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

General Description

4,4'-Dihydroxyazoxybenzene, also known as DOAB, is a chemical compound with the molecular formula C12H10N2O4. It is a red or orange solid that is insoluble in water but soluble in organic solvents. DOAB is commonly used as a radical initiator in polymerization reactions, especially for the production of acrylate and styrene-based polymers. It is also used as a dye intermediate and as a coloring agent in the plastics and rubber industries. DOAB has been shown to have moderate acute toxicity in animal studies, and it is classified as a hazardous substance by various regulatory agencies. Exposure to DOAB may cause irritation to the skin, eyes, and respiratory system, and it is important to handle and store this chemical with proper precautions.

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

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

Downstream Products

• 79030-44-7 4,4'-diacetoxyazoxybenzene 
• 86412-10-4 4,4'-bis-(<1,1-(2)H2>heptyloxy)azoxybenzene 
• 86412-13-7 4,4'-bis-(<2,2-(2)H2>octyloxy)azoxybenzene 
• 86412-09-1 4,4'-bis-(<1,1-(2)H2>octyloxy)azoxybenzene 
• 86412-23-9 4,4'-bis-(<4,4-(2)H2>octyloxy)azoxybenzene 
• 89037-70-7 4,4'-bis-(<8,8,8-(2)H3>octyloxy)azoxybenzene 
• 86468-73-7 4,4'-bis-(<2,2-(2)H2>heptyloxy)azoxybenzene 
• 86412-24-0 4,4'-bis-(<4,4-(2)H2>heptyloxy)azoxybenzene 
• 86412-25-1 4,4'-bis-(<5,5-(2)H2>heptyloxy)azoxybenzene 
• 86412-19-3 4,4'-bis-(<3,3-(2)H2>hepyloxy)azoxybenzene 
• 86412-26-2 4,4'-bis-(<6,6-(2)H2>heptyloxy)azoxybenzene 
• 86412-27-3 4,4'-bis-(<7,7,7-(2)H3>heptyloxy)azoxybenzene 
• 86412-18-2 4,4'-bis-(<3,3-(2)H2>n-octyloxy)azoxybenzene 

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 and characterization of azoxy based mesogenic diols

Azoxy based rigid mesogenic diols have been synthesized using two steps. Phenol/cresol is used as starting material. Synthesized diols are characterized by IR, 1H and 13C NMR, and mass spectroscopic methods. Thermal properties have been determined by thermo gravimetric analysis method and crystallinity patterns have been obtained by wide angle X-ray diffractogram. Substituted phenol (methyl) is used to study the effect of substitution on physical and thermal properties of rigid azoxy mesogenic diol. The detailed characterization of azoxy based rigid diols is reported in this communication, which is highly useful for fundamental and applied research, particularly in liquid crystals and liquid crystalline polymers. The experimental results reveal that phenol based rigid mesogenic diols have high thermal stability and degree of crystallinity than methyl substituted rigid mesogenic diols.

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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.