hold eyelids open, and flush with plenty of water. IF SWALLOWED and victim is CONSCIOUS, have victim drink water, or milk.

  • Fire-fighting measures: Suitable extinguishing media Extinguish with water, foam, dry chemical, carbon dioxide. Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016) 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: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Absorb on paper. Evaporate on a glass or iron dish in hood. Burn the paper.

  • 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. Ventilation along the floor.In general materials... toxic as stored or which can decompose into toxic components... should be stored in cool... ventilated place, out of... sun, away from... fire hazard... be periodically inspected and monitored. Incompatible materials should be isolated.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological 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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Relevant articles and documentsAll total 3721 Articles be found

Magnetic d-penicillamine-functionalized cellulose as a new heterogeneous support for cobalt(II) in green oxidation of ethylbenzene to acetophenone

Keshipour, Sajjad,Adak, Kamran

, (2017)

A new efficient heterogeneous catalyst is introduced for the oxidation of ethylbenzene. The catalyst was obtained in three steps: functionalization of cellulose with d-penicillamine, deposition of Fe3O4 nanoparticles on cellulose–d-p

Sodium percarbonate: A mild reagent for conversion of tosylhydrazones and nitroalkanes to carbonyl compounds


, p. 2587 - 2592 (1992)

Sodium percarbonate has been found to be a good reagent for oxidative regeneration of carbonyl compounds from tosyl hydrazones and nitroalkanes.

Debromination of α-Bromo Ketones using Polymer-supported Triphenylphosphine

Dhuru, Sameer P.,Padiya, Kamlesh J.,Salunkhe, M. M.

, p. 56 (1998)

An effective method for the debromination of α-bromo ketones using polymer-supported triphenylphosphine is described.


Mc Carty,Leeper

, p. 4245 (1970)


Atomically dispersed cobalt on graphitic carbon nitride as a robust catalyst for selective oxidation of ethylbenzene by peroxymonosulfate

Li, Jiaquan,Zhao, Shiyong,Yang, Shi-Ze,Wang, Shaobin,Sun, Hongqi,Jiang, San Ping,Johannessen, Bernt,Liu, Shaomin

, p. 3029 - 3035 (2021)

The development of a highly efficient strategy for the activation of the C-H bond in hydrocarbons is one of the most challenging tasks facing the chemical industries. The synthesis of novel catalysts with atomically dispersed active centers is highly desi



, p. C52 (1974)


Vinyl Triflimides—A Case of Assisted Vinyl Cation Formation

Schroeder, Sebastian,Strauch, Christina,Gaelings, Niklas,Niggemann, Meike

, p. 5119 - 5123 (2019)

A new concept for selectivity control in carbocation-driven reactions has been identified which allows for the chemo-, regio-, and stereoselective addition of nucleophiles to alkynes—assisted vinyl cation formation—enabled by a Li+-based supramolecular framework. Mechanistic analysis of a model complex (Li2NTf2+?3 H2O) confirms that solely the formation of a complex between the incoming nucleophile and the transition state of the alkyne protonation is responsible for the resulting selective N addition to the vinyl cation. Into the bargain, a general, operationally simple synthetic procedure to previously inaccessible vinyl triflimides is provided.


Mishima, Masaaki,Fujio, Mizue,Tsuno, Yuho

, p. 951 - 954 (1986)

The gas phase basicities of m,p-substituted methyl benzoates have been determined by means of the pulsed ICR mass spectrometer.LArSR analysis of the substituent effect provides a smaller r+ of 0.45 compared to that of acetophenone basicities, indicating a reduced resonance demand of the conjugate acid ion of methyl benzoate.

Origin of enantioselection in chiral alcohol oxidation catalyzed by Pd[(-)-sparteine]Cl2

Mueller, Jaime A.,Cowell, Anne,Chandler, Bert D.,Sigman, Matthew S.

, p. 14817 - 14824 (2005)

A kinetic investigation into the origin of enantioselectivity for the Pd[(-)-sparteine]Cl2-catalyzed aerobic oxidative kinetic resolution (OKR) is reported. A mechanism to account for a newly discovered chloride dissociation from Pd[(-)-sparteine]Cl2 prior to alcohol binding is proposed. The mechanism includes (1) chloride dissociation from Pd[(-)-sparteine]Cl2 to form cationic Pd(-)-sparteine]Cl, (2) alcohol binding, (3) deprotonation of Pd-bound alcohol to form a Pd-alkoxide, and (4) β-hydride elimination of Pd-alkoxide to form ketone product and a Pd-hydride. Utilizing the addition of (-)-sparteine HCl to control the [Cl -] and [H+] and the resulting derived rate law, the key microscopic kinetic and thermodynamic constants were extracted for each enantiomer of sec-phenethyl alcohol. These constants allow for the successful simulation of the oxidation rate in the presence of exogenous (-)-sparteine HCl. A rate law for oxidation of the racemic alcohol was derived that allows for the successful prediction of the experimentally measured krel values when using the extracted constants. Besides a factor of 10 difference between the relative rates of β-hydride elimination for the enantiomers, the main enhancement in enantiodetermination results from a concentration effect of (-)-sparteine HCl and the relative rates of reprotonation of the diastereomeric Pd-alkoxides.

