74704-39-5

Usage

Uses

Used in Pharmaceutical Industry:
THIAZOLE, 4-(BROMOMETHYL)-2-METHYLis used as a building block for the synthesis of various pharmaceuticals. Its unique chemical and biological properties make it a valuable component in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical industry, THIAZOLE, 4-(BROMOMETHYL)-2-METHYLis utilized as a key intermediate in the production of agrochemicals. Its ability to introduce functional groups into organic molecules contributes to the creation of effective and targeted agrochemical products.
Used in Organic Synthesis:
THIAZOLE, 4-(BROMOMETHYL)-2-METHYLis employed as a reagent in organic synthesis for the introduction of functional groups into organic molecules. Its bromomethyl group allows for the formation of new chemical bonds and the synthesis of a wide range of organic compounds.
Used in Research and Development:
This chemical compound is also used in research and development settings to explore its potential applications and properties. Its unique structure and reactivity make it an interesting subject for scientific investigation and the development of new technologies and applications.

InChI:InChI=1/C5H6BrNS/c1-4-7-5(2-6)3-8-4/h3H,2H2,1H3

Upstream product

• 6436-59-5 ethyl 2-methylthiazole-4-carboxylate 

Downstream Products

• 152044-54-7 epothilone B 
• 189453-10-9 epothilone D 
• 1220279-14-0 4-((1-(4-fluorophenyl)hydrazinyl)methyl)-2-methylthiazole 

Relevant academic research and scientific papers

12,13-Aziridinyl Epothilones. Stereoselective Synthesis of Trisubstituted Olefinic Bonds from Methyl Ketones and Heteroaromatic Phosphonates and Design, Synthesis, and Biological Evaluation of Potent Antitumor Agents

The synthesis and biological evaluation of a series of 12,13-aziridinyl epothilone B analogues is described. These compounds were accessed by a practical, general process that involved a 12,13-olefinic methyl ketone as a starting material obtained by ozonolytic cleavage of epothilone B followed by tungsten-induced deoxygenation of the epoxide moiety. The attachment of the aziridine structural motif was achieved by application of the Ess-Kürti-Falck aziridination, while the heterocyclic side chains were introduced via stereoselective phosphonate-based olefinations. In order to ensure high (E) selectivities for the latter reaction for electron-rich heterocycles, it became necessary to develop and apply an unprecedented modification of the venerable Horner-Wadsworth-Emmons reaction, employing 2-fluoroethoxyphosphonates that may prove to be of general value in organic synthesis. These studies resulted in the discovery of some of the most potent epothilones reported to date. Equipped with functional groups to accommodate modern drug delivery technologies, some of these compounds exhibited picomolar potencies that qualify them as payloads for antibody drug conjugates (ADCs), while a number of them revealed impressive activities against drug resistant human cancer cells, making them desirable for potential medical applications.

Total syntheses of epothilones B and D

A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.