1545-83-1

Basic information

• Product Name: Azobenzene, 4-fluoro-
• Synonyms: Azobenzene, 4-fluoro-;4-Fluoroazobenzene;(4-fluorophenyl)-phenyldiazene
• CAS NO: 1545-83-1
• Molecular Formula: C₁₂H₉FN₂
• Molecular Weight: 200.21
• Mol File: 1545-83-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 304.1°Cat760mmHg
• Flash Point: 137.7°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 0.00161mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: Azobenzene, 4-fluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: Azobenzene, 4-fluoro-(1545-83-1)
• EPA Substance Registry System: Azobenzene, 4-fluoro-(1545-83-1)

Safety Data

• Hazardous Substances Data: 1545-83-1(Hazardous Substances Data)

Usage

General Description

Azobenzene, 4-fluoro- is a chemical compound with the molecular formula C12H8FN3. It is a member of the azobenzene family, featuring a central azo group (-N=N-) that links two phenyl rings. The addition of a fluorine atom to the benzene ring gives this compound specific properties and reactivity. It is commonly used as a building block in the synthesis of various organic compounds, including dyes and pharmaceuticals. Azobenzene, 4-fluoro- is also being studied for its potential applications in molecular switches and optoelectronic devices due to its ability to undergo reversible photoisomerization. Additionally, it is important to handle and store this chemical with caution, as it may pose health and environmental hazards.

InChI:InChI=1/C12H9FN2/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 
• 371-40-4 4-fluoroaniline 
• 62-53-3 aniline 
• 51789-21-0 1-(4-fluorophenyl)-2-phenylhydrazine 
• 332-07-0 bis-(4-fluorophenyl)diazene 

Downstream Products

• 62-53-3 aniline 
• 371-40-4 4-fluoroaniline 
• 332-07-0 bis-(4-fluorophenyl)diazene 
• 135066-29-4 2-(4-fluorophenyl)-1H-indazol-3(2H)-one 
• 51789-21-0 1-(4-fluorophenyl)-2-phenylhydrazine 
• 332-00-3 (E)-1-(4-fluorophenyl)-2-phenyldiazene 
• 68110-85-0 Mn(N₂C₁₂H₈F)(CO)4 
• 68110-86-1 Mn(N₂C₁₂H₈F)(CO)4 
• 68110-87-2 Pd(N₂C₁₂H₈F)(C₅H₅) 
• 1545-85-3 4-hydroxyphenylazo-4'-fluorobenzene 

Relevant articles and documents

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

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.

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.