14731-10-3

Basic information

• Product Name: 3-(CHLOROMETHYL)-5-PHENYLISOXAZOLE
• Synonyms: 3-(CHLOROMETHYL)-5-PHENYLISOXAZOLE;3-(Chloromethyl)-5-phenylisoxazole 97%;Isoxazole,3-(chloroMethyl)-5-phenyl-
• CAS NO: 14731-10-3
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.63
• Mol File: 14731-10-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 48-49.5
• Boiling Point: 337.6°Cat760mmHg
• Flash Point: 158°C
• Appearance: /
• Density: 1.222g/cm³
• Vapor Pressure: 0.000203mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• PKA: -4.04±0.28(Predicted)
• CAS DataBase Reference: 3-(CHLOROMETHYL)-5-PHENYLISOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(CHLOROMETHYL)-5-PHENYLISOXAZOLE(14731-10-3)
• EPA Substance Registry System: 3-(CHLOROMETHYL)-5-PHENYLISOXAZOLE(14731-10-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 14731-10-3(Hazardous Substances Data)

Usage

General Description

3-(Chloromethyl)-5-phenylisoxazole is a chemical compound that contains a chlorine-methyl group and a phenylisoxazole ring. It is often used as a building block in the synthesis of various pharmaceuticals and agrochemicals. The presence of the chloromethyl group makes it a versatile intermediate for the synthesis of organic compounds, as it can undergo a variety of chemical reactions to introduce different functional groups. Additionally, the phenylisoxazole ring contributes to the compound's diverse reactivity, making it a valuable tool in the development of new molecules with potential medicinal or agricultural applications. Overall, 3-(Chloromethyl)-5-phenylisoxazole is an important chemical for the production of a wide range of useful compounds.

InChI:InChI=1/C10H8ClNO/c11-7-9-6-10(13-12-9)8-4-2-1-3-5-8/h1-6H,7H2

Upstream product

• 858489-69-7 3-(methoxymethyl)-5-phenylisoxazole 
• 1007401-94-6 (Z)-1,4-dichloro-4-phenylbut-3-en-2-one 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 98-86-2 acetophenone 
• 7063-99-2 ethyl 5-phenylisoxazole-3-carboxylate 
• 98-85-1 1-Phenylethanol 
• 100-52-7 benzaldehyde 
• 90770-96-0 3-hydroxyiminomethyl-5-phenylisoxazole 
• 59985-82-9 5-phenylisoxazole-3-carbaldehyde 
• 1619-37-0 (5-phenylisoxazol-3-yl)methanol 

Downstream Products

• 263257-35-8 4-[(5-phenylisoxazol-3-yl)methoxy]benzaldehyde 
• 250601-87-7 methyl (E)-4-phenyl-4-{4-[(5-phenylisoxazol-3-yl)methoxy]benzyloxyimino}butyrate 
• 89102-76-1 diethyl [(5-phenyl-1,2-oxazol-3-yl)methyl]phosphonate 
• 1195982-98-9 (R)-3-(1-phenylcycloheptanecarbonyloxy)-1-(5-phenylisoxazol-3-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 1195982-93-4 (R)-1-(5-phenylisoxazol-3-ylmethyl)-3-(1-thiophen-2-ylcycloheptanecarbonyloxy)-1-azoniabicyclo[2.2.2]octane chloride 
• 1195983-04-0 (R)-3-(1-phenylcyclopentanecarbonyloxy)-1-(5-phenylisoxazol-3-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 1195983-06-2 (R)-3-(1-phenylcyclohexanecarbonyloxy)-1-(5-phenylisoxazol-3-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 1201042-02-5 (R)-1-(5-phenyl-isoxazol-3-ylmethyl)-3-((S)-2-phenyl-2-piperidin-1-yl-propionyloxy)-1-azonia-bicyclo[2.2.2]octane chloride 
• 1259765-77-9 Triethyl 2-(5-phenylisoxazol-3-yl)ethane-1,1,1-tricarboxylate 
• 154016-47-4 (5-phenyl-isoxazol-3-yl)methylamine 

Relevant articles and documents

Synthesis of Fluorine-Containing Derivatives of 5-Arylisoxazoles and 4,5-Dichlorothiazole

Alkylation of fluorophenols and phenolic aldehydes with 5-phenyl(p-tolyl)-3-chloromethylisoxazole under the Williamson reaction conditions afforded the corresponding ethers. Condensation of the resulting phenolic aldehyde derivatives and 5-phenyl(p-tolyl)

Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators

Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.

Design, synthesis and biological evaluation of stilbene derivatives as novel inhibitors of protein tyrosine phosphatase 1B

By imitating the scaffold of lithocholic acid (LCA), a natural steroidal compound displaying Protein Tyrosine Phosphatase 1B (PTP1B) inhibitory activity, a series of stilbene derivatives containing phenyl-substituted isoxazoles were designed and synthesized. The structures of the title compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. Activities of the title compounds were evaluated on PTP1B and the homologous enzyme TCPTP by using a colorimetric assay. Most of the target compounds had good activities against PTP1B. Among them, compound 29 (IC50 = 0.91 ± 0.33 μM), characterized by a 5-(2,3-dichlorophenyl) isoxazole moiety, exhibited an activity about 14-fold higher than the lead compound LCA and a 4.2-fold selectivity over TCPTP. Compound 29 was identified as a competitive inhibitor of PTP1B with a Ki value of 0.78 μM in enzyme kinetic studies.