194416-45-0

Basic information

• Product Name: 4-broMo-N,N-bis(4-Methoxyphenyl)aniline
• Synonyms: 4-broMo-N,N-bis(4-Methoxyphenyl)aniline;4-BroMo-4',4'-diMethoxyltriphenylaMine;4-BroMo-4‘,4'-diMethoxytriphenylaMine
• CAS NO: 194416-45-0
• Molecular Formula: C₂₀H₁₈BrNO₂
• Molecular Weight: 384.26642
• EINECS: 1592732-453-0
• Mol File: 194416-45-0.mol
• Article Data: 63

Chemical Properties

• Melting Point: 96-98℃
• Boiling Point: 494.6±40.0 °C(Predicted)
• Appearance: /
• Density: 1.349±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.37±0.50(Predicted)
• CAS DataBase Reference: 4-broMo-N,N-bis(4-Methoxyphenyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-broMo-N,N-bis(4-Methoxyphenyl)aniline(194416-45-0)
• EPA Substance Registry System: 4-broMo-N,N-bis(4-Methoxyphenyl)aniline(194416-45-0)

Safety Data

• Hazardous Substances Data: 194416-45-0(Hazardous Substances Data)

Usage

General Description

4-Bromo-N,N-bis(4-methoxyphenyl)aniline is a chemical compound that primarily serves as an intermediate in organic synthesis. It consists of a bromine attached to a nitrogen atom, which itself is bonded by two methoxyphenyl groups (aromatic benzene rings with a methoxy group). This structure allows it to participate in various chemical reactions, particularly in pharmaceutical and dye industries where compounds of similar structural features are often used. The presence of the bromine atom makes it a good candidate for cross-coupling reactions, while the aniline component (NH2 group attached to a benzene ring) has diverse uses including the production of rubber, dyes, and pharmaceuticals. Its methoxy groups can also be a site for further functionalization, expanding its utility in organic synthesis. Proper handling and safety measures should be observed while dealing with this compound due to its potential toxicity.

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 101-70-2 bis(4-methoxyphenyl)amine 
• 67-56-1 methanol 
• 4316-58-9 tri(p-bromophenyl)amine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 100-66-3 methoxybenzene 
• 540-38-5 p-Iodophenol 
• 62-53-3 aniline 
• 106-38-7 para-bromotoluene 
• 696-62-8 para-iodoanisole 
• 106-40-1 4-bromo-aniline 
• 106-37-6 1.4-dibromobenzene 
• 20440-94-2 N,N-bis(4-methoxyphenyl)aniline 

Downstream Products

• 185014-40-8 N³,N³,N^4',N^4'-Tetrakis-(4-methoxy-phenyl)-biphenyl-3,4'-diamine 
• 89115-20-8 4-[bis(4-methoxyphenyl)amino]benzaldehyde 
• 1219091-29-8 4-methoxy-N-(4-methoxyphenyl)-N-(4-(thiophen-2-yl)phenyl)aniline 
• 1181403-97-3 4,4'-((2,4,6-triisopropylphenyl)borylene)bis(N,N-di-para-anisyl benzenamine) 
• 875667-84-8 4-methoxy-N-(4-methoxyphenyl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzenamine 
• 1253294-06-2 4-(5-(4-(N-phenyl-N-(4-(tert-butyldimethylsilyloxy)phenyl)amino)phenyl)-thien-2-yl)-7-(4-(di-(4-methoxyphenyl)-amino)phenyl)-2,1,3-benzothiadiazole 
• 1253294-07-3 4-(5-(4-(N-phenyl-N-(4-hydroxyphenyl)amino)phenyl)-thien-2-yl)-7-(4-(di-(4-methoxyphenyl)-amino)-phenyl)-2,1,3-benzothiadiazole 
• 1253294-08-4 4-(5-(4-(N-phenyl-N-(4-(tert-butyldimethylsilyloxy)phenyl)amino)phenyl)-3,4-ethylenedioxythien-2-yl)-7-(4-(di-(4-methoxyphenyl)-amino)phenyl)-2,1,3-benzothiadiazole 
• 1253294-10-8 4-(5-(4-(N-phenyl-N-(4-methoxyphenyl)amino)phenyl)-thien-2-yl)-7-(4-(di-(4-methoxyphenyl)amino)phenyl)-2,1,3-benzothiadiazole 
• 1253294-13-1 C₇₃H₆₆Br₂N₄O₃S₂ 
• 1253293-99-0 4-(7-bromobenzo[c] [1,2,5]thiadiazol-4-yl)-N,N-bis(4-methoxyphenyl)aniline 
• 1380314-77-1 4-methoxy-N-(4-methoxyphenyl)-N-(4-(5-(7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophen-2-yl)phenyl)aniline 
• 1380314-79-3 C₅₄H₄₂N₄O₄S₃ 
• 1443234-63-6 2-(4-hexyl-5-(4-(bis(4-methoxyphenyl)amino)phen-1-yl)thiophen-2-yl)-6-(4-hexyl-5-bromothiophen-2-yl)benzo[1,2-d;4,5-d']bisthiazole 

