3035-94-7

Usage

Uses

Used in Textile Industry:
4-(4-bromophenylazo)phenol is used as a dye in the textile industry for coloring synthetic fibers such as polyester, nylon, and acrylic. Its ability to impart a bright and long-lasting orange hue to fabrics makes it a popular choice for clothing, upholstery, and other textile products.
Used in Plastics Industry:
In the plastics industry, 4-(4-bromophenylazo)phenol is used as a colorant for various plastic materials, including acrylics and other synthetic resins. Its solubility in organic solvents allows for easy incorporation into the manufacturing process, resulting in plastic products with a consistent and eye-catching orange color.
Used in Biomedical Applications:
4-(4-bromophenylazo)phenol has been studied for its potential use in biomedical applications, such as drug delivery systems. Its photochemical and photophysical properties make it a candidate for the development of targeted drug delivery systems that can release therapeutic agents in response to specific stimuli.
Used in Photodynamic Therapy:
Due to its photochemical properties, 4-(4-bromophenylazo)phenol has been investigated for its potential use in photodynamic therapy. This medical treatment involves the use of light-sensitive compounds, such as Disperse Orange 3, to generate reactive oxygen species that can selectively destroy cancer cells upon exposure to light.

InChI:InChI=1/C12H9BrN2O/c13-9-1-3-10(4-2-9)14-15-11-5-7-12(16)8-6-11/h1-8,14H

Upstream product

• 16054-48-1 N-[(4-bromophenyl)imino]benzenimine oxide 
• 106-40-1 4-bromo-aniline 
• 108-95-2 phenol 
• 4418-84-2 4-bromoazobenzene 
• 123-30-8 4-amino-phenol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 17333-82-3 4-bromo-benzenediazonium ion 
• 16109-68-5 4-bromo-1-phenyl-NNO-azoxybenzene 
• 7664-93-9 sulfuric acid 
• 1215-42-5 4,4'-dibromoazoxybenzene 

Downstream Products

• 100125-69-7 2,6-dibromo-4-(4-bromo-phenylazo)-phenol 
• 35815-48-6 4-(p-bromophenylazo)phenyl tosylate 
• 7466-26-4 (4-bromo-phenyl)-(4-chloro-phenyl)-diazene 
• 860209-46-7 (4-ethoxy-phenyl)-(4-bromo-phenyl)-diazene-N-oxide 
• 1373207-54-5 (E)-1-(4-(4-bromobutoxy)phenyl)-2-(4-bromophenyl)diazene 
• 1373207-48-7 (E)-1-(4-(6-bromohexyloxy)phenyl)-2-(4-bromophenyl)diazene 
• 1373207-61-4 (E)-4-[2-{4-[4-(dodecyloxy)-3-methoxyphenyl]phenyl}diazen-1-yl]phenol 
• 1373207-62-5 4-[(E)-2-{4-[4-(dodecyloxy)-3-methoxyphenyl]phenyl}diazen-1-yl]phenyl 2-methylprop-2-enoate 
• 1373207-55-6 (E)-4'-((4-(6-bromohexyloxy)phenyl)diazenyl)-4-(hexyloxy)biphenyl-3-carbonitrile 
• 1373207-47-6 (E)-4'-((4-(6-bromohexyloxy)phenyl)diazenyl)-4-(decyloxy)biphenyl-3-carbonitrile 

Relevant academic research and scientific papers

Liquid crystal and photo-induced properties of polymers carrying pyridylazobenzene groups and iodopentafluorobenzene rings self-assembled through halogen bond

