1137-41-3

Usage

Uses

Used in Optics Industry:
4-Aminobenzophenone is used as a frequency doubler for semiconductor lasers, enhancing the performance of these devices by converting the frequency of the laser light.
Used in Chemical Synthesis:
4-Aminobenzophenone is used in the preparation of 1-[4-[N,N-bis(trimethylsilyl)amino]phenyl]-1-phenylethylene, a compound with potential applications in various chemical processes.
Used in Pharmaceutical Industry:
4-Aminobenzophenone serves as a precursor to prepare 1,2,3-triazoles, pyrimidotriazoles, benzothiazole, and pyrimidinone derivatives, which are important building blocks in the synthesis of pharmaceutical compounds.
Used in Coordination Chemistry:
4-Aminobenzophenone is involved in the formation of coordination complexes with chromium(III), which can have potential applications in various fields, such as catalysis and materials science.
Despite its high SHG efficiency, the growth of high-quality bulk crystals of 4-aminobenzophenone remains a challenging task, which may limit its widespread use in certain applications.

Synthesis Reference(s)

Tetrahedron Letters, 39, p. 1313, 1998 DOI: 10.1016/S0040-4039(97)10877-2

Safety Profile

Poison by intraperitoneal route. See also KETONES and AMINES. When heated to decomposition it emits toxic fumes of NOx,.

Purification Methods

Dissolve it in aqueous acetic acid, filter and precipitate it with ammonia. This process is repeated several times, then the amine is recrystallised from aqueous EtOH. [Beilstein 14 IV 248.]

InChI:InChI=1/C13H11NO/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9H,14H2

Upstream product

• 520-03-6 N-phenylphthalimide 
• 98-88-4 benzoyl chloride 
• 119-61-9 benzophenone 
• 1144-74-7 4-nitrobenzophenone 
• 19617-84-6 N-(4-benzoylphenyl)benzamide 
• 134-85-0 4-chlorobenzophenone 
• 873-74-5 4-Aminobenzonitrile 
• 110-89-4 piperidine 
• 36210-71-6 4-benzoylphenyl azide 
• 93-98-1 N-phenyl benzoyl amide 
• 201230-82-2 carbon monoxide 
• 124-41-4 sodium methylate 
• 33091-15-5 4-nitrophenyl(phenyl)methanol 
• 40101-60-8 2-(4-benzoylphenyl)-1H-isoindole-1,3(2H)-dione 

Downstream Products

• 4834-61-1 N-(4-benzoylphenyl)acetamide 
• 92247-43-3 1-(4-Aminophenyl)-1-phenylethanol 
• 117372-66-4 3-nitro-4,4''-imino-di-benzophenone 
• 193140-41-9 4-amino-3,5-dichloro-benzophenone 
• 16678-73-2 (salicylidene-p-amino)benzophenone 
• 19617-84-6 N-(4-benzoylphenyl)benzamide 
• 109805-15-4 N-(p-benzoylphenyl)-N'-phenylurea 
• 93-98-1 N-phenyl benzoyl amide 
• 65-85-0 benzoic acid 
• 100969-19-5 N-(4-benzoyl-phenyl)-N'-methyl-thiourea 
• 134919-56-5 Methyl N-(4-benzoylphenyl)carbamate 
• 54885-02-8 phenyl(quinolin-6-yl)methanone 
• 18267-97-5 N-acetyl-sulfanilic acid-(4-benzoyl-anilide) 
• 881738-38-1 2-(4-benzoyl-anilino)-butenedioic acid diethyl ester 

Relevant academic research and scientific papers

Selective reduction of aromatic nitro compounds to aromatic amines by Baker's yeast in basic solution

Aromatic nitro compounds containing o-, m- or p-electron withdrawing groups, such as carbonyl, halogen and nitro, were selectively and rapidly reduced to their corresponding amino derivatives in good yields using Bakers' Yeast in basic solution.

Structural and Substituent Effect on (+.) vs. (+) Formation in Fast Atom Bombardment Mass Spectra of Simple Organic Compounds

The peak intensity ratios of (+.) vs. (+) were measured in the fast atom bombardment (FAB) mass spectra of readily available test compounds with 3-nitrobenzyl alcohol as the matrix.For simple aromatic amines, the ratio increases as the ionization energy of the substrate decreases. 4-Subsituted benzophenones showed preferential formation of (+) ions, regardless of the nature of the substituents.This is probably due to the fact that the benzophenones have carbonyl groups which can form hydrogen bonds with the matrix molecule.The peak intensity ratio is roughly proportional to the Hammett ?+.Among 4-substituted biphenyls, both bromo and chloro substituents afforded abnormally high peak intensity ratios.The effects of the substituents in these compounds are discussed semi-quantitatively in terms of the Hammett correlation and the hard and soft acids and bases principle.The mechanism of ion formation in FAB and chemical ionization (CI) ion sources appeared to be different because some of the compounds studied showed an intense (+.) peak with a relatively weak (+) peak in FAB spectra but exhibited a strong (+) peak in ordinary CI spectra.

