1739-00-0

Usage

Uses

Used in Pharmaceutical Industry:
Phenethyl-phenyl-amine is used as a precursor for the synthesis of various compounds with pharmacological activities. Its ability to influence mood, energy levels, and attention makes it a potential candidate for the development of medications targeting depression and other mood disorders.
Used in Research Applications:
Phenethyl-phenyl-amine is used as a research compound to study its psychoactive and stimulant effects on the human body. This research helps in understanding the compound's mechanism of action and its potential therapeutic applications.
Used in Recreational Drug Industry:
Although not recommended due to its potential health risks, phenethyl-phenyl-amine has been used as a recreational drug for its mood-enhancing and stimulant effects.

InChI:InChI=1/C14H15N/c1-3-7-13(8-4-1)11-12-15-14-9-5-2-6-10-14/h1-10,15H,11-12H2

Upstream product

• 854634-81-4 N-phenethyl-toluene-4-sulfonanilide 
• 23052-05-3 N-phenyl-DL-phenylalanine 
• 622-24-2 2-phenylethyl chloride 
• 62-53-3 aniline 
• 100-42-5 styrene 
• 103-63-9 1-phenyl-2-bromoethane 
• 40395-41-3 phenyl-acetic acid-(N,N'-diphenyl-hydrazide) 
• 621-06-7 2,N-diphenylacetamide 
• 38253-22-4 2-(N-phenylethylanilino)cyclohexanone 
• 24760-80-3 2-phenylethyl p-nitrobenzenesulphonate 
• 4455-09-8 2-phenylethyl tosylate 
• 32376-95-7 2-phenylethyl benzenesulphonate 
• 115419-45-9 β-phenylethyldiphenylbismuth 
• 115419-46-0 tris-β-phenylethylbismuth 

Downstream Products

• 102753-63-9 phenethyl-phenyl-carbamic acid-(2-diisopropylamino-ethyl ester) 
• 101113-58-0 N-(2-(cyclohex-1-en-1-yl)ethyl)aniline 
• 76605-81-7 chloro-acetic acid-(N-phenethyl-anilide) 
• 96718-77-3 N-Phenethyl-N-phenyl-benzamide 
• 115419-49-3 N-phenyl-N-(2-phenylethyl)aniline 
• 103798-18-1 (2-cyclohex-1-enyl-ethyl)-cyclohexyl-amine 
• 38679-87-7 9-phenethyl-2,3,4,9-tetrahydro-1H-carbazole 
• 640735-03-1 1-phenethyl-indolin-2-one 
• 102449-02-5 N-(2-cyclohex-1-enyl-ethyl)-benzanilide 
• 102446-62-8 N-(2-cyclohex-1-enyl-ethyl)-N,N'-diphenyl-thiourea 
• 7001-94-7 N-Phenyl-phenaethylcarbaminsaeure-chlorid 
• 439908-02-8 3-(R)-(benzyl(phenyl)carbamoyloxy)-1(3-(thiophen-2-yl)propyl)-1-azoniabicyclo[2.2.2]octane bromide 
• 439909-11-2 phenethyl(phenyl)carbamic acid 1-azabicyclo[2.2.2]oct-3(R)-yl ester 
• 1422433-12-2 C₃₀H₂₇N₃O₃ 

Relevant academic research and scientific papers

β-phenylethylamines, indolines and isoquinolones via hydroamination of styrenes by microwave irradiation

Microwave irradiation promotes hydroamination of styrenes. This method can be used as a direct way of producing different kinds of bioactive compounds: open chain compounds like β-phenylethylamines or cyclized products like indolines or isoquinolones.

Rhodium-mediated 100% regioselective oxidative hydroamination of α-olefins

The system generated from lithium anilide and [(Et3P)2RhCl]2 caralyzes (turnover 21) the regioselective condensation of aniline with styrene to give a mixture of PhNH-CH(CH3)Ph (hydroamination product) and PhN=C(CH3)Ph (oxidative hydroamination product) in c.a. 1/2 ratio. This 100% regioselective oxidative hydroamination has been confirmed in the case of 1-hexene.

