15426-16-1

Basic information

• Product Name: 2,2'-dibromoazobenzene
• Synonyms: 2,2'-dibromoazobenzene;Bis(2-bromophenyl)diazene
• CAS NO: 15426-16-1
• Molecular Formula: C₁₂H₈Br₂N₂
• Molecular Weight: 340.01
• Mol File: 15426-16-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 131-132 °C(Solv: ethanol (64-17-5))
• Boiling Point: 413.1°C at 760 mmHg
• Flash Point: 203.6°C
• Appearance: /
• Density: 1.67g/cm³
• Vapor Pressure: 1.18E-06mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: 2,2'-dibromoazobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-dibromoazobenzene(15426-16-1)
• EPA Substance Registry System: 2,2'-dibromoazobenzene(15426-16-1)

Safety Data

• Hazardous Substances Data: 15426-16-1(Hazardous Substances Data)

Usage

Structure

A benzene ring with two bromine atoms and an azo group (-N=N-)

Classification

Organic compound

Usage

Building block in the synthesis of organic compounds, precursor in the production of dyes, pigments, and polymers, reagent and catalyst in organic synthesis

Physical properties

Red or orange color

Hazards

Potentially harmful if ingested, inhaled, or absorbed through the skin

InChI:InChI=1/C12H8Br2N2/c13-9-5-1-3-7-11(9)15-16-12-8-4-2-6-10(12)14/h1-8H/b16-15+

Upstream product

• 17333-81-2 o-bromobenzenediazonium 
• 577-19-5 2-nitrophenyl bromide 
• 19718-35-5 2,2’-dibromohydrazobenzene 
• 615-36-1 2-bromoaniline 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 1227476-15-4 Azobenzene 
• 302-01-2 hydrazine 
• 17082-12-1 trans-azobenzene 

Downstream Products

• 19718-35-5 2,2’-dibromohydrazobenzene 
• 615-36-1 2-bromoaniline 
• 1647097-08-2 (E)-1-(2-bromo-6-nitrophenyl)-2-(2-bromophenyl)diazene 
• 133871-01-9 2',2'''-(1,2-Hydrazinediyl)bis<(1,1'-biphenyl)-2-amine> 
• 133871-00-8 2',2'''-Azobis<(1,1'-biphenyl)-2-amine> 
• 1454-80-4 1,1'-biphenyl-2,2'-diamine 
• 230-17-1 benzo[c]cinnoline 

Relevant articles and documents

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Convergent Paired Electrochemical Synthesis of Azoxy and Azo Compounds: An Insight into the Reaction Mechanism

A convergent paired electrochemical method was developed for the synthesis of azoxy and azo compounds starting from the corresponding nitroarenes. We propose a unique mechanism for electrosynthesis of azoxy and azo compounds. We find that both anodic and cathodic reactions are responsible for the synthesis of these compounds. The synthesis of azoxy and azo derivatives have been successfully performed in an undivided cell, using carbon rod electrodes, by constant current electrolysis at room temperature.

Conversion of anilines into azobenzenes in acetic acid with perborate and Mo(VI): correlation of reactivities

Azobenzenes are extensively used to dye textiles and leather and by tuning the substituent in the ring, vivid colours are obtained. Here, we report preparation of a large number of azobenzenes in good yield from commercially available anilines using sodium perborate (SPB) and catalytic amount of Na2MoO4 under mild conditions. Glacial acetic acid is the solvent of choice and the aniline to azobenzene conversion is zero, first and first orders with respect to SPB, Na2MoO4 and aniline, respectively. Based on the kinetic orders, UV–visible spectra and cyclic voltammograms, the conversion mechanism has been suggested. The reaction rates of about 50 anilines at 20–50?°C and their energy and entropy of activation conform to the isokinetic or Exner relationship and compensation effect, respectively. However, the reaction rates, deduced by the so far adopted method, fail to comply with the Hammett correlation. The specific reaction rates of molecular anilines, obtained through a modified calculation, conform to the Hammett relationship. Thus, this work presents a convenient inexpensive non-hazardous method of preparation of a larger number of azobenzenes, and shows the requirement of modification in obtaining the true reaction rates of anilines in acetic acid and the validity of Hammett relationship in the conversion process, indicating operation of a common mechanism.