25389-28-0

Basic information

• Product Name: 3-(1,3-BENZOTHIAZOL-2-YL)PHENOL
• Synonyms: 3-(1,3-BENZOTHIAZOL-2-YL)PHENOL;NSC51369;3-Benzothiazol-2-yl-phenol
• CAS NO: 25389-28-0
• Molecular Formula: C₁₃H₉NOS
• Molecular Weight: 227.28166
• Mol File: 25389-28-0.mol
• Article Data: 33

Chemical Properties

• Melting Point: 165 °C
• Boiling Point: 431.2 °C at 760 mmHg
• Flash Point: 214.6 °C
• Appearance: /
• Density: 1.337 g/cm³
• Vapor Pressure: 4.83E-08mmHg at 25°C
• Refractive Index: 1.718
• PKA: 9.15±0.10(Predicted)
• CAS DataBase Reference: 3-(1,3-BENZOTHIAZOL-2-YL)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1,3-BENZOTHIAZOL-2-YL)PHENOL(25389-28-0)
• EPA Substance Registry System: 3-(1,3-BENZOTHIAZOL-2-YL)PHENOL(25389-28-0)

Safety Data

• Hazardous Substances Data: 25389-28-0(Hazardous Substances Data)

Usage

General Description

3-(1,3-benzothiazol-2-yl)phenol is a chemical compound with the molecular formula C13H9NOS. It is a derivative of phenol with a benzothiazole group attached to its aromatic ring. 3-(1,3-BENZOTHIAZOL-2-YL)PHENOL is commonly used as a fluorescent indicator, especially in the field of analytical chemistry. It has also been found to have potential applications in the development of materials with optical and electronic properties, as well as in biological research as a fluorescent probe for the detection and imaging of specific molecules or structures within cells. Additionally, 3-(1,3-benzothiazol-2-yl)phenol has been investigated for its potential pharmacological properties, including anti-cancer and anti-inflammatory effects.

InChI:InChI=1/C13H9NOS/c15-10-5-3-4-9(8-10)13-14-11-6-1-2-7-12(11)16-13/h1-8,15H

Upstream product

• 99-06-9 3-Carboxyphenol 
• 137-07-5 2-amino-benzenethiol 
• 100-83-4 meta-hydroxybenzaldehyde 
• 591-31-1 3-methoxy-benzaldehyde 
• 95-16-9 1,3-Benzothiazole 
• 620-24-6 3-Hydroxybenzyl alcohol 
• 626-02-8 3-Iodophenol 
• 10002-44-5 2-(3'-methoxyphenyl)benzothiazole 
• 103-72-0 phenyl isothiocyanate 
• 2398-37-0 3-methoxyphenyl bromide 
• 873-62-1 m-cyanophenol 

Downstream Products

• 1305316-85-1 O-[3-(1,3-benzothiazol-2-yl)phenyl]diphenylthiophosphinate 
• 1334551-91-5 C₁₇H₁₆BrNOS 
• 1334551-89-1 C₁₆H₁₄BrNOS 

Relevant articles and documents

3-(benzo[d]thiazol-2-YL)phenol and 4-(benzo[d]thiazol-2-YL)phenol: Crystal Structure Determination, DFT Calculations and Visualizing Intermolecular Interactions Using Hirshfeld Surface Analysis

This article describes the synthesis and X-ray crystal structure analysis of 3-(benzo[d]thiazol-2-yl) phenol (I) and 4-(benzo[d]thiazol-2-yl)phenol (II), crystallized in centrosymmetric triclinic and orthorhombic space groups respectively. The packing in

Discovery of new and highly effective quadruple FFA1 and PPARα/γ/δ agonists as potential anti-fatty liver agents

Non-alcoholic fatty liver disease (NAFLD) has become the most common hepatic disease, while no drug was approved until now. The previous study reported that the quadruple FFA1/PPAR-α/γ/δ agonist RLA8 provided better efficacy than obeticholic acid on NASH. In the present study, two design strategies were introduced to explore better quadruple FFA1/PPAR-α/γ/δ agonists with improved metabolic stability. These efforts ultimately resulted in the identification of ZLY18, a quadruple FFA1/PPAR-α/γ/δ agonist with twice higher metabolic half-life than RLA8 in the liver microsome. In the triton-1339W-induced hyperlipidemic model, ZLY18 reversed hyperlipidemia to an almost normal level, which exhibited far stronger lipid-lowering effects than that of RLA8. Moreover, ZLY18 significantly decreased steatosis, hepatocellular ballooning, inflammation and liver fibrosis in NASH model even better than RLA8. Further mechanism studies suggested that ZLY18 exerts stronger effects than RLA8 on the regulation of the gene related to lipid synthesis, oxidative stress, inflammation and fibrosis. In addition, ZLY18 is more effective than pirfenidone in the prevention of CCl4-induced liver fibrosis. Besides, ZLY18 has an acceptable safety profile in the acute toxicity study at a high dose of 500 mg/kg. Therefore, ZLY18 represents a novel and highly promising quadruple FFA1/PPAR-α/γ/δ agonist worth of further investigation and development.

Design, synthesis and evaluation of benzothiazole derivatives as multifunctional agents

Oxidative stress is the product or aetiology of various multifactorial diseases; on the other hand, the development of multifunctional compounds is a recognized strategy for the control of complex diseases. To this end, a series of benzothiazole derivatives was synthesized and evaluated for their multifunctional effectiveness as antioxidant, sunscreen (filter), antifungal and antiproliferative agents. Compounds were easily synthesized via condensation reaction between 2-aminothiophenols and different benzaldehydes. SAR study, particularly in position 2 and 6 of benzothiazoles, led to the identification of 4g and 4k as very interesting potential compounds for the design of multifunctional drugs. In particular, compound 4g is the best blocker of hERG potassium channels expressed in HEK 293 cells exhibiting 60.32percent inhibition with IC50 = 4.79 μM.