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Usage

Uses

Used in Pharmaceutical Industry:
Aminodiphenylmethane is used as an active pharmaceutical ingredient intermediate for chiral resolution, playing a crucial role in the development of pharmaceuticals with specific therapeutic effects.
Used in Chemical Synthesis:
Aminodiphenylmethane is used as a building block for chemical synthesis, enabling the creation of various compounds and contributing to the advancement of the chemical industry.
Used in Furan-2-carboxylic Acid Benzhydrylamide Preparation:
Aminodiphenylmethane is used as a reactant in the preparation of furan-2-carboxylic acid benzhydrylamide by reacting with furan-2-carbonyl chloride, which is an important step in the synthesis of certain pharmaceuticals and chemical products.

Synthesis

1) synthesis of diphenylketoximeAfter benzophenone 10g, oxammonium hydrochloride 6g, 95% ethanol 20mL are put into reaction flask stirring and dissolving, gradation adds sodium hydrate solid 11g.Finish, reaction solution is heated to 88 DEG C of reaction 2h, then pours in dilute hydrochloric acid solution by reaction solution, occurs white solid, filter to obtain diphenylketoxime 10.7g, yield 99%.2) synthesis of benzhydrylamineDiphenylketoxime 0.25g, 95% ethanol 5mL are put into reaction flask, after solution change is clear, adds concentration into 5 × 10 7cFU/mL waxy Bacillus solution 50mL, constant temperature 30 DEG C (rotating speed 200r/min) oscillatory reaction in shaking table.TLC detect without raw material time, add appropriate diatomite in reaction solution and carry out centrifugation, get supernatant liquid acidifying, with dichloromethane extraction, aqueous layer basified and with dichloromethane extraction concentrate to obtain benzhydrylamine 9.0g, yield 91%.

Purification Methods

Crystallise the amine from H2O. The free base absorbs CO2 from the atmosphere; store it accordingly. The hydrochloride M 219.7 m 293-295o, crystallises from H2O. [Beilstein 12 H 1323, 12 IV 3282.]

InChI:InChI=1/C13H13N/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H,14H2/p+1

Upstream product

• 1013-88-3 Benzophenone imine 
• 119-61-9 benzophenone 
• 540-69-2 ammonium formate 
• 91-01-0 1,1-Diphenylmethanol 
• 574-66-3 Benzophenone oxime 
• 4695-13-0 2,2-diphenylacetamide 
• 5350-57-2 benzophenone hydrazone 
• 3376-34-9 benzophenone oxime methyl ether 
• 100-97-0 hexamethylenetetramine 
• 776-74-9 Bromodiphenylmethane 
• 14066-73-0 benzophenone semicarbazone 
• 574-61-8 benzophenone N-phenylhydrazone 
• 21160-02-1 benzophenone O-acetyl oxime 
• 4224-00-4 3-methyl-5,5-diphenyl-imidazolidine-2,4-dione 

Downstream Products

• 102008-20-8 benzhydryl-(1-methyl-pyrrolidin-2-ylmethyl)-amine 
• 93580-01-9 1-benzhydryl-1H-pyridin-4-one 
• 6744-64-5 N,N'-dibenzhydryl-urea 
• 101288-95-3 N-benzhydryl-N'-(2-hydroxy-ethyl)-urea 
• 101785-47-1 N-benzhydryl-N'-(1-hydroxymethyl-propyl)-urea 
• 10254-15-6 nicotinic acid benzhydrylamide 
• 127568-50-7 N-benzhydrylfuran-2-carboxamide 
• 634153-68-7 piperonal-benzhydrylimine 
• 6229-28-3 5-hydroxy-3-methyl-pent-3c-enoic acid benzhydrylamide 
• 5267-35-6 N-(diphenylmethyl)acetamide 
• 66607-69-0 4-nitrobenzylidenediphenylmethylamine 
• 62506-88-1 N-benzylidenediphenylmethanamine 
• 50289-28-6 4-methoxybenzylidenediphenylmethylamine 
• 137636-01-2 1-benzhydryl-3-phenyl-urea 

Relevant academic research and scientific papers

Carbon monoxide and carbon dioxide insertion chemistry of f-block N-heterocyclic carbene complexes

The reactions of f-block silylamido N-heterocyclic carbene (NHC) complexes ([M(L)(N{SiMe3}2)2], M = Y, Ce, and U, L = bidentate alkoxy-tethered NHC ligand) with CO and CO2 have been studied and compared to each

Trihydroborates and Dihydroboranes Bearing a Pentacoordinated Phosphorus Atom: Double Ring Expansion To Balance the Coordination States

The first trihydroborate bearing a pentacoordinated phosphorus atom was synthesized as a new P?B bonded compound. Hydride abstraction of the trihydroborate gave an intermediary dihydroborane, which showed hydroboration reactivity and was trapped with pyridine whilst maintaining the P?B bond. The dihydroborane underwent a rearrangement, which involved a double ring expansion to compensate for the unbalanced coordination states of the phosphorus and boron atoms, to give a new fused bicyclic phosphine-boronate.

