92-59-1

Usage

Uses

Used in the Manufacture of Dyes:
N-Benzyl-N-ethylaniline is used as a chemical intermediate in the production of dyes, contributing to the development of various colorants for different applications.
Used in Organic Syntheses:
N-Benzyl-N-ethylaniline serves as a valuable building block in organic synthesis, enabling the creation of a range of organic compounds for diverse uses.
Used in Scientific Research:
In a study, N-Benzyl-N-ethylaniline was utilized to investigate the electron transfer quenching dynamics of excited perylene and cyanoperylene in various donating solvents, providing insights into the behavior of these compounds in different environments.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

N-Benzyl-N-ethylaniline neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Flammability and Explosibility

Notclassified

Purification Methods

Dry the amine over KOH pellets and fractionate it. The picrate crystallises from *C6H6 as lemon yellow crystals m 126-128o (softening at 120o). [Forrest et al. J Chem Soc 303 1951, IR: Hill & Meakins J Chem Soc 760 1958, Beilstein 12 H 1026, 12 IV 2176.]

InChI:InChI=1/C15H17N/c1-2-16(15-11-7-4-8-12-15)13-14-9-5-3-6-10-14/h3-12H,2,13H2,1H3

Upstream product

• 64-17-5 ethanol 
• 142-04-1 aniline hydrochloride 
• 100-44-7 benzyl chloride 
• 103-69-5 N-ethyl-N-phenylamine 
• 91-66-7 N,N-diethylaniline 
• 758640-21-0 N-Benzylaniline 
• 75-03-6 ethyl iodide 
• 16466-44-7 N-ethyl-N-phenylbenzamide 
• 65-85-0 benzoic acid 
• 7553-56-2 iodine 
• 100-39-0 benzyl bromide 
• 100-51-6 benzyl alcohol 
• 1233656-18-2 C₁₆H₁₉O₄P 
• 462-06-6 fluorobenzene 

Downstream Products

• 103276-49-9 N,N'-diethyl-N,N'-diphenyl-bibenzyl-α,α'-diyldiamine 
• 5335-85-3 N-ethyl-N-benzyl-4-thiocyanato-aniline 
• 3421-02-1 N-ethyl-N-benzyl-4-nitroso-aniline 
• 92-56-8 N-ethyl-N-benzyl-sulfanilic acid 
• 37043-80-4 N-(p-nitrobenzyl)-N-ethylaniline 
• 860701-55-9 N-benzyl-N-ethyl-2,4-dinitroaniline 
• 245321-83-9 Benzylethylaniline N-oxide 
• 67676-47-5 4-N-benzylamino-N-ethylaminobenzaldehyde 
• 84611-04-1 phosphonous dichloride 
• 92-60-4 4-(N-ethyl-anilinomethyl)-benzenesulfonic acid 
• 101-11-1 N-ethyl-N-benzylaniline-3'-sulfonic acid 
• 56919-72-3 3-(N-ethyl-anilinomethyl)-benzenesulfonic acid amide 
• 85046-51-1 N-nitroso N-benzyl-N-(4-nitroaniline) 
• 103-69-5 N-ethyl-N-phenylamine 

Relevant academic research and scientific papers

Redox-Selective Iron Catalysis for α-Amino C-H Bond Functionalization via Aerobic Oxidation

Single-electron oxidation and α-deprotonation of tertiary anilines using Fe(phen)3(PF6)3 afford α-aminoalkyl radicals, which can be coupled with electrophilic partners to afford various tetrahydroquinolines. Mechanistically, the Fe(phen)n 2+/3+ catalytic cycle is maintained by O2 or a TBHP oxidant, and the presence of the oxygen bound iron complex, Fe(III)-OO(H), was elucidated by electron paramagnetic resonance and electrospray ionization mass spectrometry. This redox-selective nonheme iron catalyst behaves similarly to bioinspired heme iron catalysts.

Direct benzylation of amines with benzylic alcohols catalyzed by palladium/phosphine-borane catalyst system

Direct catalytic benzylation of amines with benzylic alcohols to give benzylamines has been newly developed by using palladium/phosphine-borane catalyst system. In this catalytic reaction, the linking between both phosphine and borane moieties in the ligand is very important. Hydroxy group of benzylic alcohols is activated by Lewis acidic borane to form a benzylpalladium intermediate which is attacked by amines to give benzylamine products.

Method for efficiently realizing N-alkylation reaction by using cyclic iridium catalyst

The invention discloses a method for efficiently realizing N-alkylation reaction by using a cyclic iridium catalyst, and belongs to the technical field of pharmaceutical and chemical synthesis. The preparation method comprises the following steps of: taking amines and alcohol compounds as raw materials, a cyclic iridium complex as a catalyst and water or an organic solvent as a reaction medium, heating, stirring and reacting for 12-24 hours under the protection of inert gas, cooling to room temperature after the reaction is finished, carrying out reduced pressure distillation and concentrationto obtain a crude product, and carrying out column chromatography purification to obtain a series of amine compounds. The synthesis method of the amine compound is simple to operate, easily availablein raw materials and low in price; the method is high in reaction efficiency, good in N-alkylation selectivity, good in adaptability to various functional groups, wide in substrate universality and environmentally friendly, is carried out at the gram level, shows the potential of industrially synthesizing the N-alkylamine compound, and has wide application prospects in the fields of medicines, organic synthesis and the like.

