16883-16-2

Basic information

• Product Name: 5-Methyl-3-phenylisoxazole-4-carbonyl chloride
• Synonyms: 5-methyl-3-phenyl-1,2-oxazole-4-carbonylchloride;5-methyl-3-phenyl-4-isoxazolecarbonylchlorid;5-Methyl-3-phenyl-4-isoxazolecarbonylchloride;PMIC CHLORIDE;3-PHENYL-5-METHYLISOXAZOLE-4-CARBONYL CHLORIDE;5-METHYL-3-PHENYLISOXAZOLE-4-CARBONYL CHLORIDE;5-METHYL-3-PHENYL-4-CHLOROCARBONYL ISOXAZOLE;BUTTPARK 43\57-11
• CAS NO: 16883-16-2
• Molecular Formula: C₁₁H₈ClNO₂
• Molecular Weight: 221.64
• EINECS: 240-915-4
• Product Categories: Oxazole&Isoxazole
• Mol File: 16883-16-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 24 °C
• Boiling Point: 371.9 °C at 760 mmHg
• Flash Point: >100
• Appearance: /
• Density: 1.27
• Vapor Pressure: 9.97E-06mmHg at 25°C
• Refractive Index: 1.562
• Solubility: soluble in Methanol
• PKA: -4.78±0.50(Predicted)
• Water Solubility: 701.8mg/L at 25℃
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 5-Methyl-3-phenylisoxazole-4-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-3-phenylisoxazole-4-carbonyl chloride(16883-16-2)
• EPA Substance Registry System: 5-Methyl-3-phenylisoxazole-4-carbonyl chloride(16883-16-2)

Safety Data

• Hazard Codes: C,Xi
• Statements: 22-34-36
• Safety Statements: 26-36/37/39-45-26/36/37/39/45-20
• RIDADR: UN3261
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 16883-16-2(Hazardous Substances Data)

Usage

Uses

Used as Intermediate of oxacillin sodium.

Flammability and Explosibility

Notclassified

Synthesis

Benzaldehyde and hydroxylamine hydrochloride are oximeated under alkaline conditions to generate benzoxime, which is then chlorinated with chlorine to give benzoxime chloride. It is combined with ethyl acetoacetate to hydrolyze and chlorinated to obtain 5-Methyl-3-phenylisoxazole-4-carbonyl chloride.

InChI:InChI=1/C11H8ClNO2/c1-7-9(11(12)14)10(13-15-7)8-5-3-2-4-6-8/h2-6H,1H3

Upstream product

• 6249-80-5 1-phenylbut-3-en-1-one 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 31295-65-5 4-bromo-5-methyl-3-phenylisoxazole 
• 1008-74-8 5-methyl-3-phenylisoxazole 
• 68843-67-4 1-phenyl-but-3-en-1-one oxime 
• 932-90-1 Benzaldoxime 
• 698-16-8 benzohydroximoyl chloride 
• 100-52-7 benzaldehyde 
• 2065-28-3 methyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 35166-26-8 5-methyl-3-phenyl-4-isoxazoloyl carboxylic acid 
• 1136-45-4 5-methyl-3-phenylisoxazol-4-carboxylic acid 

Downstream Products

• 66-79-5 oxacillin 
• 2065-28-3 methyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 61728-31-2 5-methyl-3-phenyl-isoxazole-4-carboxylic acid 2,2,2-trifluoro-ethyl ester 
• 24477-32-5 5-methyl-3-phenyl-isoxazole-4-carboxylic acid 4-sulfamoyl-phenethylamide 
• 53646-02-9 5-methyl-3-phenyl-isoxazole-4-carboxylic acid 2-nitro-anilide 
• 68055-50-5 1,2-Bis(3'-phenyl-5'-methyl-4'-isoxazolyl)hydrazine 
• 18336-75-9 5-methyl-3-phenylisoxazole-4-carbohydrazide 
• 106833-69-6 1-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-pyrrolidine 
• 55153-42-9 4-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-morpholine 
• 268748-84-1 4-isocyanato-5-methyl-3-phenyl-1,2-oxazole 
• 93599-37-2 4-(4',5'-dihydro-4',4'-dimethyl-Δ²-oxazolin-2-yl)-5-methyl-3-phenylisoxazole 
• 93599-45-2 4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-ethyl-3-phenyl-isoxazole 
• 99298-70-1 C₁₅H₁₅⁽²⁾HN₂O₂ 
• 99298-84-7 C₁₆H₁₇⁽²⁾HN₂O₂ 

Relevant articles and documents

Design, synthesis, and bioevaluation of substituted phenyl isoxazole analogues as herbicide safeners

Herbicide safeners enhance herbicide detoxification in crops without affecting target weed sensitivity. To enhance crop tolerance to the toxicity-related stress caused by the herbicide acetochlor (ACT), a new class of substituted phenyl isoxazole derivatives was designed by an intermediate derivatization method as herbicide safeners. Microwave-assisted synthesis was used to prepare the phenyl isoxazole analogues, and all of the structures were confirmed via IR, 1H NMR, 13C NMR, and HRMS. Compound I-1 was further characterized by X-ray diffraction analysis. Bioassay results showed that most of the obtained compounds provided varying degrees of safening against ACT-induced injury by increasing the corn growth recovery, glutathione content, and glutathione S-transferase activity. In particular, compound I-20 showed excellent safener activity against ACT toxicity, comparable to that of the commercial safener benoxacor. Gaussian calculations have been performed and the results indicated that the nucleophilic ability of compound I-20 is higher than that of benoxacor, thus the activity is higher than that of benoxacor. These findings demonstrate that phenyl isoxazole derivatives possess great potential for protective management in cornfields.

Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin

A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).

Synthesis of 1,2,3-triazole substituted isoxazoles via copper (I) catalyzed cycloaddition

The synthesis of a series of 3,5-disubstituted isoxazole-4-carboxylic esters containing N-substituted 1,2,3-triazoles (V) starting from various benzaldehydes (I) is reported. Benzaldehydes undergo oximation with hydroxylamine hydrosulfate. Later, chlorination followed by condensation with methylacetoacetate and the hydrolysis of the resulting ester afforded respective carboxylic acid (II), which on chlorination with PCl5 gave the corresponding acid chlorides (III). The coraboxylic acid chlorides (III) on propargylation gave propargylic esters (IV) and these on click reaction gave the title compounds (V).