323-87-5

Basic information

• Product Name: 4-hydroxy[1,1'-biphenyl]-3-carboxylic acid
• Synonyms: 4-Hydroxy-3-biphenylcarboxylic acid;2-Hydroxy-5-phenylbenzoic acid;5-Phenyl-2-hydroxybenzoic acid
• CAS NO: 323-87-5
• Molecular Formula: C₁₃H₁₀O₃
• Molecular Weight: 214.22
• EINECS: 206-301-5
• Mol File: 323-87-5.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 4-hydroxy[1,1'-biphenyl]-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy[1,1'-biphenyl]-3-carboxylic acid(323-87-5)
• EPA Substance Registry System: 4-hydroxy[1,1'-biphenyl]-3-carboxylic acid(323-87-5)

Safety Data

• Hazardous Substances Data: 323-87-5(Hazardous Substances Data)

Usage

General Description

4-hydroxy[1,1'-biphenyl]-3-carboxylic acid, also known as 3-hydroxy-4-carboxybiphenyl, is a chemical compound with the molecular formula C13H10O3. It is a derivative of biphenyl, consisting of a hydroxyl group and a carboxylic acid group attached to the benzene rings. 4-hydroxy[1,1'-biphenyl]-3-carboxylic acid has been studied for its potential pharmaceutical and industrial applications, including its use as a starting material for the synthesis of biologically active compounds and as a building block for the production of dyes and pigments. Additionally, its antioxidant properties have garnered interest in the field of food science and nutrition. Despite its potential applications, further research is needed to fully understand and exploit the properties and potential uses of 4-hydroxy[1,1'-biphenyl]-3-carboxylic acid.

Upstream product

• 92-69-3 4-Phenylphenol 
• 15719-64-9 methylammonium carbonate 
• 89-55-4 5-bromosalicyclic acid 
• 100-58-3 phenylmagnesium bromide 
• 31044-59-4 diethyl phenylboronate 
• 143-66-8 sodium tetraphenyl borate 
• 17504-10-8 methyl 4-methoxy-[1,1'-biphenyl]-3-carboxylate 
• 4068-76-2 5-bromo-2-hydroxy-benzoic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 716-76-7 3-phenylbenzoic acid 
• 130736-30-0 6-bromo-2-morpholino-4H-1,3-benzoxazin-4-one 
• 23611-66-7 6-bromo-2-thioxo-2,3-dihydro-4H-1,3-benzoxazin-4-one 
• 17504-14-2 ethyl 4-hydroxy-[1,1'-biphenyl]-3-carboxylate 
• 2263-65-2 3-carboxy-4-hydroxybenzenediazonium tetrafluoroborate 

Downstream Products

• 17504-13-1 methyl 4-hydroxy-[1,1’-biphenyl]-3-carboxylate 
• 1855-23-8 5-cyclohexyl-2-hydroxybenzoic acid 
• 4906-68-7 3-bromo-5-phenylsalicylic acid 
• 17784-39-3 4-hydroxy-biphenyl-3-carboxylic acid phenyl ester 
• 67127-10-0 4-hydroxy-biphenyl-3-carboxylic acid 1⁽²⁾H-tetrazol-5-ylamide 
• 92-69-3 4-Phenylphenol 

Relevant articles and documents

Synthesis of the tricyclic core structure of vindoline

An efficient synthesis of the core tricyclic structure (18) of vindoline has been achieved using the strategy, which features an intramolecular 1,3-dipolar cycloaddition of the azido dienone (12) to give aziridine (13) with complete region- and stereocontrol.

Bi-aryl analogues of salicylic acids: Design, synthesis and sar study to ameliorate endoplasmic reticulum stress

Introduction: Endoplasmic reticulum (ER) stress condition is characterized as the accu-mulation of misfolded or unfolded proteins in lumen of ER. This condition has been implicated in various diseases and pathologies including β-cell apoptosis, Alzheimer’s disease and atherosclerosis. We have reported that hydroxynaphthoic acids (HNA), naphtha-lene analogues of salicylic acid (SA), reduced ER stress. In this study, we explored structural modification to bi-aryl analogues of SA. Methods: Palladium-catalyzed cross-coupling was applied to synthesize bi-aryl analogues of SA. Anti-ER stress activity was monitored by using our cell-based assay system where ER stress is induced by tunicamycin. To monitor ER stress markers, ER stress was induced physiologically relevant palmitate system. Results: Many analogues decreased ER stress signal induced by tunicamycin. Compounds creating dihedral angle between Ar group and SA moiety generally increased the activity but gave some cytotoxicity to indicate the crucial role of flat conformation of aromatic region. The best compound (16e) showed up to almost 6-fold and 90-fold better activity than 3-HNA and tauro-ursodeoxycholic acid, positive controls, respectively. ER stress markers such as p-PERK and p-JNK were accordingly decreased in Western blotting upon treatment of 16e under palmitate-induced condition. Conclusion: Anti-ER stress activity and toxicity profile of bi-aryl analogues of SA could provide a novel platform for potential therapy for protein misfolding diseases.

Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water

N-(3-Chloro-2-quinoxalinyl)-N′-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N′-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh3)4 and Pd2(dba)3/PPh3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh3)Cl2] (I) and [Pd(HL2)(PPh3)Cl2] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K2CO3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K2CO3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.