Transition-Metal-Free Three-Component Synthesis of Tertiary Aryl Amines from Nitro Compounds, Boronic Acids, and Trialkyl Phosphites

The synthesis of aromatic amines is of continuous interest in chemistry. An exceptionally versatile three-component reaction that directly transforms inexpensive nitro compounds, boronic acids, and trialkyl phosphites into tertiary aromatic amines has been realized. The reaction tolerates alkyl and aryl substituents on the nitro and boronic acid moieties, as well as functionalized phosphites. No transition-metal catalysis is required. The method is orthogonal to other classical metal-catalyzed syntheses since it tolerates the presence of halogens, and also permits the synthesis of functionalized compounds such as α-amino ester derivatives. (Figure presented.).

Photo-induced dealdehyding method

The invention provides a photo-induced dealdehyding method, and belongs to the technical field of organic synthesis. The photo-induced dealdehyding method comprises the following steps that a mixtureof a compound shown in the formula I and a solvent are reacted under an inert gas atmosphere and visible light irradiation, a dealdehyding product is obtained, and no photocatalyst is used in the whole process; wherein the structural formula of the formula I shown in the specification, R is a functional group and is selected from hydrogen, methyl, methoxyl, cyano, chlorine, bromine or fluorine. According to the photo-induced dealdehyding method, in the inert gas atmosphere, the compound shown in the formula (I) can be excited to generate carbon-oxygen bond homogeneous cracking through visiblelight irradiation, then free radical migration and double bond displacement are conducted, finally carbon monoxide is removed, aldehyde group removal is completed, no photocatalyst is needed in the whole process, operation is easy and convenient, and conditions are mild.

NEW METHOD FOR THE SYNTHESIS OF UNSYMMETRICAL TERTIARY AMINES

Disclosed is a new method for the synthesis of unsymmetrical tertiary amines using alcohol and an imine, and to new tertiary amines.

Catalyst-free photodecarbonylation ofortho-amino benzaldehyde

It is almost a consensus that decarbonylation of the aldehyde group (-CHO) needs to not only be mediated by transition metal catalysts, but also requires severe reaction conditions (high temperature and long reaction time). In this work, inspired by the “conformational-selectivity-based” design strategy, we broke this consensus and discovered a catalyst-free photodecarbonylation of the aldehyde group. It revealed that decarbonylation can be easily achieved with visible light irradiation by introducing a tertiary amine into theortho-position of the aldehyde group. A diverse array of tertiary amines is tolerated by our photodecarbonylation under mild conditions. Furthermore, the (QM) computations of the mechanism and the experiments on well-designed special substrates revealed that our photodecarbonylation depends on the conformational specificity of the aldehyde group and tertiary amine, and occurs through an unusual [1,4]-H shift and a subsequent [1,3]-H shift.

Manganese(III) Porphyrin-Catalyzed Dehydrogenation of Alcohols to form Imines, Tertiary Amines and Quinolines

Manganese(III) porphyrin chloride complexes have been developed for the first time as catalysts for the acceptorless dehydrogenative coupling of alcohols and amines. The reaction has been applied to the direct synthesis of imines, tertiary amines and quinolines where only hydrogen gas and/or water are formed as the by-product(s). The mechanism is believed to involve the formation of a manganese(III) alkoxide complex which degrades into the aldehyde and a manganese(III) hydride species. The latter reacts with the alcohol to form hydrogen gas and thereby regenerates the alkoxide complex.

Selective Synthesis of Secondary Amines from Nitriles by a User-Friendly Cobalt Catalyst

Selective hydrogenation/reductive amination of nitriles to secondary amines catalyzed by an inexpensive and user-friendly cobalt complex, (Xantphos)CoCl2, is reported. The use of (Xantphos)CoCl2 and ammonia borane (NH3?BH3) combination affords the selective reduction of nitriles to symmetrical secondary amines, whereas the employment of (Xantphos)CoCl2 and dimethylamine borane (Me2NH?BH3) along with external amines produce unsymmetrical secondary amines and tertiary amines. The general applicability of this methodology is demonstrated by the synthesis of 43 symmetrical and unsymmetrical secondary and tertiary amines bearing diverse functionalities. (Figure presented.).

Iron-Catalyzed Reductive Ethylation of Imines with Ethanol

The borrowing hydrogen strategy has been applied to the ethylation of imines with an air-stable iron complex as precatalyst. This approach opens new perspectives in this area as it enables the synthesis of unsymmetric tertiary amines from readily available substrates and ethanol as a C2 building block. A variety of imines bearing electron-rich aryl or alkyl groups at the nitrogen atom could be efficiently reductively alkylated without the need for molecular hydrogen. The mechanism of this reaction, which shows complete selectivity for ethanol over other alcohols, has been studied experimentally and by means of DFT computations.