1033-26-7

Basic information

• Product Name: bis(4-nitrophenyl)methanone
• Synonyms: bis(4-nitrophenyl)methanone
• CAS NO: 1033-26-7
• Molecular Formula: C₁₃H₈N₂O₅
• Molecular Weight: 272.21
• Mol File: 1033-26-7.mol

Chemical Properties

• Melting Point: 189 °C
• Boiling Point: 484.7°Cat760mmHg
• Flash Point: 246.3°C
• Appearance: /
• Density: 1.423g/cm³
• Vapor Pressure: 1.5E-09mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: bis(4-nitrophenyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: bis(4-nitrophenyl)methanone(1033-26-7)
• EPA Substance Registry System: bis(4-nitrophenyl)methanone(1033-26-7)

Safety Data

• Hazardous Substances Data: 1033-26-7(Hazardous Substances Data)

Usage

Uses

Used in Dye Production:
Bis(4-nitrophenyl)methanone is used as a precursor in the production of dyes, contributing to the synthesis of various colorants for different applications.
Used in Pharmaceutical Industry:
Bis(4-nitrophenyl)methanone is used as a building block in the synthesis of pharmaceuticals, aiding in the development of new drugs and improving existing ones.
Used in Polymer Production:
Bis(4-nitrophenyl)methanone is used as a component in the production of polymers, enhancing the properties and performance of various polymeric materials.
Used in Organic Synthesis for Research and Industrial Purposes:
Bis(4-nitrophenyl)methanone is used as a versatile reagent in organic synthesis, enabling the creation of complex organic molecules for research and industrial applications.
Used in the Synthesis of Other Complex Organic Molecules:
Bis(4-nitrophenyl)methanone is used as a key intermediate in the synthesis of other complex organic molecules, showcasing its importance in organic chemistry.

InChI:InChI=1/C13H8N2O5/c16-13(9-1-5-11(6-2-9)14(17)18)10-3-7-12(8-4-10)15(19)20/h1-8H

Upstream product

• 21655-75-4 1,1-dichloro-2,2-bis(4-nitrophenyl)ethene 
• 3740-55-4 2,2-bis(4-nitrophenyl)ethanoic acid 
• 596-48-5 tris(p-nitrophenyl)carbinol 
• 47797-98-8 1,1,2,2-tetrakis(4-nitrophenyl)ethene 
• 123-75-1 pyrrolidine 
• 64416-13-3 1,1,1-trifluoro-2,2-bis-(4-nitrophenyl) ethane 
• 636-98-6 p-nitrobenzene iodide 
• 201230-82-2 carbon monoxide 
• 52323-94-1 trimethyl(4-nitrophenyl)stannane 
• 1144-74-7 4-nitrobenzophenone 
• 10605-46-6 1,1-bis(4-nitrophenyl)ethylene 
• 1033-25-6 4,4'-dinitro-benzhydrol 
• 14688-37-0 cis-p,p'-dinitrostilbene oxide 
• 968-01-4 (2SR,3SR)-2,3-bis(4-nitrophenyl)oxirane 

Downstream Products

• 100970-28-3 bis(4-nitrophenyl)dimethoxymethane 
• 71777-55-4 p,p'-dinitrobenzophenone tosylhydrazone 
• 47797-98-8 1,1,2,2-tetrakis(4-nitrophenyl)ethene 
• 2642-81-1 1,1-bis(p-chlorophenyl)ethene 
• 2069-48-9 4-chloro-4'-fluoro-benzophenone 
• 108-95-2 phenol 
• 611-98-3 4,4'-diaminobenzophenone 
• 100-02-7 4-nitro-phenol 
• 62-23-7 4-nitro-benzoic acid 
• 17303-16-1 bis(4-azidophenyl)methanone 
• 112399-97-0 C₂₂H₂₄N₂O₅ 
• 112421-58-6 1-[Bis-(4-nitro-phenyl)-methoxy]-adamantane 
• 112399-98-1 (3aR,6R,6aR)-6-[Bis-(4-nitro-phenyl)-methoxymethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 112400-00-7 (3aR,5R,6S,6aR)-5-{(R)-2-[Bis-(4-nitro-phenyl)-methoxy]-1-hydroxy-ethyl}-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 

Relevant articles and documents

The formation of 4,4′-difluorobenzophenone from 4,4′-dinitrodiphenylmethane

The novel one pot oxidation/fluorodenitration of 4,4′-dinitrodiphenylmethane to form 4,4′-difluorobenzophenone has been achieved using tetramethylammonium fluoride in N,N-dimethylacetamide.

