1239589-17-3

Basic information

• Product Name: methyl 2-(4-bromophenyl)-1,3-oxazole-4-carboxylate
• Synonyms: methyl 2-(4-bromophenyl)-1,3-oxazole-4-carboxylate
• CAS NO: 1239589-17-3
• Molecular Weight: 282.093
• Mol File: 1239589-17-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 2-(4-bromophenyl)-1,3-oxazole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(4-bromophenyl)-1,3-oxazole-4-carboxylate(1239589-17-3)
• EPA Substance Registry System: methyl 2-(4-bromophenyl)-1,3-oxazole-4-carboxylate(1239589-17-3)

Safety Data

• Hazardous Substances Data: 1239589-17-3(Hazardous Substances Data)

Upstream product

• 5619-04-5 methyl 2-amino-3-hydroxypropanoate hydrochloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 

Downstream Products

• 36841-48-2 2-(4-bromophenyl)-4-hydroxymethyloxazole 
• 22091-38-9 2-(4-bromophenyl)-4-(chloromethyl)oxazole 
• 1427954-49-1 methyl 2-(p-bromophenyl)-5-phenyloxazole-4-carboxylate 
• 1427954-88-8 C₂₂H₁₄Br₂N₂O₆ 

Relevant articles and documents

Synthesis of Isoxazole- And Oxazole-4-carboxylic Acids Derivatives by Controlled Isoxazole-Azirine-Isoxazole/Oxazole Isomerization

The first synthesis of isoxazole-4-carboxylic acid derivatives by domino isoxazole-isoxazole isomerization is reported. Fe(II)-catalyzed isomerization of 4-acyl-5-methoxy-/5-aminoisoxazoles (dioxane, 105 °C) leads to the formation of isoxazole-4-carboxylic esters and amides in good yields. 4-Formyl-5-methoxyisoxazoles give methyl oxazole-4-carboxylates under the same reaction conditions. Fe(II)-catalyzed isomerization of 4-acyl-5-methoxyisoxazoles under milder conditions (MeCN, 50 °C) allows the preparation of transient 2-acyl-2-(methoxycarbonyl)-2H-azirines. The azirines isomerize quantitatively either into isoxazoles under catalytic conditions (dioxane, 105 °C) or into oxazoles under noncatalytic thermolysis (o-dichlorobenzene, 170 °C). The mechanism of the isomerization and dependence of the reaction routes on substituents at starting isoxazole core and reaction conditions are discussed on the basis of DFT calculations.

Discovery of the disubstituted oxazole analogues as a novel class anti-tuberculotic agents against MDR- and XDR-MTB

A high-throughput screening effort on 45,000 compounds resulted in the discovery of a disubstituted oxazole as a new structural class inhibitor of Mycobacterium tuberculosis (Mtb). In order to improve the activity and investigate the SAR of this scaffold, a series of disubstituted azole analogues have been designed and synthesized. The newly synthesized compounds 1a-y were evaluated for their in vitro anti-TB activity versus replicating, multi- and extensive drug resistant Mtb strains. All the compounds, except 1o, 1p and 1q, showed potent anti-TB activity with MIC of 1-64 mg/L. The test of broad spectrum panel revealed that this series are specific to Mtb. The cytotoxicity assessment indicated that the compounds were not cytotoxic against HEK 293 cells. The compounds could have a novel mechanism to anti-Mtb as they can inhibit drug sensitive and drug resistant Mtb.