Photoredox Catalysis Using Heterogenized Iridium Complexes**

Materna, Kelly L.,Hammarstr?m, Leif

, p. 16966 - 16977 (2021)

Heterogenized photoredox catalysts provide a path for sustainable chemical synthesis using highly tunable, reusable constructs. Here, heterogenized iridium complexes as photoredox catalysts were assembled via covalent attachment to metal oxide surfaces (I



, p. 471 (1979)


Influence of induced steric on the switchover reactivity of mononuclear Cu(II)-alkylperoxo complexes

Nag, Sayanta Sekhar,Mukherjee, Gourab,Barman, Prasenjit,Sastri, Chivukula V.

, p. 80 - 85 (2019)

Coordination and steric environment around a metal center plays an indispensable role in its reactivity. In this report we have synthesized two bispidine based Cu(II)-OOR (R = tBu) complexes [Cu(L1)(OOtBu)]+ and [Cu(L2)(OOtBu)]+ having different steric environment around the metal center and characterized by various spectroscopic techniques. These Cu(II)-OOR species show reactivity towards oxygen atom transfer and aldehyde deformylation reactions. In contrast to the previously reported nucleophilic oxidation, aldehyde deformylation reaction by these complexes proceed via an initial H-atom abstraction with KIE of 12 and 8 respectively. It has been observed that more steric bulk at N3 and N7 position of bispidine ligand prefers the oxygen atom transfer reaction while it hinders the H-atom abstraction for Cu(II)-alkylperoxo complexes.

Synthesis of new hybrid hydroquinone/cobalt schiff base catalysts: Efficient electron-transfer mediators in aerobic oxidation

Purse, Byron W.,Tran, Lien-Hoa,Piera, Julio,Akermark, Bjoern,Baeckvall, Jan-Erling

, p. 7500 - 7503 (2008)

A study was conducted to demonstrate the use of efficient electron-transfer mediators in aerobic oxidation. These electron-transfer mediators were used in aerobic oxidation for synthesizing new hybrid hydroquinone and Cobalt Schiff base catalysts. These n

On the Mechanism of the reduction of α-Halo-Ketones by Several Models for NADH. Reduction by a SET-Hydrogen Atom Abstraction Chain Reaction

Tanner, Dennis D.,Singh, Harrbansh Kumar,Kharrat, Abdelmajid,Stein, Allan R.

, p. 2142 - 2146 (1987)

The mechanism for the reduction of the α-haloacetophenones by four dihydronicotinamides (DHNA's) procceds by free radical chain whose initiation and propagation sequences both contain single electron transfer reactions.The use of DHNA's as models for the role of NADH in enzyme-mediated reductions is discussed.

Spacer-Independent Intramolecular Triplet Energy Transfer in Diketones

Wagner, Peter J.,Giri, Brij. P.,Frerking, Harlan W.,DeFrancesco, James

, p. 8326 - 8327 (1992)


A side-on Mn(iii)-peroxo supported by a non-heme pentadentate N3Py2ligand: Synthesis, characterization and reactivity studies

Narulkar, Dattaprasad D.,Ansari, Azaj,Vardhaman, Anil Kumar,Harmalkar, Sarvesh S.,Lingamallu, Giribabu,Dhavale, Vishal M.,Sankaralingam, Muniyandi,Das, Sandip,Kumar, Pankaj,Dhuri, Sunder N.

, p. 2824 - 2831 (2021)

A mononuclear manganese(iii)-peroxo complex [MnIII(N3Py2)(O2)]+ (1a) bearing a non-heme N,N′-dimethyl-N-(2-(methyl(pyridin-2-ylmethyl)amino)ethyl)-N′-(pyridin-2-ylmethyl)ethane-1,2-diamine (N3Py2) ligand was synthesized by the reaction of [Mn(N3Py2)(H2O)](ClO4)2 (1) with hydrogen peroxide and triethylamine in CH3CN at 25 °C. The reactivity of 1a in aldehyde deformylation using 2-phenyl propionaldehyde (2-PPA) was studied and the reaction kinetics was monitored by UV-visible spectroscopy. A kinetic isotope effect (KIE) = 1.7 was obtained in the reaction of 1a with 2-PPA and α-[D1]-PPA, suggesting nucleophilic character of 1a. The activation parameters ΔH? and ΔS? were determined using the Eyring plot while Ea was obtained from the Arrhenius equation by performing the reaction between 288 and 303 K. Hammett constants (σp) of para-substituted benzaldehydes p-X-Ph-CHO (X = Cl, F, H, and Me) were linear with a slope (ρ) = 3.0. Computational study suggested that the side-on structure of 1a is more favored over the end-on structure and facilitates the reactivity of 1a.

Iridium-catalyzed B-H insertion of sulfoxonium ylides and borane adducts: A versatile platform to α-boryl carbonyls

Zhang, Shang-Shi,Xie, Hui,Shu, Bing,Che, Tong,Wang, Xiao-Tong,Peng, Dongming,Yang, Fan,Zhang, Luyong

, p. 423 - 426 (2020)

Iridium-catalyzed boron-hydrogen bond insertion reactions of trimethylamine-borane and sulfoxonium ylides have been demonstrated, furnishing α-boryl ketones in moderate to excellent yields in most cases (51 examples; up to 84%). This practical and scalable insertion reaction showed broad substrate scope, high functional-group compatibility and could be applied in late-stage modification of structurally complex drug compounds. Further synthetic applications were also demonstrated.

