57340-21-3

Usage

Uses

Used in Chemical Synthesis:
4-(bromomethyl)azobenzene is used as a synthetic intermediate for the production of various organic compounds. Its bromomethyl group facilitates the creation of new chemical entities, making it a valuable component in the synthesis of complex molecules.
Used in Dye and Pigment Manufacturing:
In the dye industry, 4-(bromomethyl)azobenzene is utilized as a key ingredient in the manufacture of dyes and pigments. Its azo structure provides a foundation for the development of a wide range of colorants used in different applications.
Used in Pharmaceutical Production:
4-(bromomethyl)azobenzene also finds its place in the pharmaceutical sector, where it is used as a starting material for the production of pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Laboratory Research:
4-(bromomethyl)azobenzene serves as a reagent in organic reactions within laboratory settings. It is instrumental in conducting research that leads to advancements in organic chemistry and related fields.
It is crucial to handle 4-(bromomethyl)azobenzene with care due to its potential hazards. Proper ventilation and protective equipment are necessary when working with 4-(bromomethyl)azobenzene to ensure safety.

InChI:InChI=1/C13H11BrN2/c14-10-11-6-8-13(9-7-11)16-15-12-4-2-1-3-5-12/h1-9H,10H2/b16-15+

Upstream product

• 65926-74-1 1-(4-(hydroxymethyl)phenyl)-2-phenyldiazene 
• 949-87-1 4-Methylazobenzol 
• 7726-95-6 bromine 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 623-04-1 4-aminobenzenemethanol 
• 586-96-9 Nitrosobenzene 
• 150-13-0 4-amino-benzoic acid 
• 1562-93-2 4-(2-phenyldiazen-1-yl)benzoic acid 
• 106-49-0 p-toluidine 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 619-73-8 4-nitrobenzyl chloride 
• 849232-28-6 (4-nitrosophenyl)methanol 
• 62-53-3 aniline 

Downstream Products

• 114036-03-2 1-pentyl-1-(4-phenylazo-benzyl)-pyrrolidinium; bromide 
• 114036-02-1 1-butyl-1-(4-phenylazo-benzyl)-piperidinium; bromide 
• 65926-74-1 1-(4-(hydroxymethyl)phenyl)-2-phenyldiazene 
• 122724-79-2 bis-(4-phenylazo-benzyl)-ether 
• 1361228-87-6 C₅₀H₄₃N₅O₃S 
• 1361122-97-5 ethyl bis[p-(phenylazo)benzyl]isocyanoacetate 
• 1335521-11-3 trans-1-[p-(phenylazo)benzyl]pyridinium bromide 

Relevant academic research and scientific papers

Responsive Self-Assembly of Supramolecular Hydrogel Based on Zwitterionic Liquid Asymmetric Gemini Guest

A low-molecular-weight supramolecular hydrogel has been fabricated based on host–guest interactions between β-cyclodextrin (β-CD) and an asymmetric gemini zwitterionic liquid (ZIL) containing an azobenzene and bis(trifluoromethanesulfonyl)imide. Reversible sol–gel phase transitions were triggered by light and temperature. The binding stoichiometry, mainly noncovalent interactions in the hydrogel, photo- and thermoresponsive mechanisms, and mode of inclusion in the complex were studied in detail by NMR spectroscopy, UV/Vis spectroscopy, isothermal titration calorimetry, and control experiments. Interestingly, the β-CD in the complex can be photo-manipulated to shuttle along the guest molecule, accompanied by a change in the circular dichroism signals. Reversible switching of the conductivity accompanies the sol–gel phase transition, which demonstrates the stability of the supramolecular hydrogel and its potential application in multi-stimuli-responsive electric sensor materials.

Pillar[6]arene-based photoresponsive host-guest complexation

The trans form of an azobenzene-containing guest can complex with a pillar[6]arene, while it cannot complex with pillar[5]arenes due to the different cavity sizes of the pillar[6]arene and the pillar[5]arenes. The spontaneous aggregation of its host-guest complex with the pillar[6]arene can be reversibly photocontrolled by irradiation with UV and visible light, leading to a switch between irregular aggregates and vesicle-like aggregates. This new pillar[6]arene-based photoresponsive host-guest recognition motif can work in organic solvents and is a good supplement to the existing widely used cyclodextrin/azobenzene recognition motif.

Azobenzene-Based Cross-Linked Small-Molecule Vesicles for Precise Oxidative Damage Treatments Featuring Controlled and Prompt Molecular Release

Precise therapy has become prevalent in clinical practice owing to its accurate and efficient targeting treatment of diseases. Such treatments involving polymersomes as carriers have great potential to lesion sites without damage to normal tissues. However, due to the inherent thick hydrophobic layer of polymersomes, an instantaneous release response to external stimuli remains a challenge. To tackle this challenge, here, we report on the synthesis and applications of azobenzene-containing photochromic vesicles as delivery vectors. These vesicles are assembled from small-molecule amphiphiles that have been developed to provide a fast response and promote instantaneous release due to molecular size reduction compared with macromolecular polymersomes. After cross-linking, the stability of vesicles under a physiological environment is notably enhanced. By varying UV and visible light irradiation, the “gate” of vesicles can be opened and closed reversibly for the controlled release of capsuled cargoes. In vitro experiments display that the vesicles can be applied to load cysteamine for eliminating excess reactive oxygen. The synthesized vesicles here show high performance in controlled and instantaneous release in cells both in time and space. By our approach, oxidative damage to cellular biomolecules can be substantially reduced.

