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

• 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 
• 872298-25-4 2,2-bis(4-methoxyphenyl)-1-phenylethan-1-ol 
• 1066-30-4 chromium(lll) acetate 
• 639-61-2 4,4'-dimethoxybenzilic acid 
• 88837-72-3 2,2-bis(4-methoxyphenyl)-1,1,1-tribromoethane 
• 93902-86-4 1,1-bis-(4-methoxy-phenyl)-but-1-ene 
• 17435-03-9 dichloro-bis-(4-methoxy-phenyl)-methane 
• 68313-25-7 3,3,6,6-Tetrakis(4-methoxyphenyl)-1,2-dioxane 
• 100-07-2 4-methoxy-benzoyl chloride 

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 
• 500698-71-5 1,1-bis(4-methoxyphenyl)-2,2-diphenylethan-1-ol 
• 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 
• 18499-71-3 9,10-bis-[3-hydroxy-3,3-bis-(4-methoxy-phenyl)-prop-1-ynyl]-anthracene 
• 31067-02-4 1,1-Bis(p-methoxyphenyl)ethan-1-ol 
• 4663-13-2 1,1-bis(4-methoxyphenyl)propene 

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.).

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.

Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen

A simple, and practical oxidative scission of aromatic olefins to carbonyl compounds using O2as the sole oxidant with poly(ethylene glycol) dimethyl ether as a benign solvent has been developed. A wide range of monosubstituted,gem-disubstituted, 1,2-disubstituted, trisubstituted and tetrasubstituted aromatic olefins was successfully converted into the corresponding aldehydes and ketones in excellent yields even with gram-scale reaction. Some control experiments were also conducted to support a possible reaction pathway.

Method for preparing aldehyde ketone compound through olefin oxidation

The invention provides a method for preparing an aldehyde ketone compound by olefin oxidation, which relates to an olefin oxidative cracking reaction in which oxygen participates. The method comprises the following specific steps: in the presence of a solvent and an oxidant, carrying out oxidative cracking on an olefin raw material to obtain a corresponding aldehyde ketone product. Compared with the traditional method, the method does not need to add any catalyst or ligand, does not need to use high-pressure oxygen, has the advantages of simple and mild reaction conditions, environment friendliness, low cost, high atom economy and the like, is wide in substrate application range and high in yield, and has a wide application prospect in the aspects of synthesis of aldehyde ketone medical intermediates and chemical raw materials.

AIBN initiated functionalization of the benzylic sp3 C[sbnd]H and C[sbnd]C bonds in the presence of dioxygen

A sp3 C[sbnd]H bond functionalization and C[sbnd]C bond cleavage were realized by AIBN/O2 catalyst system, providing a series of benzophenones under mild reaction conditions. The mechanistic study shows that a peroxide intermediate is involved in this transformation, and in the case of diphenylmethanes, the sp3 C[sbnd]C bond is cleaved through the peroxide rearrangement, which might provides a new way to cleave relatively strong C[sbnd]C bond and be applied to more general C[sbnd]C bond activation.

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.].