2918-83-4

Basic information

• Product Name: 4'-hydroxyazobenzene-4-sulphonic acid
• Synonyms: 4'-hydroxyazobenzene-4-sulphonic acid;4-(4-Hydroxyphenylazo)benzenesulfonic acid;4-[(4-Sulfophenyl)diazenyl]phenol;4-Hydroxy-4'-sulfoazobenzene
• CAS NO: 2918-83-4
• Molecular Formula: C₁₂H₁₀N₂O₄S
• Molecular Weight: 278.2838
• EINECS: 220-856-0
• Mol File: 2918-83-4.mol

Chemical Properties

• Melting Point: 270-275 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.44g/cm³
• PKA: -1.03±0.50(Predicted)
• CAS DataBase Reference: 4'-hydroxyazobenzene-4-sulphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-hydroxyazobenzene-4-sulphonic acid(2918-83-4)
• EPA Substance Registry System: 4'-hydroxyazobenzene-4-sulphonic acid(2918-83-4)

Safety Data

• Hazardous Substances Data: 2918-83-4(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
4'-hydroxyazobenzene-4-sulphonic acid is used as a dyeing agent for fabrics, providing a deep red-orange color to the material. Its ability to bind with fibers makes it a popular choice for coloration in this industry.
Used in Paper Industry:
In the paper industry, 4'-hydroxyazobenzene-4-sulphonic acid is used as a coloring agent for paper products. Its colorfastness and ability to adhere to paper fibers contribute to its widespread use in this sector.
Used in Leather Industry:
4'-hydroxyazobenzene-4-sulphonic acid is utilized as a dye for leather, imparting a rich red-orange hue to the material. Its compatibility with leather and ability to provide a long-lasting color make it a preferred choice in this industry.
Used as a pH Indicator in Laboratory Experiments:
4'-hydroxyazobenzene-4-sulphonic acid is employed as a pH indicator due to its color-changing properties in different pH environments. This characteristic allows researchers to monitor and measure pH levels in various experimental setups.
However, there is growing concern about the environmental and health impacts of azo dyes, including 4'-hydroxyazobenzene-4-sulphonic acid. They have been found to release toxic aromatic amines when they degrade, leading to regulations on their use and disposal in many countries. This has prompted the search for safer and more eco-friendly alternatives in various applications.

Upstream product

• 305-80-6 4-diazobenzenesulfonic acid 
• 108-95-2 phenol 
• 7664-93-9 sulfuric acid 
• 1689-82-3 4-hydroxyazobenzene 
• 2154-66-7 4-sulfobenzenediazonium 
• 99-96-7 4-hydroxy-benzoic acid 
• 7732-18-5 water 
• 65036-56-8 4-(4-sulfo-phenylazo)-benzenediazonium-betaine 
• 6118-33-8 p-sulfobenzenediazonium chloride 
• 69-72-7 salicylic acid 
• 121-57-3 4-aminobenzene sulfonic acid 
• 2484-88-0 4-phenylazo-benzenesulfonic acid 
• 20972-43-4 trans-azoxybenzene 
• 104-23-4 4'-aminoazobenzene-4-sulfonic acid 

Downstream Products

• 10521-17-2 4-(4-methoxy-phenylazo)-benzenesulfonic acid 
• 2835-04-3 5-amino-2-hydroxybenzenesulfonic acid 
• 67329-17-3 2-nitro-4-(4'-sulfophenylazo)-phenol 
• 2050-16-0 4,4'-dihydroxyazobenzene 
• 98-67-9 p-hydoroxybenzenesulfonic acid 
• 118-79-6 2,4,6-tribromophenol 
• 123-30-8 4-amino-phenol 
• 121-57-3 4-aminobenzene sulfonic acid 
• 305-80-6 4-diazobenzenesulfonic acid 
• 118-75-2 chloranil 

Relevant articles and documents

Manipulating assembly of cationic dipeptides using sulfonic azobenzenes

Three sulfonic azobenzenes with tiny differences in the terminal were used to manipulate the assembly of cationic dipeptides (CDP); assemblies with diverse morphologies including urchin-like, flower-like and plate-like structures were formed.

Photo-induced reversible structural transition of cationic diphenylalanine peptide self-assembly

The photo-induced self-assembly of a cationic diphenylalanine peptide (CDP) is investigated using a photoswitchable sulfonic azobenzene as the manipulating unit. A reversible structural transition between a branched structure and a vesicle-like structure is observed by alternating between UV and visible light irradiation.