Phenyl pyrazole compound containing azo structure and preparation method and application thereof (by machine translation)

The invention discloses a phenyl pyrazole compound containing an azo structure, a preparation method thereof and application, of the phenyl pyrazole compound with the azo structure shown in the formula I in the structure, shown by the invention. The phenyl pyrazole compound containing the azo structure according to the invention has good insecticidal activity, and can be used as a pesticide for pest control. (by machine translation)

Fluorination of Photoswitchable Muscarinic Agonists Tunes Receptor Pharmacology and Photochromic Properties

Red-shifted azobenzene scaffolds have emerged as useful molecular photoswitches to expand potential applications of photopharmacological tool compounds. As one of them, tetra-ortho-fluoro azobenzene is well compatible for the design of visible-light-responsive systems, providing stable and bidirectional photoconversions and tissue-compatible characteristics. Using the unsubstituted azobenzene core and its tetra-ortho-fluorinated analogue, we have developed a set of uni- and bivalent photoswitchable toolbox derivatives of the highly potent muscarinic acetylcholine receptor agonist iperoxo. We investigated the impact of the substitution pattern on receptor activity and evaluated the different binding modes. Compounds 9b and 15b show excellent photochemical properties and biological activity as fluorination of the azobenzene core alters not only the photochromic behavior but also the pharmacological profile at the muscarinic M1 receptor. These findings demonstrate that incorporation of fluorinated azobenzenes not just may alter photophysical properties but can exhibit a considerably different biological profile that has to be carefully investigated.

A Photoswitchable Dualsteric Ligand Controlling Receptor Efficacy

The investigation of the mode and time course of the activation of G-protein-coupled receptors (GPCRs), in particular muscarinic acetylcholine (mACh or M) receptors, is still in its infancy despite the tremendous therapeutic relevance of M receptors and GPCRs in general. We herein made use of a dualsteric ligand that can concomitantly interact with the orthosteric, that is, the neurotransmitter, binding site and an allosteric one. We synthetically incorporated a photoswitchable (photochromic) azobenzene moiety. We characterized the photophysical properties of this ligand called BQCAAI and investigated its applicability as a pharmacological tool compound with a set of FRET techniques at the M1 receptor. BQCAAI proved to be an unprecedented molecular tool; it is the first photoswitchable dualsteric ligand, and its activity can be regulated by light. We also applied BQCCAI to investigate the time course of several receptor activation processes.

A facile way to achieve all-photonic logic functions and photo-printing based on a donor-acceptor Stenhouse adduct

Herein, a simple bi-photochromic molecule containing a donor-acceptor Stenhouse adduct and azobenzene moiety was synthesized. It can achieve all-photonic multimolecular logic functions and photo-printing. This molecule could provide a novel platform for exploring multifunctional molecular logic devices.

Photoswitchable azobenzene-appended iridium(III) complexes

Iridium(iii) cyclometalated complexes have been used as models to study the effect that extended conjugation and substitution pattern has on the photochromic behavior of azobenzene-appended 2-phenylpyridyl (ppy) ligands. For this purpose four azobenzene-containing ppy ligands were synthesized. With these ligands, nine iridium(iii) complexes containing up to three appended azobenzenes were synthesized. Analysis of their photochromic behaviour by means of UV-vis and 1H-NMR spectroscopy permitted us to conclude that the light-induced trans-to-cis isomerization of the azobenzene was strongly inhibited upon coordination to the Ir(iii) cation when the electronic conjugation was extended along the whole ligand. The use of an aliphatic spacer unit (either -CH2- or -OCH2-) between the azobenzene and the ppy fragment of the ligand sufficed to disrupt the electronic communication, and obtain photochromic organometallic complexes.

Photoresponsive Self-Assembly of Surface Active Ionic Liquid

A novel photoresponsive surface active ionic liquid (SAIL) 1-(4-methyl azobenzene)-3-tetradecylimidazolium bromide ([C14mimAzo]Br) with azobenzene located in the headgroup was designed. Reversible vesicle formation and rupture can be finely controlled by photostimuli without any additives in the aqueous solution of the single-tailed ionic liquid. The photoisomerization of the azobenzene derivative was investigated by 1H NMR and UV-vis spectroscopy. Density functional theory (DFT) calculations further demonstrate that trans-[C14mimAzo]Br has less negative interaction energy, which is beneficial to aggregate formation in water. The incorporation of trans-azobenzene group increases the hydrophobicity of the headgroup and reduces the electrostatic repulsion by delocalization of charge, which are beneficial to the formation of vesicles. However, the bend of cis-azobenzene makes the cis-isomers have no ability to accumulate tightly, which induces the rupture of vesicles. Our work paves a convenient way to achieve controlled topologies and self-assembly of single SAIL.

Photochromic molecule and preparing method and application thereof

The invention discloses a photochromic molecule and a preparing method and application thereof. The photochromic molecule comprises an azobenzene part and a Stenhouse adduct part. Due to the special molecular structure, the photochromic molecule has photoresponse activity no matter in an ultraviolet light area or a visible light area, and can be used for making a shading lens so as to protect eyes, or a photoprinter so as to print characters and patterns through light illumination. The photochromic molecule is obtained through chemical bonding of an azobenzene derivative containing a secondary amine group and a Stenhouse adduct containing a furan ring. The preparing method is easy to operate, reaction conditions are mild, cost is low, and the requirement of industrial production is met.