5350-47-0

Usage

Uses

Used in Pharmaceutical Industry:
(4-Nitro-phenyl)-p-tolyl-methanone is used as a building block for the synthesis of various pharmaceuticals. Its chemical structure allows for the creation of a wide range of medicinal compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Industry:
In the agrochemical industry, (4-Nitro-phenyl)-p-tolyl-methanone is employed as a starting material for the production of different agrochemicals. Its versatility in organic synthesis enables the development of compounds that can be used in agriculture to improve crop protection and yield.
Used in Material Science:
(4-Nitro-phenyl)-p-tolyl-methanone is also utilized in the field of material science. It plays a role in the development of new materials with specific properties, such as improved strength, durability, or chemical resistance, which can be applied in various industrial applications.
Used as a Reagent in Chemical Reactions:
(4-Nitro-phenyl)-p-tolyl-methanone is used as a reagent in various chemical reactions, facilitating the synthesis of complex organic molecules. Its reactivity and functional groups make it a valuable tool in the hands of chemists for advancing research and development in the chemical industry.

InChI:InChI=1/C14H11NO3/c1-10-2-4-11(5-3-10)14(16)12-6-8-13(9-7-12)15(17)18/h2-9H,1H3

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 201230-82-2 carbon monoxide 
• 937-12-2 4-tolyltrimethylstannane 
• 539-43-5 4-methylphenylmercuric chloride 
• 108-88-3 toluene 
• 116592-27-9 (4-Nitrophenyl)-(furan-2-carbonyl)-diazomethan 
• 122-04-3 4-nitro-benzoyl chloride 
• 90252-89-4 p-tolylzinc(II) chloride 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 26037-72-9 p-CH₃C₆H₄HgI 
• 5720-05-8 4-methylphenylboronic acid 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 5142-75-6 tri(p-tolyl)bismuth 
• 31614-66-1 tributyl(p-tolyl)stannane 

Downstream Products

• 33092-23-8 2-[4-(4-Methyl-benzoyl)-phenyl]-2,3-diphenyl-propionitrile 
• 33092-18-1 {4-[4-(4-Methyl-benzoyl)-phenyl-NNO-azoxy]-phenyl}-p-tolyl-methanone 
• 33757-37-8 4-methylphenyl(4-nitrophenyl)methanol 
• 62147-81-3 <4-Methyl-phenyl>-<4-nitro-phenyl>-diazomethan 
• 71777-53-2 p-Methyl-p'-nitrobenzophenon-tosylhydrazon 
• 7377-13-1 4-(4-nitrobenzoyl)benzoic acid 
• 331831-18-6 4-methyl-3,5,4'-trinitro-benzophenone 
• 79859-23-7 4-(4-nitrobenzoyl)benzoic acid methyl ester 
• 349443-22-7 4-(4-aminobenzoyl)benzoic acid methyl ester 
• 876611-16-4 4-[4-(benzylamino)benzoyl]benzoic acid methyl ester 
• 876611-17-5 4-[4-(benzoylamino)benzoyl]benzoic acid methyl ester 
• 99717-09-6 4-methyl-3,4'-dinitro-benzophenone 
• 116496-24-3 4-methyl-4'-nitro-benzophenone oxime 
• 6180-80-9 4-Amino-4'-methylbenzophenone 

Relevant academic research and scientific papers

Dirhodium-Catalyzed Enantioselective B?H Bond Insertion of gem-Diaryl Carbenes: Efficient Access to gem-Diarylmethine Boranes

The scarcity of reliable methods for synthesizing chiral gem-diarylmethine borons limits their applications. Herein, we report a method for highly enantioselective dirhodium-catalyzed B?H bond insertion reactions with diaryl diazomethanes as carbene precursors. These reactions afforded chiral gem-diarylmethine borane compounds in high yield (up to 99 % yield), high activity (turnover numbers up to 14 300), high enantioselectivity (up to 99 % ee) and showed unprecedented broad functional group tolerance. The borane compounds synthesized by this method could be efficiently transformed into diaryl methanol, diaryl methyl amine, and triaryl methane derivatives with good stereospecificity. Mechanistic studies suggested that the borane adduct coordinated to the rhodium catalyst and thus interfered with decomposition of the diazomethane, and that insertion of a rhodium carbene (generated from the diaryl diazomethane) into the B?H bond was most likely the rate-determining step.