In this work, we report on the synthesis, liquid crystal behavior and photo-induced optical properties of a polymer and a copolymer, both carrying lateral pyridylazobenzene groups and iodopentafluorobenzene (IPFB)rings self-assembled through halogen bond. The formation of the halogen-bonded complexes was confirmed by Fourier transform infrared (FTIR)spectroscopy; the mesomorphic behavior was determined by differential scanning calorimetry (DSC), polarizing optical microscopy (POM)and X-ray diffraction (XRD); and the optical properties were photo-induced with a 405 nm laser beam. The pyridylazobenzene-functionalized polymer showed a smectic-type order (smectic A and crystE phases)whereas the copolymer and the halogen-bonded complexes with IPFB rings formed aggregates whose molecular order in the z-coordinates is suppressed (no layers). The photo-isomerization (in solution)of the polymer and copolymer led to a trans-to-cis isomer conversion (%cis)of 82, and 95, respectively. In film, the %cis values resulted much inferior but still high enough to induce optical properties, as for instance, in films of the copolymer (%cis = 60)and its halogen-bonded complex (%cis = 46)that responded quite well in periodical light-induced writing/erasure experiments. Only the halogen-bonded copolymer complex allowed us to register regular surface relief gratings (SRGs)suggesting that it would be a good candidate for optical data storage applications.

Reversible dynamic full-color phototuning with a new chiral molecular switch containing linking group between chiral center and photosensitive group

In this study, a new photoresponsive chiral molecular switch, where azobenzene was not directly connected to the axially chiral binaphthyl group, was successfully synthesized and used to induce helical superstructures in the achiral nematic liquid crystal

Docking Study, Synthesis, and Anti-Inflammatory Potential of Some New Pyridopyrimidine-Derived Compounds

Background and Purpose: Because of gastrointestinal irritation and kidney toxicity associated with non-steroidal anti-inflammatory drugs and the cardiovascular problems of Coxibs use, developing novel anti-inflammatory agents with reduced toxicity and improved selectivity remains a major challenge. Depending on our previous work, a novel series of pyridopyrimidinones IIIa-i has been synthesized via reaction of 6-amino-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (I) and phenyldiazenyl aromatic aldehydes (IIa-i). All the new constructed compounds were fully characterized by elemental and spectral analysis. Methods: The target compounds IIIa–i were investigated for their potential towards COX inhibition, anti-inflammatory properties using carrageenan induced edema model in rat paw, and the ulcer indices of the most active members. Results: The ethyl pyridopyrmidinone-benzoates IIIf, IIIg and IIIh showed superior inhibitory activity of carrageenan induced edema to celecoxib. Furthermore, the pyridopyrimidinones IIId, IIIf, IIIg, and IIIi exerted improved COX-2 inhibitory activity (IC50 = 0.67–1.02 μM) comparing to celecoxib (IC50 = 1.11 μM). Moreover, the gastric ulcerogenic potential assay of compounds IIIf– h revealed their lower ulcerogenic liability than indomethacin with comparable effect to celecoxib. Conclusion: Virtual docking investigation of the most active candidates IIId, IIIf, IIIg and IIIi in the active site of COX-2 enzyme showed that these compounds implied interaction and binding motif similar to the cocrystallized ligand bromocelecoxib.

The selective synthesis ofN-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents

The solvent-controllable photoreaction of 4-methoxyazobenzenes to afford 1-aryl-1H-benzimidazoles orN-arylbenzene-1,2-diamines has been studied. The irradiation of 4-methoxyazobenzenes in DMF containing 0.5 M hydrochloric acid providedN2-aryl-4-methoxybenzene-1,2-diamines as the major product, while irradiation in acetal containing 0.16 M hydrochloric acid led to 1-aryl-6-methoxy-2-methyl-1H-benzimidazoles as the major product. A possible reaction mechanism explaining the selectivity was also discussed.

Novel Phenyldiazenyl Fibrate Analogues as PPAR α/γ/δ Pan-Agonists for the Amelioration of Metabolic Syndrome

The development of PPARα/γ dual or PPARα/γ/δ pan-agonists could represent an efficacious approach for a simultaneous pharmacological intervention on carbohydrate and lipid metabolism. Two series of new phenyldiazenyl fibrate derivatives of GL479, a previously reported PPARα/γ dual agonist, were synthesized and tested. Compound 12a was identified as a PPAR pan-agonist with moderate and balanced activity on the three PPAR isoforms (α, γ, δ). Moreover, docking experiments showed that 12a adopts a different binding mode in PPARγ compared to PPARα or PPARδ, providing a structural basis for further structure-guided design of PPAR pan-agonists. The beneficial effects of 12a were evaluated both in vitro, on the expression of PPAR target key metabolic genes, and ex vivo in two rat tissue inflammatory models. The obtained results allow considering this compound as an interesting lead for the development of a new class of PPAR pan-agonists endowed with an activation profile exploitable for therapy of metabolic syndrome.