Selective oxidation of arylalkanes with N-Graphitic-Modified cobalt nanoparticles in water

Tu, Dong-Huai,Li, Yang,Li, Jiangwei,Gu, Yu-Jie,Wang, Bo,Liu, Zhao-Tie,Liu, Zhong-Wen,Lu, Jian

, p. 130 - 133 (2017)

N-Graphitic-Modified cobalt nanoparticles supported on carbon powder (Co/phen@CB-800-L) were prepared and found to be efficient catalysts for selective oxidation of arylalkanes to aromatic ketones with tert-butyl hydroperoxide (TBHP) in water. A broad sco

Synthesis of efficient and reusable catalyst of size-controlled Au nanoparticles within a porous, chelating and intelligent hydrogel for aerobic alcohol oxidation

Wang, Yao,Yan, Rui,Zhang, Jianzheng,Zhang, Wangqing

, p. 81 - 88 (2010)

Synthesis of size-controlled Au nanoparticles for aerobic alcohol oxidation within a porous, chelating and intelligent hydrogel of poly(N-isopropylacrylamide)-co-poly[2-methacrylic acid 3-(bis-carboxymethylamino)-2-hydroxypropyl ester] (PNIPAM-co-PMACHE)


Rahman, M. T.,Hoque, A. K. M. M.,Siddique, I.,Chowdhury, D. A. N.,Nahar, S. K.,Saha, S. L.

, p. 293 - 300 (1980)

Bromomagnesium diphenylcuprate and iodomagnesium dimethylcuprate have been prepared, and their thermal stability and some of their reactions investigated.In diethyl ether, 50percent of the BrMgPh2Cu decomposes in 12 h at room temperature and 50percent of the IMgMe2Cu decomposes at 0 deg C in 14 h but the cuprates are more stable in THF at or below 0 deg C.They react with acid chlorides to give 16-76percent yields of the corresponding ketones.With bromine and iodine, BrMgPh2Cu gives bromobenzene and iodobenzene in 56 and 48percent yield, respectively.Oxidation of BrMgPh2Cu with nitrobenzeneor copper(II) chloride gives, respectively, 61 and 34percent of biphenyl.Reaction of BrMgPh2Cu with acetic or benzoic anhydride yields 46-55percent of the corresponding ketone and 34-37percent of the corresponding carboxylic acids.

Recyclable Bismuth Complex Catalyzed 1,6-Conjugate Addition of Various Nucleophiles to para-Quinone Methides: Expedient Access to Unsymmetrical Diaryl- and Triarylmethanes

Liang, Xianghao,Xu, Haiyan,Li, Hanlin,Chen, Lizhuang,Lu, Hongfei

, p. 217 - 226 (2020)

An efficient method for the 1,6-conjugate addition of para-quinone methides with readily available nucleophiles was developed. This protocol provides a straightforward access to a class of diaryl and triarylmethane derivatives with good to excellent yields in the presence of (C4H12N2)2[BiCl6]Cl·H2O. Moreover, this bismuth catalyst can be recycled for several times.


Emanuel et al.

, (1971)


Fe3O4 nanoparticles as a new efficient co-catalyst for Pd(ii) in Wacker oxidation of styrene using H2O2 as an oxidant

Keshipour, Sajjad,Nadervand, Selda

, p. 47617 - 47620 (2015)

A new highly selective and environment-friendly Wacker oxidation process employing PdCl2/Fe3O4 nanoparticles in H2O at 100°C using H2O2 as an oxidant has been developed. This approach has some advantages such as copper free reaction conditions, green solvent, high yield, excellent selectivity and green oxidant.


Hotta et al.

, p. 2413,2414 (1969)


Rapid determination of both the activity and enantioselectivity of ketoreductases

Truppo, Matthew D.,Escalettes, Franck,Turner, Nicholas J.

, p. 2639 - 2641 (2008)

(Chemical Equation Presented) Fast and furious: A rapid and inexpensive assay for determining both the activity and enantioselectivity of ketoreductases (KREDs) has beendeveloped (see scheme; HRP = horseradish peroxidase, ABTS = 2,2′-azino-di(3-ethyl benzthiazoline-6-sulfonic acid). This assay, which employs an enantioselective alcohol oxidase as a reporter enzyme, was used to screen a panel of 17 KREDs in only 10 min using less than 0.5 mg substrate.

On the Mechanism of the Reduction of α-Halo Ketones by 1,3-Dimethyl-2-phenylbenzimidazoline. Reduction by a SET-Hydrogen Atom Abstraction Chain Mechanism

Tanner, Dennis D.,Chen, Jian Jeffrey

, p. 3842 - 3846 (1989)

A series of α-halocarbonyl compounds are dehalogenated by 1,3-dimethyl-2-phenylbenzimidazoline (DMBI) to give their corresponding carbonyl compounds.Contrary to the original proposal, the mechanism for these reductions was shown to proceed via a free-radi

Silver catalyzed proto- and sila-Nakamura-type α-vinylation of silyl enol ethers with dichloroacetylene. Divergent formation of stereochemically pure tri- and tetrasubstituted olefins

Li, Lun,Wasik, Kimberly A.,Frost, Brian J.,Geary, Laina M.

, (2020)

The silver-catalyzed reaction of silyl enol ethers with dichloroacetylene (DCA) is described. When DCA was used as a solution in diethyl ether, we found that the silyl group was transferred to the vinyl group, resulting in stereochemically pure tetrasubstituted olefins. However, when DCA was used as a solution in the more polar acetonitrile, protonation was the major pathway, and trisubstituted olefins were the dominant products.