Synthesis, structure, and characterization of picolyl- and benzyl-linked biphenyl palladium N-heterocyclic carbene complexes and their catalytic activity in acylative cross-coupling reactions

N-heterocyclic carbene ligands with picolyl (L1H2Br2, L3H2Br2) and benzyl (L2H2Br2, L4H2Br2) linked biphenyl backbone were synthesized and characterized. Their palladium(II) complexes [PdL1]Br2 (1), [PdL2Br2] (2), [PdL3]Br2 (3), and [PdL4Br2] (4) were synthesized by direct method using Pd(OAc)2. All complexes (1–4) were characterized by CHN analysis, electrospray ionization-MS, nuclear magnetic resonance, and single-crystal X-ray diffraction. Molecular structures confirm the distorted square planar geometry around the Pd(II) center. All of them showed good catalytic activity in acylative Suzuki cross coupling of phenyl boronic acid with benzoyl chloride to afford benzophenone in good yields.

Carbonylative Suzuki coupling reactions catalyzed by ONO pincer–type Pd(II) complexes using chloroform as a carbon monoxide surrogate

Benzoylhydrazone Schiff base–ligated three new ONO pincer–type palladium(II) complexes, [(PdL1(PPh3)] (1), [(PdL2(PPh3)] (2), and [(PdL3(PPh3)] (3), were synthesized by the reaction of the respective ligand, N-(2-hydroxybenzylidene)benzohydrazide (HL1), N-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (HL2), or N-(5-bromo-2-hydroxybenzylidene) benzohydrazide (HL3), with Pd(OAc)2 and PPh3 in methanol and isolated as air-stable reddish-orange crystalline solids in high yields (78%–83%). All three complexes were fully characterized by elemental analysis, Fourier-transform infrared spectroscopy, UV–Visible, 1H nuclear magnetic resonance (NMR), 13C{1H} NMR, and 31P{1H} NMR spectroscopic studies. The molecular structure of all three complexes was established unambiguously by single-crystal X-ray diffraction studies which revealed a distorted square planar geometry of all three complexes. The ONO pincer–type ligands occupied three coordination sites at the palladium, while the fourth site is occupied by the monodentate triphenylphosphine ligand. The catalytic potential of all three complexes was explored in the carbonylative Suzuki coupling of aryl bromides and iodides with arylboronic acids to yield biaryl ketones, using CHCl3 as the source of carbonyl. The reported protocol is convenient and safe as it obviates the use of carbon monoxide (CO) balloons or pressured CO reactors which are otherwise needed for the carbonylation reactions. The methodology has been successfully applied to the synthesis of two antineoplastic drugs, namely, phenstatin and naphthylphenstatin, in good yields (81% and 85%, respectively). Under the optimized reaction conditions, complex 2 exhibited the best catalytic activity in the carbonylative Suzuki couplings. The reported catalysts have wide reaction scope with good functional group tolerance. All catalysts could be retrieved from the reaction after completion and recycled up to three times with insignificant loss in the catalytic activity.

Ligand-free Palladium-Catalyzed Carbonylative Suzuki Coupling of Aryl Iodides in Aqueous CH3CN with Sub-stoichiometric Amount of Mo(CO)6 as CO Source

A new method for the synthesis of diaryl and heterodiaryl ketones has been established based on the palladium-catalyzed carbonylative Suzuki coupling approach with sub-stoichiometric Mo(CO)6 as CO source. Using 0.5 mol% of Pd(TFA)2 as catalyst, 0.5 equivalent of Mo(CO)6 as solid carbonyl reagent and 3 equivalent of K3PO4 as base, a wide range of functionalized (hetero)aryl iodides and (hetero)aryl boronic acids could smoothly proceed the carbonylative cross-coupling reaction in aqueous CH3CN at 50 °C, affording the corresponding ketones in good to excellent yields. The newly developed method was easy to operate under mild conditions with high efficiency. (Figure presented.).

