23377-24-4

Basic information

• Product Name: 1-bromo-3-[(Z)-(3-bromophenyl)-NNO-azoxy]benzene
• Synonyms: Diazene, bis(3-bromophenyl)-, 1-oxide
• CAS NO: 23377-24-4
• Molecular Formula: C₁₂H₈Br₂N₂O
• Molecular Weight: 356.0127
• Mol File: 23377-24-4.mol

Chemical Properties

• Boiling Point: 445.3°C at 760 mmHg
• Flash Point: 223.1°C
• Density: 1.72g/cm³
• Vapor Pressure: 1.05E-07mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: 1-bromo-3-[(Z)-(3-bromophenyl)-NNO-azoxy]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-bromo-3-[(Z)-(3-bromophenyl)-NNO-azoxy]benzene(23377-24-4)
• EPA Substance Registry System: 1-bromo-3-[(Z)-(3-bromophenyl)-NNO-azoxy]benzene(23377-24-4)

Safety Data

• Hazardous Substances Data: 23377-24-4(Hazardous Substances Data)

Usage

Organic compound

A carbon-based molecule with a azo group linking two aromatic rings the compound is made up of elements such as carbon, hydrogen, and other non-metals, and has a specific structure featuring azo (-N=N-) and aromatic rings.

Aromatic rings

Benzene-based structure the compound belongs to the class of benzenes, which are organic compounds containing a six-carbon ring with alternating single and double bonds, and includes azobenzenes and dihydroxyazoxybenzenes.

Azo group

-N=Nlinkage between two aromatic rings the azo group is a chemical functional group consisting of a nitrogen-nitrogen double bond (-N=N-) that connects two aromatic rings, giving the compound its specific properties.

Yellow solid

The physical appearance of the compound 1-bromo-3-[(Z)-(3-bromophenyl)-NNO-azoxy]benzene is a yellow-colored solid, indicating its form and color.

Melting point

168-171°C the temperature range at which the compound transitions from a solid to a liquid state, which can be important for its handling and storage.

Sparingly soluble in water

The compound's solubility it has a low solubility in water, meaning it does not dissolve easily in aqueous solutions.

Applications

Organic synthesis and chemical reactions the compound is used in various applications, such as in the synthesis of other organic compounds and as a reagent in chemical reactions.

Potential applications

Dyes, pigments, pharmaceuticals, and materials due to its azo functionality, the compound has potential uses in the development of dyes, pigments, and other products, as well as in the pharmaceutical and materials industries.

Health and environmental hazards

Proper handling required 1-bromo-3-[(Z)-(3-bromophenyl)-NNO-azoxy]benzene may pose health and environmental risks if not handled correctly, so it is important to follow safety precautions when working with this compound.

Upstream product

• 24171-78-6 m-bromophenylhydroxylamine 
• 586-96-9 Nitrosobenzene 
• 585-79-5 m-nitrobromobenzene 
• 6831-82-9 potassium isopropoxide 
• 107986-35-6 N-(3-bromophenyl)-O-pivaloylhydroxylamine 
• 109-89-7 diethylamine 
• 114838-63-0 C₈H₈BrNO₂ 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 591-19-5 m-Bromoaniline 
• 13125-68-3 1-bromo-3-nitrosobenzene 
• 63213-03-6 1,2-bis(3-bromophenyl)diazene 

Downstream Products

• 55138-19-7 1,2-bis(3-bromophenyl)hydrazine 
• 63213-03-6 1,2-bis(3-bromophenyl)diazene 
• 84530-60-9 2,2'-dibromo-[1,1'-biphenyl]-4,4'-diamine 

Relevant articles and documents

SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution

A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.

Continuous Flow Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzenes with Gel-Bound Catalysts

In the search for a new synthetic pathway for azoxybenzenes with different substitution patterns, an approach using a microfluidic reactor with gel-bound proline organocatalysts under continuous flow is presented. Herein the formation of differently substituted azoxybezenes by reductive dimerization of nitrosobenzenes within minutes at mild conditions in good to almost quantitative yields is described. The conversion within the microfluidic reactor is analyzed and used for optimizing and validating different parameters. The effects of the different functionalities on conversion, yield, and reaction times are analyzed in detail by NMR. The applicability of this reductive dimerization is demonstrated for a wide range of differently substituted nitrosobenzenes. The effects of these different functionalities on the structure of the obtained azoxyarenes are analyzed in detail by NMR and single-crystal X-ray diffraction. Based on these results, the turnover number and the turnover frequency were determined.

Method for synthesizing oxidized azo compound through selective oxidation of aromatic amine

The invention discloses a method for synthesizing an oxidized azo compound through selective oxidation of an aromatic amine, wherein an aromatic amine is used as a raw material, hydrogen peroxide is used as an oxidizing agent, a titanium-silicon molecular sieve or a metal modified titanium-silicon molecular sieve is used as a catalyst, and the aromatic amine is subjected to selective catalytic oxidation to prepare the corresponding oxidized azobenzene compound. According to the present invention, the method has advantages of environmental protection, good selectivity, high product yield, easyseparation and recycling of the catalyst, simple instrument required by the reaction, and easy operation.

