153168-59-3

Basic information

• Product Name: 2,6-dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol
• Synonyms: 2,6-dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol
• CAS NO: 153168-59-3
• Molecular Formula: C₁₁H₉F₃N₂O₂
• Molecular Weight: 258.2
• Mol File: 153168-59-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,6-dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol(153168-59-3)
• EPA Substance Registry System: 2,6-dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol(153168-59-3)

Safety Data

• Hazardous Substances Data: 153168-59-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol is used as a potential building block for the development of new drugs due to its unique structure and properties. Its presence in pharmaceuticals can be attributed to the oxadiazole and trifluoromethyl groups, which are known for their diverse biological activities and potential to enhance drug efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical sector, 2,6-dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol is used as a precursor or intermediate in the synthesis of new pesticides. Its specific functional groups can be tailored to target pests or diseases, offering a novel approach to crop protection and potentially leading to more effective and environmentally friendly agrochemicals.
Used in Material Science:
2,6-dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol is utilized in material science for the development of materials with specific functional characteristics. Its unique molecular structure can contribute to the creation of materials with tailored properties, such as improved thermal stability, flame retardancy, or specific optical and electronic properties, depending on the intended application.
Further research is necessary to fully explore the potential uses and effects of 2,6-dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol in these industries, as well as to understand its safety profile and optimize its synthesis for large-scale applications.

Upstream product

• 162854-15-1 N',4-dihydroxy-3,5-dimethylbenzimidamide 
• 407-25-0 trifluoroacetic anhydride 
• 4198-90-7 3,5-dimethyl-4-hydroxybenzonitrile 

Downstream Products

• 174523-36-5 3-[4-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-butyl]-pyridine 
• 162854-24-2 6-methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine 
• 174523-30-9 2-chloro-5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine 
• 174523-32-1 2-methoxy-5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine 
• 174523-29-6 2-fluoro-5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine 
• 174523-35-4 2-acetyl-6-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine 
• 174523-69-4 3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-quinoline 

Relevant articles and documents

OXADIAZOLE COMPOUND AND PREPARATION METHOD THEREOF, PHARMACEUTICAL COMPOSITION AND USE THEREOF

The present invention provides an anti-Coxsackie virus oxadiazole compound as represented by formula (I), or the pharmaceutically acceptable salt thereof, a preparation method, a pharmaceutical composition, and use thereof, wherein R is CH3 or CF3; R' and R are respectively H, alkyl or halogen; A is O or S; n is a number from 1 to 6; X is O, S or NH; Y is alkyl, unsubstituted cycloalkyl, mono-substituted cycloalkyl, disubstituted cycloalkyl, poly-substituted cycloalkyl, unsubstituted aryl, mono-substituted aryl, disubstituted aryl, poly-substituted aryl, unsubstituted 5-6 membered heterocyclyl, mono-substituted 5-6 membered heterocyclyl, disubstituted 5-6 membered heterocyclyl, or poly-substituted 5-6 membered heterocyclyl. Compared to prior art, the oxadiazole compound of the present invention has excellent anti-Coxsackie virus activity, lower toxicity and high safety.

OXADIAZOLE COMPOUND AND PREPARATION METHOD THEREOF, PHARMACEUTICAL COMPOSITION AND USE THEREOF

The present invention provides an anti-Coxsackie virus oxadiazole compound as represented by formula (I), or the pharmaceutically acceptable salt thereof, a preparation method, a pharmaceutical composition, and use thereof, wherein R is CH3 or CF3; R′ and

Picornavirus Inhibitors: Trifluoromethyl Substitution Provides a Global Protective Effect against Hepatic Metabolism

Several modifications of the oxazoline ring of WIN 54954, a broad spectrum antipicornavirus compound, have been prepared in order to address the acid lability and metabolic instability of this compound.We have previously shown that the oxadiazole analogue 3 displayed comparable activity against a variety of rhinoviruses and appeared to be stable to acid.A monkey liver microsomal assay was developed to examine the metabolic stability in vitro of both compounds, and it was determined that WIN 54954 displayed 18 metabolic products while 3 was converted to 8 products.Two major products of 3 were determined by LC-MS/MS to be monohydroxylated at each of the terminal methyl groups.Replacement of the methyl on the isoxazole ring with a trifluoromethyl group, while preventing hydroxylation at this position, did not reduce the sensitivity of the molecule to microsomal metabolism at other sites.However, the (trifluoromethyl)oxadiazole 9 not only prevented hydroxylation at this position but also provided protection at the isoxazole end of the molecule, resulting in only two minor products to the extent of 4percent.The major product was identified as the monohydroxylated compound 23.The global metabolic protective effect of trifluoromethyl group on the oxadiazole ring was further demonstrated by examining a variety of analogues including heterocyclic replacements of the isoxazole ring.In each case, the trifluoromethyl analogue displayed a protective effect when compared to the corresponding methyl analogue.

1,2,4-OXADIAZOLYL-PHENOXYALKYLISOXAZOLES AND THEIR USE AS ANTIVIRAL AGENTS

Compounds of the formula wherein: R1 is alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, or cyanomethyl; Y is alkylene of 3 to 9 carbon atoms, R2 and R3 independently are hydrogen, alkyl, alkoxy, halo, cyano, trifluoromethyl and nitro; R4 is alkoxy, hydroxy, halomethyl, dihalomethyl, trihalomethyl, dihaloethyl, cycloalkyl, heterocyclyl, alkoxycarbonyl, hydroxyalkyl, alkoxyalkyl, alkanecarbonyloxyalkyl, cyano, halo, thioalkyl, alkylthioalkyl, alkylthio, thio, 2,2,2-trifluoro-ethyl, (4-methylphenyl)sulfonyloxymethyl, N=Q or CON=Q, where N=Q is amino, alkylamino or dialkylamino; R5 is hydrogen or halo or alkyl