1545-83-1

Usage

Uses

Used in Organic Synthesis:
Azobenzene, 4-fluorois utilized as a key building block in the synthesis of various organic compounds, including dyes and pharmaceuticals. Its unique properties and reactivity contribute to the development of novel and improved materials with specific functions and applications.
Used in Molecular Switches:
Due to its reversible photoisomerization ability, Azobenzene, 4-fluorois being studied for its potential use in molecular switches. These switches can be triggered by light, allowing for the control of molecular properties and functions, which can be applied in various fields, such as materials science and nanotechnology.
Used in Optoelectronic Devices:
Azobenzene, 4-fluorois also being explored for its potential applications in optoelectronic devices. Its photoisomerization capability can be harnessed to create devices that respond to light, such as sensors, displays, and photovoltaic cells, contributing to the advancement of optoelectronic technology.
Used in Research and Development:
Azobenzene, 4-fluoroserves as an important compound in research and development, particularly in the fields of chemistry, materials science, and physics. Its unique properties and potential applications make it a valuable subject for scientific investigation and innovation.

InChI:InChI=1/C12H9FN2/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H/b15-14+

Upstream product

• 586-96-9 Nitrosobenzene 
• 371-40-4 4-fluoroaniline 
• 62-53-3 aniline 
• 332-07-0 bis-(4-fluorophenyl)diazene 
• 51789-21-0 1-(4-fluorophenyl)-2-phenylhydrazine 

Downstream Products

• 1545-85-3 4-hydroxyphenylazo-4'-fluorobenzene 
• 68110-87-2 Pd(N₂C₁₂H₈F)(C₅H₅) 
• 68110-85-0 Mn(N₂C₁₂H₈F)(CO)4 
• 68110-86-1 Mn(N₂C₁₂H₈F)(CO)4 
• 332-00-3 (E)-1-(4-fluorophenyl)-2-phenyldiazene 
• 51789-21-0 1-(4-fluorophenyl)-2-phenylhydrazine 
• 135066-29-4 2-(4-fluorophenyl)-1H-indazol-3(2H)-one 
• 62-53-3 aniline 
• 371-40-4 4-fluoroaniline 
• 332-07-0 bis-(4-fluorophenyl)diazene 

Relevant academic research and scientific papers

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

Photosensitive and Photoswitchable TRPA1 Agonists Optically Control Pain through Channel Desensitization

Transient receptor potential ankyrin 1 (TRPA1) channel, as a nonselective ligand-gated cation channel robustly in dorsal root ganglion sensory neurons, is implicated in sensing noxious stimuli and nociceptive signaling. However, small-molecule tools targeting TRPA1 lack temporal and spatial resolution, limiting their use for validation of TRPA1 as a therapeutic target for pain. In our previous work, we found that 4,4′-(diazene-1,2-diyl)dianiline (AB1) is a photoswitchable TRPA1 agonist, but the poor water solubility and activity hinder its further development. Here, we report a series of specific and potent azobenzene-derived photoswitchable TRPA1 agonists (series 1 and 2) that enable optical control of the TRPA1 channel. Two representative compounds 1g and 2c can alleviate capsaicin-induced pain in the cheek model of mice through channel desensitization but not in TRPA1 knockout mice. Taken together, our findings demonstrate that photoswitchable TRPA1 agonists can be used as pharmacological tools for study of pain signaling.

Hydrogen peroxide based oxidation of hydrazines using HBr catalyst

Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.

Visible-light-promoted oxidative dehydrogenation of hydrazobenzenes and transfer hydrogenation of azobenzenes

Azo compounds are widely used in the pharmaceutical and chemical industries. Here, we report the use of a non-metal photo-redox catalyst, Eosin Y, to synthesize azo compounds from hydrazine derivatives. The use of visible-light with air as the oxidant makes this process sustainable and practical. Moreover, the visible-light-driven, photo-redox-catalyzed transfer hydrogenation of azobenzenes is compatible with a series of hydrogen donors such as phenyl hydrazine and cyclic amines. Compared with traditional (thermal/transition-metal) methods, our process avoids the issue of over-reduction to aniline, which extends the applicability of photo-redox catalysis and confirms it as a useful tool for synthetic organic chemistry.

Photocatalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

Visible light mediated oxidative dehydrogenation of hydrazobenzenes under an ambient atmosphere using an organic dye as a photocatalyst was reported for the first time. The reaction provides an environmentally benign method for the preparation of azobenzenes in excellent yields with good functional group tolerance.

T BuOK-triggered bond formation reactions

Recently, inexpensive and readily available tBuOK has seen widespread use in transition-metal-free reactions. Herein, we report the use of tBuOK for S-S, S-Se, NN and CN bond formations, which significantly extends the scope of tBuOK in chemical synthesis. Compared with traditional methods, we have realized mild and general methods for disulfide, azobenzenes imine etc. synthesis.

Preparation method of aromatic azo organic compounds

The invention discloses a preparation method of aromatic azo compounds so as to achieve high-yield preparation of the azo compounds from diaryl hydrazine low in cost and easy to obtain through oxydehydrogenation by an organic oxidant. According to different raw materials, the symmetrical or asymmetric azo compounds can be obtained, a catalyst is not needed, the reaction raw materials and the organic oxidant are low in cost and easy to obtain, conditions are mild and efficient, a reaction can be complete through only a few minutes, the reaction process is smooth and safe, products are easy to separate, and the preparation method accords with the development concept of green chemistry.

Photocatalysis Enabling Acceptorless Dehydrogenation of Diaryl Hydrazines at Room Temperature

Aromatic azo compounds are privileged structural motifs, and they exhibit a myriad of pharmaceutical as well as industrial applications. Here, we report a catalytic acceptorless dehydrogenation of diarylhydrazine derivatives to access a wide variety of aryl-azo compounds with the removal of molecular hydrogen as the sole byproduct. This distinctive reactivity has been achieved under dual catalytic conditions by merging the visible-light active [Ru(bpy)3]2+ as the photoredox catalyst and Co(dmgH)2(py)Cl as the proton-reduction catalyst. The reaction proceeds smoothly under very mild and benign conditions and operates at ambient temperature. This dual catalytic approach is highly compatible with many different functional groups and has a broad substrate scope. We have also demonstrated the reversible hydrogen storage and release phenomenon on hydrazobenzene/azobenzene couple to show the utility of these compounds as hydrogen storage materials. Further diversification of azobenzene was shown by a transition-metal-catalyzed azo-group-directed ortho-C-H bond functionalization.

Dehydrogenation of the NH?NH Bond Triggered by Potassium tert-Butoxide in Liquid Ammonia

A novel strategy for the dehydrogenation of the NH?NH bond is disclosed using potassium tert-butoxide (tBuOK) in liquid ammonia (NH3) under air at room temperature. Its synthetic value is well demonstrated by the highly efficient synthesis of aromatic azo compounds (up to 100 % yield, 3 min), heterocyclic azo compounds, and dehydrazination of phenylhydrazine. The broad application of this strategy and its benefit to chemical biology is proved by a novel, convenient, one-pot synthesis of aliphatic diazirines, which are important photoreactive agents for photoaffinity labeling.

Palladium-Catalyzed Carbonylative Cyclization of Azoarenes

In this communication, we established an interesting palladium-catalyzed carbonylation protocol for the intramolecular cyclization of azoarenes. With Mo(CO)6 as the solid CO source and through C(sp2)?H bond activation, a series of azoarenes were transformed into the corresponding 2-arylindazolones in moderate to good yields. Notably, not only symmetrical azoarenes, but also unsymmetrical substrates underwent the reaction with excellent regioselectivity.