36602-01-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenylamino-benzonitrile is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties.
Used in Dye Industry:
In the dye industry, 4-Phenylamino-benzonitrile is utilized as a precursor in the production of dyes, contributing to the creation of colorants with unique characteristics.
Used in Materials Science:
4-Phenylamino-benzonitrile is used as a component in the development of polymers and optoelectronic devices, where its chemical structure plays a role in enhancing the performance and properties of these materials.

Upstream product

• 18523-41-6 4-azidobenzonitrile 
• 71-43-2 benzene 
• 36800-95-0 p-cyanophenyl p-toluenesulfonate 
• 62-53-3 aniline 
• 623-00-7 4-bromobenzenecarbonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 375815-93-3 diiodo-di-(1-methyl-3-(ethoxycarbonylpropyl)-imidazolin-2-ylidene)-palladium 
• 4477-28-5 diphenylamine-4-diazonium hydrosulfate 
• 108-90-7 chlorobenzene 
• 873-74-5 4-Aminobenzonitrile 
• 591-50-4 iodobenzene 
• 3058-39-7 4-iodobenzonitrile 
• 923799-23-9 C₁₆H₁₄N₂O₂ 
• 100-63-0 phenylhydrazine 

Downstream Products

• 1392831-43-4 1-(4-cyanophenyl)-3-methyl-1,3-diphenylurea 
• 741709-22-8 4-(2-phenyl-1H-indol-1-yl)benzonitrile 
• 849806-05-9 (4-aminomethyl-phenyl)-phenyl-amine 

Relevant academic research and scientific papers

High-efficiency exciplex-based white organic light-emitting diodes with a new tripodal material as a co-host

Exciplex-forming co-hosts have been reported to be a potentially suitable material for organic light-emitting diodes (OLEDs). However, they might not be able to provide optimal low voltage and maximal power efficiency (PE), when used in white organic light-emitting diodes (WOLEDs). Herein, a novel strategy using multi-exciplex-forming co-hosts (MEHs) is introduced to achieve enhanced efficiency and low operating voltage. To realize this strategy, a new tripodal bipolar compound CNTPA-DPA was synthesized and used as a co-host in the devices. As a result, the orange light-emitting component in WOLEDs provides 27% external quantum efficiency (EQE), 2.1 V turn-on voltage, and 115.5 lm W-1 PE, which are among the best values of orange color emission in OLEDs. And then this orange light emitting component was adopted in the MEH strategy to construct WOLEDs, achieving 19.5% EQE and 73 lm W-1 PE at the maximum, which are 45.7% and 19.6% higher than those using a single exciplex as the host, respectively. Moreover, the well-matched energy alignment endows the device with a very low operating voltage of 3.8 V at 1000 cd m-2. These results indicate that the performance of the exciplex-based WOLEDs can be remarkably enhanced by using the MEH strategy.

Modulation of p-type units in tripodal bipolar hosts towards highly efficient red phosphorescent OLEDs

Three novel tripodal bipolar compounds (CNTPA-CZ, CNTPA-PXZ and CNTPA-PTZ) were designed and synthesized, where three functional groups were attached to 1,3,5-positions of the central benzene ring, respectively. In these three compounds, carbazole/phenoxazine/phenothiazine (CZ/PXZ/PTZ) and benzonitrile were applied as electron-donating and electron-withdrawing groups, respectively, to achieve bipolar transport functionality, which was confirmed by the hole-only and electron-only device results. Due to the efficient energy transfer from these compounds to the dopant (Ir(MDQ)2(acac)), the red phosphorescent OLEDs demonstrated high device performance with maximum external quantum efficiency (EQE) over 20%. Particularly, the red OLED hosted by CNTPA-PTZ achieved a maximum efficiency of 42.5 cd/A, 44.3 lm/w and 23.4% with the EQE roll-off ratio of 3.4% from the peak value to that at a brightness of 500 cd/m2.