Highly efficient synthesis of aryl ketones by PEPPSI-palladium catalyzed acylative Suzuki coupling of amides with diarylborinic acids

An improved acylative cross-coupling of various N-methyl-N-tosyl amides with diarylborinic acids for synthesis of aryl ketones is developed. In most cases, aryl ketones could be obtained in excellent yields by using 1 mol% 2,6-diisopropylphenylimidazolylidene and 3-chloropyridine co-supported palladium chloride as catalyst in the presence of 3 equiv. K2CO3 as base in refluxing THF. The readily prepared and cost-effective substrates, N-methyl-N-tosylamides and diarylborinic acids, and the commercially available catalyst system promise a practical and efficient access to aryl ketones.

Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment

A series of novel benzophenone derivatives containing a thiazole heterocyclic nucleus were designed by molecular hybridization. Molecular docking studies have demonstrated the inhibitory potential of the designed compounds against cyclooxygenase (COX) isoenzymes. These compounds were synthesized, characterized, and evaluated for their anti-inflammatory properties by the croton oil-induced ear edema assay to examine their effect on both prostaglandin (PG) production and neutrophils recruitment. The thiazole derivatives displayed a potent effect in terms of reducing ear edema. The analysis suggested that the presence of 4-phenyl-2-hydrazinothiazole and the absence of C40-OCH3 on the benzophenone derivative structure are strongly related to the inhibition of PG production. In addition, the derivatives 2e, 3a and 3c concomitantly inhibit PG production and neutrophil recruitment, which may be a mechanism of action better than of common NSAIDs due to their inability to inhibit the neutrophil recruitment. Thus, these compounds can be considered as potential lead compounds toward the development of new anti-inflammatory drugs with an innovating mechanism of action.

Kinetic studies on tetrabutylammonium bromochromate oxidation of some mono-and di-substituted benzhydrols

The oxidation of 12 mono- and di-substituted benzhydrols (BH) by tetrabutylammonium bromochromate (TBABC) have been studied in aqueous acetic acid medium. Absence of any effect of added acrylonitrile on the reaction discounts the possibility of a one-electron oxidation, leading to the formation of free radicals. The tetrabutylammonium bromochromate oxidation of 12 mono- and di-substituted benzhydrols complies with the isokinetic relationship and Hammett relationship. The overall mechanism is proposed to involve a cyclic concerted symmetrical transition state leading to the product.

Transition-Metal-Free Regiospecific Aroylation of Nitroarenes Using Ethyl Arylacetates at Room Temperature

A novel regiospecific C(sp3)-C(sp2) coupling between ethyl arylacetates and nitroarenes has been developed to deliver biaryl ketones in excellent yields. The protocol is metal-free, mild, and compatible with a number of functional groups on both of the reacting partners.

At normal pressure fragrant ketone copper catalytic synthesis method

The invention discloses a method of synthesizing diaryl ketone under normal pressure by virtue of copper catalysis. The method is as follows: in a solvent alcohol or aqueous liquor of alcohol, under action of alkali and acid, adding a copper catalyst, alkyl iodide, alkyl boric acid and carbon monoxide to directly carry out crossed coupling reaction to prepare diaryl ketone compounds. According to the invention, the method of preparing diaryl ketone compounds by carbonylation Suzuki coupling reaction has the advantages as follows: the catalyst is wide in source, cheap and small in toxicity; the reaction is free of ligand in reaction and good in activity; the reaction is carried out under the normal pressure and selectivity is high; a substrate source is wide and stable; functional group compatibility is good and scope of application for the substrate is wide; a reaction medium is environment-friendly and recyclable. Under the condition of optimizing reaction conditions, the target product separating yield is 95%.

At normal pressure fragrant ketone nickel catalytic synthesis method

The invention discloses a method for synthesizing diarylketone under the catalysis of nickel at normal pressure. The method comprises the steps of enabling aryl iodide, arylboronic acid and carbon monoxide to be subjected to direct cross-coupling reaction in a solvent polyethylene glycol or a water solution of polyethylene glycol under the catalysis of a nickel catalyst and the combined action of alkaline and acid at normal pressure to prepare a diarylketone compound. The method has the advantages of wide catalyst source, low price, little toxicity, reaction at normal pressure, high selectivity, no need of ligands in reaction, good activity, good functional group compatibility, wide substrate application range, wide substrate source, stable substrate, green and recyclable reaction medium and the like. The separation yield of target products is up to 93% under an optimized reaction condition.