A Manganese(IV)-Hydroperoxo Intermediate Generated by Protonation of the Corresponding Manganese(III)-Superoxo Complex

Lin, Yen-Hao,Kutin, Yury,Van Gastel, Maurice,Bill, Eckhard,Schnegg, Alexander,Ye, Shengfa,Lee, Way-Zen

, p. 10255 - 10260 (2020)

Earlier work revealed that metal-superoxo species primarily function as radicals and/or electrophiles. Herein, we present ambiphilicity of a MnIII-superoxo complex revealed by its proton- A nd metal-coupled electron-transfer processes. Specifically, a MnIV-hydroperoxo intermediate, [Mn(BDPBrP)(OOH)]+ (1, H2BDPBrP = 2,6-bis((2-(S)-di(4-bromo)phenylhydroxylmethyl-1-pyrrolidinyl)methyl)pyridine) was generated by treatment of a MnIII-superoxo complex, Mn(BDPBrP)(O2a¢) (2) with trifluoroacetic acid at-120 °C. Detailed insights into the electronic structure of 1 are obtained using resonance Raman and multi-frequency electron paramagnetic resonance spectroscopies coupled with density functional theory calculations. Similarly, the reaction of 2 with scandium(III) triflate was shown to give a Mn(IV)/Sc(III) bridging peroxo species, [Mn(BDPBrP)(OO)Sc(OTf)n](3-n)+ (4). Furthermore, it is found that deprotonation of 1 quantitatively regenerates 2, and that one-electron oxidation of the corresponding MnIII-hydroperoxo species, Mn(BDPBrP)(OOH) (3), also yields 1.

In situ spectroscopic studies related to the mechanism of the Friedel-Crafts acetylation of benzene in ionic liquids using AlCl3 and FeCl3

Csihony, Szilard,Mehdi, Hasan,Homonnay, Zoltan,Vertes, Attila,Farkas, Oedoen,Horvath, Istvan T.

, p. 680 - 685 (2002)

Several aspects of the mechanism of the Friedel-Crafts acetylation of benzene were studied by in situ spectroscopic methods in ionic liquids, prepared from MCl3 (M = Al or Fe) and 1-butyl-3-methylimidazolium chloride ([bmim]Cl). Moessbauer measurements have revealed that the addition of FeCl3 to [bmim]Cl leads to an equilibrium mixture that contains solid FeCl3, [bmim][Fe2Cl7], and Fe2Cl6 and/or [bmim][FeCl4], depending on the molar ratio of FeCl3 and [bmim]Cl. The formation of [(CH3CO)2CHCO]+[MCl4] -, a potential side product in the Friedel-Crafts acetylation of benzene, was shown to require the presence of both the acetylium ion [CH3CO]+[MCl4]- and free acetyl chloride. We have confirmed that [(CH3CO)2CHCO]+[MCl4]- does not involve in the Friedel-Crafts acetylation of benzene. Experimental data and theoretical calculations indicate that the acetylium ion [CH3CO]+[MCl4]- is the key intermediate in the Friedel-Crafts acetylation of benzene and the reaction proceeds through an ionic mechanism.

Mechanistic Aspects of Photocycloaddition Chemistry. An Interesting Relationship between Substituent Effects on 1,4-Biradical Closure-to-Cleavage Ratios and Photocycloaddition Regioselectivity

Savino, Thomas G.,Chenard, Lois Konicki,Swenton, John S.

, p. 4055 - 4058 (1983)

The influence of β-substituents on closure-to-cleavage ratios of triplet 1,4-biradicals has been recorded and compared with how these substituents influence the regiochemistry of photocycloaddition of isobutylene and 5-substituted uracils.

Facile conversion of tosylhydrazones to carbonyl compounds by the potassium peroxymonosulfate-acetone system


, p. 1583 - 1587 (1992)

Tosylhydrazones of carbonyl compounds were found to be readily cleaved into the corresponding carbonyl compounds in good yields under the mild conditions by treatment with dimethyldioxirane which is generated in situ from the reaction of acetone with potassium peroxymonosulfate.

Nucleophilic versus Electrophilic Reactivity of Bioinspired Superoxido Nickel(II) Complexes

Panda, Chakadola,Chandra, Anirban,Corona, Teresa,Andris, Erik,Pandey, Bhawana,Garai, Somenath,Lindenmaier, Nils,Künstner, Silvio,Farquhar, Erik R.,Roithová, Jana,Rajaraman, Gopalan,Driess, Matthias,Ray, Kallol

, p. 14883 - 14887 (2018)

The formation and detailed spectroscopic characterization of the first biuret-containing monoanionic superoxido-NiII intermediate [LNiO2]? as the Li salt [2; L=MeN[C(=O)NAr)2; Ar=2,6-iPr2C6H3)] is reported. It results from oxidation of the corresponding [Li(thf)3]2[LNiIIBr2] complex M with excess H2O2 in the presence of Et3N. The [LNiO2]? core of 2 shows an unprecedented nucleophilic reactivity in the oxidative deformylation of aldehydes, in stark contrast to the electrophilic character of the previously reported neutral Nacnac-containing superoxido-NiII complex 1, [L′NiO2] (L′=CH(CMeNAr)2). According to density-functional theory (DFT) calculations, the remarkably different behaviour of 1 versus 2 can be attributed to their different charges and a two-state reactivity, in which a doublet ground state and a nearby spin-polarized doublet excited-state both contribute in 1 but not in 2. The unexpected nucleophilicity of the superoxido-NiII core of 2 suggests that such a reactivity may also play a role in catalytic cycles of Ni-containing oxygenases and oxidases.

