2873-89-4

Usage

Uses

Used in Chemical Synthesis Industry:
N-(4-chlorophenyl)-N,N-diethylamine is used as an intermediate in the synthesis of various dyes, pharmaceuticals, and other chemicals. Its unique structure allows it to serve as a building block for the development of a wide range of products.
Used in Catalyst Applications:
N-(4-chlorophenyl)-N,N-diethylamine is also utilized as a reaction catalyst in various chemical processes. Its ability to facilitate and speed up reactions makes it a valuable component in the production of different chemical compounds.

InChI:InChI=1/C4H4/c1-3-4-2/h1-2H2

Upstream product

• 78-40-0 triethyl phosphate 
• 106-47-8 4-chloro-aniline 
• 74-96-4 ethyl bromide 
• 13519-75-0 N-ethyl-4-chloro-aniline 
• 106-39-8 bromochlorobenzene 
• 1066-87-1 (N,N-diethylamino)tributyltin 
• 613-48-9 N,N-diethyl-p-toluidine 
• 99-97-8 Dimethyl-p-toluidine 
• 64-17-5 ethanol 
• 214470-03-8 2-(2-methoxyethoxy)ethyl ethyl carbonate 
• 91-66-7 N,N-diethylaniline 
• 75-03-6 ethyl iodide 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 64-19-7 acetic acid 

Downstream Products

• 1008-93-1 4-chloro-N-ethyl-N-nitrosoaniline 
• 22037-07-6 N,N-Diethyl-p-selenocyanatoaniline 
• 28491-95-4 N-ethyl-4-chloro-2-nitro-aniline 
• 86309-90-2 N-(4-Chloro-2-nitrophenyl)diethylamine 
• 86309-91-3 (4-Chloro-2-nitrophenyl)ethylnitrosamine 
• 613-48-9 N,N-diethyl-p-toluidine 
• 99-97-8 Dimethyl-p-toluidine 
• 6860-63-5 N,N,N',N'-tetraethylbenzidine 
• 5335-79-5 bis-(4-diethylamino-phenyl)-disulfide 
• 1169841-36-4 N-(4-chlorophenyl)-N-ethyl-N'-tosylformimidamide 
• 1169841-43-3 C₁₆H₁₇ClN₂O₃S 

Relevant academic research and scientific papers

Highly Active Ni Nanoparticles on N-doped Mesoporous Carbon with Tunable Selectivity for the One-Pot Transfer Hydroalkylation of Nitroarenes with EtOH in the Absence of H2

Cost-effective and environmentally friendly conversion of nitroarenes into value-added products is desirable but still challenging. In this work, highly dispersed Ni nanoparticles (NPs) supported on N-doped mesoporous carbon (Ni/NC-x) were synthesized via novel ion exchange-pyrolysis strategy. Their catalytic performance was investigated for one-pot transfer hydroalkylation of nitrobenzene (NB) with EtOH in absence of H2. Interestingly, the catalytic performance could be easily manipulated by tuning the morphology and electronic state of Ni NPs via varying the pyrolysis temperature. It was found that the Ni/NC-650 achieved 100 % nitrobenzene conversion and approx. 90 % selectivity of N,N-diethyl aniline at 240 °C for 5 h, more active than those of homogeneous catalysts or supported Ni catalysts prepared by impregnation (Ni/NC-650-IM, Ni/SiO2). This can be ascribed to the higher dispersion and better reducibility as well as richer surface basicity of the catalyst. More interestingly, the Ni/NC-650 catalyst achieved complete conversion of various nitroarenes, yielding imines, secondary amines, or tertiary amines selectively by simply controlling the reaction temperature at 180, 200 and 240 °C, respectively. The one-pot hydrogen-free process with non-noble metal catalysts, as demonstrated in this work, shows great promise for selective conversion of nitroarenes with ethanol to various anilines at industrial scale, from an economic, environmental, and safety viewpoint.

N-alkylation using sodium triacetoxyborohydride with carboxylic acids as alkyl sources

A versatile N-alkylation was performed using sodium triacetoxyborohydride and carboxylic acid as an alkyl source. The combination of these reagents furnished products different from those given previously by a similar reaction. Moreover, the mild conditions of our method allowed some functional groups to remain through the reaction, whereas they would react and be converted into other moieties in the similar reductive N-alkylation reported previously. Herein, we provide a new procedure for the preparation of various compounds containing nitrogen atoms.

Copper-Mediated monochlorination of anilines and nitrogen-containing heterocycles

A simple and selective copper(II) chloride-mediated monochlorination of anilines and nitrogen-containing heterocycles has been developed. Stirring a mixture of aniline, copper(II) chloride, lithium chloride in EtOH under reflux condition produced 4-chloroaniline with high yield. Eighteen substrates including substituted anilines, N-substituted anilines, N,N-disubstituted anilines, 5-nitroindole and carbazole were all reactive and afforded desired products in moderate to excellent yields (52%–98%).

