90-90-4

Usage

Uses

Used in Analytical Applications:
4-Bromobenzophenone is used as a component in high-performance liquid chromatography (HPLC) and gas chromatography (GC) for the separation and analysis of various compounds. Its unique chemical properties make it suitable for use as a stationary phase or derivatization agent, enhancing the selectivity and sensitivity of these analytical techniques.
Used in Chemical Synthesis:
As a chemical reagent, 4-bromobenzophenone plays a crucial role in the synthesis of various organic compounds. Its reactivity allows it to undergo a range of chemical reactions, such as nucleophilic substitution, electrophilic aromatic substitution, and coupling reactions, making it a versatile building block for the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
4-Bromobenzophenone serves as an important intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity enable the development of new drugs with improved therapeutic properties. It is used in the production of various drug candidates, including antidepressants, anti-inflammatory agents, and other therapeutic agents.

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 2708, 1966 DOI: 10.1021/jo01346a526Tetrahedron Letters, 27, p. 929, 1986 DOI: 10.1016/S0040-4039(00)84140-4

Purification Methods

Crystallise the phenone from EtOH. The 2,4-dinitrophenylhydrazone forms orange-red leaflets from dioxane/EtOH with m 207-209o. [Allen & Van Allan J Am Chem Soc 66 7 1944, Beilstein 7 H 422, 7 III 2079, 7 IV 1378.]

InChI:InChI=1/C13H9BrO/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9H

Upstream product

• 108-86-1 bromobenzene 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 5472-32-2 1,2-bis-(4-bromo-phenyl)-1,2-diphenyl-ethane-1,2-diol 
• 103-73-1 Phenetole 
• 29334-16-5 phenyl(4-bromophenyl)methanol 
• 2116-36-1 1-benzyl-4-bromo-benzene 
• 18066-89-2 1-bromo-4-<(bromophenyl)methyl>benzene 
• 201230-82-2 carbon monoxide 
• 595-90-4 tetraphenyltin(IV) 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 99763-24-3 (Z)-4-bromobenzophenone oxime 
• 98-07-7 Benzotrichlorid 
• 586-75-4 4-chlorobenzoyl chloride 

Downstream Products

• 101606-21-7 (4-bromo-phenyl)-phenyl-[2]pyridyl-methanol 
• 4333-76-0 1-(4-bromophenyl)-1-phenylethene 
• 132568-80-0 4-(4-bromo-phenyl)-4-hydroxy-4-phenyl-but-2-ynoic acid amide 
• 115915-86-1 1-(4-bromo-phenyl)-1,5,5-triphenyl-pent-2-yne-1,5-diol 
• 6813-30-5 4-biphenyl-2-yl-benzophenone 
• 51608-66-3 1-(4-bromophenyl)-1-phenylpropan-1-ol 
• 127787-74-0 p-bromophenyltrityl chloride 
• 61623-62-9 1-(p-bromophenyl)-1,1-diphenylcarbinol 
• 717881-57-7 4-bromo-trityl bromide 
• 119-61-9 benzophenone 
• 33090-29-8 4,4'-dibenzoyl-1,1'-biphenyl 
• 29334-16-5 phenyl(4-bromophenyl)methanol 
• 2116-36-1 1-benzyl-4-bromo-benzene 
• 5472-32-2 1,2-bis-(4-bromo-phenyl)-1,2-diphenyl-ethane-1,2-diol 

Relevant academic research and scientific papers

Recyclable Transition Metal Catalysis using Bipyridine-Functionalized SBA-15 by Co-condensation of Methallylsilane with TEOS

Well-defined recyclable Pd- and Rh-bipyridyl group-impregnated SBA-15 catalysts were prepared for C?C bond coupling reaction and selective hydrogenation reactions, respectively. These SBA-15 derived ligands for the catalysts were prepared by direct and indirect co-condensation method using bipyridyl-linked methallylsilane. This indirect method, involving methoxysilane generated from methallylsilane shows higher loading efficiency of transition metal catalysts on SBA-15 than the direct use of methallylsilane.

