4418-84-2

Basic information

• Product Name: (4-Bromo-phenyl)-phenyl-diazene
• Synonyms: (4-Bromo-phenyl)-phenyl-diazene;p-Bromoazobenzene
• CAS NO: 4418-84-2
• Molecular Formula: C₁₂H₉BrN₂
• Molecular Weight: 261.11726
• Mol File: 4418-84-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 89 °C
• Boiling Point: 351.8°Cat760mmHg
• Flash Point: 166.5°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 8.15E-05mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: (4-Bromo-phenyl)-phenyl-diazene(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Bromo-phenyl)-phenyl-diazene(4418-84-2)
• EPA Substance Registry System: (4-Bromo-phenyl)-phenyl-diazene(4418-84-2)

Safety Data

• Hazardous Substances Data: 4418-84-2(Hazardous Substances Data)

Usage

Description

(4-Bromo-phenyl)-phenyl-diazene, also known as bromobenzene diazonium, is a chemical compound with the molecular formula C12H9BrN2. It belongs to the class of diazonium salts, which are widely utilized in various fields due to their versatile chemical properties. This particular compound is characterized by its ability to undergo diazotization and subsequent coupling with other aromatic compounds, making it a valuable intermediate in the synthesis of different products.

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

• 60-29-7 diethyl ether 
• 16109-68-5 4-bromo-1-phenyl-NNO-azoxybenzene 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 98-95-3 nitrobenzene 
• 1823-91-2 1-phenylethyl cyanide 
• 62-53-3 aniline 
• 106-40-1 4-bromo-aniline 
• 586-96-9 Nitrosobenzene 
• 7664-93-9 sulfuric acid 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 1227476-15-4 Azobenzene 
• 16054-48-1 N-[(4-bromophenyl)imino]benzenimine oxide 
• 103-84-4 Acetanilid 

Downstream Products

• 16054-48-1 N-[(4-bromophenyl)imino]benzenimine oxide 
• 1070337-91-5 (E)-1-Phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)diazene 
• 6141-96-4 (E)-1-(4-bromophenyl)-2-phenyldiazene 
• 1382867-58-4 C₁₈H₁₄N₂O₂ 
• 1215-42-5 4,4'-dibromoazoxybenzene 
• 59360-38-2 2-(4-bromo-phenylazo)-phenol 
• 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 

Relevant articles and documents

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.

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.