118-44-5

Usage

Uses

1. Used in Chemical Synthesis:
N-Ethyl-1-naphthylamine is used as an intermediate in the chemical synthesis of various compounds. Its ability to participate in cross-coupling reactions makes it a valuable component in the production of a range of chemical products.
2. Used in Analytical Chemistry:
N-Ethyl-1-naphthylamine is used as a reagent in the characterization of nitrite-dependent genotoxins and tumor promoter-like substances in fermented fish sauce. It aids in the identification process through cross-coupling reactions, which result in the formation of colored azo dyes.
3. Used in Pharmaceutical Research:
N-Ethyl-1-naphthylamine may also be utilized in the identification of triazenes metabolites in urine samples. This application is particularly relevant in the field of pharmaceutical research, where understanding the metabolic pathways of various compounds is crucial for drug development and safety assessment.

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

Upstream product

• 86-57-7 1-Nitronaphthalene 
• 925-90-6 ethylmagnesium bromide 
• 10319-80-9 thioacetic acid 1-naphthyl amide 
• 94943-86-9 2-(1-naphthylamino)propionic acid 
• 15309-82-7 N-(naphthalen-1-yl)benzenesulfonamide 
• 74-96-4 ethyl bromide 
• 134-32-7 1-amino-naphthalene 
• 64-17-5 ethanol 
• 74-85-1 ethene 
• 75-00-3 chloroethane 
• 75-07-0 acetaldehyde 
• 110-91-8 morpholine 
• 75-03-6 ethyl iodide 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 60375-32-8 ethyl-(4-phenylazo-[1]naphthyl)-amine 
• 101111-62-0 2-chloro-propionic acid-(ethyl-[1]naphthyl-amide) 
• 110-91-8 morpholine 
• 84-95-7 N,N-diethyl-1-naphthylamine 
• 6930-96-7 N-ethyl-N-[1]naphthyl-acetamide 
• 87175-64-2 (4-ethylamino-[1]naphthyl)-bis-(4-dimethylamino-phenyl)-methane 
• 887336-04-1 N-ethyl-N-naphthalen-1-ylguanidine 

Relevant academic research and scientific papers

Conformational Studies by Dynamic NMR. 32. Enantiomerization of Chiral Conformers in Hindered Naphthylamines and Naphthyl Nitroxides

Observation of anisochronous NMR signals in N-alkyl-N-methyl-1-naphthylamines at low temperature indicates that these molecules adopt a twisted conformation (yielding enantiomeric conformers at the equilibrium) as opposed to the corresponding N-alkyl-N-methyl-2-naphthylamines which give two planar (thus achiral) conformers.The barriers to enantiomerization in 1-naphthylamines have been measured by line-shape analysis for those amines containing prochiral substituents.The use at low temperature of one of the Pirkle's chiral alcohols as a discriminating agent allowed these barriers to be measured even in absence of prochiral grpups.Related alkyl 1-naphthyl nitroxides were also shown to prefer a twisted conformation, but the enantiomerization barriers are too low to be measured by ESR.Examination of a much more hindered nitroxide (2-tert-butyl-1-naphthyl ethyl nitroxide) showed that the methylenic hydrogens were anisochronous even at room temperature, indicating that this radical exist as a racemic mixture.The existence of an exponential relationship between the free energies of enantiomerization in the 1-naphthylamines and the nitrogen hyperfine splittings in the analogous nitroxides allowed the barrier for N,N-dimethyl-1-naphthylamine to be estimated.This barrier could not be measured directly because of the symmetry of the amine.

Continuous-Flow Amide and Ester Reductions Using Neat Borane Dimethylsulfide Complex

Reductions of amides and esters are of critical importance in synthetic chemistry, and there are numerous protocols for executing these transformations employing traditional batch conditions. Notably, strategies based on flow chemistry, especially for amide reductions, are much less explored. Herein, a simple process was developed in which neat borane dimethylsulfide complex (BH3?DMS) was used to reduce various esters and amides under continuous-flow conditions. Taking advantage of the solvent-free nature of the commercially available borane reagent, high substrate concentrations were realized, allowing outstanding productivity and a significant reduction in E-factors. In addition, with carefully optimized short residence times, the corresponding alcohols and amines were obtained in high selectivity and high yields. The synthetic utility of the inexpensive and easily implemented flow protocol was further corroborated by multigram-scale syntheses of pharmaceutically relevant products. Owing to its beneficial features, including low solvent and reducing agent consumption, high selectivity, simplicity, and inherent scalability, the present process demonstrates fewer environmental concerns than most typical batch reductions using metal hydrides as reducing agents.

