150-61-8

Usage

Uses

Used in Chemical Synthesis:
1,2-Dianilinoethane is used as a chemical intermediate for the formation of crystalline imidazolidines with aldehydes, which can be important in the synthesis of various organic compounds and pharmaceuticals. The reaction occurs in the presence of acetic acid, making it a valuable component in chemical processes.
Used as a Trapping Agent:
In the field of chemistry, 1,2-Dianilinoethane serves as a trapping agent for aldehydes. This application is particularly useful in the study and analysis of aldehydes, as it allows for their isolation and further investigation.
Used in Coordination Chemistry:
As an N-donating ligand, 1,2-Dianilinoethane can be utilized in coordination chemistry to form complexes with metal ions. These complexes can have various applications, such as catalysts, sensors, or materials with unique properties.

Synthesis Reference(s)

Synthetic Communications, 22, p. 1081, 1992 DOI: 10.1080/00397919208019300

Purification Methods

Crystallise the reagent from aqueous EtOH or MeOH. [Beilstein 12 H 543, 12 IV 986.]

InChI:InChI=1/C14H16N2/c15-11-12-16(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,11-12,15H2

Upstream product

• 107-06-2 1,2-dichloro-ethane 
• 62-53-3 aniline 
• 106-93-4 ethylene dibromide 
• 762-50-5 1-chloro-2-fluoroethane 
• 107-07-3 2-chloro-ethanol 
• 620-81-5 N,N'-Diphenyloxamid 
• 56018-47-4 1,1',3,3'-Tetraphenyl-2,2'-biimidazolidin 
• 540-63-6 ethane-1,2-dithiol 
• 108-98-5 thiophenol 
• 86453-49-8 1,2,2,3-Tetraphenylimidazolidin 
• 74401-94-8 2-(p-dimethylaminostyryl)-N,N'-diphenyl-1,3-imidazolidine 
• 107-21-1 ethylene glycol 
• 56-23-5 tetrachloromethane 
• 80-41-1 2-chloroethyl tosylate 

Downstream Products

• 88828-39-1 2-(1,3-diphenyl-imidazolidin-2-yl)-pyridine 
• 59282-04-1 4-(1,3-diphenyl-imidazolidin-2-yl)-pyridine 
• 59282-03-0 3-(1,3-diphenyl-imidazolidin-2-yl)-pyridine 
• 102174-92-5 1,3-diphenyl-2-[2]thienyl-imidazolidine 
• 118765-56-3 3-(1,3-diphenyl-imidazolidin-2-ylmethyl)-4-(2-methyl-[1,3]dioxolan-2-ylmethyl)-indole 
• 858850-94-9 1,4-diphenyl-piperazine-2,3-dione 
• 613-39-8 1,4-diphenyl-piperazine 
• 32411-73-7 N,N'-ethanediyl-bis-acetanilide 
• 59281-86-6 N-(2-anilino-ethyl)-acetanilide 
• 103-84-4 Acetanilid 
• 96772-30-4 1,3,1',3'-tetraphenyl-2,2'-p-phenylene-bis-imidazolidine 
• 94867-39-7 2-(2-chloro-phenyl)-1,3-diphenyl-imidazolidine 
• 54172-96-2 N,N′-diphenyl-N,N′-bis(pyridin-2-ylmethyl)ethane-1,2-diamine 
• 56018-53-2 2-(4-methoxy-phenyl)-1,3-diphenyl-imidazolidine 

Relevant academic research and scientific papers

Synthesis and antioxidant properties of a novel arylamine antioxidant

A novel oil-soluble arylamine antioxidant N1,N2-diphenylethane-1,2-diamine (ND) was successfully synthesized, and the potential antioxidant behavior of which had never been reported before. The structure of ND was characterized via nuclear magnetic resonance (1H NMR, 13C NMR) and electron ionization mass spectrometry. The antioxidant performance of ND and its synergistic effect with 2,6-di-tert-butyl-4-methylphenol (BHT) in di-2-ethylhexyl sebacate were evaluated by pressurized differential scanning calorimetry, thermogravimetry analysis, and hot oil oxidation test. All the results indicated that the synthesized antioxidant ND exhibited outstanding antioxidant performance and showed prominent synergistic effect with BHT in ester base oil. Furthermore, the probable synergistic anti-oxidative effect between ND and BHT was discussed, which was mainly induced by the formation of a fresh BHT radical and the regeneration of ND antioxidant.