Meta conjugation effect on the torsional motion of aminostilbenes in the photoinduced intramolecular charge-transfer state

The photochemical behavior of a series of trans-3-(N-arylamino)stilbenes (m1, aryl = 4-substituted phenyl with a substituent of cyano (CN), hydrogen (H), methyl (Me), or methoxy (OM)) in both nonpolar and polar solvents is reported and compared to that of the corresponding para isomers (p1CN, p1H, p1Me, and p10M). The distinct propensity of torsional motion toward a low-lying twisted intramolecular charge-transfer (TICT) state from the planar ICT (PICT) precursor between the meta and para isomers of 1CN and 1Me reveals the intriguing meta conjugation effect and the importance of the reaction kinetics. Whereas the poor charge-redistribution (delocalization) ability through the meta-phenylene bridge accounts for the unfavorable TICT-forming process for m1CN, it is such a property that slows down the decay processes of fluorescence and photoisomerization for m1Me, facilitating the competition of the single-bond torsional reaction. In contrast, the quinoidal character for p1Me in the PICT state kinetically favors both fluorescence and photoisomerization but disfavors the single-bond torsion. The resulting concept of thermodynamically allowed but kinetically inhibited TICT formation could also apply to understanding the other D-A systems, including trans-4-cyano-4′-(N,N-dimethylamino)stilbene (DCS) and 3-(N,N-dimethylamino)benzonitrile (3DMABN).

Red electroluminescent compound as well as preparation method and application thereof

The invention discloses a red electroluminescent compound as well as a preparation method and application thereof, belonging to the technical field of organic photoelectricity. The red electroluminescent compound has a chemical structural formula shown in the specification. The red electroluminescent compound has the advantages of cheap monomer raw materials, simple synthesis route, convenient purification, convenience in research on a structure-performance relationship, and easiness in industrial scale-up production. The red electroluminescent compound disclosed by the invention is simple in synthetic route, convenient to purify, novel in structure and good in electroluminescent property; the compound has good solubility and can be used for preparing a large-area flexible display device by adopting a solution processing technology; and the compound has huge development potential and prospects in the field of organic electronic display.

Reductive C?N Coupling of Nitroarenes: Heterogenization of MoO3 Catalyst by Confinement in Silica

The construction of C?N bonds with nitroaromatics and boronic acids using highly efficient and recyclable catalysts remains a challenge. In this study, nanoporous MoO3 confined in silica serves as an efficient heterogeneous catalyst for C?N cross-coupling of nitroaromatics with aryl or alkyl boronic acids to deliver N-arylamines and with desirable multiple reusability. Experimental results suggest that silica not only heterogenizes the Mo species in the confined mesoporous microenvironment but also significantly reduces the reaction induction period and regulates the chemical efficiency of the targeted product. The well-shaped MoO3@m?SiO2 catalyst exhibits improved catalytic performance both in yield and turnover number, in contrast with homogeneous Mo catalysts, commercial Pd/C, or MoO3 nanoparticles. This approach offers a new avenue for the heterogeneous catalytic synthesis of valuable bioactive molecules.

Schiff bases-titanium (III) & (IV) complex compounds: Novel photocatalysts in Buchwald-Hartwig C–N cross-coupling reaction

Nine novel Schiff bases were derived from salicylic aldehyde and oxalic aldehyde, isolated, and their molecular and spatial structure were explored by a set of experiments (IR, CNMR, HNMR, CHN, SEM, XRD) and theoretical simulation (DFT def2-TZVP). A high potential was predicted in metal cations chelating. The isolated organic species were applied as the ligands in the reaction of complex formation with titanium (III) chloride and (IV) bromide and 12 novel complexes were synthesized and studied experimentally and theoretically. Using the UV–vis spectroscopic titration, the solution stability of the complexes was indicated. Depending on the nature of the Schiff base ligand, their formation constants were calculated in the range of 6.84–17.32. Using the DFT def2-TZVP theoretical method together with the experimental spectroscopic data, the coordination types of the ligands were investigated, and the structure of the complexes was proposed. The photocatalytic ability of the isolated complexes was tested in the C-N cross-coupling reaction under sunlight. Complexes exhibited high visible-light photocatalytic activity for a wide range of aromatic and benzylic amines including electron-withdrawing and electron-donating groups from moderate to good yields ranging in 50–85 %. The use of an inexpensive, clean, and renewable energy source (visible light) is the superiority of the developed photocatalytic systems.

Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions

Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Herein, we report the implementation of substoichiometric quantities of redox mediators to address limitations to Cu-catalyzed electrosynthesis. Mechanistic studies reveal that mediators serve multiple roles by (i) rapidly oxidizing low-valent Cu intermediates, (ii) stripping Cu metal from the cathode to regenerate the catalyst and reveal the active Pt surface for proton reduction, and (iii) providing anodic overcharge protection to prevent substrate oxidation. This strategy is applied to Chan-Lam coupling of aryl-, heteroaryl-, and alkylamines with arylboronic acids in the absence of chemical oxidants. Couplings under these electrochemical conditions occur with higher yields and shorter reaction times than conventional reactions in air and provide complementary substrate reactivity.

Ni/Pd-catalyzed Suzuki-Miyaura cross-coupling of alcohols and aldehydes and C-N cross-coupling of nitro and amines: via domino redox reactions: base-free, hydride acceptor-free

Domino oxidation-Suzuki-Miyaura cross-coupling of benzyl alcohols with phenylboronic acid and domino reduction-C-N cross-coupling of the nitro compounds with aryl halides were carried out using a strong Ni/Pd bimetallic redox catalyst. The catalyst bearing a copolymer with two Ni/Pd coordinated metals in porphyrin (derived from demetalated chlorophyll b) and salen-type ligands, and pyridine moiety as a base functionality all immobilized on magnetite NPs was synthesised and characterized. The domino oxidation cross-coupling reaction was accomplished under molecular O2 in the absence of any hydride acceptor or/and base. Also, the domino reduction C-N cross-coupling reaction was performed in the presence of NaBH4 without the need for any base and co-reductant. This multifunctional catalyst gave moderate to good yields for both coupling reactions with high chemoselectivity. A wide investigation was conducted to determine its mechanism and chemoselectivity.

Design, preparation and characterization of aerogel NiO-CuO-CoO/SiO2 nanocomposite as a reusable catalyst for C-N cross-coupling reaction

Aerogels are porous, non-crystalline solid materials with high specific surface space, plentiful three-dimensional (3D) porous construction, ultra-low density and significant porosity. The aerogel nanocomposite is produced using sol-gel and supercritical drying processes. CO2 supercritical drying (SCD) is the most powerful process, ensuring optimal product properties such as high porosity, low density, and high thermal conductivity. On this account, we used the CO2 supercritical drying method to produce NiO-CuO-CoO/SiO2 nanocomposite aerogels and applied it as a reusable catalyst for the C-N cross-coupling reaction (Buchwald-Hartwig amination). Powerful catalytic activity for the C-N cross-coupling reaction was obtained for the new nanocomposite aerogel, that is, NiO-CuO-CoO/SiO2. The catalyst was characterized by X-ray Powder Diffraction (XRD), field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDS), elemental mapping and Brunauer-Emmett-Teller (BET). Also, organic compounds were identified by melting point, Fourier-transform infrared spectroscopy (FT-IR) and hydrogen-1 nuclear magnetic resonance (1H NMR) analyses.

Exploring Homogeneous Conditions for Mild Buchwald-Hartwig Amination in Batch and Flow

Cross-couplings are among the most frequently used reactions in complex molecule synthesis. However, the requirement of stoichiometric base can cause challenges. Harsh, insoluble inorganic bases can lead to poor tolerance of sensitive functional groups, scale-up issues, and difficult adaptation to continuous flow platforms. Herein, we describe the use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g., XantPhos) with DBU as a soluble, functional-group-tolerant, homogeneous base. Application of this system to diverse aminations in batch and flow are demonstrated, as is the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions.