4418-84-2

Usage

Uses

Used in Textile Industry:
(4-Bromo-phenyl)-phenyl-diazene is used as an intermediate for the production of various azo dyes, which are essential colorants in the textile industry. These dyes are known for their vibrant colors and ability to produce a wide range of hues, making them highly desirable for use in fabrics and other textile products.
Used in Food Industry:
In the food industry, (4-Bromo-phenyl)-phenyl-diazene is utilized as an intermediate in the synthesis of azo dyes that are used as additives to impart color to various food products. These dyes enhance the visual appeal of the products, making them more attractive to consumers.
Used in Pharmaceutical Research:
(4-Bromo-phenyl)-phenyl-diazene is employed in pharmaceutical research as a reagent for the synthesis of various pharmaceutical compounds. Its ability to undergo diazotization and coupling reactions with other aromatic compounds makes it a valuable tool in the development of new drugs and therapeutic agents.
Used in Organic Reactions:
As a diazonium salt, (4-Bromo-phenyl)-phenyl-diazene is used as a reagent in various organic reactions, including the synthesis of complex organic molecules and the modification of existing compounds. Its versatility in undergoing different types of reactions makes it a valuable asset in the field of organic chemistry.

InChI:InChI=1/C12H9BrN2/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 
• 106-40-1 4-bromo-aniline 
• 64-17-5 ethanol 
• 7466-30-0 1-(4-bromophenyl)-1,2-diphenylhydrazine 
• 62-53-3 aniline 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 98-95-3 nitrobenzene 
• 1823-91-2 1-phenylethyl cyanide 
• 7664-93-9 sulfuric acid 
• 16109-68-5 4-bromo-1-phenyl-NNO-azoxybenzene 
• 60-29-7 diethyl ether 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 1227476-15-4 Azobenzene 

Downstream Products

• 59360-38-2 2-(4-bromo-phenylazo)-phenol 
• 59360-37-1 5-bromo-2-phenylazo-phenol 
• 3035-94-7 4-((p-bromophenyl)diazenyl)phenol 
• 16109-68-5 4-bromo-1-phenyl-NNO-azoxybenzene 
• 16054-48-1 N-[(4-bromophenyl)imino]benzenimine oxide 
• 97870-64-9 1-(4-bromophenyl)-2-ethyl-1H-benzo[d]imidazole 
• 21650-64-6 (4-bromo-phenyl)-(4-nitro-phenyl)-diazene 
• 40932-75-0 N¹-(4-bromophenyl)benzene-1,4-diamine 
• 343952-87-4 5-bromo-N¹-phenylbenzene-1,2-diamine 
• 169834-88-2 5-bromo-biphenyl-2,4'-diyldiamine 
• 92-87-5 p,p'-diaminobiphenyl 
• 1070337-91-5 (E)-1-Phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)diazene 

Relevant academic research and scientific papers

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.

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.

Substitution of a nitro group by diazonium salts in σH-Adducts of carbanions to mono-nitrobenzenes. Formation of substituted azobenzenes and indazoles

σH-Adducts formed at low temperature from nitrobenzene derivatives and carbanions stabilized by cyano, alkoxycarbonyl or sulfonyl groups react with benzenediazonium salts as nucleophiles, forming a new C–N bond preferentially at carbon atom bearing the nitro group. The so-formed intermediates eliminate HNO2 molecule under action of base, yielding substituted azobenzenes. Adducts of secondary carbanions, stabilized by cyano or sulfonyl groups to the ortho positions of nitrobenzenes, cyclize in situ to substituted indazoles. Some ortho σH-adducts of 1-chloroethyl phenyl sulfone carbanion add diazonium cations at meta position to the nitro group. In this case, the subsequent elimination of HCl leads to azo compounds retaining the nitro group in its original position.

TEMPO catalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

A metal-free direct oxidative dehydrogenation approach for the synthesis of azobenzenes from hydrazobenzenes has been developed by using TEMPO as an organocatalyst for the first time. The reaction proceeded in open air under mild reaction conditions. A wide range of hydrazobenzenes readily undergo dehydrogenation to give the corresponding azobenzenes in excellent yields.

Light-Driven Crawling of Molecular Crystals by Phase-Dependent Transient Elastic Lattice Deformation

The light-driven crawling of a molecular crystal that can form three phases, (α, β, and γ) is presented. Laser irradiation of the molecular crystal can generate phase-dependent transient elastic lattice deformation. The resulting elastic lattice deformati

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.

Method for oxidizing and synthesizing azo compounds by taking hydrazine compounds as raw materials

The invention provides a method for synthesizing azo compounds, and the method takes hydrazine compounds as raw materials and trichloroisocyanuric acid as an oxidant to synthesize the azo compounds ina one-pot high-yield and high-efficiency manner in an organic solvent in an air atmosphere at room temperature. According to the method, the trichloroisocyanuric acid, which is low in price, green, nontoxic and highly efficient in oxidation, is used as the oxidant, and the trichloroisocyanuric acid is low in price, green and environment-friendly, stable in performance and high in use safety; thereaction solvent does not need special treatment, no byproduct is generated, the post reaction treatment is simple, the environmental pollution is small, the method is green and environment-friendly,and the method is suitable for industrial production.

Transition Metal-Free Oxidative Coupling of Primary Amines in Polyethylene Glycol at Room Temperature: Synthesis of Imines, Azobenzenes, Benzothiazoles, and Disulfides

A transition metal-free protocol has been developed for the oxidative coupling of primary amines to imines and azobenzenes, thiols to disulfides, and 2-aminothiophenols to benzothiazoles, offering excellent yields. The advantageous features of the present environmentally benign methodology include the usage of biocompatible and green reaction conditions such as, solvent, room temperature reactions and transition metal-free approach. Moreover, it offers a broader substrate scope.

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.

Rh(III)-catalyzed [4?+?1]-annulation of azobenzenes with α- carbonyl sulfoxonium ylides toward 3-acyl-(2H)-indazoles

A Rh(III)-catalyzed [4 + 1]-annulation of azobenzenes with α- carbonyl sulfoxonium ylides was developed to access 2H-indazoles in moderate to excellent yields with good functional group compatibilities. It proceeded with the sequential insertion of the Rh(III) carbene to the C?H bond and cyclization steps, where sulfoxonium ylides served as efficient and stable carbene precursor.