Kinetic and quantum chemical studies of the mechanism of dehydrochlorination of 2,2-diaryl-1,1,1-trichloroethanes with nitrite ions

The E2 mechanism has been proposed for the dehydrochlorination of 2,2-diaryl-1,1,1-trichloroethanes with nitrite ion, leading to 2,2-diaryl-1,1-dichloroethenes, on the basis of experimental kinetic study and quantum chemical simulation.

Transformation of 1,1-Dichloro-2,2-bis(4-nitrophenyl)ethene in the Reaction with Nitrite Ion in Polar Aprotic Solvents

The reaction of 1,1-dichloro-2,2-bis(4-nitrophenyl)ethene with sodium nitrite in polar aprotic solvents has been studied. Products of the reaction have been identified, and effects of different factors, including reactant dissociation and solvation, on the reaction rate constants have been analyzed. Thermodynamic parameters of the reaction have been determined, the multistep process has been simulated by quantum chemical calculations, and a plausible mechanism has been proposed.

OXIDATION OF SUBSTRATES HAVING LABILE HYDROGENS BY SUPEROXIDE IN THE PRESENCE OF PHOSGENE DIMER

Superoxide (O2(-.)) oxidized substrates having labile hydrogens to ketones in the presence of phosgene dimer.Oxidation with similar treatment of alkynes were examined.The reaction mechanism was also discussed.

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.].

Aerobic Oxygenation of Alkylarenes over Ultrafine Transition-Metal-Containing Manganese-Based Oxides

The oxygenation of alkylarenes to the corresponding aryl ketones is an important reaction, and the development of efficient heterogeneous catalysts that can utilize O2 as the sole oxidant is highly desired. In this study, we developed an efficient alkylarene oxygenation process catalyzed by ultrafine transition-metal-containing Mn-based oxides with spinel or spinel-like structures (M-MnOx, M=Fe, Co, Ni, Cu). These M-MnOx catalysts were prepared by a low-temperature reduction method in 2-propanol-based solutions using tetra-n-butyl ammonium permanganate (TBAMnO4) as the Mn source, and they exhibited high Brunauer–Emmett–Teller surface areas (typically >400 m2 g?1). Using fluorene as the model substrate, the catalytic activities of M-MnOx and Mn3O4 were compared. The catalytic activities of M-MnOx were significantly higher than that of Mn3O4, which demonstrates that the incorporation of transition metals in manganese oxide was critical. Among the series of M-MnOx catalysts examined, Ni-MnOx exhibited the highest catalytic activity for the oxygenation. In addition, the catalytic activity of Ni-MnOx was higher than that of a physical mixture of Mn3O4 and NiO. Furthermore, Ni-MnOx exhibited a broad substrate scope with respect to various types of structurally diverse (hetero)alkylarenes (16 examples). The observed catalysis was truly heterogeneous, and the Ni-MnOx catalyst was reusable for the oxygenation of fluorene at least three times and its high catalytic performance was preserved, for example, the reaction rate, final product yield, and product selectivity. The present Ni-MnOx-catalyzed oxygenation process is possibly initiated by a single-electron oxidation process, and herein a plausible oxygen-transfer mechanism is proposed based on several pieces of experimental evidence.

Nanostructured Manganese Oxides within a Ring-Shaped Polyoxometalate Exhibiting Unusual Oxidation Catalysis

Nanosized manganese oxides have recently received considerable attention for their synthesis, structures, and potential applications. Although various synthetic methods have been developed, precise synthesis of novel nanostructured manganese oxides are st

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.

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.

Method for preparing symmetric diarylketone through catalytic oxidative carbonylation

The invention discloses a method for preparing symmetric diarylketone of a formula (I) as shown in the description. The method comprises the following steps: mixing arylboronic acid (II) (Ar-B(OH)2 (II)), a palladium catalyst, a promoter and an organic solvent in a reactor, introducing air and CO having a volume ratio of (7-19):1, reacting under the conditions of a pressure of 1-6 atm and a temperature of 30-80 DEG C for 8-16 hours, and performing after-treatment on the reaction solution, thereby obtaining the product symmetric diarylketone. According to the method disclosed by the invention,the air directly serves as an oxidizing agent to replace the O2 to be applied to oxidative carbonylation of the arylboronic acid, and the ratio of the air to CO is beyond an explosion limit. Therefore, the catalytic system is safe and economic. The palladium catalyst is small in dosage and simple in separation and can be recycled for several times. The method disclosed by the invention is mild inreaction condition, excellent in substrate suitability and high in yield.