90-96-0

Usage

Uses

Used in Organic Synthesis:
4,4'-Dimethoxybenzophenone is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for the creation of a wide range of molecules, making it an essential component in the synthesis process.
Used in Pharmaceutical Industry:
4,4'-Dimethoxybenzophenone is used as a pharmaceutical intermediate, playing a crucial role in the development and production of various medications. Its properties enable it to be incorporated into drug molecules, contributing to their efficacy and safety.
Used in Agrochemicals:
In the agrochemical industry, 4,4'-Dimethoxybenzophenone is used as a raw material and intermediate for the synthesis of various agrochemical products. Its involvement in the production of these substances helps to ensure the development of effective and safe agricultural solutions.
Used in Dyestuff Industry:
4,4'-Dimethoxybenzophenone is also utilized in the dyestuff industry, where it serves as an important raw material and intermediate for the production of dyes and pigments. Its presence in these products contributes to their colorfastness and stability.
Overall, 4,4'-Dimethoxybenzophenone is a multifaceted compound with a diverse range of applications across various industries, including organic synthesis, pharmaceuticals, agrochemicals, and dyestuff. Its unique properties and versatility make it an indispensable component in the development and production of numerous products.

Preparation

btained by photocatalytic oxidation of 4,4–′-dimethoxybenzhydrol (m.p. 69–71°) catalyzed by H3PW12O40/SiO2 in acetonitrile under oxygen atmosphere at r.t. for 1 h (90%).

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 3037, 1969 DOI: 10.1021/ja01039a036Tetrahedron Letters, 30, p. 1277, 1989 DOI: 10.1016/S0040-4039(00)72735-3

Purification Methods

Crystallise the ketone from absolute EtOH, aqueous EtOH or EtOH/AcOH. The 2,4-dinitrophenylhydrazone has m 199-200o. [Beilstein 8 H 317, 8 I 641, 8 II 355, 8 III 2649, 8 IV 2453.]

Upstream product

• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 65201-95-8 hexa-N-methyl-4,4'-carbonyl-di-anilinium; dichloride 
• 93-59-4 Perbenzoic acid 
• 4356-69-8 1,1-bis-(4-methoxyphenyl)ethylene 
• 67-66-3 chloroform 
• 60-29-7 diethyl ether 
• 4663-13-2 1,1-bis(4-methoxyphenyl)propene 
• 19920-00-4 1,1,2,2-tetrakis(4-methoxyphenyl)ethane-1,2-diol 
• 726-18-1 4,4'-dianisylmethane 
• 872298-25-4 2,2-bis(4-methoxyphenyl)-1-phenylethan-1-ol 
• 1066-30-4 chromium(lll) acetate 
• 2186-93-8 4,4’-dimethoxybenzophenone dimethyl acetal 
• 639-61-2 4,4'-dimethoxybenzilic acid 

Downstream Products

• 100-09-4 4-methoxybenzoic acid 
• 110663-65-5 1,1-bis-(4-methoxy-phenyl)-2-[2]pyridyl-ethanol 
• 67916-54-5 di[4'',4'''-di(methoxy)phenyl](2'-pyridyl)methanol 
• 17181-62-3 1,1-Bis(4-hydroxyphenyl)pentane 
• 859079-13-3 bis(4-methoxyphenyl)-(2-methylphenyl)methanol 
• 4356-69-8 1,1-bis-(4-methoxyphenyl)ethylene 
• 103512-95-4 1,1,6,6-tetrakis(p-methoxyphenyl)hexa-2,4-diyne-1,6-diol 
• 19920-00-4 1,1,2,2-tetrakis(4-methoxyphenyl)ethane-1,2-diol 
• 17435-03-9 dichloro-bis-(4-methoxy-phenyl)-methane 
• 500698-71-5 1,1-bis(4-methoxyphenyl)-2,2-diphenylethan-1-ol 
• 109723-66-2 4-hydroxy-4,4-bis-(4-methoxy-phenyl)-but-2-ynoic acid amide 
• 883836-83-7 (4,4'-dimethoxy-benzhydrylidene)-succinic acid-1-tert-butyl ester 
• 121816-51-1 1,1-bis-(4-methoxy-phenyl)-5,5-diphenyl-pentane-1,4-dien-3-one 
• 18499-68-8 1,4-bis-[3-hydroxy-3,3-bis-(4-methoxy-phenyl)-prop-1-ynyl]-benzene 

