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Usage

Uses

Used in Pharmaceutical Industry:
4-Nitrobenzophenone is used as an organic chemical synthesis intermediate for the development of various pharmaceutical compounds. Its versatile chemical structure allows for further functionalization and modification, making it a valuable building block in the synthesis of a range of drugs.
Used in Antimalarial Applications:
In the field of antimalarial drug development, 4-Nitrobenzophenone is employed in the quantitative structural activity relationship (QSAR) analysis of benzophenone derivatives. This analysis helps researchers understand the relationship between the chemical structure of benzophenone derivatives and their antimalarial activity, guiding the design of more effective and targeted treatments against malaria.
Used in Chemical Synthesis:
4-Nitrobenzophenone serves as a crucial intermediate in the synthesis of various organic compounds, including dyes, pigments, and other specialty chemicals. Its reactivity and functional group make it a versatile component in the creation of a wide array of products across different industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 4634, 1983 DOI: 10.1021/jo00172a038Tetrahedron Letters, 27, p. 113, 1986 DOI: 10.1016/S0040-4039(00)83955-6

InChI:InChI=1/C13H9NO3/c15-13(10-4-2-1-3-5-10)11-6-8-12(9-7-11)14(16)17/h1-9H

Upstream product

• 119-61-9 benzophenone 
• 1817-77-2 4-benzyl-1-nitrobenzene 
• 94521-53-6 benzophenone; nitrate 
• 122-04-3 4-nitro-benzoyl chloride 
• 71-43-2 benzene 
• 636-98-6 p-nitrobenzene iodide 
• 201230-82-2 carbon monoxide 
• 15525-13-0 tetramethylammonium tetraphenylborate 
• 934-56-5 trimethyl(phenyl)stannane 
• 841-76-9 triphenylaluminium 
• 62673-29-4 phenyl(diisobutyl)aluminium 
• 58482-37-4 triphenylaluminium etherate 
• 33091-15-5 4-nitrophenyl(phenyl)methanol 
• 7599-05-5 4-nitrophenylphenylcyanomethane 

Downstream Products

• 101439-73-0 1-(4-nitro-phenyl)-1-phenyl-penta-2,4-diyn-1-ol 
• 115915-87-2 1-(4-nitro-phenyl)-1,5,5-triphenyl-pent-2-yne-1,5-diol 
• 33091-15-5 4-nitrophenyl(phenyl)methanol 
• 2999-01-1 4-nitro-benzophenone-seqtrans-oxime 
• 23554-71-4 (E)-cyclohexyl(phenyl)methanone oxime 
• 63068-97-3 dichloro-(4-nitro-phenyl)-phenyl-methane 
• 106652-57-7 dibromo-(4-nitro-phenyl)-phenyl-methane 
• 1137-41-3 (4-aminophenyl)(phenyl)methanone 
• 19617-86-8 bis-(4-benzoyl-phenyl)-diazene 
• 119852-63-0 4-[4-(4-nitro-phenyl)-1,4-diphenyl-butatrienyl]-anisole 
• 22057-84-7 1-(4-nitrophenyl)-1-phenylethylene 
• 115165-05-4 4-hydroxy-4-(4-nitro-phenyl)-4-phenyl-but-2-ynoic acid 
• 33092-21-6 2-(4-benzoylphenyl)-2-phenylbutanenitrile 
• 68063-82-1 1-((Z)-2-Methanesulfonyl-1-phenyl-vinyl)-4-nitro-benzene 

Relevant academic research and scientific papers

Carbonylative cross-coupling reaction of ethynylstibane with aryl iodides

Palladium-catalyzed carbonylative cross-coupling reaction of ethynylstibane (Ph-=-SbPh2) and aryl iodides (Ar-I) is described. The reaction of the stibanes and the halides under 1 atm of carbon monoxide in N,N-dimethylacetamide using a combination of 5 mol% Pd(OAc)2 and 4 equivalents (20 mol%) of PPh3 brought about carbonylative cross-coupling reaction to afford arylethynylketones [ArC(O)-=-Ph] in good yields along with a small amount of directly coupled products, aryl acetylens (Ar-=-Ph). Formation of the side product was completely suppressed by conducting the reaction under high CO pressure (20 atm) conditions. The present method provides a variety of carbonylated products in good yield even with electron-deficient aryl iodides which usually give inferior results due to their tendency to undergo decarbonylation in the cross-coupling reaction of ethynylstibanes and acyl halides.

