4-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid
[CAS# 864725-62-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives
• Name: 4-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid
• Molecular Formula: C₁₈H₁₂Cl₂F₃NO₃
• Molecular Weight: 418.19
• CAS Registry Number: 864725-62-2
• EC Number: 888-585-6
• SMILES: CC1=C(C=CC(=C1)C2=NOC(C2)(C3=CC(=CC(=C3)Cl)Cl)C(F)(F)F)C(=O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

4-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid is a complex organic compound characterized by a substituted benzoic acid moiety linked to a dihydroisoxazole ring, which is further substituted with dichlorophenyl and trifluoromethyl groups. The molecular structure incorporates multiple functional groups that contribute to its chemical behavior and potential biological activity.

The compound belongs to a class of molecules containing the isoxazole ring system, a five-membered heterocycle consisting of three carbon atoms, one nitrogen atom, and one oxygen atom. The 4,5-dihydroisoxazole designation indicates partial saturation of the isoxazole ring, altering its electronic properties and reactivity. The presence of electron-withdrawing groups such as trifluoromethyl and dichlorophenyl substituents influences the molecule’s lipophilicity, metabolic stability, and interaction with biological targets.

Synthetically, the construction of this molecule typically involves cycloaddition or condensation reactions to form the isoxazole ring, followed by selective substitution to introduce the dichlorophenyl and trifluoromethyl groups. The benzoic acid portion is functionalized with a methyl group at the 2-position, which can affect acidity and steric interactions.

Such compounds have been explored in medicinal chemistry due to their potential as modulators of various biological pathways, including enzyme inhibition and receptor binding. The trifluoromethyl group is known to enhance metabolic stability and membrane permeability, making these molecules attractive candidates for drug development. Additionally, the dichlorophenyl substituent may contribute to increased binding affinity through hydrophobic interactions.

Applications of molecules with similar structural features include use as anti-inflammatory agents, agrochemicals, and components of material science research. The benzoic acid moiety provides a handle for further chemical modifications, enabling the design of derivatives with tailored pharmacokinetic and pharmacodynamic properties.

Physicochemical properties such as solubility, melting point, and spectral characteristics are determined by the balance of hydrophobic and polar groups. Analytical methods like nuclear magnetic resonance spectroscopy, mass spectrometry, and infrared spectroscopy confirm the structure and purity of the compound.

In summary, 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid is a heterocyclic compound featuring multiple substituents that influence its chemical and potential biological properties. Its synthesis and functionalization make it a valuable molecule in the context of pharmaceutical and chemical research.

References

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