Synergetic activation of CO2by the DBU-organocatalyst and amine substrates towards stable carbamate salts for synthesis of oxazolidinones

The development of an efficient methodology to transform CO2 into valuable chemicals has attracted increasing attention concerning the challenging issues of CO2-utilization. Herein, an efficient approach for the preparation of oxazolidinones from CO2, primary (aliphatic/aromatic) amines and 1,2-dichloroethane (or its derivatives) catalyzed by DBU organo-superbase was achieved with yields of 47-97% under mild conditions (80-100 °C, 12 h, 1.0 MPa CO2). Control experiments demonstrated that the formation of an ion-pair carbamate salt intermediate IS-B derived from the reaction of CO2, DBU (catalyst) and an amine (substrate) was the key step for this three-component reaction. The available DBU-amine-CO2 adduct intermediate (like IS-B-2) with fair stability will evolve into the thermodynamically stable product oxazolidinones upon attack of 1,2-dichloroethane (or its derivatives), along with the regeneration of the DBU catalyst. Alternatively, the decomposition of the DBU-aryl amine-CO2 adduct (like IS-B-1) with relatively poor stability also could result in the competitive substitution reaction of 1,2-dichloroethane (or its derivatives) with the aryl amine. This work provides insights into synergetic CO2-activation by the DBU-catalyst and a nucleophilic amine-substrate via the formation of robust carbamate salt intermediates responsible for the final production of oxazolidinones. This journal is

A Nanocrystal Catalyst Incorporating a Surface Bound Transition Metal to Induce Photocatalytic Sequential Electron Transfer Events

Heterogeneous photocatalysis is less common but can provide unique avenues for inducing novel chemical transformations and can also be utilized for energy transductions, i.e., the energy in the photons can be captured in chemical bonds. Here, we developed a novel heterogeneous photocatalytic system that employs a lead-halide perovskite nanocrystal (NC) to capture photons and direct photogenerated holes to a surface bound transition metal Cu-site, resulting in a N-N heterocyclization reaction. The reaction starts from surface coordinated diamine substrates and requires two subsequent photo-oxidation events per reaction cycle. We establish a photocatalytic pathway that incorporates sequential inner sphere electron transfer events, photons absorbed by the NC generate holes that are sequentially funneled to the Cu-surface site to perform the reaction. The photocatalyst is readily prepared via a controlled cation-exchange reaction and provides new opportunities in photodriven heterogeneous catalysis.

Visible-light-promoted decarboxylative addition cyclization of: N -aryl glycines and azobenzenes to access 1,2,4-triazolidines

Methods for the synthesis of 1,2,4-triazolidines are scarce. Herein, we report a visible-light-promoted decarboxylative addition cyclization of N-aryl glycines and azobenzenes to access such important compounds. Using commercially available methylene blue (MB) as an organic photocatalyst, the reaction proceeded smoothly in the absence of transition-metal catalysts at ambient temperature, affording the corresponding products, 1,2,4-triaryl 1,2,4-triazolidines, in good to excellent yields. This work demonstrates a new synthetic application of readily available azobenenes and provides a novel strategy for constructing 1,2,4-triazolidines.

Copper-Catalyzed Propargylation of Nitroalkanes

Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N-heterocycles such as pyrroles and 2-pyrrolines.

B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane

The first B(C6F5)3-catalyzed deoxygenative reduction of amides into the corresponding amines with readily accessible and stable ammonia borane (AB) as a reducing agent under mild reaction conditions is reported. This metal-free protocol provides facile access to a wide range of structurally diverse amine products in good to excellent yields, and various functional groups including those that are reduction-sensitive were well tolerated. This new method is also applicable to chiral amide substrates without erosion of the enantiomeric purity. The role of BF3 ? OEt2 co-catalyst in this reaction is to activate the amide carbonyl group via the in situ formation of an amide-boron adduct. (Figure presented.).

