14542-16-6

Basic information

• Product Name: 4-Methyl-1,3-thiazole-2-carboxylic acid
• Synonyms: 4-Methyl-1,3-thiazole-2-carboxylic acid;4-Methylthiazole-2-carboxylic acid;methyl 4-methyl-1,3-thiazole-2-carboxylate;2-Carboxy-4-methyl-1,3-thiazole;4-Methyl-2-thiazole-carboxylic acid
• CAS NO: 14542-16-6
• Molecular Formula: C₅H₅NO₂S
• Molecular Weight: 143.1637
• Product Categories: Carboxylic Acids;Thiazoles, Isothiazoles &Benzothiazoles;Carboxylic Acids;Thiazoles, Isothiazoles & Benzothiazoles
• Mol File: 14542-16-6.mol

Chemical Properties

• Melting Point: 99 °C
• Boiling Point: 317.135 °C at 760 mmHg
• Flash Point: 145.598 °C
• Appearance: White/Crystalline Powder
• Density: 1.418 g/cm³
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 0.55±0.10(Predicted)
• CAS DataBase Reference: 4-Methyl-1,3-thiazole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-1,3-thiazole-2-carboxylic acid(14542-16-6)
• EPA Substance Registry System: 4-Methyl-1,3-thiazole-2-carboxylic acid(14542-16-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 14542-16-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
4-Methyl-1,3-thiazole-2-carboxylic acid is utilized as a key intermediate in the synthesis of pharmaceutical drugs, particularly for those targeting bacterial infections and inflammatory conditions. Its unique structure allows for the creation of novel drug candidates with improved efficacy and reduced side effects.
Used in Organic Synthesis:
In the field of organic chemistry, 4-Methyl-1,3-thiazole-2-carboxylic acid serves as a valuable building block for the synthesis of complex organic molecules. Its reactivity and functional groups enable the formation of diverse chemical entities, contributing to the advancement of organic synthesis techniques.
Used in the Synthesis of Bioactive Compounds:
4-Methyl-1,3-thiazole-2-carboxylic acid is employed as a starting material in the preparation of bioactive compounds with potential therapeutic applications. Its incorporation into these compounds can enhance their biological activity, leading to the discovery of new treatments for various diseases and conditions.
Used in Anti-bacterial Applications:
4-Methyl-1,3-thiazole-2-carboxylic acid is used as an anti-bacterial agent, exhibiting activity against a range of bacterial pathogens. Its incorporation into pharmaceutical formulations can help combat bacterial infections and contribute to the development of new antibiotics.
Used in Anti-inflammatory Applications:
Due to its potential anti-inflammatory properties, 4-Methyl-1,3-thiazole-2-carboxylic acid is used in the development of anti-inflammatory drugs. It can be incorporated into formulations to alleviate inflammation and reduce the associated symptoms, offering a promising avenue for the treatment of inflammatory disorders.

Upstream product

• 13750-68-0 4-methyl-thiazole-2-carbaldehyde 
• 7586-99-4 2-(α-hydroxyethyl)-4-methylthiazole 
• 7210-73-3 4-Methylthiazol-2-carbonsaeure-ethylester 
• 693-95-8 4-Methylthiazole 
• 124-38-9 carbon dioxide 
• 541-58-2 2,4-dimethylthiazole 
• 24622-44-4 (E)-4-methyl-2-styrylthiazole 

Downstream Products

• 693-95-8 4-Methylthiazole 
• 14542-15-5 methyl 4-methyl-1,3-thiazole-2-carboxylate 
• 100516-76-5 4-methyl-1,3-thiazole-2-carbohydrazide 
• 79312-42-8 C₅H₄ClNOS 
• 1446003-98-0 C₃₉H₆₂N₄O₁₅S 
• 1628847-80-2 N-((1s,4s)-4-(2-(4'-(((3S,5R)-3,5-dimethylpiperazin-1-yl)methyl)-2'-(morpholinomethyl)biphenyl-3-yloxy)-5-fluoronicotinamido)cyclohexyl)-4-methylthiazole-2-carboxamide trifluoroacetic acid salt 

Relevant articles and documents

Synthesis and biological evaluation of picolinamides and thiazole-2-carboxamides as mGluR5 (metabotropic glutamate receptor 5) antagonists

We described here the synthesis and biological evaluation of picolinamides and thiazole-2-carboxamides as potential mGluR5 antagonists. We found that a series of thiazole derivatives 6 showed better inhibitory activity against mGluR5. Compounds 6bc and 6bj have been identified as potent antagonists (IC50 = 274 and 159 nM) showing excellent in vitro stability profile. Molecular docking study using the crystal structure of mGluR5 revealed that our compounds 6bc and 6bj fit the allosteric binding site of mavoglurant well.

Discovery of functionally selective 7,8,9,10-tetrahydro-7,10-ethano-1,2,4- triazolo[3,4-a]phthalazines as GABAA receptor agonists at the α3 subunit

We have previously identified the 7,8,9,10-tetrahydro-7,10-ethano-1,2,4- triazolo[3,4-a]phthalazine (1) as a potent partial agonist for the 0.3 receptor subtype with 5-fold selectivity in binding affinity over α1. This paper describes a detailed investigation of the substituents on this core structure at both the 3- and 6-positions. Despite evaluating a wide range of groups, the maximum selectivity that could be achieved in terms of affinity for the α3 subtype over the α1 subtype was 12-fold (for 57). Although most analogues showed no selectivity in terms of efficacy, some did show partial agonism at α1 and antagonism at α3 (e.g., 25 and 75). However, two analogues tested (93 and 96), both with triazole substituents in the 6-position, showed significantly higher efficacy for the α3 subtype over the α1 subtype. This was the first indication that selectivity in efficacy in the required direction could be achieved in this series.

An Infrared Study of Rotational Isomerism in Thiazole-2-carboxylates

A series of alkyl thiazole-2-carboxylates containing a range of substituents at the 4- and 5-positions has been prepared.Solutions of these esters (mostly new compounds) show well resolved doublets in the i.r.C=O region which arise from rotational isomers.The higher wavenumber components are assigned to the more polar carbonyl O,S-anti-s-trans-rotamers and the lower wavenumber components to the carbonyl O,S-syn-s-trans-forms.Small, but systematic, differences between the methyl esters are noted.