Mechanistic studies of magnetically recyclable Pd-Fe3O4 heterodimeric nanocrystal-catalyzed organic reactions

Byun, Sangmoon,Chung, Jooyoung,Kwon, Jungmin,Moon Kim

, p. 982 - 988 (2015)

Recently, we have reported several catalytic applications of new Pd-Fe3O4 heterodimeric nanocrystals as magnetically separable catalysts. Successful applications of the nanocrystals towards various useful organic reactions such as Suzuki, Heck, and Sonogashira coupling reactions, direct C-H arylation, and Wacker oxidation have been recorded. However, detailed mechanistic courses of the reactions have not been delineated, and it was not clear whether these processes proceeded through a homogeneous or heterogeneous mechanism. Here, we report detailed mechanistic investigations of the reactions employing the Pd-Fe3O4 nanoparticle catalysts. Suzuki coupling and Wacker oxidation reactions were chosen as two representative heterogeneous reactions employing the Pd-Fe3O4 catalysts, and general kinetic studies, hot filtration tests, and three-phase tests were carried out for the two reactions. The studies showed that the reactions most probably proceed via a solution-phase mechanism.

Mononuclear manganese-peroxo and bis(m-oxo)dimanganese complexes bearing a common N-methylated macrocyclic ligand

Kang, Hyeona,Cho, Jaeheung,Cho, Kyung-Bin,Nomura, Takashi,Ogura, Takashi,Nam, Wonwoo

, p. 14119 - 14125 (2013)

Mononuclear MnIII-peroxo and dinuclear bis(μ-oxo)Mn III2 complexes that bear a common macrocyclic ligand were synthesized by controlling the concentration of the starting MnII complex in the reaction of H2O2 (i.e., a Mn III-peroxo complex at a low concentration (≤ 1 mM) and a bis(μ-oxo)MnIII2 complex at a high concentration (≥30mM)). These intermediates were successfully characterized by various physicochemical methods such as UV-visible spectroscopy, ESI-MS, resonance Raman, and X-ray analysis. The structural and spectroscopic characterization combined with density functional theory (DFT) calculations demon-strated unambiguously that the peroxo ligand is bound in a side-on fashion in the MnIII-peroxo complex and the Mn2O2 diamond core is in the bis(μ-oxo)MnIII2 complex. The reactivity of these intermediates was investigated in electrophilic and nucleophilic reactions, in which only the MnIII-peroxo complex showed a nucleophilic reactivity in the deformylation of aldehydes.

Kinetics of acetophenone reduction to (R)-1-phenylethanol by a whole-cell Pichia capsulata biocatalyst

Homola, Patrik,Kurák, Tomá?,Illeová, Viera,Polakovi?, Milan

, p. 323 - 332 (2015)

(R)-1-phenylethanol is an important substance in fragrance and flavor industry. In this work, the reduction of acetophenone to (R)-1-phenylethanol in an aqueous medium was examined using Pichia capsulata as a whole-cell biocatalyst. Progress curve and initial rate measurements were used to obtain kinetic data. The experiments were carried out at pH 5, temperature of 25 °C, and in the presence of glucose to maintain in vivo regeneration of NADH. A model of the reversible reaction kinetics considering the substrate inhibition of the forward reaction was developed. Five kinetic parameters of this model were determined by a simultaneous fit of a reaction rate dependence on substrate concentration and 18 substrate and product concentration progress curves with very good accuracy. Equilibrium constant of the reaction and equilibrium conversion of acetophenone to (R)-1-phenylethanol were 13.7 and 93%, respectively.

Rapid and selective removal of Hg(II)ions and high catalytic performance of the spent adsorbent based on functionalized mesoporous silica/poly(m-aminothiophenol)nanocomposite

, ()

The toxic Hg(II)being released excessively into the water body from various sources has threatened the environment and human health. The aim of this study is to design a rapid and selective adsorbent, and propose an alternative way to dispose the spent ad

Transition-Metal-Free N-O Reduction of Oximes: A Modular Synthesis of Fluorinated Pyridines

Huang, Huawen,Cai, Jinhui,Xie, Hao,Tan, Jing,Li, Feifei,Deng, Guo-Jun

, p. 3743 - 3746 (2017)

An NH4I-based reductive system has been explored to promote the oxime N-O bond cleavage and thereby enable a modular synthesis of a broad range of pharmacologically significant fluorinated pyridines. Compared with traditional condensation methods for pyridine assembly, this protocol was found to be highly regio- and chemoselective and presented broad functional group tolerance.

Ruthenium-Catalyzed Flash Oxidation of Allenes to α,α′-Dihydroxyketones

Laux, Michael,Krause, Norbert

, p. 765 - 766 (1997)

The ruthenium-catalyzed flash oxidation of β-allenic esters 1 furnishes α,α′-dihydroxyketones 2 in 24-72% yield. In the case of the chiral allene 1e, the oxidation proceeds with good diastereoselectivity (88% de), i.e. with efficient axis to center chirality transfer. The flash oxidation can also be used for the synthesis of corticosteroids, as exemplified by the transformation of allenic steroid 4 into dihydroxyketone 5.

'Amphiphilic' cleavage of γ-stannyl ketones with ATPH/RLi: Application to enone fragmentation by the conjugate addition - Cleavage sequence

Kondo, Yuichiro,Kon-i, Kana,Iwasaki, Atsuko,Ooi, Takashi,Maruoka, Keiji

, p. 414 - 416 (2000)

The use of a combined Lewis acid/base system consisting of aluminum tris(2,6-diphenylphenoxide) (ATPH) and MeLi has allowed the electrophilically activated nucleophilic ('amphiphilic') cleavage of C(α)-C(β) bonds in γ- stannyl ketones. Through combination with the conjugate addition of α- stannyl carbanion to enone, this approach constitutes a novel two-step conjugate addition-cleavage sequence that leads to functionalized ketones (see reaction).