Azo Dyes: New Palladium- and Copper-Catalysed Coupling Reactions on an Old Template

The elaboration of azo dyes using a variety of transition-metal-catalysed reactions (Stille, Heck, Ullmann, and Suzuki couplings) is reported. This methodology has been applied to the synthesis of functionalised coumarin azo dye conjugates, substrates which may find potential application in the development of new sensors.

Synthesis and anticancer activities of 4-[(Halophenyl)diazenyl]phenol and 4-[(Halophenyl)diazenyl]phenyl aspirinate derivatives against nasopharyngeal cancer cell lines

Aspirin and azo derivatives have been widely studied and have drawn considerable attention due to diverse biological activities. In this study, a series of 4-[(halophenyl)diazenyl]phenyl aspirinate derivatives were synthesized from the reaction of aspirin

CHROMOPHORES FOR PHOTOCHROMIC COMPOSITIONS USEFUL FOR THREE DIMENSIONAL DISPLAY APPLICATIONS

Described herein are novel azo-benzene type chromophores. The chromophores are useful in photochromic compositions comprising a polymer matrix and a chromophore, wherein the chromophore is a novel azo-benzene type structure. The photochromic composition i

Synthesis and phase transitions of monomers carrying a biphenyleneazobenzene or an azotolane group. Precursors of photo-responsive liquid crystal polymers

Four functional methacrylate monomers, two of them carrying a biphenyleneazobenzene group, and the other two an azotolane group, were synthesized. The synthetic route involved several reactions, among which are the Suzuki-Miyaura and Sonogashira cross-coupling reactions that allowed us to prepare long rigid rodlike azobenzene cores. The chemical structure of these new azo-monomers was confirmed by proton nuclear magnetic resonance (1H NMR) spectroscopy, and the thermotropic liquid-crystalline behavior was determined from differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (XRD) analyses. The four monomers showed a mesomorphic behavior that extends over a broad temperature range. The phase transitions of the monomers carrying a biphenyleneazobenzene core were much broader and weaker than those of monomers carrying an azotolane group. Also, the former showed no crystallization in cooling to room temperature. The four studied monomers displayed liquid crystal phases with lamellar order (SmA and SmC), but only those carrying an azotolane core developed an additional nematic phase. The lamellar stacking of monomers is discussed in terms of lateral interactions between the rigid rodlike cores. Both types of monomers showed a trans to cis photo-conversion of around 90% when irradiated with UV–light. These new monomers are precursors of photo-responsive liquid crystal polymers.

Photocontrol of Antibacterial Activity: Shifting from UV to Red Light Activation

The field of photopharmacology aims to introduce smart drugs that, through the incorporation of molecular photoswitches, allow for the remote spatial and temporal control of bioactivity by light. This concept could be particularly beneficial in the treatment of bacterial infections, by reducing the systemic and environmental side effects of antibiotics. A major concern in the realization of such light-responsive drugs is the wavelength of the light that is applied. Studies on the photocontrol of biologically active agents mostly rely on UV light, which is cytotoxic and poorly suited for tissue penetration. In our efforts to develop photoswitchable antibiotics, we introduce here antibacterial agents whose activity can be controlled by visible light, while getting into the therapeutic window. For that purpose, a UV-light-responsive core structure based on diaminopyrimidines with suitable antibacterial properties was identified. Subsequent modification of an azobenzene photoswitch moiety led to structures that allowed us to control their activity against Escherichia coli in both directions with light in the visible region. For the first time, full in situ photocontrol of antibacterial activity in the presence of bacteria was attained with green and violet light. Most remarkably, one of the diaminopyrimidines revealed an at least 8-fold difference in activity before and after irradiation with red light at 652 nm, showcasing the effective "activation" of a biological agent otherwise inactive within the investigated concentration range, and doing so with red light in the therapeutic window.