Relevant articles and documents

Arylamino-fluorene derivatives: Optically induced electron transfer investigation, redox-controlled modulation of absorption and fluorescence

A series of biarylaminofluorene-based systems with donor-π-donor (D-π-D) structure have been designed and synthesized in order to study the dependence on the π-conjugated bridge length of the intervalence charge-transfer transitions (IV-CT) and of the electronic coupling between the redox centers. To this purpose cyclic voltammetry, UV/Vis-NIR, fluorescence spectroscopy and computational investigations have been carried out to characterize the electronic structure of the compounds in the neutral as well as in the mono- and dication states. Additionally, a study of related D-π compounds has been performed to elucidate the effect of the interaction between two redox centers. Interestingly it was observed that the mono- and dication species exhibit intense transition bands in the NIR region, in the 10000-15000 cm?1 range, whose intensity depends on the oxidation state and thus it can be reversibly tuned by an applied potential. In a similar way, all compounds show an oxidation state dependent fluorescence which leads to electrofluorochromism. Particularly significant is the mixed valence behavior that provides these systems singular optoelectronic properties, making them excellent active components for electrochromic and electrofluorochromic applications.

Acene-based organic semiconductors for organic light-emitting diodes and perovskite solar cells

In this work, three novel acene-based organic semiconductors, including 2,7-bis(trimethylstannyl)naphtho[2,1-b:6,5-b′]dithiophene (TPA-NADT-TPA), 4,4′-(anthracene-2,6-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) (TPA-ANR-TPA) and N2,N2,N6,N6-tetrakis(4-methoxyphenyl)anthracene-2,6-diamine (DPA-ANR-DPA), are designed and synthesized for use in organic light-emitting diodes (OLEDs) and perovskite solar cells (PSCs). In OLEDs, devices based on TPA-NADT-TPA, TPA-ANR-TPA and DPA-ANR-DPA showed pure blue, blue green, and green emission, respectively. Also, the maximum brightness of the devices with a turn-on voltage of 3.8 V reached 8682 cd m-2 for TPA-NADT-TPA, 11180 cd m-2 for TPA-ANR-TPA, and 18 600 cd m-2 for DPA-ANR-DPA. These new materials are also employed as hole transporting materials (HTMs) in inverted PSCs, where they were used without additives. The inverted devices based on these HTMs achieved an overall efficiency of 10.27% for TPA-NADT-TPA, 7.54% for TPA-ANR-TPA, and 6.05% for DPA-ANR-DPA under identical conditions (AM 1.5G and 100 mW cm-2). While the PSCs with TPA-NADT-TPA as the HTM achieved the highest efficiency, the DPA-ANR-DPA-based OLED devices showed the brightest emission and efficiency. Based on the obtained promising performance, it is clear that this molecular design presents a new research strategy to develop materials that can be used in multiple types of devices.

A novel dibenzimidazole-based fluorescent probe with high sensitivity and selectivity for copper ions

A novel fluorescence probe TPA-BMZ for Cu2+, based on intramolecular charge transfer, was designed and synthesized. Probe was composed of triphenylamine as the fluorophore and benzimidazole derivative as the receptor. AFM measurement exhibits that TPA-BMZ possess an amorphous state without any crystallization, which benefits to its long-term stability due to application. Meanwhile, its optical character was studied and the results shown that TPA-BMZ could be used to recognize cupric ions in consequence of intramolecular charge transfer (ICT) and it even could be used to detect the presence of cupric ions in seawater. The Job's plot curve demonstrated the molar ratio of probe to copper is 1:1. Moreover, from the fluorescence titration spectrum of copper ions to probe, the limit of detection of probe is obtained (0.094 μM) and the complex constant is 6.57 × 10?8 M?1 which shows a high sensibility towards copper ions. In addition, probe was also used to detect copper ions in tap water, river water and seawater which demonstrated a potential application in seawater. More importantly, the response time of the probe to copper ions is within 1 s.

