2362-79-0

Usage

Uses

Used in Pharmaceutical Research:
1-(4-chlorophenyl)-N-phenyl-methanimine is used as a research compound for its potential therapeutic applications in the treatment of medical conditions like depression and obesity. Its action as a releasing agent for serotonin, norepinephrine, and dopamine makes it a subject of interest for scientists exploring novel treatments for these conditions.
Used in Psychopharmacology:
In the field of psychopharmacology, 1-(4-chlorophenyl)-N-phenyl-methanimine is used as a research tool to study the effects of stimulants and hallucinogens on the brain's neurotransmitter systems. Understanding its mechanism of action can contribute to the development of new drugs with fewer side effects and lower potential for abuse.
Used in Controlled Substance Regulation:
Due to its stimulant and hallucinogenic properties, 1-(4-chlorophenyl)-N-phenyl-methanimine is considered a controlled substance in many countries. It is used in the regulatory industry to develop and enforce policies and laws related to the control and prevention of substance abuse and addiction.

InChI:InChI=1/C13H10ClN/c14-12-8-6-11(7-9-12)10-15-13-4-2-1-3-5-13/h1-10H/b15-10+

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 62-53-3 aniline 
• 4750-61-2 N-(p-chlorobenzyl)aniline 
• 121876-99-1 1-phenyl-4-(p-chlorophenyl)-1,2-diazabutadiene 
• 39184-66-2 (4-chlorophenyl)chlorodiazirine 
• 5909-74-0 (4-chlorobenzylidene)phenylamine N-oxide 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 37613-10-8 4-chloro-N-phenyl-benzimidoyl chloride 
• 107-06-2 1,2-dichloro-ethane 
• 3768-55-6 N-trimethylsilylaniline 
• 873-76-7 para-Chlorobenzyl alcohol 
• 1204601-47-7 C₁₆H₁₂ClN₂O₂⁽¹⁺⁾ 
• 78186-21-7 C₁₇H₁₂F₃N₂O₂⁽¹⁺⁾ 

Downstream Products

• 10480-00-9 5-(4-chloro-phenyl)-1-phenyl-4,5-dihydro-1H-[1,2,3]triazole 
• 4390-55-0 N-[(4-chloro-phenyl)-[2]pyridyl-methyl]-aniline 
• 72867-37-9 (N-benzoyl-anilino)-(4-chloro-phenyl)-acetonitrile 
• 4750-61-2 N-(p-chlorobenzyl)aniline 
• 16178-08-8 2-{4-[(E)-2-(4-chlorophenyl)vinyl]phenyl}-5-phenyloxazole 
• 16157-17-8 2-[4-(4-chloro-trans-styryl)-phenyl]-5-phenyl-[1,3,4]oxadiazole 
• 54397-10-3 2-(4-chloro-phenyl)-3-phenyl-thiazolidin-4-one 
• 66427-68-7 2-(4-chloro-phenyl)-3-methyl-4-morpholin-4-yl-1,2,3,4-tetrahydro-quinoline 
• 16143-31-0 2-[4-(4-chloro-trans-styryl)-phenyl]-naphtho[1,2-d]oxazole 
• 93872-62-9 N-[1-(4-chlorophenyl)pentyl]aniline 
• 16177-98-3 2-biphenyl-4-yl-6-(4-chloro-trans-styryl)-5-methyl-benzooxazole 
• 16157-41-8 2-[4-(4-chloro-trans-styryl)-phenyl]-5-(4-trans-styryl-phenyl)-[1,3,4]oxadiazole 
• 2131-85-3 1-(4-chloro-trans-styryl)-4-trans-styryl-benzene 
• 23798-57-4 trans-1-<4-Methoxy-phenyl>-2-<4'-chlor-stilben-4-yl>-acetylen 

Relevant academic research and scientific papers

Experimental and theoretical investigation of benzyl-N-pyrrolylketene, one- step procedure for preparing of new β-lactams by [2 +2] cycloaddition reaction