A novel manganese(III)-peroxo complex bearing a proline-derived pentadentate aminobenzimidazole ligand

Du, Junyi,Miao, Chengxia,Xia, Chungu,Sun, Wei

, p. 1869 - 1871 (2018)

Manganese(III)-peroxo complexes are invoked as key intermediates in the enzymatic cycles of Mn-containing enzymes, and the synthesis of reactive manganese(III)-peroxo complexes with rationally designed ligand has been of great interest in the communities of bioinorganic and biomimetic chemistry. Herein, we designed a novel pentadentate aminobenzimidazole ligand and obtained its manganese(II) complex, which was successfully applied in the synthesis of a reactive manganese(III)-peroxo complex by treatment with hydrogen peroxide in the presence of triethylamine. The manganese(III)-peroxo complex was well characterized with various spectroscopic techniques, including ultraviolet–visible (UV-vis) spectrophotometry, coldspray ionization time-of-flight mass spectrometry (CSI-TOF MS), and continuous wave electron paramagnetic resonance (CW-EPR) spectroscopy. Besides, its reactivity in aldehyde deformylation was investigated, demonstrating second-order kinetics in the reaction with 2-phenylpropionaldehyde and affording acetophenone as the sole product.

Structure-based enzyme tailoring of 5-hydroxymethylfurfural oxidase

Dijkman, Willem P.,Binda, Claudia,Fraaije, Marco W.,Mattevi, Andrea

, p. 1833 - 1839 (2015)

5-Hydroxymethylfurfural oxidase (HMFO) is a flavin-dependent enzyme that catalyzes the oxidation of many aldehydes, primary alcohols, and thiols.The three-step conversion of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid is relevant for the industrial production of biobased polymers.The remarkable wide substrate scope of HMFO contrasts with the enzymes precision in positioning the substrate to perform catalysis.We have solved the crystal structure of HMFO at 1.6 ? resolution, which guided mutagenesis experiments to probe the role of the active-site residues in catalysis.Mutations targeting two active-site residues generated engineered forms of HMFO with promising catalytic features, namely enantioselective activities on secondary alcohols and improved 2,5-furandicarboxylic acid yields.

Hypervalent iodine in synthesis XIV-facile conversion of tosylhydrazones to carbonyl compounds with phenyliodine (III) diacetate (PID)


, p. 2497 - 2502 (1993)

Treatment of tosylhydrazones of ketones with PID in wet acetonitrile affords the corresponding parent ketones in excellent yields under mild conditions.

Hydration of phenylacetylene on sulfonated carbon materials: Active site and intrinsic catalytic activity

Yan, Pengqiang,Xie, Zailai,Tian, Siyuan,Li, Fan,Wang, Dan,Su, Dang Sheng,Qi, Wei

, p. 38150 - 38156 (2018)

A series of sulfonated carbon materials (sulfonated glucose-derived carbon, carbon nanotubes, activated carbon and ordered mesoporous carbon, denoted as Sglu, SCNT, SAC and SCMK, respectively) were synthesized and applied as acid catalysts in phenylacetyl

Functionalized-1,3,4-oxadiazole ligands for the ruthenium-catalyzed Lemieux-Johnson type oxidation of olefins and alkynes in water

Hkiri, Shaima,Touil, Soufiane,Samarat, Ali,Sémeril, David

, (2021/11/30)

Three arene-ruthenium(II) complexes bearing alkyloxy(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-trifluoromethylphenyl)methyl ligands were quantitatively obtained through the reaction of (E)-1-(4-trifluoromethylphenyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-methanimine with the ruthenium precursor [RuCl2(η6-p-cymene)]2 in a mixture of the corresponding alcohol and CH2Cl2 at 50 °C. The obtained complexes were fully characterized by elemental analysis, infrared, NMR and mass spectrometry. Solid-state structures confirmed the coordination of the 1,3,4-oxadiazole moiety to the ruthenium center via their electronically enriched nitrogen atom at position 3 in the aromatic ring. These complexes were evaluated as precatalysts in the Lemieux-Johnson type oxidative cleavage of olefins and alkynes in water at room temperature with NaIO4 as oxidizing agent. Good to full conversions of olefins into the corresponding aldehydes were measured, but low catalytic activity was observed in the case of alkynes. In order to get more insight into the mechanism, three analogue arene-ruthenium complexes were synthesized and tested in the oxidative cleavage of styrene. The latter tests clearly demonstrated the importance of the hemilabile alkyloxy groups, which may form more stable (N,O)-chelate intermediates and increase the efficiency of the cis-dioxo-ruthenium(VI) catalyst.