A convenient Hofmann reaction of carboxamides and cyclic imides mediated by trihaloisocyanuric acids

A simple, efficient and pot-economic approach in a single vessel has been developed for conversion of aromatic and aliphatic carboxamides into primary amines with one fewer carbom atom (Hofmann reaction) in 38–89 % yield by reacting with trichloro- or tribromoisocyanuric acid and sodium hydroxide in aqueous acetonitrile. Under the same reaction conditions, cyclic imides gave amino acids (69–83 %). The role of the trihaloisocyanuric acids is the in situ generation of N-haloamides, key-intermediates for the Hofmann reaction. The scalability of the methodology was demonstrated by a multigram-scale transformation of phthalimide into anthranilic acid in 77 % yield.

Lewis Acid-Catalyzed Nucleophilic Substitutions of Benzylic Alcohols with Sulfamides

Nucleophilic substitutions of benzylic alcohols with sulfamides were achieved using an FeCl3 Lewis acid catalyst in MeNO2. It was necessary to adjust the reaction conditions to obtain efficient yields depending on the stability of the carbocation intermediates. The reaction could easily be performed, and it was revealed that a variety of diarylmethanols and benzylic alcohols were applicable to the reaction, irrespective of the type and position of the substituents. The sulfamide moieties were easily deprotected and converted into amine groups.

Implication of a Silyl Cobalt Dihydride Complex as a Useful Catalyst for the Hydrosilylation of Imines

Here, we describe the formation and use of silyl cobalt (III) dihydride complexes as powerful catalysts for the hydrosilylation of a variety of imines starting from a low-valent well-defined cobalt (I) complex. The reaction is efficient at low catalyst loadings with a diverse range of imines bearing various protecting groups, as well as aliphatic ketimines and quinoline. Kinetics, DFT calculations, NMR spectroscopic studies, deuteration experiments, and X-ray diffraction analyses allowed us to propose a catalytic cycle based on silyl dihydrocobalt (III) complexes performing a hydrocobaltation.

Electrochemical Oxidative C(sp3)-H/N-H Coupling of Diarylmethanes with Sulfoximines or Benzophenone Imine

Herein, we report an efficient electrochemical method for the synthesis of N-alkylated sulfoximines by electrochemical oxidative C(sp3)-H/N-H coupling of sulfoximines and diarylmethanes. In addition, we used the same conditions for electrochemical dehydrogenative amination of diarylmethanes with benzophenone imine as an aminating agent. The reactions showed good functional group tolerance and afforded the corresponding products in moderate to good yields without the use of a stoichiometric oxidant, a metal catalyst, or an activating agent.

Effects of ruthenium hydride species on primary amine synthesis by direct amination of alcohols over a heterogeneous Ru catalyst

Heterogeneously catalysed synthesis of primary amines by direct amination of alcohols with ammonia has long been an elusive goal. In contrast to reported Ru-based catalytic systems, we report that Ru-MgO/TiO2 acts as an effective heterogeneous catalyst for the direct amination of a variety of alcohols to primary amines at low temperatures of ca. 100 °C without the introduction of H2 gas. The present system could be applied to a variety of alcohols and provides an efficient synthetic route for 2,5-bis(aminomethyl)furan (BAMF), an attention-getting biomonomer. The high catalytic performance can be rationalized by the reactivity tuning of Ru-H species using MgO. Spectroscopic measurements suggest that MgO enhances the reactivity of hydride species by electron donation from MgO to Ru.

Rh(III)-catalyzed synthesis of isoquinolines using the N-Cl bond of N-chloroimines as an internal oxidant

The Rh(III)-catalyzed coupling of N-chloroimines with alkynes for the efficient synthesis of isoquinolines is reported. This represents the first use of the N-Cl bond of N-chloroimines as an internal oxidant for construction of the isoquinoline skeleton. The synthesis features atom and step economy, a green solvent (EtOH), mild reaction conditions, and a broad substrate scope.

Hydrogenation reaction method

The invention relates to a hydrogenation reaction method, and belongs to the technical field of organic synthesis. The hydrogenation reaction method provided by the invention comprises the following steps: carrying out a hydrogen transfer reaction on a hydrogen acceptor compound, pinacol borane and a catalyst in a solvent in the presence of proton hydrogen, so that the hydrogen acceptor compound is subjected to a hydrogenation reaction; the catalyst is one or more than two of a palladium catalyst, an iridium catalyst and a rhodium catalyst; the hydrogen acceptor compound comprises one or morethan two functional groups of carbon-carbon double bonds, carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogentriple bonds and epoxy. The method is mild in reaction condition, easy to operate, high in yield, short in reaction time, wide in substrate application range, suitable for carbon-carbon double bonds,carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogen triple bonds and epoxy functional groups, good in selectivity and high in reaction specificity.

Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).