Catalytic N-Alkylation of Amines Using Carboxylic Acids and Molecular Hydrogen

A convenient, practical and green N-alkylation of amines has been accomplished by applying readily available carboxylic acids in the presence of molecular hydrogen. Applying an in situ formed ruthenium/triphos complex and an organic acid as cocatalyst, a broad range of alkylated secondary and tertiary amines are obtained in good to excellent yields. This novel method is also successfully applied for the synthesis of unsymmetrically substituted N-methyl/alkyl anilines through a direct three-component coupling reaction of the corresponding amines, carboxylic acids, and CO2 as a C1 source.

Room temperature N-alkylation of amines with alcohols under UV irradiation catalyzed by Cu-Mo/TiO2

It is highly desirable to develop efficient heterogeneous photocatalysts for organic reactions. Here, we show the preparation and catalytic performance of a novel TiO2 (P25) supported Cu and Mo photocatalyst (Cu-Mo/TiO2) for N-alkylation of amines with alcohols under UV irradiation at room temperature. A variety of aromatic and aliphatic amines were selectively converted into the corresponding secondary amines or tertiary amines in moderate to excellent yields without the addition of any co-catalysts such as bases and organic ligands. Noteworthy, this catalytic system is feasible in the alkylation of anilines containing halogen substituents with alcohols and the yields of the desired products are up to 95%.

Homogeneous catalytic hydrogenation of amides to amines

Hydrogenation of amides in the presence of [Ru(acac)3] (acacH=2,4-pentanedione), triphos [1,1,1-tris- (diphenylphosphinomethyl)ethane] and methanesulfonic acid (MSA) produces secondary and tertiary amines with selectivities as high as 93 % provided that there is at least one aromatic ring on N. The system is also active for the synthesis of primary amines. In an attempt to probe the role of MSA and the mechanism of the reaction, a range of methanesulfonato complexes has been prepared from prepared from [Ru(acac) 3], triphos and MSA, or from reactions of [RuX-(OAc)(triphos)] (X=H or OAc) or [RuH2(CO)(triphos)] with MSA. Crys-tallographically characterised complexes include: [Ru(OAc-κ1O) 2(H2O)-(triphos)], [Ru(OAc-κ2O,O') (CH3SO3-κ1O)(triphos)], [Ru(CH 3SO3-κ1O)2-(H 2O)(triphos)] and [Ru2(μ-CH3SO 3)3-(triphos)2][CH3SO3], whereas other complexes, such as [Ru(OAc-κ1O)(OAc- κ2O,O')(triphos)],[Ru(CH3SO3- κ1O)(CH3SO3-κ2O,O')- (triphos)], H[Ru(CH3SO3-κ1O) 3-(triphos)], [RuH(CH3SO3-κ1O) (CO)-(triphos)] and [RuH(CH3SO3-k2O,O')- (triphos)] have been characterised spectroscopically. The interactions between these various complexes and their relevance to the catalytic reactions are discussed.

Understanding reactivity patterns of the dialkylaniline radical cation

N,N-Dimethylaniline and N,N-diethylaniline react with Cu2+ to form the corresponding amine radical cations. The radical cations were characterized by their absorption spectra. In the absence of any nucleophiles, the radical cations dimerize to give tetraalkylbenzidines, and this reaction can be monitored by absorption spectroscopy, In the presence of nucleophiles such as Cl, Br, or SCN, the radical cations undergo nucleophilic substitution to give para-substituted dialkylanilines in good yields.

Bis(triarylmethylium)-mediated diaryl ether synthesis: Oxidative arylation of phenols with N,N-dialkyl-4-phenylthioanilines

Various aryl 4-dialkylaminophenyl ethers were readily synthesized without heating in good yield from phenols and N,N-dialkyl-4-phenylthioanilines. This oxidative arylation of phenols was successfully promoted by a bis(diphenylmethylium)naphthalenediyl dication via ipso-substitution of the phenylthio group in the anilines through a radical process. Copyright

A novel and efficient ceric ammonium nitrate catalyzed oxidative nuclear chlorination of activated aromatic compounds by acetyl chloride

A mild and efficient oxidative chlorination of activated aromatic compounds have been achieved in excellent yields using acetyl chloride in the presence of a catalytic amount of ceric ammonium nitrate at room temperature. However, chlorination failed to occur with deactivated aromatic rings.

Reaction of primary aromatic amines with alkyl carbonates over NaY faujasite: A convenient and selective access to mono-N-alkyl anilines

At atmospheric pressure and at 130-160°C, primary aromatic amines (p-XC6H4NH2, X = H, Cl, NO2) are mono-N-alkylated in a single step, with symmetrical and asymmetrical dialkyl carbonates [ROCOOR′, R = Me, R′ = MeO(CH2)2O(CH2)2; R = R′ = Et; R = R′ = benzyl; R = R′ = allyl; R = Et, R′ = MeO(CH2)2O(CH2)2], in the presence of a commercially available NaY faujasite. No solvents are required. Mono-N-alkyl anilines are obtained with a very high selectivity (90-97%), in good to excellent yields (68-94%), on a preparative scale. In the presence of triglyme as a solvent, the mono-N-alkyl selectivity is independent of concentration and polarity factors. The reaction probably takes place within the polar zeolite cavities, and through the combined effect of the dual acid-base properties of the catalyst.