Unmodified Fe3O4 nanostructure promoted with external magnetic field: safe, magnetically recoverable, and efficient nanocatalyst for N- and C-alkylation reactions in green conditions

Transition metal compounds have emerged as suitable catalysts for organic reactions. Magnetic compounds as soft Lewis acids can be used as catalysts for organic reactions. In this report, the Fe3O4 nanostructures were obtained from Fe2+ and Fe3+-salts, under an external magnetic field (EMF) without any protective agent. The X-ray photoelectron spectroscopy, scanning electron microscopy, and energy dispersive X-ray spectroscopy tools were used to characterize these magnetic compounds. The two-dimensional (2-D, it showed nanometric size in the two dimensions, nanorod structure) Fe3O4 compound showed high catalytic activity and stability in N- and C-alkylation reactions. A diverse range of N- and C-alkylation products were obtained in moderate to high yield under green and mild conditions in air. Also the N- and C-alkylation products can be obtained with different selectivity and yield by exposure reactions with EMF. Results of alkylation reactions showed that the presence of Fe(II) and Fe(III) species on the surface of magnetic catalysts (phase structure of magnetic compounds) are essential as very cheap active sites. Also, morphology of magnetic catalysts had influence on their catalytic performances. After the reaction, the catalyst/product(s) separation could be easily achieved with an external magnet and more than 95% of catalyst could be recovered. The catalyst was reused at least four times without any loss of its high catalytic activity for N- and C-alkylation reactions.

Synthesis of Arylamines via Non-Aerobic Dehydrogenation Using a Palladium/Carbon-Ethylene System

The reaction of cyclohexanones with amines proceeded under an ethylene atmosphere in the presence of a catalytic amount of palladium/carbon to afford a variety of arylamines in good to high yields. The present reaction was carried out under completely non-aerobic conditions, and which is in contrast with the previously reported aerobic system. has wide applicability affording a variety of aromatic amines, and co-product of the reaction is only gaseous ethane. Thus, this method is environmentally friendly. This protocol was applied intramolecularly to provide a novel method for the construction of quinoline and isoquinoline compounds. (Figure presented.).

Improved microwave synthesis of unsymmetrical N,N'-diaryl-1,2-aminoethane and imidazolidinium salts as precursors of N-heterocyclic carbenes

Lithium aluminium hydride reduction of bis-unsymmetric-diaryloxamides 3 is difficult to accomplish especially for the sterically hindered mesityl derivative. Using microwaves LAH reduction of 3a,d was successful in a short time, however, with cleavage of the ether linkage to give compounds 11a,d. Extension of this method enabled the reduction of bis-oxamide derivatives 13 to the corresponding tetraamine derivative 14 which was then converted to the bis-imidazolidinium salt 15. Application of this method led to rapid reduction of unsymmetric N,N'-diaryloxamides 16 to the corresponding N,N'- diarylethylenediamines 17 which were converted to their corresponding imidazolidinium salts 18. the Partner Organisations 2014.

New phosphine-functionalized NHC ligands: Discovery of an effective catalyst for the room-temperature amination of aryl chlorides with primary and secondary amines

We report convenient and high-yielding syntheses of new phosphine-functionalized dihydroimidazolium salts and demonstrate their utility as ligand precursors for Buchwald-Hartwig amination. Several examples of the general formula [1-Mes-3-{2-(PR2)phenyl}imidazolidin-2-ylium][BF 4] have been prepared, where phosphines of varying steric and electronic properties (R = Ph (9), Cy (10), 1-Ad (11)) are tethered by an o-phenylene group. The synthesis was not adaptable to N-aryl groups other than mesityl, giving unexpected phosphonium salt species instead. The synthesis was adapted to flexible benzyl-linked variants of the formula [1-Ar-3-{2-(PCy 2)benzyl}imidazolidin-2-ylium][BF4], which allowed more steric variation of the dihydroimidazolium N-aryl group (Ar = Mes (21), Dipp (22)). A preliminary study of these hybrid NHC/P ligands in Buchwald-Hartwig amination catalysis (in situ precatalyst formation) revealed 11 to be the most active of the series. Premixing the isolated free NHC ligand 1-Mes-3-{2-(PAd2)phenyl}imidazolidin-2-ylidene (23) with [Pd(cinnamyl)Cl]2 provided a highly active precatalyst that performed well at room temperature and 1 mol % catalyst loading. The system was shown to have an unprecedented ability to arylate both primary alkylamines (monoarylation) and secondary dialkylamines with aryl chlorides at room temperature. Electron-rich and -poor aryl and heteroaryl halides, as well as those featuring ortho substitution, were well tolerated, while substrates featuring both primary and secondary amine groups were selectively arylated at the NH2 position. Furthermore, a preliminary examination of performance in ammonia arylation and acetone α-arylation showed promising results, giving good conversion and high selectivity for monoarylation in both cases.