A highly efficient transformation from cumene to cumyl hydroperoxide via catalytic aerobic oxidation at room temperature and investigations into solvent effects, reaction networks and mechanisms

Chen, Chong,Ji, Lijun,Lu, Qiuting,Shi, Guojun,Yuan, Enxian,Zhou, Hongyu

, (2021/12/04)

Cumyl hydroperoxide (CHP) is an important intermediate for the production of phenol/acetone, but suffers from severe reaction conditions and a low yield industrially. Here, an efficient transformation from cumene to CHP was developed. Different solvents were modulated for cumene oxidation catalyzed by NHPI/Co, and reaction network and mechanisms were investigated methodically. Hexafluoroisopropanol (HFIP) markedly promoted the transformation from cumene to CHP compared to other solvents at room temperature. A cumene conversion high up to 64.3% were observed with a selectivity to CHP of 71.7%. The solvent HFIP exhibited a significant promotion on cumene oxidation due to its contribution to the enhancement of the concentration of PINO radicals. Moreover, cumyl, cumyl oxyl and methyl radicals were captured by TEMPO and analyzed by HRMS, and the reaction paths and mechanisms from cumene to products were inferred. The preparation method discovered in this work may open an access to the production of CHP.

A Nanographene-Based Two-Dimensional Covalent Organic Framework as a Stable and Efficient Photocatalyst

Jin, Enquan,Fu, Shuai,Hanayama, Hiroki,Addicoat, Matthew A.,Wei, Wenxin,Chen, Qiang,Graf, Robert,Landfester, Katharina,Bonn, Mischa,Zhang, Kai A. I.,Wang, Hai I.,Müllen, Klaus,Narita, Akimitsu

supporting information, (2021/12/22)

Synthesis of covalent organic frameworks (COFs) with desirable organic units furnishes advanced materials with unique functionalities. As an emerging class of two-dimensional (2D) COFs, sp2-carbon-conjugated COFs provide a facile platform to build highly stable and crystalline porous polymers. Herein, a 2D olefin-linked COF was prepared by employing nanographene, namely, dibenzo[hi,st]ovalene (DBOV), as a building block. The DBOV-COF exhibits unique ABC-stacked lattices, enhanced stability, and charge-carrier mobility of ≈0.6 cm2 V?1 s?1 inferred from ultrafast terahertz photoconductivity measurements. The ABC-stacking structure was revealed by the high-resolution transmission electron microscopy and powder X-ray diffraction. DBOV-COF demonstrated remarkable photocatalytic activity in hydroxylation, which was attributed to the exposure of narrow-energy-gap DBOV cores in the COF pores, in conjunction with efficient charge transport following light absorption.

Two-step sequential energy transfer of molecular assemblies based on host-guest interactions for the construction of photochemically catalyzed artificial light-harvesting systems

Jiang, Man,Li, Xing-Long,Liu, Hui,Wang, Rong-Zhou,Wang, Ying,Xing, Ling-Bao,Yu, Shengsheng,Zhang, Ming-Hui

, (2022/01/14)

In the present work, a highly efficient artificial light-harvesting system with a two-step sequential energy transfer process based on host-guest interactions between cyano-substituted p-phenylenevinylene derivative (PPTA) and cucurbit [7]uril (CB [7]) ha

AuCu/ZnO heterogeneous photocatalysts: Photodeposited AuCu alloy effect on product selectivity in alkene epoxidation

Brock, Aidan J.,Deshan, Athukoralalage Don K.,Sarina, Sarina,Waclawik, Eric R.,Weerathunga, Helapiyumi,Zhu, Huai-Yong

, (2021/12/24)

AuCu metal alloy nanoparticles were photodeposited on ZnO nanorods (ZnO_NRs) which proved to be effective photocatalysts for alkene epoxidation. The alloy nanoparticles were photodeposited onto ZnO nanorods with controlled ratios of gold and copper, with the deposition monitored in situ by UV-Vis spectroscopy. The alloy catalyst hybrids were tested for activity toward styrene epoxidation and HMF oxidative esterification, where the photoreactions were both optimized for time, temperature, and metal ratio content of the catalyst. The Au0.54Cu1/ZnO_NR alloy catalysts showed excellent photocatalytic activity and were most effective for conversion of styrene to styrene epoxide, where the product selectivity could be controlled by varying the metal ratio. Cu content in the alloy NP was essential to this process, as shown by the extrema in terms of metal content, using Au/ZnO only, where 100% benzaldehyde was obtained as the product. Au/ZnO evidenced best photocatalytic activity for HMF esterification, with conversion rapidly diminishing upon alloying of Au with Cu. A detailed XPS study was carried out to investigate reaction mechanism based on these studies, in particular, mechanisms are proposed for styrene epoxidation and oxidation cycles using the AuCu/ZnO_NR photocatalysts.

Process route upstream and downstream products

Process route





propyl sodium

propyl sodium









Conditions Yield
weiteres Produkt: Propan;






Conditions Yield
at 280 - 300 ℃; im geschlossenen Rohr;






Conditions Yield
With nickel; at 200 ℃;
With nickel; In benzene; for 0.5h; Title compound not separated from byproducts; Heating;
With oxygen; tricalcium diphosphate; palladium; at 120 ℃; for 2h; under 760 Torr; Further Variations:; Catalysts; Temperatures; Product distribution;
With triethylamine; cyclohexene; palladium/alumina; In cyclohexane; at 80 ℃; Further Variations:; Reagents; Catalysts; Solvents; Temperatures; Product distribution;
With oxygen; In water; at 80 ℃; for 24h; under 760.051 Torr;
With oxygen; at 160 ℃; for 1h; neat (no solvent);
With palladium on carbon; [emim][NTf2]; oxygen; at 160 ℃; for 1h; Kinetics; Ionic liquid;
With 5% palladium on Al2O3; In ethyl acetate; at 70 ℃; Inert atmosphere;
With ammonium formate; In ethanol; water; at 60 ℃; for 0.5h;
With 5% Pd/C; In water; at 100 ℃; for 12h; under 750.075 Torr; Time; Solvent; Inert atmosphere; Autoclave;
With formic acid; 5%-palladium/activated carbon; In ethanol; water; at 80 ℃; for 0.5h; Reagent/catalyst; Time; Inert atmosphere;
With carbon dioxide; 5%-palladium/activated carbon; In water; at 100 ℃; for 3h; under 47254.7 Torr; Pressure; Time;
With doubly supported catalyst Pd(at)MIL-88B-NH2(at)nano-SiO2; air; In toluene; at 110 ℃; for 168h; under 675.068 - 1500.15 Torr; Catalytic behavior;
With sodium hydroxide; In water; toluene; at 100 ℃; for 4h; under 760.051 Torr; Reagent/catalyst;
With palladium on activated carbon; In para-xylene; at 130 ℃; for 0.16h; Temperature; Kinetics; Catalytic behavior; Inert atmosphere;
28.8 %Chromat.
diethyl ether

