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Usage

Uses

Used in Pharmaceutical Industry:
Benzhydrylamine is utilized as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex organic molecules that can have medicinal properties.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, Benzhydrylamine serves as a precursor in the production of compounds that can be used in the development of pesticides and other agricultural chemicals.
Used in Chemical Industry for Dyes and Pigments:
Benzhydrylamine is also employed in the chemical industry for the production of dyes and pigments, where its chemical structure allows for the creation of a variety of colorants used in different applications.
Used in the Production of Other Industrial Chemicals:
Its versatility extends to other areas within the chemical industry, where Benzhydrylamine is used in the synthesis of a range of industrial chemicals, highlighting its importance as a building block in chemical manufacturing processes.

Upstream product

• 62506-88-1 N-benzylidenediphenylmethanamine 
• 141-52-6 sodium ethanolate 
• 36728-39-9 N-(α-benzylamino-benzhydryl)-propionamide 
• 13261-62-6 N,N-dimethyl-2-aminofluorene 
• 140-29-4 phenylacetonitrile 
• 2235-01-0 dimethoxydiphenylmethane 
• 100-46-9 benzylamine 
• 119-61-9 benzophenone 
• 62506-88-1 (E)-N-(phenylmethylene)benzhydrylamine 
• 18406-59-2 N-benzyl-N,N-bis(trimethylsilyl)amine 
• 2051-90-3 Dichlorodiphenylmethane 
• 110-86-1 pyridine 
• 101370-75-6 1-Benzyl-4-methyl-5,5-diphenyl-4,5-dihydro-1H-tetrazole 
• 574-66-3 Benzophenone oxime 

Downstream Products

• 119-61-9 benzophenone 
• 103-67-3 benzyl-methyl-amine 
• 110321-80-7 6-(Benzhydrylidene-amino)-2,2-dimethyl-5,6-diphenyl-hexan-3-one 
• 97625-65-5 N¹-Benzhydrylidene-1,N²-diphenyl-2-p-tolyl-ethane-1,2-diamine 
• 140-29-4 phenylacetonitrile 
• 13261-62-6 N,N-dimethyl-2-aminofluorene 
• 101-97-3 Ethyl 2-phenylethanoate 
• 106727-49-5 3-benzyl-3,4-dihydro-2,2-diphenyl-2H-1,3-oxazin-4-one 
• 105602-10-6 (Z)-3-(1-Benzyl-4-oxo-2,2-diphenyl-azetidin-3-ylamino)-but-2-enoic acid ethyl ester 
• 62506-88-1 N-benzylidenediphenylmethanamine 
• 401834-00-2 4-(Benzhydrylidene-amino)-1,3,4-triphenyl-butan-1-one 
• 97625-64-4 N-Benzhydrylidene-N'-(4-chloro-phenyl)-1,2-diphenyl-ethane-1,2-diamine 
• 110321-76-1 4-(Benzhydrylidene-amino)-1-(4-methoxy-phenyl)-3,4-diphenyl-butan-1-one 
• 5669-43-2 N-benzylbenzhydrylamine 

Relevant academic research and scientific papers

Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2 H-Pyrroles via Intermediate Pyrrolines

N-Benzyl ketimines undergo [3 + 2] cycloaddition with arylacetylenes in the KOBut/DMSO solution to 2,3,5-triarylpyrrolines, which are oxidized (chloranil, DDQ) in situ to 2,3,5-triaryl-2H-pyrroles in 53-71% yields. The intermediate 1-pyrrolines can be isolated in 31-91% yields and separately oxidized to the corresponding 2H-pyrroles.

Direct C(sp3)-N Radical Coupling: Photocatalytic C-H Functionalization by Unconventional Intermolecular Hydrogen Atom Transfer to Aryl Radical

An unconventional approach for intermolecular direct C(sp3)-N radical coupling has been developed by photocatalytic C(sp3)-H activation of simple alkyl substrates using O-benzoyl oximes. The selective photocatalytic energy-transfer-driven homolysis followed by decarboxylation generates the persistent iminyl radical and aryl radical, which would undergo an unprecedented intermolecular hydrogen atom abstraction from the alkyl substrate to provide the key C(sp3) radical. Selective radical-radical C-N cross-coupling furnishes imines which are valuable amine building blocks.

Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines

Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)2 or Pd(PPh3)4 to afford imines and/or α-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas α-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/α-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or α-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.

Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water

A novel carbanionic reactivity of imines mediated by photoredox catalysis is demonstrated. The umpolung imine reactivity is exemplified by proton abstraction from water as a key step in the reduction of benzophenone ketimines to amines (up to 98% yield). Deuterium is introduced into amines efficiently using D2O as an inexpensive deuterium source (≥95% D ratio). The mechanism of this unusual transformation is probed.

Photocatalytic and Chemoselective Transfer Hydrogenation of Diarylimines in Batch and Continuous Flow

A visible-light photocalytic method for the chemoselective transfer hydrogenation of imines in batch and continuous flow is described. The reaction utilizes Et3N as both hydrogen source and single-electron donor, enabling the selective reduction of imines derived from diarylketimines containing other reducible functional groups including nitriles, halides, esters, and ketones. The dual role of Et3N was confirmed by fluorescence quenching measurements, transient absorption spectroscopy, and deuterium-labeling studies. Continuous-flow processing facilitates straightforward scale-up of the reaction.