Benzotriazole-containing donor-acceptor-acceptor type cyclometalated iridium(III) complex for solution-processed near-infrared polymer light emitting diodes

A novel near-infrared-emitting cyclometalated iridium(III) complex of (CH3OTPA-BTz-Iq)2Irpic containing benzotriazole unit with a donor-acceptor-acceptor (D-A-A) chromophore was synthesized and characterized. The optophysical, electrochemical and electroluminescent characteristics were primarily studied. A near-infrared emission peaked at 716 nm with a shoulder at 790 nm was exhibited in the (CH3OTPA-BTz-Iq)2Irpic dichloromethane solution at 298 K. In its optimized solution-processed polymer light-emitting diodes, a near-infrared electroluminescent emission peaked at 723 nm with a shoulder at 780 nm was observed with a maximum external quantum efficiency of 0.41% at 8.14 mA cm-2. This work indicates that introducing appropriate D and A units to develop D-A-A structure is an efficient approach to construct near-infrared-emitting iridium(III) complex in the polymer light-emitting diodes with suppressive efficiency roll-off.

Boosting inverted perovskite solar cell performance by using 9,9-bis(4-diphenylaminophenyl)fluorene functionalized with triphenylamine as a dopant-free hole transporting material

In this study, two newly developed small molecules based on 9,9-bis(4-diphenylaminophenyl)fluorene functionalized with triphenylamine moieties, namely TPA-2,7-FLTPA-TPA and TPA-3,6-FLTPA-TPA, are designed, synthesized and characterized. The electrochemical, optical and thermal properties of both materials are investigated using various techniques. Afterwards, these materials are employed as dopant-free hole transporting materials (HTMs) in planar inverted perovskite solar cell devices with the aim of determining the device performance and studying their stability in comparison with reference N4,N4,N4′′,N4′′-tetra([1,10-biphenyl]-4-yl)-[1,1′:4′,1′′-terphenyl]-4,4′′-diamine (TaTm)-based devices. Under 1 sun conditions, TPA-3,6-FLTPA-TPA-based devices achieve a power conversion efficiency (PCE) of 13.9% whereas TPA-2,7-FLTPA-TPA-based devices exhibit the highest PCE of 17.1% mainly due to an improvement in the fill factor (FF). Meanwhile, the devices prepared using TaTm as the reference HTM exhibit an overall efficiency of 15.9%. In addition to the higher efficiency, our newly developed HTM TPA-2,7-FLTPA-TPA-based devices demonstrate good stability which is comparable to those with TaTm under similar aging test conditions.

Hole transport material containing isoindigo compound as well as preparation method and application thereof

The hole transport material takes isoindigo-containing compound as a core, the alkyl chain is introduced to improve the solubility, different donor groups are introduced to regulate the energy level, and the hole transport capacity is improved. The synthesized hole transport and transmission material is low in cost and good in hole transport capacity, and has high application value in the field of solar cells. The hole transport material has good hole transport performance and good solubility, is applied to a perovskite solar cell as a hole transport layer, and improves the photoelectric conversion efficiency of the solar cell.

Photo-Electroswitchable Arylaminoazobenzenes

Azobenzenes appended with a redox-active arylamino group (redox auxiliary, RA) are prepared and shown to undergo fast, complete, and catalytic Z→E azo isomerization upon electron loss from the RA unit of the azobenzene. The RA-azo structures can be reversibly (E→Z→E)n cycled by sequential photo- and electrostimulation. Due to the robust nature of the RA?+-azo radical cation chain carrying species, initiation of electron transfer (ET) catalysis occurs at low levels (1.0-0.04 mol %) of catalytic loading and is effective even at Z-RA-azo concentrations of 10-4-10-5 M, yielding TONs (turnover numbers) of 100-2300 under such dilute conditions. The RA-azo Z→E conversion is demonstrated using chemical oxidation (redox switching), electrochemical oxidation (electro switching), and photochemical oxidation (photoredox switching). The Z→E acceleration is shown to be at least 2 × 109-fold for RA-azo 5. DFT calculations on methyl yellow suggest that a N-centered radical cation of the RA group stabilizes the Z→E N-N twist transition state of the RA?+-azo, yielding a large reduction in the barrier for RA?+-azo compared to neutral RA-azo. The RA-azo structure class has nanomechanical features that can be toggled with photo- and electrostimulation, the latter offering a quick switch for complete Z→E conversion.