Relevant academic research and scientific papers

Chemical capture of an unprecedented oxatetramethyleneethane radical cation with a through-space electronic coupling

A photoinduced electron-transfer reaction of 2,2-dianisyl-4-isopropylidene- 3,3-dimethylcyclobutanone (5) in acetonitrile containing molecular oxygen or water gave 4,4′-dimethoxybenzophenone (7) and 2,2-dianisyl-4- isopropylidene-5,5-dimethylhydrofuran-3-one (8), demonstrating the chemical capture of an unprecedented oxatetramethyleneethane-type radical cation intermediate (6?+). A density functional theory calculation suggests through-space electronic coupling between the tetramethylallyl and joined dianisylmethyl carbonyl subunits in 6?+.

1,3-Oxathiolanes from the reaction of aromatic and enolized thioketones with monosubstituted oxiranes

The reactions of 4,4′-dimethoxythiobenzophenone (1) with (S)-2-methyloxirane ((S)-2) and (R)-2-phenyloxirane ((R)-6) in the presence of a Lewis acid such as BF3·Et2O, ZnCl2, or SiO2 in dry CH2Cl2 led to the corresponding 1:1 adducts, i.e., 1,3-oxathiolanes (S)-3 with Me at C(5), and (S)-7 and (R)-8 with Ph at C(4) and C(5), respectively. A 1:2 adduct, 1,3,6-dioxathiocane (4S,8S)-4 and 1,3-dioxolane (S)-9, respectively, were formed as minor products (Schemes 3 and 5, Tables 1 and 2). Treatment of the 1:1 adduct (S)-3 with (S)-2 and BF3·Et2O gave the 1:2 adduct (4S,8S)-4 (Scheme 4). In the case of the enolized thioketone 1,3-diphenylprop-1-ene-2-thiol (10) with (S)-2 and (R)-6 in the presence of SiO2, the enesulfanyl alcohols (1′Z,2S)-11 and (1′E,2S)-11, and (1′Z,2S)-13, (1′E,2S)-13, (1′Z,1R)-15, and (1′E,1R)-15, respectively, as well as a 1,3-oxathiolane (S)-14 were formed (Schemes 6 and 8). In the presence of HCl, the enesulfanyl alcohols (1′Z,2S)-11, (1′Z,2S)-13, (1′E,2S)-13, (1′Z,1R)-15, and (1′E,1R)-15 cyclize to give the corresponding 1,3-oxathiolanes (S)-12, (S)-14, and (R)-16, respectively (Schemes 7, 9, and 10). The structures of (1′E,2S)-11, (S)-12, and (S)-14 were confirmed by X-ray crystallography (Figs. 1-3). These results show that 1,3-oxathiolanes can be prepared directly via the Lewis acid-catalyzed reactions of oxiranes with non-enolizable thioketones, and also in two steps with enolized thioketones. The nucleophilic attack of the thiocarbonyl or enesulfanyl S-atom at the Lewis acid-complexed oxirane ring proceeds with high regio- and stereoselectivity via an SK2-type mechanism.

Preparation, redox properties, and x-ray structures of electrochromic 11,11,12,12-tetraarylanthraquinodimethane and its bianthraquinodimethane analogue: Drastic geometrical changes upon interconversion with dicationic dyes

Tetrakis(4-methoxyphenyl)anthraquinodimethane 1(b) with a bent geometry undergoes reversible redox interconversion with twisted dication 1(t) 2+ exhibiting a vivid change in color (electrochromism) accompanied by a drastic structural change. Electrochemical oxidation of bianthraquinodimethane 2(b) with a doubly bent structure to bianthrylidene-type twisted dication 2(t)2+ proceeded smoothly, whereas the reverse conversion was less effective because 2(t)2 generated upon reduction of 2(t)2+ is a long-lived species to undergo side reactions.

Supramolecular amphiphiles based on cyclodextrin and hydrophobic drugs

Herein we report a novel “supra-prodrug-type” superamphiphile design: via a redox-sensitive self-immolative linker, a hydrophobic drug molecule was labeled with an azobenzene moiety, which was designed to be capped by a hydrophilic cyclodextrin (CD) molec

Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide

A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).

