143209-04-5

Basic information

• Product Name: (S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid
• Synonyms: (S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid
• CAS NO: 143209-04-5
• Molecular Weight: 223.252
• Mol File: 143209-04-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid(143209-04-5)
• EPA Substance Registry System: (S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid(143209-04-5)

Safety Data

• Hazardous Substances Data: 143209-04-5(Hazardous Substances Data)

Usage

Description

(S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid is an organic compound with a unique molecular structure that features a thiazole ring and a hydroxyphenyl group. It is characterized by its potential applications in various industries due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
(S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid is used as an active pharmaceutical ingredient for the development of new drugs targeting various medical conditions. Its unique structure allows for the modulation of specific biological pathways, making it a promising candidate for therapeutic applications.
Used in Chemical Synthesis:
(S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid is used as a key intermediate in the synthesis of various complex organic molecules. Its versatile structure enables the creation of a wide range of compounds with different properties and applications.
Used in Material Science:
(S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid is used as a building block for the development of novel materials with specific properties. Its incorporation into polymers or other materials can lead to enhanced performance characteristics, such as improved stability or functionality.
Used in Agricultural Industry:
(S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid is used as a component in the development of new agrochemicals, such as pesticides or herbicides. Its potential to target specific biological pathways can contribute to the creation of more effective and environmentally friendly products.

Upstream product

• 611-20-1 salicylonitrile 
• 52-89-1 l-cysteine hydrochloride 
• 32443-99-5 D-cysteine hydrochloride 

Downstream Products

• 338461-20-4 (4S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid N-methoxy-N-methylamide 
• 1269638-17-6 (S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carbaldehyde 
• 1269638-41-6 C₁₃H₁₄N₂O₃S₂ 
• 1269638-40-5 C₁₃H₁₄N₂O₃S₂ 
• 143209-09-0 N,N'-bis<<<2-(2'-hydroxyphenyl)-2-thiazolin-4-yl>carbonyl>-2-aminoethyl>amine 
• 143209-08-9 1,2-bis<<<2-(2'-hydroxyphenyl)-2-thiazolin-4-yl>carbonyl>amino>ethane 
• 143209-07-8 1,5,10-tris<<2-(2'-hydroxyphenyl)-2-thiazolin-4-yl>carbonyl>-1,5,10-triazadecane 

Relevant articles and documents

Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+Complex

The siderophore piscibactin is a key virulence factor involved in the iron uptake of pathogenic bacteria Photobacterium damselae subsp. piscicida and Vibrio anguillarum, responsible for the fish diseases photobacterioisis (pasteurellosis) and vibriosis, respectively. A convergent total synthesis of its Ga3+ complex using l-/d-cysteine as chiral agents and Meldrum's acid is described. A Staudinger reduction/Aza-Wittig process in the synthesis of the acid-sensitive β-hydroxy-2,4-disubstituted thiazoline moiety and the convenient protecting groups was a key step in this synthesis.

Design and synthesis of new 2-aryl-4,5-dihydro-thiazole analogues: In vitro antibacterial activities and preliminary mechanism of action

Sixty 2-aryl-4,5-dihydrothiazoles were designed and synthesized in yields ranging from 64% to 89% from cysteine and substituted-benzonitriles via a novel metal- and catalyst-free method. The structures of the title compounds were confirmed mainly by NMR spectral data analysis. Antibacterial activity assays showed that the compounds (S)-2-(2′-hydroxyphenyl)-4-hydroxy-methyl-4,5-dihydrothiazole (7h) and (R)-2-(2′-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydro-thiazole (7h′) exhibited significant inhibition against Ralstonia solanacearum, Pseudomonas syringae pv. actinidiae, Bacillus subtilis and Bacillus cereus, with minimum inhibitory concentrations (MICs) ranging from 3.91 to 31.24 μg·mL-1. The effect of substituents showed that not only electron-withdrawing groups, but also electron-donating groups could abolish the antibacterial activities unless a 2′-hydroxy group was introduced on the 2-aryl substituent of the 4,5-dihydrothiazole analogues. The results of scanning electron microscope (SEM) and fatty acid exposure experiments indicated that these antibacterial compounds influence fatty acid synthesis in the tested bacteria.

Design and Synthesis of Multidentate 2-(2'-Hydroxyphenyl)-2-thiazolines for Biomedical Application

A variety of multidentate ligands based on the 2-(2'-hydroxyphenyl)-2-thiazoline functionality have been synthesized by the formation of amide linkages at the carboxyl moiety in 2-(2'-hydroxyphenyl)-2-thiazoline-4-carboxylic acid 1 with a number of polyam