59418-09-6

Basic information

• Product Name: METHYL 4-THIAZOLECARBOXYLATE
• Synonyms: 4-(Methoxycarbonyl)-1,3-thiazole;2-Methyl-1,3-thiazole-4-carboxylate;4-Thiazolecarboxylic acid, Methyl ester;Methyl1,3-thiazole-4-carboxylate97%;THIAZOLE-4-CARBOXYLIC ACID METHYL ESTER;METHYL 4-THIAZOLECARBOXYLATE;METHYL 1,3-THIAZOLE-4-CARBOXYLATE;METHYL THIAZOLE-4-CARBOXYLATE
• CAS NO: 59418-09-6
• Molecular Formula: C₅H₅NO₂S
• Molecular Weight: 143.16
• Product Categories: Carboxes;Thiazoles;blocks
• Mol File: 59418-09-6.mol

Chemical Properties

• Melting Point: 38-42
• Boiling Point: 219.8 °C at 760 mmHg
• Flash Point: 86.8 °C
• Appearance: /
• Density: 1.301 g/cm³
• PKA: 0.24±0.10(Predicted)
• CAS DataBase Reference: METHYL 4-THIAZOLECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-THIAZOLECARBOXYLATE(59418-09-6)
• EPA Substance Registry System: METHYL 4-THIAZOLECARBOXYLATE(59418-09-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 59418-09-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Synthesis:
METHYL 4-THIAZOLECARBOXYLATE is used as a key intermediate in the synthesis of various pharmaceuticals and biological compounds. Its presence of sulfur and nitrogen atoms allows it to form connections with a wide range of other elements, making it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Reactions:
METHYL 4-THIAZOLECARBOXYLATE is used as a reactive compound in various chemical reactions. Its reactivity and the diverse molecules it can produce when reacting with other compounds make it a useful tool in the synthesis of complex organic molecules and the exploration of novel chemical pathways.
Used in Drug Development:
METHYL 4-THIAZOLECARBOXYLATE is used as a building block in the development of new drugs. Its unique structure and the ability to form stable connections with other molecules contribute to the creation of innovative pharmaceutical formulations with potential therapeutic applications.
Used in Material Science:
METHYL 4-THIAZOLECARBOXYLATE is used as a component in the synthesis of advanced materials, such as polymers and composites, that exhibit unique properties. Its incorporation into these materials can lead to the development of new products with improved performance characteristics in various industries, including electronics, aerospace, and automotive.

Upstream product

• 67-56-1 methanol 
• 3973-08-8 Thiazole-4-carboxylic acid 
• 42258-90-2 (R)-thiazolidine-4-carboxylic acid methyl ester 
• 60667-24-5 (4R)-thiazolidine-4-carboxylic acid,methyl ester 
• 186581-53-3 diazomethane 

Downstream Products

• 10538-10-0 thiazole-4-carboxylic acid 4-bromo-anilide 
• 173979-04-9 methyl 2-trimethylsilyl-4-thiazolecarboxylate 
• 99972-45-9 methyl 5-phenylthiazole-4-carboxylate 
• 133415-16-4 methyl 2,5-diphenylthiazole-4-carboxylate 
• 7113-02-2 2-phenyl-1,3-thiazole-4-carboxylic acid methyl ester 
• 1315510-12-3 C₁₁H₈ClNO₂S 
• 3973-08-8 Thiazole-4-carboxylic acid 
• 76862-26-5 2-(methylthio)-4-thiazolecarboxylic acid methyl ester 
• 1362690-92-3 methyl 5-(2-cyanophenyl)thiazole-4-carboxylate 
• 1372926-40-3 C₁₉H₁₁N₃O₂S 
• 1362690-91-2 methyl 5-(3-formylphenyl)thiazole-4-carboxylate 
• 1362690-90-1 methyl 5-(4-cyanophenyl)thiazole-4-carboxylate 
• 1372925-70-6 C₁₉H₁₁N₃O₂S 

Relevant articles and documents

Anti-biofilm effect of novel thiazole acid analogs against Pseudomonas aeruginosa through IQS pathways

IQS has been proven to be a new quorum sensing (QS) system against bacterial biofilm formation, which is activated in the common phosphate-limiting environment of infected tissues taking over the central las system. Up to now, numerous biofilm inhibitors which function by affecting traditional QS system have been reported. However, no compound has been reported to exert anti-biofilm activity through IQS system. Herein, various novel IQS derivatives were synthesized by the reaction of thiazole-4-carboxylic acid with different linear alcohols (R-OH) or amines (R-NH2). IQS derivatives with four carbon chain length of R group were found to present the best biofilm inhibition activity. Compound B-11 as the model molecule was observed to inhibit biofilm formation only under phosphate-limiting condition, and increase in B-11 concentration significantly reduced the expression of rhlA-gfp and pqsA-gfp, but lasB-gfp. Moreover, B-11 reduced production of virulence factors of rhamnolipid and pyocyanin under phosphate limitation. These observations indicated that the synthesized compounds possessed the anti-biofilm activity through IQS pathways rather than traditional QS pathways, which pave a path for future molecular design against bacterial biofilm formation.

Method for preparing thiazole-4-formic acid

The invention discloses a method for preparing thiazole-4-formic acid. By the aid of the method, the problems of relatively high prices of raw materials used in old processes for thiabendazole which is one of important traditional pesticide and bactericide varieties and low yield of the thiabendazole can be solved. The method includes steps of generating thiazolidine-4-formic acid from L-cysteinehydrochloride, formaldehyde and pyridine; carrying out reaction on the thiazolidine-4-formic acid, methyl alcohol and HCl gas to generate thiazolidine-4-methyl formate; carrying out reaction on the thiazolidine-4-methyl formate, acetonitrile and MnO2 to generate thiazole-4-methyl formate; hydrolyzing the thiazole-4-methyl formate under the effect of sodium hydroxide to obtain the thiazole-4-formicacid which is a product. The method has the advantages of simple process synthetic route, mild reaction condition, low cost, environmental protection, safety, excellent application prospect, good social benefit and high economic benefit.

Mechanism selection for regiocontrol in base-assisted, palladium-catalysed direct C-H coupling with halides: First approach for oxazole- and thiazole-4-carboxylates

Both base-assisted non-concerted metallation-deprotonation (nCMD) and concerted metallation-deprotonation (CMD) have been identified as two potent operating mechanisms in palladium-catalysed direct C-H coupling of oxazole and thiazole-4-carboxylate esters

Direct C-2 arylation of alkyl 4-thiazolecarboxylates: New insights in synthesis of heterocyclic core of thiopeptide antibiotics

(Chemical Equation Presented) The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4- thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.

Synthesis of thiazole compounds via lithiation: An unexpected rearrangement

A novel rearrangement was discovered during an investigation of the lithium-bromine exchange reactions of bromothiazole derivatives and their subsequent reactions with various electrophiles.

A FACILE SYNTHETIC APPROACH TO THE FRAGMENT D OF ANTIBIOTIC NOSIHEPTIDE, 2--THIAZOLE-4-CARBOXYLIC ACID

The lactam corresponding to fragment D of a polypeptide antibiotic nosiheptide was prepared via oxidation of the corresponding thiazolidine-4-carboxylate obtained by the condensation of 2-azido-2,3-dideoxy-D-threo-pentoalduronate with L-cysteine methyl ester.