diethyl ether

methylmagnesium iodide

methylmagnesium iodide









benzyl alcohol

benzyl alcohol

Conditions Yield
Erwaermen des Reaktionsprodukts mit Benzaldehyd und nach Zersetzung mit verd.Schwefelsaeure;Produkt5: Dibenzoylmethan;
Conditions Yield
With oxygen; tetraethylammonium borohydride; 5,10,15,20-tetraphenyl porphyrin iron; In 1,2-dimethoxyethane; isopropyl alcohol; for 25h; Product distribution; Ambient temperature; further transition metal catalysts; effect of catalyst on the product yield/distribution;
Conditions Yield
With oxygen; cobalt acetylacetonate; In isopropyl alcohol; at 75 ℃; for 1h;
48 % Chromat.
2 % Chromat.
24 % Chromat.
With oxygen; cobalt acetylacetonate; In isopropyl alcohol; at 75 ℃; for 1h; Product distribution;
48 % Chromat.
24 % Chromat.
2 % Chromat.
Conditions Yield
styrene; With RhCl(PPh3)3; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 0 - 5 ℃; for 1h;
With oxygen; triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 12h;
With phenylsilane; oxygen; In tetrahydrofuran; at 60 ℃; for 16h; under 750.075 Torr; Reagent/catalyst; Time;
With phenylsilane; oxygen; cobalt acetylacetonate; In tetrahydrofuran; for 20h; Ambient temperature;
With triethylsilane; (1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyaninato)iron(II); oxygen; In ethanol; at 20 ℃; for 23h; under 760.051 Torr; chemoselective reaction; Sealed tube; Green chemistry;
With triethylsilane; porphyrin‐Co(II); oxygen; In dichloromethane; for 24h; Ambient temperature;
With oxygen; tetraethylammonium borohydride; 5,10,15,20-tetraphenyl-21H,23H-porphine cobalt(II); In 1,2-dimethoxyethane; isopropyl alcohol; at -50 ℃; for 46h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With oxygen; cobalt(II) bis(salicylidene-γ-iminopropyl)methylamine;
With triethylsilane; oxygen; bis(trifluoroacetylacetonato)cobalt(II); In propan-1-ol; at 75 ℃; for 12h;
53 % Chromat.
29 % Chromat.
With air; tetrabutylammonium borohydride; (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride; Yield given. Multistep reaction. Yields of byproduct given; 1) CH2Cl2, 2) CH2Cl2, r.t., 24 h;
With oxygen; tetraethylammonium borohydride; 5,10,15,20-tetraphenyl-21H,23H-porphine cobalt(II); In 1,2-dimethoxyethane; isopropyl alcohol; at -50 ℃; for 46h; Mechanism; Product distribution; other catalysts, other reaction conditions;
With triethylsilane; [5,10,15,20-tetra(2,6-dichlorophenyl)porphyrinato]cobalt(II); oxygen; phosphorous acid trimethyl ester; Yield given. Multistep reaction; 1.) 2-propanol, dichloromethane, 28 deg C, 1 atm, 10 min, 2.) 2-propanol, dichloromethane, RT, 2 h;
With pyridine; oxygen; bis(salicylidene)-based Co(2+); In ethanol; at 70 ℃; for 8h; under 760 Torr;
45.88 % Chromat.
54.12 % Chromat.
With dichloro bis(acetonitrile) palladium(II); 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); water; p-benzoquinone; In methanol; isopropyl alcohol; at 35 - 85 ℃; for 34h; Inert atmosphere; Glovebox;
61 %Chromat.
17 %Chromat.
With cis-[((R,R)-N,N'-dimethyl-N,N'-bis(pyridin-2-ylmethyl)cyclohexane-1,2-diamine)RuVI(O)2](ClO4)2; In acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;
26 %Chromat.
55 %Chromat.
With phenylsilane; oxygen; lithium ethoxide; In tetrahydrofuran; at 60 ℃; for 16h; under 750.075 Torr; Reagent/catalyst; Catalytic behavior;
79 %Chromat.
16 %Chromat.
With oxygen; potassium carbonate; isopropyl alcohol; at 130 ℃; for 6h; under 3000.3 Torr; Reagent/catalyst; Temperature; Catalytic behavior;
79.6 %Chromat.
8 %Chromat.
Conditions Yield
With oxygen; CoSMDPT; Product distribution; var. reag.: H2O2, CH3COOH or K2O/18-crown-6; var. solv.;










Conditions Yield
With oxygen; for 10h; Irradiation;
230 %
diethyl ether

diethyl ether











Conditions Yield
for 2h; Product distribution; Irradiation;

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