Palladium-catalyzed coupling of benzoyl halides with aryltrifluorosilanes leading to diaryl ketones

Acyl-aryl Hiyama coupling of acyl halides with arylsilanes has been achieved by employing a palladium/phosphine catalyst system. A variety of acyl chlorides and fluorides can be applied for coupling with arylsilicon reagents, and unsymmetrical benzophenone derivatives can be prepared using this protocol.

Highly efficient etherification and oxidation of aromatic alcohols using supported and unsupported phosphorus pentoxide as a heterogeneous reagent

A highly efficient procedure for etherification and oxidation of aromatic alcohol is described using unsupported and supported P2O5 on alumina and/or silica gel. The silica gel and alumina proved to be the most suitable support among the supports examined in our experiments. It was illustrated that the etherification and oxidative performance in reactions depend largely upon variables including reaction temperature, the nature of the P2O5 used (supported or unsupported P2O 5), and whether solvent-free conditions are applied. It was shown that P2O5 not only can convert the aromatic alcohols into corresponding ethers and/or aldehyde and ketone but also can convert aromatic ethers into aldehyde or ketone via oxidative cleavage. Finally, quantum mechanical calculations were performed to rationalized these events, and it was indicated that aldehyde and ketone are more favorable products on the basis of the heat of formation (Hf).

Synthesis, structure, and characterization of picolyl- and benzyl-linked biphenyl palladium N-heterocyclic carbene complexes and their catalytic activity in acylative cross-coupling reactions

N-heterocyclic carbene ligands with picolyl (L1H2Br2, L3H2Br2) and benzyl (L2H2Br2, L4H2Br2) linked biphenyl backbone were synthesized and characterized. Their palladium(II) complexes [PdL1]Br2 (1), [PdL2Br2] (2), [PdL3]Br2 (3), and [PdL4Br2] (4) were synthesized by direct method using Pd(OAc)2. All complexes (1–4) were characterized by CHN analysis, electrospray ionization-MS, nuclear magnetic resonance, and single-crystal X-ray diffraction. Molecular structures confirm the distorted square planar geometry around the Pd(II) center. All of them showed good catalytic activity in acylative Suzuki cross coupling of phenyl boronic acid with benzoyl chloride to afford benzophenone in good yields.

Room-temperature palladium-catalyzed and copper(I)-mediated coupling reactions of acid chlorides with boronic acids under neutral conditions

The palladium-catalyzed cross-coupling reactions of acid chlorides with arylboronic acids in the presence of copper(I) thiophene-2-carboxylate (CuTC) as an activator under strictly non-basic and mild reaction conditions afford the unsymmetrical ketones in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring is compatible. Georg Thieme Verlag Stuttgart.

Phosphane-free palladium-catalyzed carbonylative suzuki coupling reaction of aryl and heteroaryl iodides

The carbonylative cross-coupling reaction of an arylboronic acid with an aryl iodide and a heteroaryl iodide to give unsymmetrical biaryl ketones was carried out by using Pd(tmhd)2/Pd (OAc)2 as a phosphane-free catalyst. Various aryl and heteroaryl iodides with different arylboronic acid derivatives provided, good, to excellent yields of the desired products under optimized reaction conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

Silica-supported phosphine palladium(0) complex catalyzed phenylation of acid chlorides and aryl iodides by sodium tetraphenylborate

In the presence of a catalytic amount of silica - supported phosphine palladium(0) complex, sodium tetraphenylborate (NaBPh4) reacts with acid chlorides under mild conditions to give the corresponding phenyl ketones in 57-80% yields; it also reacts with aryl iodides to afford the corresponding biaryls in 75-84% yields.

A convenient method for preparing aromatic ketones from acyl chlorides and arylboronic acids via Suzuki-Miyaura type coupling reaction

Aromatic ketones are synthesized efficiently via palladium-catalyzed cross-coupling reaction of boronic acids with acyl chlorides in the presence of K3PO4 hydrate in toluene. This allows the use of aliphatic acyl chlorides as the starting material. Hydrated water plays a significant role as an H2O source to activate the catalytic system.

Palladium-catalyzed direct conversion of carboxylic acids into ketones with organoboronic acids promoted by anhydride activators

A new type of catalytic process to convert carboxylic acids and organoboron compounds into unsymmetrical ketones in one-pot under mild and neutral conditions was presented. The method allowed the use of an α, β-unsatuarted carboxylic acids such as trans-c

Nucleophilic acylation of arylfluorides catalyzed by imidazolidenyl carbene

Imidazolidenyl carbene catalyzes nucleophilic acylation reaction of arylfluorides with electron withdrawing groups to give benzophenone derivatives.