3-Phenyl-2-(1-H-pyrrol-1-yl) propanoic acid has been used as a ketene source in synthesizing of monocyclic-2-azetidinones. Hindrance in ketene and imines successfully controlled the diastereoselectivity of the reaction. For example, in some cases only one isomer was achieved. By using Mukaiyama reagent, the leaving group in acid was activated and the by-products were separated by simple aqueous work-up. DFT calculation indicated that the benzyl-N-pyrrolylketene has nonconjugated structure and the pyrrolyl ring is perpendicular to the ketene plane in both the twisted and planar structures.

Stereoselective synthesis of new β-lactams from the main functional group of indomethacin

New β-lactams were synthesized in moderate yields from indomethacin, which is currently used as a drug to relieve pain such as arthritis, muscle and bone damage. The reaction was carried out by [2 + 2] cycloaddition of the in situ formed indomethacinyl ke

Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides

The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.

Nanomagnetic catalysis (Fe3O4@S–TiO2): a novel magnetically nano catalyst for the synthesis of new highly substituted tetrahydropyridine derivatives under solvent-free conditions

A novel nanomagnetic catalyst (Fe3O4@S–TiO2) was prepared by the hydrothermal method. At the first, Fe3O4 nanoparticles were synthesized, then iron oxide nanoparticles (IONPs) were dispersed in ethano

Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams

We report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory diastereoselectivities in most cases. This reaction also features good functional-group tolerance, facile scalability and product diversification. Experimental and computational studies suggest that α-ketoacylsilanes can serve as photochemical precursors by engaging in a 1,3 silicon shift to the distal carbonyl group.

Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4

An efficient, quick, and environment-friendly one-pot reductive amination of aldehydes or ketones was developed. In ethanol at 70 °C, a imination catalyzed by sulfated polyborate and further reduced by sodium borohydride yields various amines. The present method has many significant benefits, including a shorter reaction time, excellent yields, and a hassle-free, straightforward experimental process. The reaction has a wide range of applications due to its flexibility, including secondary amine for reductive amination.

Aza-peterson olefinations: Rapid synthesis of (E)-alkenes

An aza-Peterson olefination methodology to access 1,3-dienes and stilbene derivatives from the corresponding allyl- or benzyltrimethylsilane is described. Silanes can be deprotonated using Schlosser's base and added to N -phenyl imines or ketones to directly give the desired products in high yields.

Rhodium catalyzed multicomponent dehydrogenative annulation: one-step construction of isoindole derivatives

A strategy for one-pot synthesis of isoindoles is describedviaa catalytic multicomponent dehydrogenative annulation of diarylimines, vinyl ketones and simple amines. In the presence of a rhodium catalyst and Cu oxidant, four C-H and two N-H bonds are activated along with the formation of one new C-C and two new C-N bonds, leading to a series of isoindole derivatives in good to very high isolated yields.

Arene diruthenium(II)-mediated synthesis of imines from alcohols and amines under aerobic condition

The utility and selectivity of the newly synthesized dinuclear arene Ru(II) complex were demonstrated towards the synthesis of imines from coupling of alcohols and amines in the aerobic condition. Analytical and various spectral methods have been used to establish the unprecedented formation of the new thiolato-bridged dinuclear ruthenium complex. The molecular structure of the titled complex was evidenced with aid of X-ray crystallographic technique. A wide range of imines were obtained in good-to-excellent yields up to 98% and water as the by-product through an acceptorless dehydrogenative coupling of alcohols with amines. The catalytic reaction operated a concise atom economical without any oxidant with 1 mol% of the catalyst load. Further, the role of base, solvent and catalyst loading of the coupling reaction has been investigated. A plausible mechanism has been described and was found to proceed via the formation of an aldehyde intermediate. Short synthesis of antibacterial drug N-(salicylidene)-2-hydroxyaniline illustrated the utility of the present protocol.

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.