A new cobalt triangular prism supramolecular flask: Encapsulation of a quinhydrone cofactor for hydrogenation of nitroarenes with high selectivity and efficiency

A new M6L3 metal-organic triangular prism host Co–L1 was synthesized that contains a sufficiently large cavity for encapsulation of a quinhydrone (QHQ) electron transporter to form charge-transfer complexes for accelerating electron delivery. Through the strong coordinating ability of the ONP chelator, a suitable redox potential was obtained for the combination of light-driven proton reduction with the selective hydrogenation of nitro groups. The experimental results showed that the regulation of redox potential is very beneficial for hydrogen production and that the introduction of QHQ accelerates electron transfer and increases the reaction rate. Control experiments based on an inhibitor and a mononuclear compound resembling the cobalt corner of the triangular prism suggest enzyme-like behaviour. This synthetic platform, in which the supramolecular systems exhibit high activity and stability, provides an alternative strategy to selectively hydrogenate nitroarenes using light as a clean energy source.

Xantphos-ligated palladium dithiolates: An unprecedented and convenient catalyst for the carbonylative Suzuki–Miyaura cross-coupling reaction with high turnover number and turnover frequency

Xantphos- and dithiolate-ligated macrocyclic palladium complexes as an efficient and stable catalyst for the carbonylative Suzuki–Miyaura cross-coupling reaction have been synthesized. The catalysts were characterized by 1H-nuclear magnetic resonance (NMR), CHNS (carbon, hydrogen, nitrogen, and sulfur) analysis, melting point analysis, and 31P-NMR spectroscopy. Several sensitive functional groups (e.g., –NO2, –F, –Cl, –Br, –NH2, and –CN) on the aromatic ring were well tolerated in the carbonylative Suzuki–Miyaura coupling reaction. The present palladium complexes produce six times higher turnover number (TON) and five times higher turnover frequency (TOF) compared with conventional homogeneous palladium precursors. Maximum TONs in the range of 105 to 106 and TOF in the range of 104 to 105 could be generated by a very low amount of catalyst loading (10–5?mol%).

Fe2O3/NGr@C- and Co-Co3O4/NGr@C-catalysed hydrogenation of nitroarenes under mild conditions

An improved hydrogenation of nitroarenes using nano-structured iron- and cobalt-based catalysts is presented. Modifications of the heterogeneous catalysts by N-doped graphene-flakes are crucial for the success of selective reductions. The use of polar solvents and basic additives has a significant positive influence on the rate of reduction of nitroarenes. This allows performing non-noble metal-catalysed hydrogenations under very mild reaction conditions (e.g. 70 °C and 20 bar). On the basis of the obtained catalytic results a heterolytic mechanism for the hydrogenation process is postulated, too.

Silver-catalyzed decarboxylative acylation of arylglyoxylic acids with arylboronic acids

The silver-catalyzed coupling of arylboronic acids with arylglyoxylic acids was found to be an extremely efficient route for the synthesis of unsymmetrical diaryl ketones. It can be conducted on a gram scale under mild and open-flask conditions with good functional group compatibility, avoiding the addition of expensive and/or toxic metals. This journal is

TITANIUM-MEDIATED REDUCTION OF NITROBENZENES AND BENZIL WITH DIALKYL TELLURIDE

In the presence of titanium(IV) chloride, nitrobenzenes are easily reduced with dialkyl telluride to give the corresponding amines in good to moderate yields.Benzil is reduced to benzoin which, on a further treatment, is converted to desoxybenzoin.

A practical and chemoselective reduction of nitroarenes to anilines using activated iron

Reduction of nitroarenes to anilines using activated iron generated by Fe/HCl or Zn/FeSO4 is described. A variety of functional groups such as alkyne, ketone, enone, nitrile, lactone, and aromatic halide are well tolerated under these conditions.

Silica gel supported AlCl3 catalyzed Friedel-Crafts acylation of aromatic compounds

Silica gel supported aluminium trichloride (SiO2-AlCl3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for the acylation of aromatic compounds with acid chlorides. The catalyst can be reused up to five times after simple washing with ether and is stable (as a bench top catalyst).

Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane

The metal-free reduction of nitro compounds to amines mediated by trichlorosilane was successfully performed for the first time under continuous-flow conditions. Aromatic as well as aliphatic nitro derivatives were converted to the corresponding primary amines in high yields and very short reaction times with no need for purification. The methodology was also extended to the synthesis of two synthetically relevant intermediates (precursors of baclofen and boscalid).