611-97-2

Usage

Uses

Used in Petrochemical Industry:
4,4'-Dimethylbenzophenone is utilized as a catalytic agent and petrochemical additive. Its role in this industry is crucial due to its ability to enhance the efficiency and effectiveness of various chemical reactions that are integral to the production of different petrochemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4,4'-Dimethylbenzophenone is employed as a key intermediate in the synthesis of various drugs. Its unique chemical structure allows it to serve as a building block in the creation of a wide range of pharmaceutical compounds, thereby contributing to the development of new and improved medications.

Synthesis Reference(s)

Tetrahedron, 50, p. 12821, 1994 DOI: 10.1016/S0040-4020(01)81203-5Tetrahedron Letters, 27, p. 3911, 1986 DOI: 10.1016/S0040-4039(00)83914-3

Purification Methods

Purify the benzophenone by zone refining or distllation, preferably in a vacuum. [Beilstein 7 III 2181, 7 IV 1434.]

Upstream product

• 530-45-0 1,1-di(4-methylphenyl)ethane 
• 913-86-0 tetra(4-methylphenyl)-1,2-ethanediol 
• 4957-14-6 4,4'-dimethyldiphenylmethane 
• 16620-75-0 4,4'-dimethylbenzophenone imine 
• 876498-21-4 9-(α-hydroxy-4,4'-dimethyl-benzhydryl)-fluoren-9-ol 
• 103-71-9 phenyl isocyanate 
• 874-60-2 4-methyl-benzoyl chloride 
• 108-88-3 toluene 
• 50891-00-4 dichloro-di-p-tolyl-methane 
• 64-19-7 acetic acid 
• 99-94-5 p-Toluic acid 
• 75-44-5 phosgene 
• 79-37-8 oxalyl dichloride 
• 103-73-1 Phenetole 

Downstream Products

• 102474-77-1 2-[2]pyridyl-1,1-di-p-tolyl-ethanol 
• 111089-30-6 (4-Methyl-[2]pyridyl)-di-p-tolyl-methanol 
• 6266-56-4 bis(4-methylphenyl)phenylmethanol 
• 500345-09-5 5-bromomethyl-5-methyl-2,2-di-p-tolyl-[1,3]dioxane 
• 6629-83-0 4,4',4-(ethene-1,1,2-triyl)tris(methylbenzene) 
• 82313-75-5 4-tert-Butyl-4',4''-dimethyltriphenylmethanol 
• 18763-47-8 ph3Si(OCH(4-toy)2) 
• 791-31-1 triphenylhydroxysilane 
• 2919-20-2 1,1-di(p-tolyl)ethylene 
• 4333-55-5 4,4'-(prop-1-ene-1,1-diyl)bis(methylbenzene) 
• 768295-67-6 1,1-di-p-tolylpropan-1-ol 
• 859777-49-4 2,2-diphenyl-1,1-di-p-tolyl-ethanol 
• 114889-49-5 4,4'-(2-(4-bromophenyl)ethene-1,1-diyl)bis(methylbenzene) 
• 885-77-8 4,4'-dimethylbenzhydrol 

Relevant academic research and scientific papers

Ethoxysilane appended M(II) complexes and their SiO2/MCM-41 supported forms as catalysts for efficient oxidation of secondary alcohols

Divalent transition metal complexes ML2 (M = Mn 1; Co 2; Cu 3; Zn 4), possessing an ethoxysilane group as a part of the bidentate Schiff base ((E)-1-((3-(triethoxysilyl)propylimino)methyl)naphthalen-2-ol (L)), have been synthesized. While the copper complex 3 has been isolated in an analytically pure form and characterized by spectroscopic and single crystal XRD studies, the formation of complexes 1, 2, and 4 in solution has been verified by ESI mass spectroscopy and subsequently used for further catalyst preparation without their isolation. Treatment of the in situ formed 1–4 with pre-activated silica in boiling toluene produces the catalysts 5–8, respectively. The copper complex 3 was also treated with MCM-41 in boiling toluene to obtain CuL2@MCM-41 (9). Elemental analysis (CHN), ESI MS, IR, UV–vis., 13C & 29Si NMR, EPR, P-XRD, TGA, BET, SEM and TEM have been used to characterize the compounds. Compounds 3 (homogeneous) and 5–9 (heterogeneous) have been utilized as catalysts in the oxidation of secondary alcohols to corresponding carbonyls in the presence of H2O2, t-BuOOH, and C6H5C(CH3)2OOH. 3 and 9 have shown better catalytic activity than the rest of the catalysts investigated. Combination of 9 with H2O2 is the best catalytic system due to its efficiency and reusability besides being environment friendly.

