15596-57-3

Basic information

• Product Name: 4,4'-Dihydroxyazoxybenzene
• Synonyms: 4,4'-Dihydroxyazoxybenzene
• CAS NO: 15596-57-3
• Molecular Formula: C₁₂H₁₀N₂O₃
• Molecular Weight: 230.22
• Mol File: 15596-57-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 224 °C (decomp)
• Boiling Point: 464.2°C at 760 mmHg
• Flash Point: 234.5°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 2.05E-09mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: 4,4'-Dihydroxyazoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dihydroxyazoxybenzene(15596-57-3)
• EPA Substance Registry System: 4,4'-Dihydroxyazoxybenzene(15596-57-3)

Safety Data

• Hazardous Substances Data: 15596-57-3(Hazardous Substances Data)

Usage

Description

4,4'-Dihydroxyazoxybenzene, also known as DOAB, is a chemical compound characterized by its molecular formula C12H10N2O4. It is a red or orange solid that exhibits insolubility in water but is soluble in organic solvents. DOAB is recognized for its role as a radical initiator in various chemical processes, particularly in the polymerization of acrylate and styrene-based polymers. Additionally, it serves as a dye intermediate and a coloring agent in the plastics and rubber industries. Despite its utility, DOAB has been identified as a hazardous substance with moderate acute toxicity in animal studies, necessitating careful handling and storage to prevent irritation to the skin, eyes, and respiratory system.

Uses

Used in Polymerization Industry:
4,4'-Dihydroxyazoxybenzene is used as a radical initiator for the polymerization of acrylate and styrene-based polymers, facilitating the formation of these polymers through the initiation of radical reactions.
Used in Dye and Pigment Industry:
4,4'-Dihydroxyazoxybenzene is used as a dye intermediate, contributing to the synthesis of various dyes and pigments.
Used in Plastics and Rubber Industry:
4,4'-Dihydroxyazoxybenzene is used as a coloring agent in the plastics and rubber industries, providing coloration to these materials during their production processes.

InChI:InChI=1/C12H10N2O3/c15-11-5-1-9(2-6-11)13-14(17)10-3-7-12(16)8-4-10/h1-8,16-17H

Upstream product

• 79030-44-7 4,4'-diacetoxyazoxybenzene 
• 108-95-2 phenol 
• 123-30-8 4-amino-phenol 
• 100-02-7 4-nitro-phenol 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 
• 2050-16-0 4,4'-dihydroxyazobenzene 
• 60-29-7 diethyl ether 
• 637-62-7 p-benzoquinone oxime 
• 100-63-0 phenylhydrazine 
• 104-91-6 p-nitrosophenol 
• 110-86-1 pyridine 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 90239-53-5 C₂₄H₃₀N₂O₅ 
• 2050-16-0 (E)-4,4'-dihydroxyazobenzene 

Relevant articles and documents

Synthesis of photo-responsive azobenzene molecules with different hydrophobic chain length for controlling foam stability

To obtain an aqueous foam photo-switch, azobenzene molecules [4-hydroxy-4′-oxoalkyl azobenzene (HCnAzo) n = 4, 8, and 12] were synthesized. The hydrophobic chain length affected both photo-responsive properties and foam stability controllability. trans → cis isomerization of HCnAzo occurred by exposing to UV light for 1 s and the cis → trans process for HC4Azo, HC8Azo and HC12Azo was carried out by visible light irradiation for 12 min, 13 min and 14 min, respectively. The reversible isomerization was repeatable, maintaining high sensitivity. Due to the small steric effect and isomerization barrier, photo-isomerization of HC4Azo was more rapid than HC8Azo and HC12Azo. With the increase of the hydrophobic chain length, the decrease of thermal isomerization barrier resulted in less cis isomer and more trans isomer in photo-stationary state via UV and visible light irradiation, respectively. The combination of visible light and heat can accelerate the cis → trans isomerization speed. trans HC4Azo, HC8Azo and HC12Azo increased foam life from 6.67 min to 10.38, 9.91 and 7.74 min, respectively, resulting from the absorption on the air-water interface and a high affinity. cis HC4Azo, HC8Azo and HC12Azo decreased foam life from 6.67 min to 5.12, 5.49 and 6.02 min, respectively, attributed to the interfacial desorption and increase of surface tension. HC4Azo with sensitive photo-isomerization and effective foam stability controllability was the best choice for an aqueous foam photo-switch.

Synthesis, characterization and biological evaluation of novel diesters of 4,4'-dihydroxy azoxy benzene with long chain carboxylic acids

Synthesis of novel symmetrical azoxy diesters have been prepared by the reaction of 4,4'-dihydroxyazoxy benzene with aliphatic acid halides of varying chain lengths. The synthesized compounds have been characterized by spectral and analytical data. These symmetrical azoxy diesters exhibit good antifungal activity against six fungal strains (Mucor species, Aspergillus niger, Aspergillus flavus, Alternaria solani, Fusarium solani and Aspergillus fumigatus) and antitumor activities while no significant antibacterial activity has been observed. These synthesized compounds are also potent free radical scavengers.

-

The synthesis of aromatic azoxydiethers was realized from 4,4′-dihidroxybenzene with electromagnetic microwaves not only without solvent but also without inorganic absorbent support. This result is atributed to the polar structure of the reagents.