2497-38-3

Basic information

• Product Name: 4-HYDROXY-AZOBENZENE-4'-CARBOXYLICACID
• Synonyms: 4-HYDROXY-AZOBENZENE-4'-CARBOXYLICACID;4-(4-Hydroxyphenylazo)benzoic acid;4-[(4-Carboxyphenyl)diazenyl]phenol;4-[(4-Hydroxyphenyl)azo]benzoic acid;4-Hydroxy-4'-carboxyazobenzene;4-[(4'-hydroxyphenyl)diazenyl] benzoic acid;4'-Hydroxyazobenzene-4-carboxylic Acid Hydrate;4- benzoic acid
• CAS NO: 2497-38-3
• Molecular Formula: C₁₃H₁₀N₂O₃
• Molecular Weight: 242.2301
• Mol File: 2497-38-3.mol

Chemical Properties

• Melting Point: 266 °C (decomp)(Solv: ethanol (64-17-5))
• Boiling Point: 439.3°Cat760mmHg
• Flash Point: 219.5°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 1.72E-08mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.77±0.10(Predicted)
• CAS DataBase Reference: 4-HYDROXY-AZOBENZENE-4'-CARBOXYLICACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-AZOBENZENE-4'-CARBOXYLICACID(2497-38-3)
• EPA Substance Registry System: 4-HYDROXY-AZOBENZENE-4'-CARBOXYLICACID(2497-38-3)

Safety Data

• Hazardous Substances Data: 2497-38-3(Hazardous Substances Data)

Usage

Uses

Used in Dye and Pigment Industry:
4-HYDROXY-AZOBENZENE-4'-CARBOXYLIC ACID is used as a chemical intermediate for the synthesis of azo dyes, which are widely used in the dye and pigment industry for coloring textiles, plastics, and other materials.
Used in Materials Science:
4-HYDROXY-AZOBENZENE-4'-CARBOXYLIC ACID is used as a precursor for the production of photochromic and thermochromic materials, which change color in response to light or temperature changes, respectively. These materials have potential applications in smart textiles, sensors, and optical devices.
Used in Pharmaceutical Industry:
4-HYDROXY-AZOBENZENE-4'-CARBOXYLIC ACID is used as a photoresponsive compound in drug delivery systems, where its ability to change properties under light exposure can be utilized for controlled release of drugs. This can improve the efficiency and targeting of drug delivery, reducing side effects and increasing therapeutic efficacy.
Used in Biomedical Research:
4-HYDROXY-AZOBENZENE-4'-CARBOXYLIC ACID has potential applications in biomedical imaging, where its photoresponsive properties can be exploited for the development of imaging agents that can be activated or quenched by light. This can enhance the contrast and resolution of imaging techniques, aiding in the diagnosis and monitoring of diseases.

InChI:InChI=1/C13H10N2O3/c16-12-7-5-11(6-8-12)15-14-10-3-1-9(2-4-10)13(17)18/h1-8,14H,(H,17,18)

Upstream product

• 1837-05-4 4-benzenediazonium-carboxylate 
• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 582-69-4 azoxybenzene-4,4'-dicarboxylic acid 
• 1562-93-2 4-(2-phenyldiazen-1-yl)benzoic acid 
• 123-30-8 4-amino-phenol 
• 94-09-7 p-aminoethylbenzoate 
• 108-95-2 phenol 
• 150-13-0 4-amino-benzoic acid 
• 17333-88-9 4-Carboxy-phenyl-diazonium 
• 105595-96-8 4-phenyl-NNO-azoxybenzoic acid 

Downstream Products

• 154825-45-3 p-benzoic acid 
• 1151690-76-4 C₂₅H₂₆BN₃O₄ 
• 3517-20-2 4'-methoxyazobenzene-4-carboxylic acid 
• 79570-20-0 4'-Acetoxy-azobenzol-carbonsaeure-⁽⁴⁾ 

Relevant articles and documents

Direct and Divergent Solid-Phase Synthesis of Azobenzene and Spiropyran Derivatives

Here, we report a solid-phase approach to synthesize azobenzene and spiropyran derivatives. The divergent synthesis process requires no purification steps to obtain the desired product with a 28-55% yield, depending on the specific compound. For the spiropyran compounds, solid-phase resin cleavage is performed under mild conditions to minimize spiropyran ring opening. The solid-phase method enables the synthesis of a library of azobenzene and spiropyran derivatives without the need to develop purification strategies for each derivative.

On the azo dyes derived from benzoic and cinnamic acids used as photosensitizers in dye-sensitized solar cells

In order to get a better insight into the relationship between molecular structure and photovoltaic performance, six monoazo dye molecules containing benzoic and cinnamic acid moieties were synthesized and their photovoltaic properties were studied. Three of them have not been previously used in solar cells. Spectroscopic measurements of the investigated compounds coupled with theoretical calculations were performed. Short-circuit current density, open-circuit voltage, and fill-factor were determined. It was found that a larger amount of short-circuit current density will be generated if the HOMO–LUMO energy gap is lower, determined by the stability of the molecule and the electronic effect of the donor moiety. Among both series of synthesized dye molecules, the highest obtained values of short-circuit current density were achieved with (2-hydroxynaphthalene-1-ylazo)benzoic acid and (2-hydroxynaphthalene-1-ylazo)cinnamic acid, and thus they were regarded as promising candidates for application in dye-sensitized solar cells.

Synthesis of Kojic Ester Derivatives as Potential Antibacterial Agent

The search for lead product with beneficial pharmacological properties has become a great challenge and costly. Extraction and synthetic modification of bioactive compounds from natural resources has gained great attention and is cost effective. In this study, kojic acid was produced from fungal fermentation, using sago waste as substrate, and chemically incorporated with chalcones and azobenzene to form a series of kojic ester derivatives and evaluated for antibacterial activities. Kojic ester bearing halogenated chalcone demonstrated active inhibition against Staphylococcus aureus compared to that of standard ampicillin. The inhibition increased as the electronegativity of halogens decreased, while incorporation of azobenzene derivatives on kojic acid backbone demonstrated fair antibacterial activity against Escherichia coli with minimum inhibitory concentration (MIC) of 190-330 ppm. The presence of C=C and N=N reactive moieties in both chalcone and azo molecules contributed to the potential biological activities of the kojic acid ester.

Synthesis and optical properties of poly[4-methacryloxy-(4′-carboxy)-azobenzene]

In the present work, the homopolymer built from the free radical polymerization of methacrylic monomer incorporating an azobenzene side-group has been synthesized and structurally characterized. The optical properties such as refractive index, extinction

Design and Function of Supramolecular Recognition Systems Based on Guest-Targeting Probe-Modified Cyclodextrin Receptors for ATP

In this study, we have developed a rational design strategy to obtain highly selective supramolecular recognition systems of cyclodextrins (CyDs) on the basis of the lock and key principle. We designed and synthesized dipicolylamine (dpa)-modified -CyD-Cu

The photochemical behavior of polyhydroxy styrene with azofragments containing free methacrylic double bounds

Polymer material which combines advantages of photoaligning azo-compounds with thermal stability of the induced anisotropy provided by free methacryloyl groups was synthesised. FTIR spectroscopy was employed for clarification its photochemical behavior. T

A Carbon Dioxide Bubble-Induced Vortex Triggers Co-Assembly of Nanotubes with Controlled Chirality

It is challenging to prepare co-organized nanotube systems with controlled nanoscale chirality in an aqueous liquid flow field. Such systems are responsive to a bubbled external gas. A liquid vortex induced by bubbling carbon dioxide (CO2) gas was used to stimulate the formation of nanotubes with controlled chirality; two kinds of achiral cationic building blocks were co-assembled in aqueous solution. CO2-triggered nanotube formation occurs by formation of metastable intermediate structures (short helical ribbons and short tubules) and by transition from short tubules to long tubules in response to chirality matching self-assembly. Interestingly, the chirality sign of these assemblies can be selected for by the circulation direction of the CO2 bubble-induced vortex during the co-assembly process.

A reactive azobenzene liquid-crystalline block copolymer as a promising material for practical application of light-driven soft actuators

Cross-linked liquid-crystalline polymers containing azobenzene have been drawing great research interest of scientists due to their significant values in the design of light-driven soft actuators. However, poor processabilities due to the chemical cross-l

Supramolecular functionalized polybenzoxazines from azobenzene carboxylic acid/azobenzene pyridine complexes: Synthesis, surface properties, and specific interactions

In this study we synthesized Azo-COOH BZ, a new benzoxazine derivative containing both azobenzene and carboxylic acid units, through the reaction of 4-(4-hydroxphenylazo)benzoic acid (Azo-COOH, itself prepared through a diazonium reaction of 4-aminobenzoi

Multifunctional polybenzoxazine nanocomposites containing photoresponsive azobenzene units, catalytic carboxylic acid groups, and pyrene units capable of dispersing carbon nanotubes

In this study, we synthesized a new multifunctional benzoxazine monomer Azo-COOH-Py BZ - featuring an azobenzene unit, a carboxylic acid group, and a pyrene moiety - through the reaction of 4-(4-hydroxyphenylazo)benzoic acid (Azo-COOH), paraformaldehyde, and aminopyrene (Py-NH2) in 1,4-dioxane. Fourier transform infrared (FTIR) spectroscopy and 1H and 13C nuclear magnetic resonance spectroscopy confirmed the structure of this new monomer. Using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and FTIR spectroscopy, we monitored the curing behavior of Azo-COOH-Py BZ leading to the formation of poly(Azo-COOH-Py BZ); we found that the carboxylic acid and azobenzene units acted as catalysts for the ring opening reaction of the benzoxazine unit. The pyrene moiety of Azo-COOH-Py BZ enhanced the dispersibility of carbon nanotubes (CNTs) in THF, leading to the formation of highly dispersible Azo-COOH-Py BZ/CNT nanocomposites stabilized through π-π stacking of the pyrene and CNT units, as detected through fluorescence emission spectroscopy. We also used DSC and TGA to examine the curing behavior of Azo-COOH-Py BZ/CNTs to form poly(Azopy-COOH-Py BZ)/CNTs nanocomposites. Interestingly, DSC profiles revealed that the maximum exothermic peak representing the ring opening polymerization of the benzoxazine unit of Azo-COOH-Py BZ shifted to much lower temperature upon increasing the content of single-walled CNTs (SWCNTs) or multiwalled CNTs (MWCNTs), suggesting that the CNTs acted as catalysts for the ring opening reaction of the benzoxazine. In addition, the curing temperatures for the SWCNT composites were lower than those for the MWCNT composites, suggesting that the SWCNTs were dispersed better than the MWCNTs in their composites and that the thermal stability of the SWCNT nanocomposites was higher than that of the MWCNT nanocomposites. The combination of photoresponsive azobenzene units, carboxylic acid groups, and CNTs enhanced the thermal stability and char yields of the polybenzoxazine matrixes, as determined through TGA analyses.