180597-83-5

Basic information

• Product Name: 4-(BROMOMETHYL)-5-METHYL-3-PHENYLISOXAZOLE
• Synonyms: 4-(BROMOMETHYL)-5-METHYL-3-PHENYLISOXAZOLE
• CAS NO: 180597-83-5
• Molecular Formula: C11H10BrNO
• Molecular Weight: 252.11
• Mol File: 180597-83-5.mol

Chemical Properties

• Melting Point: 61 °C
• Boiling Point: 369.8°C at 760 mmHg
• Flash Point: 177.5°C
• Appearance: /
• Density: 1.428g/cm³
• Vapor Pressure: 2.46E-05mmHg at 25°C
• Refractive Index: 1.579
• CAS DataBase Reference: 4-(BROMOMETHYL)-5-METHYL-3-PHENYLISOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(BROMOMETHYL)-5-METHYL-3-PHENYLISOXAZOLE(180597-83-5)
• EPA Substance Registry System: 4-(BROMOMETHYL)-5-METHYL-3-PHENYLISOXAZOLE(180597-83-5)

Safety Data

• Statements: 34-36
• Safety Statements: 26-36/37/39
• RIDADR: 3261
• WGK Germany: 3
• Hazardous Substances Data: 180597-83-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(BROMOMETHYL)-5-METHYL-3-PHENYLISOXAZOLE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to form carbon-carbon and carbon-heteroatom bonds, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(BROMOMETHYL)-5-METHYL-3-PHENYLISOXAZOLE is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides, due to its reactivity and structural features that can be incorporated into active molecules with desired biological properties.
Used in Organic Synthesis:
As a versatile building block, 4-(BROMOMETHYL)-5-METHYL-3-PHENYLISOXAZOLE is employed in organic synthesis for the creation of complex organic molecules and compounds, taking advantage of its reactivity and the presence of functional groups that facilitate various chemical transformations.

InChI:InChI=1/C11H10BrNO/c1-8-10(7-12)11(13-14-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3

Upstream product

• 100-52-7 benzaldehyde 
• 932-90-1 Benzaldoxime 
• 698-16-8 benzohydroximoyl chloride 
• 2065-28-3 methyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 18718-79-1 5-methyl-3-phenyl-4-isoxazolylmethanol 

Downstream Products

• 1240494-56-7 N-(4-fluorophenyl)-6-((5-methyl-3-phenylisoxazol-4-yl)methylthio)nicotinamide 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of Novel Nonsteroidal Farnesoid X Receptor (FXR) Antagonists: Molecular Basis of FXR Antagonism

Farnesoid X receptor (FXR) plays an important role in the regulation of cholesterol, lipid, and glucose metabolism. Recently, several studies on the molecular basis of FXR antagonism have been reported. However, none of these studies employs an FXR antagonist with nonsteroidal scaffold. On the basis of our previously reported FXR antagonist with a trisubstituted isoxazole scaffold, a novel nonsteroidal FXR ligand was designed and used as a lead for structural modification. In total, 39 new trisubstituted isoxazole derivatives were designed and synthesized, which led to pharmacological profiles ranging from agonist to antagonist toward FXR. Notably, compound 5s (4′-[(3-{[3-(2-chlorophenyl)-5-(2-thienyl)isoxazol-4-yl]methoxy}-1H-pyrazol-1-yl)methyl]biphenyl-2-carboxylic acid), containing a thienyl-substituted isoxazole ring, displayed the best antagonistic activity against FXR with good cellular potency (IC50=12.2±0.2μM). Eventually, this compound was used as a probe in a molecular dynamics simulation assay. Our results allowed us to propose an essential molecular basis for FXR antagonism, which is consistent with a previously reported antagonistic mechanism; furthermore, E467 on H12 was found to be a hot-spot residue and may be important for the future design of nonsteroidal antagonists of FXR. X marks the spot: 39 trisubstituted isoxazoles were designed and synthesized, leading to compounds with pharmacological profiles ranging from agonist to antagonist at the farnesoid X receptor (FXR). By using the most potent antagonist as a probe, the essential molecular basis of FXR antagonism is proposed, and E467 on H12 can be regarded as a hot-spot residue for the future design of nonsteroidal antagonists of FXR.