1201-74-7

Usage

Uses

Used in Pharmaceutical Industry:
1-NAPHTHALEN-2-YL-ETHYLAMINE is used as an intermediate in the production of pharmaceuticals for its ability to facilitate the synthesis of various medicinal compounds.
Used in Organic Synthesis:
1-NAPHTHALEN-2-YL-ETHYLAMINE is used as a key component in the synthesis of a variety of organic compounds, contributing to the development of new chemical entities.
Used in Dye Manufacturing:
1-NAPHTHALEN-2-YL-ETHYLAMINE is used as a raw material in the manufacturing of dyes, where its chemical properties contribute to the creation of diverse colorants.
Used in Plastics Industry:
1-NAPHTHALEN-2-YL-ETHYLAMINE is utilized in the production of plastics, enhancing the properties of the final products and expanding the range of applications for plastic materials.
Used in Organic Synthesis and Medicinal Chemistry:
1-NAPHTHALEN-2-YL-ETHYLAMINE has potential applications in the field of organic synthesis and medicinal chemistry, where it can be employed to develop new compounds with therapeutic or other beneficial properties.

InChI:InChI=1/C12H13N/c1-9(13)11-7-6-10-4-2-3-5-12(10)8-11/h2-9H,13H2,1H3/p+1/t9-/m0/s1

Upstream product

• 540-69-2 ammonium formate 
• 77287-34-4 formamide 
• 93-08-3 methyl 2-naphthyl ketone 
• 613-46-7 2-naphthalenecarbonitrile 
• 75-16-1 methylmagnesium bromide 
• 16712-16-6 ammonium formate 
• 492-41-1 (1R,2S)-norephedrine 
• 51705-88-5 E de l'ether methylique de l'oxime de l'acetyl-2 naphthalene 
• 104354-38-3 1-(naphthalen-2-yl)ethanone O-methyloxime 
• 1201-74-7 1-(2-Naphthyl)ethylamine 
• 67021-79-8 (R)-α-(2-naphthyl)propionic acid 
• 3082-62-0 (1S)-1-(2-naphthyl)ethylamine 
• 939-27-5 2-ethylnaphthalene 
• 7228-47-9 2-(2-naphthyl)ethanol 

Downstream Products

• 3082-62-0 (1S)-1-(2-naphthyl)ethylamine 
• 1201-74-7 (R)-[1-(naphthalen-2-yl)ethyl]amine 
• 100381-63-3 (+/-)-(1-[2]naphthyl-ethyl)-urea 
• 103280-28-0 1,4-bis-(1-[2]naphthyl-ethyl)-piperazine 
• 117920-93-1 N,N'-bis-(1-[2]naphthyl-ethyl)-ethylenediamine 
• 87783-01-5 (S)-N-acetyl-1-(2-naphthyl)ethylamine 
• 87783-02-6 N-((S)-1-Naphthalen-2-yl-ethyl)-butyramide 
• 100728-02-7 1-(2-naphthyl)ethyl isothiocyanate 
• 93-08-3 methyl 2-naphthyl ketone 
• 188682-59-9 C₁₅H₁₇NO₂ 

Relevant academic research and scientific papers

Resolution of 1-arylethylamines with 5-(1,2-O-isopropylidene-3,6-anhydro- α-D-glucofuranosyl) hydrogen phthalate

The potential of the hydrogen phthalate of 1,2-O-isopropylidene-3,6- anhydro-α-D-glucofuranose 1 obtainable by the reaction of phthalic anhydride with 1,2-O-isopropylidene-3,6-anhydro-α-D-glucofuranose 8 as a new resolving agent is shown. The salts between 1 and (RS)-1-arylethylamines 2-6 and (RS)-1-arylpropylamine 7 selectively crystallize 1·(R)-salts allowing the recovery of the corresponding (R)-amines 2-7. The more soluble 1·(S)-salts were analogously processed to obtain (S)-amines, respectively. In all of the cases (R)- and (S)-amines 2-7 were obtained in high chemical yield and enantiomeric excess >98%. Resolving agent 1 has been recovered in a quantitative yield and high purity.

Enantioselective electrocatalytic oxidation of racemic amines using a chiral 1-azaspiro[5.5]undecane N-oxyl radical

A preparative electrocatalytic oxidation of racemic amines, which contain a chiral centre α to the amino group, on (6S, 7R, 10R)-4-acetylamino-2,2,7-trimethyl-10-isopropyl-1-aza-spiro[5.5]undecane N-oxyl yielded mixtures of carbonyl compounds (54.3-66.1%) and amines (33.9-45.7%) after 5 h of electrolysis, in which the current efficiency, turnover number, enantiopurity of the remaining (R)-isomers and S values were 90.7-94.8%, 21.7-26.5, 62-78% and 4.7-5.8, respectively.

