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Usage

Uses

Used in Pharmaceutical Industry:
1,4-Dibenzoylbenzene is used as a reactant in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medications. Its chemical properties make it a valuable intermediate in the production of a range of therapeutic agents.
Used in Dye and Fragrance Industry:
In the dye and fragrance industry, 1,4-dibenzoylbenzene is used as a component in the production of various dyes and fragrances. Its unique chemical structure allows it to contribute to the color and scent profiles of these products, enhancing their quality and performance.
Used in Sunscreen Products:
1,4-Dibenzoylbenzene is used as an ultraviolet light absorber in sunscreen products. It helps protect the skin from the harmful effects of UV radiation, reducing the risk of sunburn and skin damage. Its effectiveness in absorbing UV light makes it a valuable ingredient in a variety of sunscreen formulations.
Used in Organic Synthesis:
As a versatile organic compound, 1,4-dibenzoylbenzene is used as a reactant in the synthesis of other organic compounds. Its chemical reactivity and structural features make it a useful building block in the creation of a wide range of organic molecules for various applications, including chemical research and industrial processes.

InChI:InChI=1/C20H14O2/c21-19(15-7-3-1-4-8-15)17-11-13-18(14-12-17)20(22)16-9-5-2-6-10-16/h1-14H

Upstream product

• 7375-38-4 4-benzhydrylbenzophenone 
• 100-47-0 benzonitrile 
• 100-20-9 terephthaloyl chloride 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 201230-82-2 carbon monoxide 
• 624-38-4 para-diiodobenzene 
• 934-56-5 trimethyl(phenyl)stannane 
• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 98-88-4 benzoyl chloride 
• 6136-66-9 4-iodobenzophenone 
• 587-85-9 diphenylmercury(II) 
• 100-21-0 terephthalic acid 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 1605-19-2 1,4-bis(1-phenylvinyl)benzene 
• 1849-27-0 1,4-bis(2-phenylethynyl)benzene 
• 57542-59-3 phenyl(4-(2-phenylethynyl)phenyl)methanone 
• 138062-34-7 1,4-bis(6-phenylfulven-6-yl)benzene 
• 792-68-7 1,2-dibenzylbenzene 
• 793-23-7 1,4-dibenzylbenzene 
• 31024-89-2 α,α'-diphenyl-1,4-benzenedimethanol 
• 58280-04-9 (4-benzylphenyl)(phenyl)methanone 
• 455952-11-1 1,4-di(benzoyl)benzene-3',3-disulfonyl chloride 
• 15880-27-0 1-[4-(1-hydroxy-1-phenylprop-2-ynyl)phenyl]-1-phenylprop-2-yn-1-ol 
• 874365-06-7 1,4-di-(8-bromo-3-phenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 
• 874365-11-4 1,4-di-(2,6-diphenyl-5-ethoxycarbonyl-[2H]-naphtho[2,1-b]pyran-2-yl)-benzene 
• 792-67-6 1,2-Bis-cyclohexylmethyl-cyclohexan 

Relevant academic research and scientific papers

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

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.

Pd-Catalysed carbonylative Suzuki-Miyaura cross-couplings using Fe(CO)5under mild conditions: generation of a highly active, recyclable and scalable ‘Pd-Fe’ nanocatalyst

The dual function and role of iron(0) pentacarbonyl [Fe(CO)5] has been identified in gaseous CO-free carbonylative Suzuki-Miyaura cross-couplings, in which Fe(CO)5supplied COin situ, leading to the propagation of catalytically active Pd-Fe nanoparticles. Compared with typical carbonylative reaction conditions, CO gas (at high pressures), specialised exogenous ligands and inert reaction conditions were avoided. Our developed reaction conditions are mild, do not require specialised CO high pressure equipment, and exhibit wide functional group tolerance, giving a library of biaryl ketones in good yields.

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.].

Recyclable polyetheretherketone fiber-supported N-heterocyclic carbene catalysts for nucleophilic acylation of fluorobenzenes

We report for the first time a novel support of polyetheretherketone fiber for the synthesis of recyclable N-heterocyclic carbene (NHC) catalysts. The fiber catalysts were verified in nucleophilic acylation of fluorobenzenes with superior catalytic activities, and successfully recycled by a tiny pair of tweezers over 21 cycles with minimal loss of performance.

Ruthenium-Catalyzed Dehydrogenation of Alcohols with Carbodiimide via a Hydrogen Transfer Mechanism

Ruthenium-catalyzed oxidative dehydrogenation of alcohols using carbodiimide as an efficient hydrogen acceptor has been developed. The protocol exhibits wide substrate scope with good to excellent yields. The results of the kinetic analysis indicated that the reaction mechanism includes the hydrogen transfer process and that the addition of carbodiimide is essential for the reaction system, and the resulting amidine also could react as a hydrogen acceptor.

Novel and efficient bridged bis(N-heterocyclic carbene)palladium(II) catalysts for selective carbonylative Suzuki–Miyaura coupling reactions to biaryl ketones and biaryl diketones

Bridged N,N′-substituted bisbenzimidazolium bromide salts (L1, L2, and L3) were synthesized and fully characterized. Reactions of palladium acetate with L1, L2, and L3 afforded corresponding new bridged bis(N-heterocyclic carbene)palladium(II) complexes (C1, C2, and C3) in high yields. The X-ray structure of complex C1 showed that the Pd(II) ion is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromido ligands are in the cis position, resulting in a distorted square planar geometry. The three Pd(NHC)2Br2 complexes C1, C2, and C3 were evaluated in carbonylative Suzuki–Miyaura coupling reactions of aryl boronic acids with aryl halides and displayed high catalytic activity with low catalyst loading. The coupling reactions of aryl bromides were selective towards the carbonylation product at higher carbon monoxide pressure.

Endergonic addition of N -methylamines to aromatic ketones driven by photochemical offset of the entropic cost

Intermolecular addition reactions are generally accompanied by an entropic penalty due to the decrease of molecular numbers during the reaction, which sometimes makes the reaction endergonic. Here we demonstrate that such an endergonic reaction can be promoted with light-energy as a driving force; N-methylamines were added to aromatic ketones to produce aminoalcohols under UV-light irradiation. The reaction represents an obvious example showing that the photochemical approach is effective to offset such an entropic cost, and thereby to drive thermodynamically uphill addition reactions. Moreover the present reactions are highly expedient from the synthetic view point, being transition-metal-catalyst-free, scalable, highly atom economical, and regioselective. The product amines can be converted in one step to functional multi-arylated enamines, which are potentially valuable compounds in electronic materials.

Reactions of hydrazones and hydrazides with Lewis acidic boranes

The reaction of (diphenylmethylene)hydrazone or 1,4-bis-hydrazone-ylidene(phenylmethyl)benzene with Lewis acidic boranes B(2,4,6-F3C6H2)3 or B(3,4,5-F3C6H2)3 generates the Lewis acid-base adducts. Alternatively, when (9H-fluoren-9-ylidene)hydrazone is employed several products were isolated including 1,2-di(9H-fluoren-9-ylidene)hydrazone, the 2:1 borane adduct of NH2-NH2 and the 1-(diarylboraneyl)-2-(9H-fluoren-9-ylidene)hydrazone in which one ArH group has been eliminated. The benzhydrazide starting material also initially gives an adduct when reacted with Lewis acidic boranes which upon heating eliminates ArH generating a CON2B heterocycle.

Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols

An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.