21650-51-1

Basic information

• Product Name: (E)-4,4'-Dichloroazobenzene
• Synonyms: (E)-4,4'-Dichloroazobenzene;XHQLXCFUPJSGOE-FOCLMDBBSA-N
• CAS NO: 21650-51-1
• Molecular Formula: C₁₂H₈Cl₂N₂
• Molecular Weight: 251.11
• Mol File: 21650-51-1.mol
• Article Data: 54

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-4,4'-Dichloroazobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4,4'-Dichloroazobenzene(21650-51-1)
• EPA Substance Registry System: (E)-4,4'-Dichloroazobenzene(21650-51-1)

Safety Data

• Hazardous Substances Data: 21650-51-1(Hazardous Substances Data)

Usage

Description

(E)-4,4'-Dichloroazobenzene, also known as trans-4,4'-dichloroazobenzene, is an organic compound characterized by its chemical formula C12H8Cl2N2. It presents as a yellow crystalline solid and is recognized for its applications in various industries due to its unique properties.

Uses

Used in Textile Industry:
(E)-4,4'-Dichloroazobenzene is used as a dye in the textile industry for coloring fabrics. Its vibrant yellow hue and ability to adhere to fibers make it a valuable component in the production of textiles.
Used in Plastics Industry:
In the plastics industry, (E)-4,4'-Dichloroazobenzene is utilized as a dye to impart color to various plastic products. Its compatibility with plastic materials and stability during processing contribute to its widespread use in this sector.
Used in Paints and Coatings Industry:
(E)-4,4'-Dichloroazobenzene is also employed as a dye in the manufacturing of paints and coatings. Its colorfastness and resistance to fading make it a preferred choice for enhancing the visual appeal and durability of painted surfaces.
Used as a Precursor in Synthesis:
(E)-4,4'-Dichloroazobenzene serves as a precursor in the synthesis of other azo compounds. Its chemical structure allows for further reactions and modifications, leading to the creation of a diverse range of azo-based products.
Used as a Reagent in Organic Chemistry:
(E)-4,4'-Dichloroazobenzene is also used as a reagent in organic chemical reactions, where it can participate in various processes, such as coupling or substitution reactions, to produce desired products.
Safety and Environmental Considerations:
It is crucial to handle (E)-4,4'-Dichloroazobenzene with care due to its toxicity. It can cause irritation to the eyes, skin, and respiratory system. Additionally, it is considered a potential environmental hazard, and proper disposal measures should be taken to prevent contamination of water and soil.

Upstream product

• 106-47-8 4-chloro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 614-26-6 4,4'-bis(chloro)azoxybenzene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 624-31-7 4-tolyl iodide 
• 696-62-8 para-iodoanisole 
• 603-71-4 nitromesitylene 
• 156741-60-5 17-Nitro-tricyclo[11.3.1.1^5,9]octadeca-1⁽¹⁶⁾,5,7,9⁽¹⁸⁾,13⁽¹⁷⁾,14-hexaene 
• 156741-59-2 6-Nitro-tricyclo[11.3.1.1^5,9]octadeca-1⁽¹⁶⁾,5,7,9⁽¹⁸⁾,13⁽¹⁷⁾,14-hexaene 
• 3296-05-7 1-azido-4-chlorobenzene 
• 30926-04-6 cis-4,4'-dichloroazobenzene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 108-88-3 toluene 
• 614-26-6 (Z)-1,2-bis(4-chlorophenyl)diazene 1-oxide 

Downstream Products

• 52598-02-4 2,3-diphenyl-5-chloro-1H-indole 
• 953-14-0 N,N'-bis(4-chlorophenyl)hydrazine 
• 106-47-8 4-chloro-aniline 
• 165663-10-5 1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione 
• 914478-93-6 1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (4-methoxyphenyl)amide 

Relevant articles and documents

Oxidative dehydrogenation of hydrazines and diarylamines using a polyoxomolybdate-based iron catalyst

We report an efficient method for the oxidative dehydrogenation of hydrazines and diarylamines in aqueous ethanol using Anderson-type polyoxomolybdate-based iron(iii) as a catalyst and hydrogen peroxide as an oxidant. A series of azo compounds and tetraarylhydrazines were obtained in moderate to excellent yields. The reaction conditions and substrate scopes are complementary or superior to those of more established protocols. In addition, the catalyst shows good stability and reusability in water. The preliminary mechanistic studies suggest that a radical process is involved in the reaction.

Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst

Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C4H9)4]2[Mo6O19] (1), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.

Trichloroisocyanuric Acid Mediated Oxidative Dehydrogenation of Hydrazines: A Practical Chemical Oxidation to Access Azo Compounds

A highly efficient, metal-free, chemical oxidation of hydrazines has been implemented using environmentally friendly TCCA as oxidant. This benign protocol provides straightforward access to a wide range of azo compounds in THF in excellent yield. Altogether, 35 azo compounds were obtained in this way and scale-up preparations were performed. Additionally, a plausible mechanism was also proposed. Step-economical process, mild reaction conditions, operational simplicity, high reaction efficiency, and easy scale-up highlight the practicality of this methodology.