Palladium nanoparticles on amino-modified silica-catalyzed C–C bond formation with carbonyl insertion

Abstract: A practical and heterogeneously catalyzed Stille, homo-coupling, and Suzuki carbonylation reaction has been reported using Pd nanoparticles supported on amino-vinyl silica-functionalized magnetic carbon nanotube (CNT@Fe3O4@SiO2-Pd) for the efficient synthesis of symmetrical and unsymmetrical diaryl ketones from aryl iodides. A wide variety of symmetrical and unsymmetrical diaryl ketones were obtained in high yields under CO gas-free conditions using Mo(CO)6 as an efficient carbonyl source. Considering the atom economy of Ph3SnCl, less than an equimolar amount can be applied in Stille transformation, which is of great importance due to the toxicity of organotin derivatives. Moreover, no phosphine ligand and external reducing agent were necessary in these coupling carbonylation reactions. This heterogeneous Pd catalyst offers high activity with very low palladium leaching. Finally, the catalyst can be reused and recycled for six steps without loss in activity, exhibiting good example of sustainable methodology. Graphic abstract: [Figure not available: see fulltext.].

Palladium imine-pyridine-imine complex immobilized on graphene oxide as a recyclable catalyst for the carbonylative homo-coupling of aryl halides

A heterogeneous 3-N,N,N-(II) Pd(OAc)2 catalyst was prepared from the reaction of Pd(OAc)2 with Si-Prn-N = C-Py-C = N-Prn-Si immobilized on graphene oxide (GO-Si-Prn-N = C-Py-C = N-Prn-Si-GO). The prepared catalyst was characterized by inductively coupled plasma optical emission spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, Raman spectroscopy, energy dispersive X-ray spectroscopy, X-ray diffraction, UV-vis spectroscopy, BET surface area, scanning electron microscopy, transmission electron microscopy, and thermogravimetric analysis. The catalyst was employed as a heterogeneous catalyst for carbonylative homo-coupling of aryl iodides and bromides under carbon monoxide gas-free condition. Cr(CO)6 was used as the carbon monoxide source and the desired symmetrical diaryl ketones were achieved in good to excellent yields. Moreover, the catalyst was reused up to five consecutive cycles without significant loss of activity.

Organotellurium-catalyzed oxidative deoximation reactions using visible-light as the precise driving energy

Irradiated by visible light, the recyclable (PhTe)2-catalyzed oxidative deoximation reaction could occur under mild conditions. In comparison with the thermo reaction, the method employed reduced catalyst loading (1 mol% vs. 2.5 mol%), but afforded elevated product yields with expanded substrate scope. This work demonstrated that for the organotellurium-catalyzed reactions, visible light might be an even more precise driving energy than heating because it could break the Te–Te bond accurately to generate the active free radical catalytic intermediates without damaging the fragile substituents (e.g., heterocycles) of substrates. The use of O2 instead of explosive H2O2 as oxidant affords safer reaction conditions from the large-scale application viewpoint.

PhSe(O)OH/NHPI-catalyzed oxidative deoximation reaction using air as oxidant

A novel oxidative deoximation method was developed in this article. Compared with the reported organoselenium-catalyzed oxidative deoximation reaction, this reaction employed N-hydroxyphthalimide (NHPI) as the co-catalyst, so that the oxidative deoximation reaction could utilize air as oxidant in the green DMC solvent under mild reaction conditions. Control experiments and X-ray photoelectron spectroscopy (XPS) analysis results indicated that NHPI was essential for activating the catalytic organoselenium species. It could accelerate the activation of molecular oxygen in air to promote the reaction process. The reaction can avoid metal residues in product and is of potential application values in pharmaceutical industry due to the transition metal-free process.

Synthesis of biaryl ketones and biaryl diketones via carbonylative Suzuki-Miyaura coupling reactions catalyzed by bridged bis(N-heterocyclic carbene)palladium(II) catalysts

This disclosure relates to bridged bis(N-heterocyclic carbene)palladium(II) complexes, methods of preparing the complexes, and methods of using the complexes in Suzuki-Miyaura coupling reactions.