Benzhydrylamine: An effective aminating agent for the synthesis of primary amines

Aldehydes, ketones, alkyl toluene-p-sulfonates and halides are converted into the corresponding primary amines with benzhydrylamine as a valuable ammonia synthon in moderate to excellent yields.

P-N Cooperative Borane Activation and Catalytic Hydroboration by a Distorted Phosphorous Triamide Platform

Studies of the stoichiometric and catalytic reactivity of a geometrically constrained phosphorous triamide 1 with pinacolborane (HBpin) are reported. The addition of HBpin to phosphorous triamide 1 results in cleavage of the B-H bond of pinacolborane through addition across the electrophilic phosphorus and nucleophilic N-methylanilide sites in a cooperative fashion. The kinetics of this process of were investigated by NMR spectroscopy, with the determined overall second-order empirical rate law given by ν = -k[1][HBpin], where k = 4.76 × 10-5 M-1 s-1 at 25 °C. The B-H bond activation process produces P-hydrido-1,3,2-diazaphospholene intermediate 2, which exhibits hydridic reactivity capable of reacting with imines to give phosphorous triamide intermediates, as confirmed by independent synthesis. These phosphorous triamide intermediates are typically short lived, evolving with elimination of the N-borylamine product of imine hydroboration with regeneration of the deformed phosphorous triamide 1. The kinetics of this latter process are shown to be first-order, indicative of a unimolecular mechanism. Consequently, catalytic hydroboration of a variety of imine substrates can be realized with 1 as the catalyst and HBpin as the terminal reagent. A mechanistic proposal implicating a P-N cooperative mechanism for catalysis that incorporates the various independently verified stoichiometric steps is presented, and a comparison to related phosphorus-based systems is offered.

Synthesis of 4-Isoxazolines via Visible-Light Photoredox-Catalyzed [3 + 2] Cycloaddition of Oxaziridines with Alkynes

A method for [3 + 2] cycloaddition of oxaziridines with alkynes to form 4-isoxazolines via visible-light photoredox catalysis is described. This method is a greener, atom-economical reaction that tolerates various functional groups and provides good to excellent yield. Moreover, the cyclization products can be conveniently converted into tetrasubstituted allylic alcohols and enamines. A mechanistic study suggests that the reaction involves photoredox-catalyzed in situ generation of a nitrone from the oxaziridine by SET.

Access to α-Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide

A straightforward and transition-metal-free approach for the efficient synthesis of α-arylglycine derivatives from aromatic imines and carbon dioxide was enabled by an umpolung carboxylation reaction. Various substituted diphenylmethimines underwent the carboxylation smoothly with carbon dioxide in the presence of potassium tert-butoxide and 18-crown-6 to give the corresponding carboxylated products in good to high yields. Besides the enhancement of the solubility of potassium tert-butoxide in THF, 18-crown-6 also plays key roles in suppressing the reverse protonation or 1, 3-proton shift isomerization as well as by stabilizing the carboxylated intermediate.

Cyclopalladated benzophenone imines: Synthesis, antitumor activity, cell accumulation, dna interaction, and cathepsin b inhibition

The synthesis of the endo five-membered cyclo-ortho-palladated benzophenone imines [Pd{C6H4(Ph)C=NR}]2(μ-X)2 [1 (X = OAc), 2 (X = Cl), a (R = phenyl), b (R = 1-naphthyl), c (R = benzyl), d (R = α-methylbenzyl)], and trans-N,P-[Pd{C6H4(Ph)C=NR}X(PPh3)] [3 (X = OAc), 4 (X = Cl), a (R = phenyl), b (R = 1-naphthyl), c (R = benzyl), d (R = α-methylbenzyl)] and the X-ray molecular structure of 1a, 1c, 1d, 4a, 4b, and 4c are reported. The antitumor activity, DNA interaction, and cathepsin B inhibition of palladium compounds a-d were studied and compared with those previously reported for palladium compounds e with R = H and compound 4f analogous to 4e but with a platinum(II) center. The IC50 values against a panel of human cancer cell lines allowed the establishment of a qualitative relationship between their structure and antitumor activity. Compounds 3e, 4e, and 4f were the most active ones in relation to their in vitro anticancer activity. Compounds 3e and 4e were about 4 times more active than cisplatin against the MDA-MB-231 and MCF-7 breast human cancer lines, and compound 4f was about 4 times more active than cisplatin against the cisplatin-resistant HCT-116 colon human cancer cell line. In addition, compound 3e was 3 times less cytotoxic than cisplatin toward the quiescent HUVEC cells. Accumulation of palladium compounds e and b in the MDA-MB-231 cell line was considerably greater than that of cisplatin in the same cell line, but palladium compounds b were noncytotoxic. Some of these complexes altered the DNA tertiary structure in a similar way to cisplatin but at higher concentration, and most cytotoxic ones did not present a high efficiency as cathepsin B inhibitors.