Anti-Markovnikov hydroaminations of styrene catalyzed by palladium(II) N-heterocyclic carbene complexes under conventional and microwave heating

Six palladium(II) complexes with benzimidazole-based N-heterocyclic carbene ligands were synthesized by transmetallation reactions between silver(I) N-heterocyclic carbene complexes and PdCl2(PhCN)2. The complexes were characterized by physicochemical and spectroscopic methods. The palladium complexes were tested as catalysts for intermolecular hydroamination reactions of styrene with various anilines in ionic liquids under both conventional and microwave heating. All of these complexes proved to be catalytically active in these reactions. The anti-Markovnikov addition products were selectively obtained by using 1?mol% of the palladium complex.

Markownikoff and anti-Markownikoff hydroamination with palladium catalysts immobilized in thin films of silica supported ionic liquids

The concept of immobilising organometallic complexes in a thin film of supported ionic liquids was utilised to synthesise novel bi-functional catalysts combining soft Lewis acidic and strong Bronsted acidic functions; the materials showed exceptional catalytic activity for the addition of aniline to styrene, providing the Markownikoff product under kinetically controlled conditions and mainly the anti-Markownikoff product in the thermodynamic regime. The Royal Society of Chemistry 2006.

Titanium amido- and imido-complexes supported by a tridentate pyrrolyl ligand: Syntheses, characterisation and catalytic activities

The complexes [Ti(NMe2)2(pmpmi)] [H2pmpmi = (2-pyrrolylmethene)-(2-pyrrolylmethyl)imine], [Ti(NtBu)(pmpmi)(py) 2], [Ti(NtBu)(pmpmi)(dpy)] and [Ti(NPh)(pmpmi)(py) 2] have been prepared, characterised and shown to be pre-catalysts for the hydroamination of phenylacetylene with aniline and p-chloroaniline. The X-ray structures of [Ti(NMe2)2(pmpmi)], [Ti(N tBu)(pmpmi)(dpy)] and [Ti(NPh)(pmpmi)(py)2] have been determined.

Dibutyltin chloride hydride complex as a novel reductant for chemoselective reductive amination

Imine-selective reducing agent Bu2SnClH-HMPA (I) performed effective reductive amination of carbonyl compounds. Various functionalized amines could be prepared in a one-pot procedure. Noteworthy is that highly chemoselective reactions were achieved with the co-existence of other functionalities such as halogen, carbon-carbon double bond and hydroxyl groups.

Minimization of Back-Electron Transfer Enables the Elusive sp3 C?H Functionalization of Secondary Anilines

Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N-Dialkyl-derivatives enable radical generation α to the N-atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back-electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence of an exogenous alkylamine. This approach synergistically aids aniline SET oxidation and then accelerates the following deprotonation. In this way, the generation of α-anilinoalkyl radicals is now possible and these species can be used in a general sense to achieve divergent sp3 C?H functionalization.

A base-free Chan–Lam reaction catalyzed by an easily assembled Cu(II)-carboxylate metal-organic framework

A new copper(II) metal-organic framework is constructed as a sustainable copper heterogeneous catalyst. Cu-DPTCA, with high catalytic activity, can effectively promote the Chan–Lam coupling reaction of arylboronic acids and amines without adding any base or additive.

Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D

N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs in the brains of freely moving mice and modulated emotional behavior [ Mock et al. Nat Chem. Biol., 2020, 16, 667-675 ]. Here, we describe the structure-activity relationship (SAR) of a library of pyrimidine-4-carboxamides as inhibitors of NAPE-PLD that led to the identification of LEI-401. A high-throughput screening hit was modified at three different substituents to optimize its potency and lipophilicity. Conformational restriction of an N-methylphenethylamine group by replacement with an (S)-3-phenylpiperidine increased the inhibitory potency 3-fold. Exchange of a morpholine substituent for an (S)-3-hydroxypyrrolidine reduced the lipophilicity and further increased activity by 10-fold, affording LEI-401 as a nanomolar potent inhibitor with drug-like properties. LEI-401 is a suitable pharmacological tool compound to investigate NAPE-PLD function in vitro and in vivo.

Iron-catalyzed N-alkylation of aromatic amines via borrowing hydrogen strategy

Earth-abundant transition metals could be used as a noble metal replacement in catalysis not only for different catalytic reactivity but environmentally benign methodology. We report here on the iron-catalyzed synthesis of N-alkylated amines via borrowing hydrogen strategy and differently functionalized aniline derivatives are alkylated in good yields.