Highly selective reduction of nitrobenzenes to azoxybenzenes with a copper catalyst

A convenient protocol for highly selective delivery of azoxybenzenes from reduction of nitrobenzenes was developed by utilizing a copper catalyst. A variety of functional groups and substitution were well tolerated.

Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzene

Herein we report an effective and simple preparation method of substituted azoxybenzenes by reductive dimerization of nitrosobenzenes. This procedure requires no additional catalyst/reagent and can be applied to substrates with a wide range of substitution patterns.

Silica encapsulated magnetic nanoparticles-supported Zn(II) nanocatalyst: A versatile integration of excellent reactivity and selectivity for the synthesis of azoxyarenes, combined with facile catalyst recovery and recyclability

A novel and highly efficient zinc based nanocatalyst has been synthesized by covalent grafting of 2-acetylpyridine on amine functionalized silica@magnetite nanoparticles, followed by metallation with zinc acetate. The resulting nano-composite was found to be highly efficient for oxidation of various aromatic amines to give azoxyarenes. The prepared nanocatalyst was characterized by Electron microscopy techniques (SEM and TEM with EDS), X-ray diffraction (XRD), vibrational sampling magnetometer (VSM), Fourier transform infrared spectroscopy (FT-IR) and atomic absorption spectroscopy (AAS) techniques. High turnover number (TON), mild reaction conditions and high selectivity for azoxyarenes with sustained catalytic activity makes present protocol worthy and highly compliant as compared to the other non-magnetic heterogeneous catalytic system. The acquisition of this nanocatalyst is also exemplified by employing the catalyst in leaching and reusability test and the results from the tests showing negligible zinc leaching and recycling was achieved multiple times just by sequestering using an external magnet.

Switchable selectivity during oxidation of anilines in a ball mill

A solvent-free method for the direct oxidation of anilines to the corresponding azo and azoxy homocoupling products by using a planetary ball mill was developed. Various oxidants and grinding auxiliaries were tested and a variety of substituted anilines were investigated. It was possible to form chemoselectively either azo, azoxy, or the nitro compounds from reaction of aromatic anilines. The selectivity of the solvent-free reaction is switchable by applying a combination of oxidant and grinding auxiliary. Furthermore, a comparison with other methods of energy input (microwave, classical heating, and ultrasound) highlighted the advantages of the ball mill approach and its high energy efficiency. Grinding reactions: Highly efficient oxidative homocoupling of aromatic amines was performed under solvent-free conditions in a planetary ball mill (see scheme). The choice of solid oxidants and grinding auxiliaries allowed selective generation of the oxidized products. Other methods of energy input are compared with respect to reaction time and energy consumption.

High-intensity ultrasound and microwave, alone or combined, promote Pd/C-catalyzed aryl-aryl couplings

Pd-catalyzed homo- and cross-couplings of boronic acids and aryl halides were successfully carried out both in aqueous media under high-intensity ultrasound (US) and in DME under microwave (MW). Heterogeneous catalysis with Pd/C was employed, avoiding phosphine ligands and phase-transfer catalysts. In a trial series involving 15 different iodo- and bromoaryls and 7 boronic acids, both energy sources drastically reduced reaction times affording biaryls in acceptable to good yields. With palladium(II) acetate as catalyst, electron-deficient aryl chlorides also reacted, affording a few biaryls in acceptable yields. Ullmann-type zinc-mediated homocoupling of iodo- and bromoaryls in the presence of Pd/C under CO2 atmosphere was achieved in aqueous media under US, though not under MW. Suzuki homo- and cross-couplings were also carried out in a new reactor developed in our laboratory, featuring combined US and MW irradiation, further improving a green synthetic method.

Anti-androgenic activity of substituted azo- and azoxy-benzene derivatives.

Substituted phenylazo and phenylazoxy compounds were systematically prepared and their anti-androgenic activity was measured in terms of (1) the growth-inhibiting effect on an androgen-dependent cell line, SC-3, and (2) the binding affinity to nuclear androgen receptor. Generally, azo/azoxy compounds showed cell toxicity, and the growth-inhibiting effects on SC-3 cells correlated with the toxicity. However, some compounds, including 4,4'-dinitroazobenzene (25), 4,4'-dimethoxyazobenzene (33), and 2,2'-dichloroazoxybenzene (47), possessed potent anti-androgenic activity without apparent cell toxicity.

Reactions of 2-acylthiazolium salts with N-arylhydroxylamines

2-Acylthiazolium salts, easily obtained by alkylation of the corresponding 2-acylthiazoles with methyl triflate, react with N- arylhydroxylamines to furnish the O-acyl derivatives of relevance in the induction of cancer by aromatic mines.