2437-03-8

Usage

InChI:InChI=1/C12H13N/c1-2-13-12-8-7-10-5-3-4-6-11(10)9-12/h3-9,13H,2H2,1H3

Upstream product

• 75-03-6 ethyl iodide 
• 91-59-8 naphthalen-2-ylamine 
• 74-96-4 ethyl bromide 
• 64-17-5 ethanol 
• 64-67-5 diethyl sulfate 
• 4423-74-9 2-formamidonaphthalene 
• 581-97-5 2-acetylaminonaphthalene 
• 76587-93-4 3-methyl-2-ethylisoquinolinium iodide 
• 74-89-5 methylamine 
• 20937-86-4 2-azidonaphthalene 
• 920-39-8 isopropylmagnesium bromide 
• 99631-78-4 N-(2-naphthyl)alanine 
• 7647-01-0 hydrogenchloride 
• 101-02-0 triphenyl phosphite 

Downstream Products

• 42352-79-4 ethyl-(1-phenylazo-[2]naphthyl)-amine 
• 102449-40-1 ethyl-[2]naphthyl-[2-(toluene-4-sulfonyl)-ethyl]-amine 
• 19485-86-0 ethyl-(1,2,3,4-tetrahydro-[2]naphthyl)-amine 
• 856213-39-3 ethyl-(5,6,7,8-tetrahydro-[2]naphthyl)-amine 
• 86488-48-4 N-ethyl-N-[2]naphthyl-toluene-4-sulfonamide 
• 6368-72-5 N-ethyl-1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenylamine 

Relevant academic research and scientific papers

Amide-tethered quinoline-resorcinol conjugates as a new class of HSP90 inhibitors suppressing the growth of prostate cancer cells

The study is focused on the design and synthesis of amide tethered quinoline-resorcinol hybrid constructs as a new class of HSP90 inhibitor. In-vitro studies of the synthetic compounds led to the identification of compound 11, which possesses potent cell growth inhibitory effects against HCT116, Hep3B and PC-3 cell lines, exerted through HSP90 inhibition. Compound 11 triggers degradation of HSP90 client proteins along with concomitant induction of HSP70, demonstrates apoptosis inducing ability and causes G2M phase cell cycle arrest in PC-3 cells. Molecular modeling was used to dock compound 11 into the HSP90 active site and key interactions with the amino acid residues of the HSP90 chaperone protein were determined.

Stable triazenes derived from 2-alkylaminonaphthalenes and 5-nitrobenzo[c]-1,2-thiazole-3-diazonium hydrogensulfate

A calculation using the DFT method confirmed that the extraordinary stability of the triazenes formed by an azo coupling reaction of 5-nitrobenzo[c]-1,2-thiazole-3-diazonium with primary or secondary aromatic amines is caused by the fact that these substances are protonated at the heterocyclic nitrogen atom and not at the nitrogen atom of the triazene grouping -N=N-N(R)Ar. Stable triazenes are also formed by reaction of 5-nitrobenzo[c]-1,2-thiazole-3-diazonium with 2-alkylaminonaphthalenes. In the cases of the azo coupling reaction with 2-methylamino- and 2- ethylaminonaphthalene, the content of triazenes is almost 50% in the product mixture with the isomeric azo compounds. The structures of the triazenes were confirmed by X-ray analysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Selective N -monomethylation of primary anilines with the controllable installation of N -CH2D, N -CHD2, and N -CD3units

The selective N-monomethylation of primary anilines was realized by the use of the Me3N-BH3/N,N-dimethylformamide (DMF) system as the methyl source. This method also allows for the controllable introduction of N-CH2D, N-CHD2, and N-CD3 units with high lev

Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment

Six Cp?Ir complexes containing NN-bitentate chelate ligands [Cp?IrCl(C5H4CH2C5H3OH)][Cl] (1), [Cp?IrCl(C5H4CH2C5H3O)] (2), [Cp?IrCl(C5H4C5H3OH)] [Cl] (3), [Cp?IrCl(C5H4CH2C5H4)][Cl] (4), [Cp?IrCl(CH3OC5H3CH2C5H3OCH3)][Cl] (5), and [Cp?IrCl(CH3OC5H3CH2C5H3OH)][Cl] (6) were synthesized and characterized. Complex 1 could be transformed to 2 when reacted with NaOtBu or NEt3 via -OH deprotonation. These six complexes were tested as catalysts for mono-N-alkylation of amines with trialkyl amines, and complex 1 exhibited highest activity. The coupling reactions proceed under air condition, with 1 mol % catalyst loading without extra base in methanol at 120 °C and can be further accelerated by adding NR3·HCl.

Nickel-Catalyzed Amination of Aryl Carbamates with Ammonia

Aryl carbamates were employed in the nickel-catalyzed monoarylation of ammonia. The applied, well-defined single-component nickel(II) precatalyst contains a Josiphos ligand, is air-stable, and operates without any ancillary reductant. This catalyst system

Selective N-alkylation of amines using nitriles under hydrogenation conditions: Facile synthesis of secondary and tertiary amines

Nitriles were found to be highly effective alkylating reagents for the selective N-alkylation of amines under catalytic hydrogenation conditions. For the aromatic primary amines, the corresponding secondary amines were selectively obtained under Pd/C-catalyzed hydrogenation conditions. Although the use of electron poor aromatic amines or bulky nitriles showed a lower reactivity toward the reductive alkylation, the addition of NH4OAc enhanced the reactivity to give secondary aromatic amines in good to excellent yields. Under the same reaction conditions, aromatic nitro compounds instead of the aromatic primary amines could be directly transformed into secondary amines via a domino reaction involving the one-pot hydrogenation of the nitro group and the reductive alkylation of the amines. While aliphatic amines were effectively converted to the corresponding tertiary amines under Pd/C-catalyzed conditions, Rh/C was a highly effective catalyst for the N-monoalkylation of aliphatic primary amines without over-alkylation to the tertiary amines. Furthermore, the combination of the Rh/C-catalyzed N-monoalkylation of the aliphatic primary amines and additional Pd/C-catalyzed alkylation of the resulting secondary aliphatic amines could selectively prepare aliphatic tertiary amines possessing three different alkyl groups. According to the mechanistic studies, it seems reasonable to conclude that nitriles were reduced to aldimines before the nucleophilic attack of the amine during the first step of the reaction.

Reductive and catalytic monoalkylation of primary amines using nitriles as an alkylating reagent

(Chemical Equation Presented) A selective and catalytic mono-N-alkylation method of both aromatic and aliphatic amines using nitriles as an alkylating agent with Pd/C or Rh/C as a catalyst is described. This method is particularly attractive to provide an environmentally benign and applicable alkylation method of amines without using toxic and corrosive alkylating agents such as alkyl halides and carbonyl compounds.

A novel and efficient approach to mono-N-alkyl anilines via addition of Grignard reagents to aryl azides

Mono-N-alkyl anilines were obtained in high yields within a short reaction time when various aromatic azides were reacted with alkyl magnesium halides at room temperature.

A new phase transfer catalyst (PTC) for N-alkylation reactions

Hexamethylene tetramine bromide HMTA+ Br- - a new phase transfer catalyst is reported for N-Alkylation reactions of industrially important anilides.

Recyclization of 3-Alkyl- and 1,3-Dialkylisoquinolinium Salts to Naphthylamines

3-Methyl- and 3-benzylisoquinolinium salts undergo rearrangement to 2-alkylaminonaphthalenes under the influence of alcohol solutions of alkylamines.The rearrangement of 1,3-dimethyl- and 1-methyl-3-benzylisoquinolinium salts leads to both 1- and 2-alkylaminonaphthalenes with predominance of the former.