23598-72-3

Basic information

• Product Name: 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid
• Synonyms: 3-(2-CHLOROPHENYL)-5-METHYL-4-ISOZAZOLECARBOXYLIC ACID;3-(2-CHLOROPHENYL)-5-METHYLISOXAZOLE-4-CARBOXYLIC ACID, 98+%;3-(2-CHLOROPHENYL)-5-METHYLISOXAZOLE-4-CARBOXYLIC ACID (CMIC ACID);5-Methyl-3-(2-chlorophenyl)isoxazole-4-carboxylic acid;3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid;3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid (CMIC aci;4-Carboxy-3-(2-chlorophenyl)-5-methylisoxazole;4-Isoxazolecarboxylic acid, 3-(2-chlorophenyl)
• CAS NO: 23598-72-3
• Molecular Formula: C₁₁H₈ClNO₃
• Molecular Weight: 237.64
• EINECS: 245-770-0
• Product Categories: Oxazole&Isoxazole
• Mol File: 23598-72-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 186 °C
• Boiling Point: 374.5 °C at 760 mmHg
• Flash Point: 180.3 °C
• Appearance: Cream solid
• Density: 1.385 g/cm³
• Vapor Pressure: 2.83E-06mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 2.07±0.25(Predicted)
• BRN: 791928
• CAS DataBase Reference: 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid(23598-72-3)
• EPA Substance Registry System: 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid(23598-72-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-37/38-36
• Safety Statements: 26-36-36/37/39-22
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 23598-72-3(Hazardous Substances Data)

Usage

Description

3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid, also known as Cloxacillin EP Impurity D, is an organic compound with a chemical structure that features a chlorophenyl group, a methyl group, and an isoxazole-4-carboxylic acid moiety. It is characterized by its cream solid appearance and is known for its pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid is used as a key intermediate in the synthesis of isoxazolecarboxamides, which are a class of TGR5 agonists. These compounds have potential applications in the treatment of various metabolic disorders, such as non-alcoholic steatohepatitis (NASH), obesity, and type 2 diabetes, due to their ability to modulate bile acid signaling and improve energy homeostasis.
Additionally, 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid is utilized in the preparation of β-lactamase inhibitors. These inhibitors are essential in the development of antibiotics, as they protect β-lactam antibiotics from enzymatic degradation by bacterial β-lactamases, thereby enhancing the effectiveness of the antibiotics against bacterial infections.

InChI:InChI=1/C11H8ClNO3/c1-6-9(11(14)15)10(13-16-6)7-4-2-3-5-8(7)12/h2-5H,1H3,(H,14,15)

Upstream product

• 4357-94-2 methyl 3-(2'-chlorophenyl)-5-methylisoxazole-4-carboxylate 
• 83817-50-9 ethyl 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylate 
• 29568-74-9 2-chloro-N-hydroxybenzimidoyl chloride 
• 3717-28-0 2-chloro benzaldehyde oxime 
• 89-98-5 2-chloro-benzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 25629-50-9 3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride 
• 4414-58-8 3-(2-chloro-5-nitro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 91747-72-7 3-(2-Chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid cyclohexylamide 
• 25369-02-2 3-(2-Chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid phenylamide 
• 93666-06-9 2-[3-(2-Chloro-phenyl)-5-methyl-isoxazol-4-yl]-benzooxazole 
• 69047-46-7 3-(2-Chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid o-tolylamide 
• 80825-06-5 N-<3-(2-chlorophenyl)-5-methoxyisoxazol-4-carbonyl>phthalimide 
• 23891-95-4 C₂₂H₁₄Cl₂N₂O₅ 
• 352686-68-1 3-(2-chlorophenyl)-N-[4-(diethylamino)phenyl]-5-methylisoxazole-4-carboxamide 
• 61-72-3 cloxacillin 
• 4414-60-2 3-(2-chloro-5-hydroxy-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 4414-63-5 3-(2-chloro-5-hydroxy-phenyl)-5-methyl-isoxazole-4-carboxylic acid anilide 
• 53013-51-7 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamide 
• 4414-59-9 3-(5-amino-2-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 

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.

PHENYL-ISOXAZOL DERIVATIVES AND PREPARATION PROCESS THEREOF

Disclosed are a phenyl-isoxazol derivative compound, which is useful as a treatment material for virus infection, especially, infection of an influenza virus, or its pharmaceutically acceptable derivative, a preparation method thereof, and an illness treatment pharmaceutical composition including the compound as an active ingredient.

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).