298694-30-1

Basic information

• Product Name: 4-BROMO-2-METHYLTHIAZOLE
• Synonyms: 4-BROMO-2-METHYLTHIAZOLE;4-Bromo-2-methyl-1,3-thiazole;4-Bromo-2-(methyl-d3)-thiazole;298694-30-1
• CAS NO: 298694-30-1
• Molecular Formula: C₄H₄BrNS
• Molecular Weight: 178.05
• Mol File: 298694-30-1.mol

Chemical Properties

• Boiling Point: 199.2 °C at 760 mmHg
• Flash Point: 74.3 °C
• Appearance: /
• Density: 1.702 g/cm³
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 0.66±0.10(Predicted)
• CAS DataBase Reference: 4-BROMO-2-METHYLTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-METHYLTHIAZOLE(298694-30-1)
• EPA Substance Registry System: 4-BROMO-2-METHYLTHIAZOLE(298694-30-1)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 298694-30-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-BROMO-2-METHYLTHIAZOLE is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its reactivity and versatility in forming chemical bonds make it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical industry, 4-BROMO-2-METHYLTHIAZOLE is utilized as a key intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties allow for the creation of effective and targeted agricultural products.
Used in Flavors and Fragrances Industry:
4-BROMO-2-METHYLTHIAZOLE is used as a component in the production of flavors and fragrances, adding unique scents and tastes to various consumer products. Its chemical structure contributes to the creation of novel and appealing sensory experiences.
Used in Research and Development:
4-BROMO-2-METHYLTHIAZOLE is employed in research and development for the exploration of new materials and chemical compounds. Its reactivity and potential for forming new bonds make it an essential tool in scientific investigations and innovation.

Upstream product

• 4175-77-3 2,4-dibromo-1,3-thiazole 
• 77-78-1 dimethyl sulfate 
• 333-27-7 methyl trifluoromethanesulfonate 
• 616-42-2 dimethylsulfite 
• 13061-96-6 dihydroxy-methyl-borane 

Downstream Products

• 1036988-73-4 1-{3-[7-(2-methyl-thiazol-4-yl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea 
• 1239586-80-1 (E)-3-((2-methylthiazol-4-yl)ethynyl)cyclohex-2-enone oxime 
• 329203-85-2 2-methyl-4-[(trimethylsilyl)ethynyl]-1,3-thiazole 
• 653564-10-4 tributyl-(2-methylthiazol-4-yl)stannane 

Relevant articles and documents

Synthesis of epothilone 16,17-alkyne analogs by replacement of the C13-C15(O)-ring segment of natural epothilone C

Ring-opening cross metathesis of epothilone C (4a) with ethylene, followed by silyl protection and ester hydrolysis, yielded an eastern ring segment C1-C12 as the carboxylic acid 10. Separately, a western ring segment 12 carrying a C16-C17 triple bond was synthesized and coupled with 10 to form the ester 13. Ring closure by olefin metathesis, deprotection, and then epoxidation, gave the 16,17-alkyne analogs (14b, 3b) of epothilone C and epothilone A. The identity of 3b was proven by hydrogenation to (16Z)-epothilone A8 (17) and comparison with an authentic sample prepared from natural epothilone A8 (18). The biological activity of the new epothilones was determined. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

2-AMINO-N-(AMINO-OXO-ARYL-LAMBDA6-SULFANYLIDENE)ACETAMIDE COMPOUNDS AND THEIR THERAPEUTIC USE

The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain 2-amino-N-(amino-oxo-aryl-λ6- sulfanylidene)acetamide compounds (referred to herein as ANASIA compounds) that, inter alia, inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase (aaRS) (e.g., bacterial leucyl-tRNA synthetase, LeuRS). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase; to treat disorders that are ameliorated by the inhibition (e.g., selective inhibition) of bacterial aminoacyl-tRNA synthetase; to treat bacterial infections; etc.

Small-molecule anticancer agents kill cancer cells by harnessing reactive oxygen species in an iron-dependent manner

In the course of generating a library of open-chain epothilones, we discovered a new class of small molecule anticancer agents that has no effect on tubulin but instead kills selected cancer cell lines by harnessing reactive oxygen species in an iron-dependent manner. Results of the preliminary studies are consistent with the recently described cell death mechanism ferroptosis. Studies are in progress to confirm ferroptosis as the cell death mechanism and to identify the specific molecular targets of these small molecule anticancer agents.

Synthesis and in vitro/in vivo pharmacological evaluation of [ 11C]-ThioABP, a novel radiotracer for imaging mGluR5 with PET

We have designed a novel positron emission tomography (PET) radiotracer, [11C]-ThioABP, a thiazole based derivative for imaging the metabotropic glutamate receptor subtype 5 (mGluR5), and prepared the hydroxy oxime precursor 4 in a 15% overall yield. [11C]-ThioABP was radiosynthesized in the Veenstra module and obtained in a decay corrected radiochemical yield of 40% and specific activity of 80-250 GBq μmol -1 at the end of synthesis. ThioABP exhibited excellent binding affinity (Ki) in vitro of 1.9 ± 0.9 nM and [ 11C]-ThioABP showed an optimal log D7.4 of 2.4. The autoradiographic studies on rat brain slices revealed specific binding to mGluR5. In vivo evaluation of [11C]-ThioABP including a displacement study with MMPEP in a dynamic PET scan showed a specificity of [ 11C]-ThioABP for mGluR5. Radio-TLC metabolite studies showed a good metabolic stability of [11C]-ThioABP in vivo. The comparison of biological properties of [11C]-ThioABP and [11C]-ABP688 revealed similarity between these two compounds.

Synthesis of epothilones molecule fragment (15R)-C13-C 21 from D-mannitol

Efficient synthesis of an epothilone molecules fragment (15R)-C 13-C21 was carried out from D-mannitol through its conversion into methyl 2,3-O-cyclohexylidene-D-glycerate followed by the cyclopropanation of the ester group with ethy

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, or stereoisomers thereof, wherein each dashed line (represented by ------) represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR6, -NH-SO2R7; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, or C3-7cycloalkyl; n is 3, 4, 5, or 6; R4 and R5 independently from one another are hydrogen, halo, hydroxy, nitro, cyano, carboxyl, C1-6alkyl, C1-6alkoxy, C1-6alkoxyC1-6alkyl, C1-6alkylcarbonyl, C1-6alkoxy- carbonyl, amino, azido, mercapto, C1-6alkylthio, polyhaloC1-6alkyl, aryl or Het; W is aryl or Het; R6 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R7 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl or naphthyl, each optionally substituted with 1-3 substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 - 4 heteroatoms each independently selected from N, O or S, and optionally substituted with 1 -3 substituents; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.

HETEROCYCLIC COMPOUNDS

Compounds of formula I : and pharmaceutically-acceptable salts thereof, wherein Ar and R are as defined in the specification, compositions containing such compounds and the use of such compounds and compositions for use in therapy.