Photooxygenation of 1,1-Diarylethylenes via Addition of Oxygen to the 1,4-Dimer Radical Cations, Catalyzed by 10-Methylacridinium Ion

Photooxygenation of 1,1-diarylethylene occurs efficiently using 10-methylacridinium ion as a photocatalyst to yield the 1,2-dioxane and/or the diaryl ketone depending on the substituents on the aryl groups. The reaction mechanism is revealed based on the dependence of the quantum yields on the concentrations of the alkene and oxygen, the fluorescence quenching of 10-methylacridinium ion by the alkene, and the direct detection of reactive intermediates by applying laser flash spectroscopy as well as pulse radiolysis. The photooxygenation proceeds via photoinduced electron transfer from the alkene to the singlet excited state of 10-methylacridinium ion. The alkene radical cation formed by the photoinduced electron transfer reacts with alkene to give the 1,4-dimer radical cation, which then reacts with oxygen to produce the oxygenated 1,6-radical cation. The subsequent one-electron reduction of the 1,6-radical cation results in formation of the 1,6-biradical which cyclizes to yield 1,2-dioxane derivative or fragmentates to yield diaryl ketone. When the 1,6-biradical is reduced by the alkene itself, the alkene radical cation is regenerated to repeat the radical chain process.

Mechanism of Photochemical Reaction of Contact Charge Transfer Pair between 1,1-Diarylethene and Oxygen

Selective excitation of the contact charge transfer band between 1,1-diarylethene and oxygen in dichloromethane and acetonitrile gave 3,3,6,6-tetraaryl-1,2-dioxane and benzophenone derivative through an electron transfer reaction.The proposed mechanism was confirmed by the direct observation of the dimer cation radical of the olefin trapped by a triplet oxygen in pulse radiolysis.

Investigations of the Influence of Molecular Geometry on the Spectroscopic and Photochemical Properties of α-Oxoparacyclophanes (Cyclophanobenzophenones)

The spectroscopic and photochemical properties of a family of α-oxoparacyclophanes (8-12) for n=8-12, respectively) have been investigated.Compared to a model structure possessing a nominal T1(n?*) state (4,4'-dimethylbenzophenone, DM-BZ), photochemical and photophysical evidence is presented that the n?* character of T1 decreases as the cyclophane ring size decreases.For example, the rate constants for hydrogen atom abstraction from 1,4-cyclohexadiene in acetonitrile are 1.6E8, 0.93E8, 0.30E8, 0.06E8, and 0.04E8 M-1s-1 for triplet 12-8, respectively, a result consistent with decreasing n?* character and decreasing reactivity toward hydrogen atom abstraction with decreasing value of n.The spectroscopic properties (vibrational structure of the phosphorescence spectrum, phosphorescence lifetime, phosphorescence excitation spectra, triplet-triplet absorption spectra) also vary in a manner consistent with decreasing n?* character as the cyclophane ring size decreases.

Preparation method of diaryl ketone

The invention relates to the field of organic compound preparation chemistry, and particularly discloses a preparation method of diaryl ketone. The preparation method comprises the following steps: reacting tartrate with an aryl Grignard reagent to prepare 1,1,4,4-tetraaryl butantetraol; the method comprises the following steps: in the presence of an organic alkali and under a specific temperature condition, carrying out a highly regioselective 2, 3-cyclic sulfite esterification reaction on the 1,1,4,4-tetraaryl butantetraol and thionyl chloride to generate dichloro aryl cyclic sulfite; and reacting the dichloro aryl cyclic sulfite with inorganic alkali liquor at a certain temperature in a certain organic solvent to generate the diaryl ketone. The preparation method avoids the use of an expensive heavy metal-containing catalyst, and has the remarkable characteristics of easily available raw materials, simplicity and convenience in operation, excellent reaction region selectivity, easiness in treatment, high yield and the like.

Fe-S Catalyst Generated in Situ from Fe(III)- And S3?--Promoted Aerobic Oxidation of Terminal Alkenes

An iron-sulfur complex formed by the simple mixture of FeCl3 with S3?- generated in situ from K2S is developed and applied to selective aerobic oxidation of terminal alkenes. The reaction was carried out under an atmosphere of O2 (balloon) and could proceed on a gram scale, expanding the application of S3?- in organic synthesis. This study also encourages us to explore the application of an Fe-S catalyst in organic reactions.

Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis

A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.

Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water

With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.

Visible-Light-Driven Selective Air-Oxygenation of C?H Bond via CeCl3 Catalysis in Water

Visible-light-induced C?H aerobic oxidation is an important chemical transformation that can be applied for the synthesis of aromatic ketones. High-cost catalysts and toxic solvents were generally needed in the present methodologies. Here, an efficient aqueous C?H aerobic oxidation protocol was reported. Through CeCl3-mediated photocatalysis, a series of aromatic ketones were produced in moderate to excellent yields. With air as the oxidant, this reaction could be performed under mild conditions in water and demonstrated high activity and functional group tolerance. This method is economical, highly efficient, and environmentally friendly, and it will provide inspiration for the development of aqueous photochemical synthesis reactions.

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.].