Nitrosoarene-Catalyzed HFIP-Assisted Transformation of Arylmethyl Halides to Aromatic Carbonyls under Aerobic Conditions

A rare metal-free nucleophilic nitrosoarene catalysis accompanied by highly hydrogen-bond-donor (HBD) solvent, 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), organocatalytically converts arylmethyl halides to aromatic carbonyls. This protocol offers an effective means to access a diverse array of aromatic carbonyls with good chemoselectivity under mild reaction conditions. The activation of arylmethyl halides by HFIP to generate stable carbocation and autoxidation of in situ generated hydroxylamine to nitrosoarene in the presence of atmospheric O2 are the keys to success.

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.

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 of olefins in water

The carbonyl compounds, synthesized by the oxidative cleavage of their corresponding olefins, are of great significance in organic synthesis, especially aryl ketones. We have developed a gentle and effective protocol, using acid red 94 as the organic metal-free photocatalyst, O2 as the oxidant, and water as the solvent. Under visible light irradiation, aryl ketone derivatives were obtained in moderate to excellent yields, showing good economic and environmental advantages.

Halogen Bonding Tetraphenylethene Anion Receptors: Anion-Induced Emissive Aggregates and Photoswitchable Recognition

A series of tetraphenylethene (TPE) derivatives functionalized with highly potent electron-deficient perfluoroaryl iodo-triazole halogen bond (XB) donors for anion recognition are reported. 1H NMR titration experiments, fluorescence spectroscopy, dynamic light scattering measurements, TEM imaging and X-ray crystal structure analysis reveal that the tetra-substituted halogen bonding receptor forms luminescent nanoscale aggregates, the formation of which is driven by XB-mediated anion coordination. This anion-coordination-induced aggregation effect serves as a powerful sensory mechanism, capable of luminescence chloride sensing at parts per billion concentration. Furthermore, the doubly substituted geometric isomers act as unprecedented photoswitchable XB donor anion receptors, where the composition of the photostationary state can be modulated by the presence of a coordinating halide anion.

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 supported on MRGO@CoAl-LDH catalyzed reductive carbonylation of nitroarenes and carbonylative Suzuki coupling reactions using formic acid as liquid CO and H2 source

In the present study, a heterogeneous palladium catalyst system, Pd nanoparticles supported on MRGO@CoAl-LDH, was synthesized and employed in reductive carbonylation of nitroarenes and carbonylative Suzuki coupling reactions using formic acid as CO and H2 source. The as-obtained heterogeneous catalyst was characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray analysis (EDAX), thermal gravimetric analysis (TGA), and vibrating sample magnetometer (VSM). The nanocatalyst was reused for 5 cycles with a negligible reduction in the yield of products. All reactions were carried out with high yields and under suitable and safe conditions. Also, we have successfully applied formic acid as a good and safe alternative to CO and H2 gases.

Self-Assembled 2,3-Dicyanopyrazino Phenanthrene Aggregates as a Visible-Light Photocatalyst

In this study, 2,3-dicyanopyrazino phenanthrene (DCPP), a commodity chemical that can be prepared at an industrial scale, was used as a photocatalyst in lieu of Ru or Ir complexes in C-X (X = C, N, and O) bond-forming reactions under visible-light irradiation. In these reactions, [DCPP]n aggregates were formed in situ through physical π-πstacking of DCPP monomers in organic solvents. These aggregates exhibited excellent photo- and electrochemical properties, including a visible light response (430 nm), long excited-state lifetime (19.3 μs), high excited-state reduction potential (Ered([DCPP]n*/[DCPP]n·-) = +2.10 V vs SCE), and good reduction stability. The applications of [DCPP]n aggregates as a versatile visible-light photocatalyst were demonstrated in decarboxylative C-C cross-coupling, amidation, and esterification reactions.

A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones

We herein report the fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe-Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe-N-C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion.