106203-24-1

Basic information

• Product Name: 5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester
• Synonyms: 5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester ;ETHYL4-(TRIFLUOROMETHYL)-5-THIAZOLECARBOXYLATE;ethyl 4-(trifluoromethyl)thiazole-5-carboxylate;4-Trifluoromethyl-thiazole-5-carboxylic acid ethyl ester;Ethyl 4-(trifluoromethyl)-1,3-thiazole-5-carboxylate
• CAS NO: 106203-24-1
• Molecular Formula: C7H6F3NO2S
• Molecular Weight: 225.1882496
• Mol File: 106203-24-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 38.5-39.5 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 264.167°C at 760 mmHg
• Flash Point: 113.564°C
• Appearance: /
• Density: 1.407g/cm³
• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.463
• PKA: -2.14±0.10(Predicted)
• CAS DataBase Reference: 5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester(106203-24-1)
• EPA Substance Registry System: 5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester(106203-24-1)

Safety Data

• Hazardous Substances Data: 106203-24-1(Hazardous Substances Data)

Usage

Description

5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester is a colorless liquid chemical compound with a molecular formula of C10H8F3NO2S and a molecular weight of 261.24 g/mol. It is commonly used in organic synthesis and pharmaceutical research due to its potent biological activity and is often used as an intermediate in the production of various pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester is used as an intermediate in the production of various pharmaceuticals for its potent biological activity.
Used in Agrochemical Industry:
5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester is used as an intermediate in the production of various agrochemicals for its potent biological activity.
Used in Dye and Pigment Industry:
5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester is used in the manufacturing of dyes, pigments, and other specialty chemicals.
Used in Material Science:
5-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester has potential applications in the development of new materials, such as polymers and functionalized surfaces.

InChI:InChI=1/C7H6F3NO2S/c1-2-13-6(12)4-5(7(8,9)10)11-3-14-4/h3H,2H2,1H3

Upstream product

• 72850-52-3 ethyl 2-chloro-4-(trifluoromethyl)thiazole-5-carboxylate 
• 72850-53-4 ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-5-thiazole-carboxylate 
• 372-29-2 ethyl 3-amino-4,4,4-trifluoro-2-butenoate 
• 344-72-9 ethyl 2-amino-4-(trifluoromethyl)-5-thiazole-carboxylate 
• 363-58-6 ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate 

Downstream Products

• 167548-89-2 4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid 

Relevant articles and documents

Optimization of Triarylpyridinone Inhibitors of the Main Protease of SARS-CoV-2 to Low-Nanomolar Antiviral Potency

Non-covalent inhibitors of the main protease (Mpro) of SARS-CoV-2 having a pyridinone core were previously reported with IC50 values as low as 0.018 μM for inhibition of enzymatic activity and EC50 values as low as 0.8 μM for inhibition of viral replication in Vero E6 cells. The series has now been further advanced by consideration of placement of substituted five-membered-ring heterocycles in the S4 pocket of Mpro and N-methylation of a uracil ring. Free energy perturbation calculations provided guidance on the choice of the heterocycles, and protein crystallography confirmed the desired S4 placement. Here we report inhibitors with EC50 values as low as 0.080 μM, while remdesivir yields values of 0.5-2 μM in side-by-side testing with infectious SARS-CoV-2. A key factor in the improvement is enhanced cell permeability, as reflected in PAMPA measurements. Compounds 19 and 21 are particularly promising as potential therapies for COVID-19, featuring IC50 values of 0.044-0.061 μM, EC50 values of ca. 0.1 μM, good aqueous solubility, and no cytotoxicity.

Syntheses and Reactions of 2-Halo-5-thiazolecarboxylates

A variety of 2-halo-5-thiazolecarboxylates was prepared from substituted-3-aminoacrylates and 3-ketoesters.Selective reduction of 2-chloro-5-thiazolecarboxylates 4a, 4i and 4j with sodium borohydride in ethanol provided the corresponding 2-halo-5-thiazolemethanols 27 - 29.Nucleophilic displacement on methyl methanesulfonate (32c) occured selectivity at the 5-substituent to provide 2-chloro-4-(trifluoromethyl)-5-(heteroatom-substituted methyl)thiazoles 32d-f.