13541-00-9

Usage

Uses

Used in Pharmaceutical Industry:
BENZYL-(4-CHLORO-BENZYL)-AMINE is used as an active pharmaceutical ingredient for the development of treatments targeting various diseases, including cancer, AIDS, and other inflammatory conditions. Its chemical structure allows for the modulation of biological pathways and interactions with specific targets, making it a promising candidate for therapeutic applications.
Used in Cancer Treatment:
BENZYL-(4-CHLORO-BENZYL)-AMINE is employed as a chemotherapeutic agent, particularly for the treatment of various types of cancer. It may work by interfering with cellular processes, such as DNA replication and protein synthesis, ultimately leading to the inhibition of tumor growth and the induction of cell death.
Used in AIDS Treatment:
In the context of AIDS treatment, BENZYL-(4-CHLORO-BENZYL)-AMINE may be utilized as an antiviral agent, targeting the replication and spread of the human immunodeficiency virus (HIV). Its amine functional groups could potentially interact with viral enzymes or receptors, thereby disrupting the viral life cycle and reducing the viral load in infected individuals.
Used in Inflammatory Disease Treatment:
BENZYL-(4-CHLORO-BENZYL)-AMINE is also used as an anti-inflammatory agent, helping to alleviate symptoms associated with various inflammatory diseases. It may exert its effects by modulating the immune response, reducing inflammation, and mitigating the associated pain and discomfort.

InChI:InChI=1/C14H14ClN/c15-14-8-6-13(7-9-14)11-16-10-12-4-2-1-3-5-12/h1-9,16H,10-11H2/p+1

Upstream product

• 100-44-7 benzyl chloride 
• 104-86-9 4-chlorobenzylamine 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 100-46-9 benzylamine 
• 622-95-7 4-chlorobenzyl bromide 
• 100-52-7 benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 873-76-7 para-Chlorobenzyl alcohol 
• 100-51-6 benzyl alcohol 
• 623-03-0 4-Cyanochlorobenzene 
• 100-47-0 benzonitrile 
• 874-90-8 4-methoxybenzonitrile 
• 7461-34-9 N-benzyl-p-chlorobenzamide 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 55280-30-3 C₁₅H₁₃Cl₂NO 
• 55196-82-2 5-[Benzyl-(4-chloro-benzyl)-amino]-pentanenitrile 
• 634889-11-5 C₁₆H₁₅ClN₂ 
• 130517-96-3 N-[(1E)-(4-chlorophenyl)methylidene]benzenemethanamine 
• 14310-22-6 4-chlorobibenzyl 

Relevant academic research and scientific papers

Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions

A simple and efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine-BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to 95%. The strategy was applied to the synthesis of 15N labeled in 89% yield.

Synthesis, characterization, and antibacterial activity of dibenzildithiocarbamate derivates and Ni(II)–Cu(II) coordination compounds

In this work, the study of the synthesis methodology to obtain dibenzylamine derivates as intermediates for the formation of dithicarbamate ligands (DTC) and its coordination compounds was conducted. Four molecules derived from dibenzylamine were synthesized by two methodologies: classical (reflux) and microwave. From these amines, Four dithiocarbamate ligands (DTC): dibenzyldithiocarbamate, N-benzyl-1-(4-methoxyphenyl)dithiocarbamate, N-benzyl-1-(4-chlorophenyl)dithiocarbamate, and N-benzyl-1-(3-nitrophenyl)dithiocarbamate, and eight coordination complexes with general formula [M(DTC)2]nH2O (M= Cu(II) and Ni(II)) were obtained. All the compounds were characterized using different spectroscopic and thermal techniques such as Fourier-transform infrared spectroscopy (FT-IR), ultraviolet–visible spectroscopy (UV–VIS), proton and carbon-13 nuclear magnetic resonance (1H and 13C NMR), thermogravimetric analysis–differential scanning calorimetry (TGA-DSC). Additionally, it was possible to characterize two new crystalline phases of salts through single-crystal X-ray diffraction: dibenzyl ammonium nitrate and N-benzyl-1-(3-nitrophenyl)ammonium chloride. Additionally, microbial inhibition tests were conducted using the dibenzildithiocarbamate derivates. All DTC compounds showed important activity against Pseudomonas aeruginosa and Staphylococcus aureus but less sensitivity against Escherichia coli and Mycobacterium smegmatis. Among the coordination compounds, only [Cu(N-benzyl-1-(3-nitrophenyl)dithiocarbamate)2] presented a moderate activity against M. smegmatis mc2 155.

Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines

Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.

Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination

Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.

Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia-Borane

Herein we report the synthesis of primary and secondary amines by nitrile hydrogenation, employing a borrowing hydrogenation strategy. A class of phosphine-free manganese(I) complexes bearing sulfur side arms catalyzed the reaction under mild reaction conditions, where ammonia-borane is used as the source of hydrogen. The synthetic protocol is chemodivergent, as the final product is either primary or secondary amine, which can be controlled by changing the catalyst structure and the polarity of the reaction medium. The significant advantage of this method is that the protocol operates without externally added base or other additives as well as obviates the use of high-pressure dihydrogen gas required for other nitrile hydrogenation reactions. Utilizing this method, a wide variety of primary and symmetric and asymmetric secondary amines were synthesized in high yields. A mechanistic study involving kinetic experiments and high-level DFT computations revealed that both outer-sphere dehydrogenation and inner-sphere hydrogenation were predominantly operative in the catalytic cycle.

Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride

A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.

Synthesis and characterization of Ni(II) complexes with functionalized dithiocarbamates: New single source precursors for nickel sulfide and nickel-iron sulfide nanoparticles

Six Ni(II) complexes, bis(N-benzyl-N-substituted benzyldithiocarbamato-S,S′)nickel(II) (1–3), (N-benzyl-N-substituted benzyldithiocarbamato-S,S′)(thiocyanato-N)(triphenylphosphine)nickel(II) (4–6), [Substituted benzyl=4-hydroxybenzyl (1, 4), 4-methoxybenzyl (2, 5), 4-chlorobenzyl (3, 6)] complexes have been synthesized and characterized by elemental analysis, IR, UV–Vis and NMR (1H and 13C) spectroscopy. Upfield shift of NCS2 carbon signals of heteroleptic complexes compared to homoleptic complexes supports the back bonding effect of triphenylphosphine. Structures of complexes 1, 4, 5 and 6 have been obtained by single crystal X-ray diffraction. The coordination geometry around nickel is a distorted square planar in all the complexes. Intramolecular Ni?H-C anagostic interaction is observed in 4. Various non-covalent interactions such as C-H?π(chelate), C-H?π and C-H?X (X = O and Cl) lead to supramolecular aggregation. [Ni(dbdtc)2] and [Ni(dbdtc)3][FeCl4] (dbdtc = N,N-dibenzyldithiocarbamate) were used to prepare monometallic sulfide (nickel sulfide), bimetallic sulfide (iron-nickel sulfide) nanoparticles. TEM images of nickel sulfide and iron-nickel sulfide reveal that the particles are oval shape and ultrafine (～5–10 nm), respectively.

Cobalt complex, preparation method thereof, and application thereof in selective catalysis of transfer hydrogenation reaction of cyano group

The invention discloses a cobalt complex, a preparation method thereof, and an application thereof in the selective catalysis of a transfer hydrogenation reaction of a cyano group. The structural formula of the cobalt complex is represented by formula I. The cobalt complex is prepared through a reaction of a cobalt salt and an NNP ligand or a PNP ligand under the protection of an inert atmosphere;and the chemical formula of the cobalt salt is CoX12, wherein X1 represents halogen, a sulfate radical, a perchlorate radical, a hexafluorophosphate radical, a hexafluoroantimonate radical, a tetrafluoroborate radical, a trifluoromethanesulfonate radical or a tetra(pentafluorophenyl)borate radical. The cobalt complex can be used in the selective catalysis of the transfer hydrogenation reaction ofthe cyano group to obtain a primary amine compound, a secondary amine compound and a tertiary amine compound, the primary amine compound, the secondary amine compound and the tertiary amine compoundare important intermediates in a series of subsequent functionalizing reactions, and the cobalt complex has a very high catalysis activity, and has great research values and a great application prospect.

A facile synthesis of stable β-amino-N-/O-hemiacetals through a catalyst-free three-component Mannich-type reaction

A practical, straightforward and one-step procedure for the synthesis of novel and stable β-amino-N-/O-hemiacetals (i.e. γ-aminoalcohols) is provided. The title compounds were obtained in good to excellent yields through an uncatalyzed three-component reaction by treatment of secondary amines with polyformaldehyde and electron-rich alkenes in acetonitrile as solvent at ambient temperature. The reactions proceeded with the formation of iminium ions, through a Mannich-type reaction, as the key intermediates for the generation of the target products. Single crystal X-ray analysis of derivative 4l confirmed unequivocally the structure and stability of the obtained compounds.

Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls

The development of a boron/nitrogen-centered frustrated Lewis pair (FLP) with remarkably high water tolerance is presented. As systematic steric tuning of the boron-based Lewis acid (LA) component revealed, the enhanced back-strain makes water binding increasingly reversible in the presence of relatively strong base. This advance allows the limits of FLP's hydrogenation to be expanded, as demonstrated by the FLP reductive amination of carbonyls. This metal-free catalytic variant displays a notably broad chemoselectivity and generality.