Synthesis and structures of chiral halo mercury(II) complexes

HgCl2 reacts with enantiomerically pure 3-lithio-(S)-(-) or (R)-(+)-N,N-dimethyl-α-(2-naphthyl)ethylamine, (S) or (R)-LiTMNA, to produce (S)C(R)Hg-(HgCl), 2a', or (S)C(R)Hg-(HgCl), 2a, in fair yields. The bromide (2b) and iodide (2c) analogs were prepared in good yields by reaction of 2a with NaBr and NaI, respectively. The crystal structures of 2a', 2b and 2c show that the Hg atom in each compound is three-coordinate, T-shaped, and slightly pyramidal in the solid state. These three compounds form exclusively as the (S)C(R)Hg or (R)C(S)Hg diastereomers with average Hg-C and Hg-N distances of 2.08 (2) Angstroem and 2.65 (2) Angstroem, respectively. The Hg-N bond is weak and is easily cleaved in solution to form temperature-dependent equilibrium mixtures of two- and three-coordinate species as deduced from variable temperature NMR spectroscopy. - Keywords: Orthometallation; Mercury; Chiral complexes; CD spectroscopy; X-ray crystallography

Synthesis and pKa determination of new enantiopure dimethyl-substituted acridino-crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

New enantiopure dimethyl-substituted acridino-18-crown-6 and acridino-21-crown-7 ethers containing a carboxyl group at position 9 of the acridine ring [(S,S)-8, (S,S)-9, (R,R)-10] were synthesized. The pKa values of the new crown ethers [(S,S)-8, (S,S)-9, (R,R)-10] and of an earlier reported macrocycle [(R,R)-2] were determined by UV-pH titrations. Crown ether (S,S)-8 was attached to silica gel by covalent bonds and the enantiomeric separation ability of the newly prepared chiral stationary phase [(S,S)-CSP-12] was studied by high-performance liquid chromatography (HPLC). Homochiral preference was observed and the best separation was achieved for the enantiomers of 1-NEA. Ligands (S,S)-9 and (R,R)-10 are precursors of enantioselective sensor and selector molecules for the enantiomers of protonated primary amines, amino acids, and their derivatives.

Direct reductive amination of ketones with ammonium salt catalysed by Cp*Ir(iii) complexes bearing an amidato ligand

A series of half-sandwich Ir(iii) complexes1-6bearing an amidato bidentate ligand were conveniently synthesized and applied to the catalytic Leuckart-Wallach reaction to produce racemic α-chiral primary amines. With 0.1 mol% of complex1, a broad range of ketones, including aryl ketones, dialkyl ketones, cyclic ketones, α-keto acids, α-keto esters and diketones, could be transformed to their corresponding primary amines with moderate to excellent yields (40%-95%). Asymmetric transformation was also attempted with chiral Ir complexes3-6, and 16% ee of the desired primary amine was obtained. Despite the unsatisfactory enantio-control achieved so far, the current exploration might stimulate more efforts towards the discovery of better chiral catalysts for this challenging but important transformation.

Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones

Half-sandwich iridium complexes bearing bidentate urea-phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α-position.

Iterative Alanine Scanning Mutagenesis Confers Aromatic Ketone Specificity and Activity of L-Amine Dehydrogenases

Direct reductive amination of prochiral ketones catalyzed by amine dehydrogenases is attractive in the synthesis of active pharmaceutical ingredients. Here, we report the protein engineering of L-Bacillus cereus amine dehydrogenase to allow reactivity on synthetically useful aromatic ketone substrates using an iterative, multiple-site alanine scanning mutagenesis approach. Mutagenesis libraries based on molecular docking, iterative alanine scanning, and double-proximity filter approach significantly expand the scope of active pharmaceutical ingredients relevant building blocks. The eventual quintuple mutant (A115G/T136A/L42A/V296A/V293A) showed reactivity toward aromatic ketones 12 a (5-phenyl-pentan-2-one) and 13 a (6-phenyl-hexan-2-one), which have not been reported to serve as targets of reductive amination by currently available amine dehydrogenases. Docking simulation and tunnel analysis provided valuable insights into the source of the acquired specificity and activity.

HETEROCYCLIC COMPOUNDS AS MUTANT IDH INHIBITORS

The present disclosure relates generally to compounds useful in treatment of conditions associated with mutant isocitrate dehydrogenase (mt-IDH), particularly mutant IDH1 enzymes. Specifically, the present invention discloses compound of formula (IA), which exhibits inhibitory activity against mutant IDH1 enzymes. Method of treating conditions associated with excessive activity of mutant IDH1 enzymes with such compound is disclosed. Uses thereof, pharmaceutical composition, and kits are also disclosed.

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.

The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst

The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis of primary amines. The use of catalysts, especially reusable catalysts, based on earth-abundant metals is similarly appealing. Here, the iron-catalyzed synthesis of primary amines through reductive amination was realized. A broad scope and a very good tolerance of functional groups were observed. Ketones, including purely aliphatic ones, aryl–alkyl, dialkyl, and heterocyclic, as well as aldehydes could be converted smoothly into their corresponding primary amines. In addition, the amination of pharmaceuticals, bioactive compounds, and natural products was demonstrated. Many functional groups, such as hydroxy, methoxy, dioxol, sulfonyl, and boronate ester substituents, were tolerated. The catalyst is easy to handle, selective, and reusable and ammonia dissolved in water could be employed as the nitrogen source. The key is the use of a specific Fe complex for the catalyst synthesis and an N-doped SiC material as catalyst support.