Graphene quantum dot grafting azo derivative composite material, and preparation method and application of same

The invention discloses a graphene quantum dot grafting azo derivative composite material, and a preparation method and an application of same. The preparation method comprises the steps of: 1) dispersing graphene quantum dots (GQDs) in thionyl chloride and N,N-dimethylformamide (DMF) and performing a reflux reaction to obtain an acylchloridized graphene quantum dot material (GQDs-COCl); 2) performing a reaction to sulfanilic acid azo-phenol (SUL-Ph) with the GQDs-COCl in tetrahydrofuran to produce the graphene quantum dot grafting azo derivative composite material. The graphene quantum dot grafting azo derivative composite material has strong recognizing capability, high selectivity and good stability on metal ions in molecular fluorescence, so that the material may be applied to the fields such as biomedicines, sensors, optical and electronic devices, solar cells, electronic equipment, optical fuels, composite particle systems, etc.

An environmentally friendly, photocontrollable and highly recyclable catalyst for use in a one-pot three-component Mannich reaction

An environmentally friendly, photocontrollable and highly recyclable catalyst (ZrOPPAZOSO3H) has been synthesized by the immobilization of 4-[4-(6-phosphonic acid-hexanoxyl)phenylazo]benzenesulfonic acid onto zirconium phosphonate. This catalyst was characterized by Fourier transform infrared, scanning electron microscopy, X-ray powder diffraction, nitrogen adsorption-desorption and UV-vis analyses. The catalytic activity of ZrOPPAZOSO3H was investigated towards the one-pot three-component Mannich-type reaction of benzaldehyde, aniline and cyclohexanone in water at room temperature, and gave excellent yields. Interestingly, the catalytic activity could be regulated by photoirradiation. Furthermore, upon completion of the reaction, the product could be readily separated by extraction, and the water phase reused in the next run. Lastly, the catalyst could be readily recovered by centrifugation and reused up to six times without any discernible impact on its activity.

A small molecule binding to the coactivator CREB-binding protein blocks apoptosis in cardiomyocytes

As a master transcription factor in cellular responses to external stress, tumor suppressor p53 is tightly regulated. Excessive p53 activity during myocardial ischemia causes irreversible cellular injury and cardiomyocyte death. p53 activation is dependent on lysine acetylation by the lysine acetyltransferase and transcriptional coactivator CREB-binding protein (CBP) and on acetylation-directed CBP recruitment for p53 target gene expression. Here, we report a small molecule ischemin, developed with a structure-guided approach to inhibit the acetyl-lysine binding activity of the bromodomain of CBP. We show that ischemin alters post-translational modifications on p53 and histones, inhibits p53 interaction with CBP and transcriptional activity in cells, and prevents apoptosis in ischemic cardiomyocytes. Our study suggests small molecule modulation of acetylation-mediated interactions in gene transcription as a new approach to therapeutic interventions of human disorders such as myocardial ischemia.

Optimization of the azobenzene scaffold for reductive cleavage by dithionite; development of an azobenzene cleavable linker for proteomic applications

In this paper we conducted an extensive reactivity study to determine the key structural features that favour the dithionite-triggered reductive cleavage of the azo-arene group. Our stepwise investigation allowed identification of a highly reactive azo-arene structure 25 bearing a carboxylic acid, at the ortho position of the electron-poor arene and an ortho-Oalkyl-resorcinol as the electron-rich arene. Based on this 2(2′-alkoxy-4′-hydroxyphenylazo) benzoic acid (HAZA) scaffold, the orthogonally protected difunctional azo-arene cleavable linker 26 was designed and synthesized. Selective linker deprotection and derivatization was performed by introducing an alkyne reactive group and a biotin affinity tag. This optimized azo-arene cleavable linker led to a total cleavage in less than 10 s with only 1 mM dithionite. Similar results were obtained in biological media.

ELECTROPHILIC CATALYSIS BY CYCLODEXTRINS

The catalysis of an aromatic electrophilic substitution reaction by cyclodextrins is reported.The catalysis can be explained on the basis of the electron rich character of the interior of the cyclodextrin cavity.Kinetic analysis of this reaction in the presence of cyclodextrins indicate binding and catalysis.