Homogeneous cobalt-catalyzed deoxygenative hydrogenation of amides to amines

The first general and efficient cobalt-catalyzed deoxygenative hydrogenation of amides to amines is presented. The optimal catalytic system based on a combination of [Co(NTf2)2] and (p-anisyl)triphos (L3) in the presence of [Me3SiOTf] as acidic co-catalyst facilitates the direct hydrogenation of a broad range of amides to the corresponding amines under mild conditions. A set of control experiments indicate that, after the initial reduction of the amide carboxylic group to the well-known hemiaminal intermediate, the reaction mainly proceeds through C-O bond cleavage though other pathways might be also involved to a minor extent. This journal is

Ru-Catalyzed Deoxygenative Transfer Hydrogenation of Amides to Amines with Formic Acid/Triethylamine

A ruthenium(II)-catalyzed deoxygenative transfer hydrogenation of amides to amines using HCO2H/NEt3 as the reducing agent is reported for the first time. The catalyst system consisting of [Ru(2-methylallyl)2(COD)], 1,1,1-tris(diphenylphosphinomethyl) ethane (triphos) and Bis(trifluoromethane sulfonimide) (HNTf2) performed well for deoxygenative reduction of various secondary and tertiary amides into the corresponding amines in high yields with excellent selectivities, and exhibits high tolerance toward functional groups including those that are reduction-sensitive. The choice of hydrogen source and acid co-catalyst is critical for catalysis. Mechanistic studies suggest that the reductive amination of the in situ generated alcohol and amine via borrowing hydrogen is the dominant pathway. (Figure presented.).

Cobalt-Catalyzed Reductive Alkylation of Amines with Carboxylic Acids

Direct reductive alkylation of amines with carboxylic acid is carried out by using an inexpensive, air-stable cobalt/triphos catalytic system with molecular hydrogen as the reductant. This efficient synthetic method proceeds through reduction and condensation, followed by reduction of the in situ-generated imine into the amine in a green catalytic process.

Deoxygenative Hydrogenation of Amides Catalyzed by a Well-Defined Iridium Pincer Complex

The iridium-catalyzed highly chemoselective hydrogenation of amides to amines has been developed. Using a well-defined iridium catalyst bearing a P(O)C(O)P pincer ligand combined with B(C6F5)3, the C-O cleavage products are formed under mild reaction conditions. The reaction provides a new method for the preparation of amines from amides in good yield with high selectivity.

Alanine triazole iridium-catalyzed C–N bond formation through borrowing hydrogen strategy

An efficient synthesis of secondary amines has been described through alanine triazole iridium-catalyzed C–N bond formation of an aromatic amine and an alkyl amine using the borrowing hydrogen strategy. In addition, it was observed that alanine triazole iridium is also an efficient catalyst to promote C–N bond formation of an aromatic amine and alcohols with good to excellent yields.

Direct N-alkylation of aromatic amines using a microflow reactor: Enhancement of selectivity and reactivity

A simple and highly atom-economical method for the direct N-alkylation of aromatic amines by using a microflow reactor was developed to overcome the problem of over-alkylation. In the developed method, high-yield conversion (up to 100%) was achieved in a relatively short reaction time. The ratio of mono- to di-benzylated products (3.57:1) was higher than that achieved with batch reactions conducted in a 1 L scale flask (0.87:1). The structural features of the microflow reactor meant that short-chain alkyl halides could be converted into products with high reactivity and selectivity under superheating conditions, although their boiling point was much lower than the reaction temperature. This method was successfully applied to the synthesis of a range of secondary amines including an intermediate of indobufen synthesis.

Nickel-catalyzed amination of Aryl chlorides with ammonia or ammonium salts

The nickel-catalyzed amination of aryl chlorides to form primary arylamines occurs with ammonia or ammonium sulfate and a well-defined single-component nickel(0) precatalyst containing a Josiphos ligand and an η2-bound benzonitrile ligand. This system also catalyzes the coupling of aryl chlorides with gaseous amines in the form of their hydrochloride salts. Simple alternative: The title reaction, which results in primary arylamines, is catalyzed by well-defined single-component nickel(0) precatalysts containing a Josiphos ligand and an η2-bound benzonitrile ligand. This system also catalyzes the coupling of aryl chlorides with gaseous amines in the form of their hydrochloride salts.

Palladium-catalyzed amination of aryl chlorides and bromides with ammonium salts

We report the palladium-catalyzed coupling of aryl halides with ammonia and gaseous amines as their ammonium salts. The coupling of aryl chlorides and ortho-substituted aryl bromides with ammonium sulfate forms anilines with higher selectivity for the primary arylamine over the diarylamine than couplings with ammonia in dioxane. The resting state for the reactions of aryl chlorides is different from the resting state for the reactions of aryl bromides, and this change in resting states is proposed to account for a difference in selectivities for reactions of the two haloarenes.