1868-48-0

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Bis(trifluoromethyl)-1,3,4-oxadiazole is used as a building block for the synthesis of new drug candidates due to its strong electron-withdrawing properties, which can enhance the pharmacological activity and selectivity of the resulting compounds.
Used in Agrochemical Industry:
In the agrochemical field, 2,5-Bis(trifluoromethyl)-1,3,4-oxadiazole is utilized as a component in the development of novel agrochemicals, leveraging its electron-withdrawing properties to improve the efficacy and selectivity of these compounds.
Used in Materials Science:
2,5-Bis(trifluoromethyl)-1,3,4-oxadiazole is employed as a building block for the construction of functional materials, where its electron-withdrawing nature can contribute to the creation of materials with unique properties for various applications.
Used in Organic Electronic Devices:
2,5-BIS(TRIFLUOROMETHYL)-1,3,4-OXADIAZOLE has been studied for its potential application in organic electronic devices, where its strong electron-withdrawing properties can be harnessed to improve the performance of these devices.
Used in Molecular Architecture:
2,5-Bis(trifluoromethyl)-1,3,4-oxadiazole is also used as a building block for the construction of novel molecular architectures, where its unique properties can lead to the development of innovative chemical entities with diverse applications in chemical and materials science.

InChI:InChI=1/C4F6N2O/c5-3(6,7)1-11-12-2(13-1)4(8,9)10

Upstream product

• 354-32-5 trifluoracetyl chloride 
• 2925-21-5 5-(trifluoromethyl)tetrazole 
• 76-05-1 trifluoroacetic acid 
• 667-35-6 1,2-bis(trifluoroacetyl)hydrazine 
• 155184-23-9 (Z,Z)-2,5-diiodo-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 758-84-9 1--2--hydrazin 
• 121607-96-3 3,5-bis(trifluoromethyl)-4-(3'-methoxyphenyl)-4H-1,2,4-triazole 
• 121607-97-4 3,5-bis(trifluoromethyl)-4-(2'-methoxyphenyl)-4H-1,2,4-triazole 
• 121608-07-9 3,5-bis(trifluoromethyl)-4-(2',4'-dichlorophenyl)-4H-1,2,4-triazole 
• 121608-02-4 3,5-bis(trifluoromethyl)-4-(3'-trifluoromethylphenyl)-4H-1,2,4-triazole 
• 121607-98-5 3,5-bis(trifluoromethyl)-4-(4'-methylphenyl)-4H-1,2,4-triazole 
• 121608-06-8 3,5-bis(trifluoromethyl)-4-(4'-chlorophenyl)-4H-1,2,4-triazole 
• 121607-95-2 3,5-bis(trifluoromethyl)-4-(4'-methoxyphenyl)-4H-1,2,4-triazole 
• 121607-94-1 3,5-bis(trifluoromethyl)-4-(4'-chlorophenylmethyl)-4H-1,2,4-triazole 
• 128097-70-1 2,5-endo,endo-diphenyl-1,4-bis(trifluoromethyl)-7-oxabicyclo<2.2.1>heptane 
• 121608-05-7 3,5-bis(trifluoromethyl)-4-(3'-fluorophenyl)-4H-1,2,4-triazole 
• 121608-11-5 3,5-bis(trifluoromethyl)-4-(2',6'-diethylphenyl)-4H-1,2,4-triazole 
• 121608-01-3 3,5-bis(trifluoromethyl)-4-(4'-trifluoromethylphenyl)-4H-1,2,4-triazole 
• 88579-71-9 3,5-bis(trifluoromethyl)-4-phenyl-4H-1,2,4-triazole 

Relevant academic research and scientific papers

Improved synthesis of perfluoroalkyl substituted 1,3,4-oxadiazoles as precursors for corresponding 1,2,4-triazoles

An improved and more efficient synthesis of 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole (2a), 2,5-bis(perfluoroethyl)-1,3,4-oxadiazole (2b), 2-(perfluoroethyl)-5-(trifluoromethyl)-1,3,4-oxadiazole (2d) and 2-(perfluoroheptyl)-5-(trifluoromethyl)-1,3,4-oxadi

Synthesis of a series of trifluoromethylazoles and determination of pKa of acidic and basic trifluoromethyl heterocycles by 19F NMR spectroscopy

Trifluoroacetylation at the 5-position of 3,4-dihydro-2H-pyran and the 3-position of 4,5-dihydrofuran, followed by treatment with hydrazine, gave 3-(3-trifluoromethyl-1H-pyrazol-4-yl)propanol and 2-(3-trifluoromethyl-1H-pyrazol-4-yl)ethanol, respectively.In the latter case, an intermediate dimer was isolated.Isomeric 2-(3-trifluoromethyl-1H-pyrazol-5-yl)ethanol was formed by reaction of hydrazine with 6-benzyloxy-1,1,1-trifluorohex-3-yn-2-one and deprotection.Reaction of 3-benzyloxypropylamine with 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole, followed by deprotection, afforded 3-propanol.A series of 2-trifluoromethyl-1H-benzimidazoles and 2-trifluoromethyl-3H-imidazopyridines were prepared by condensation of the appropriate ortho-arenediamine with trifluoroacetic acid.Analysis of the 19F NMR spectra of the trifluoromethylazoles and of 3-trifluoromethylpyridine in aqueous solution at different pHs enabled determination of pKa values.All the compounds evaluated had one or more pKa between 1 and 13, except the triazole.Several compounds were identified as having potential use in measuring pH in biological media by 19F NMR spectroscopy.

Perfluoro-1,3,4-oxadiazoles

Some new polyfluorinated 1,3,4-oxadiazoles have been obtained via a two-step method.The cycloadditions of the 1,3,4-oxadiazoles have been studied and an analysis of the energies of the frontier orbitals calculated by the MNDO method indicates a LUMO-dependent pathway for cycloaddition.

Unsaturated nitrogen compounds containing fluorine. Part 10. Reaction of 2,5-dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene with halide ion and oxygen- and sulphur-centred nucleophiles and of its 2,5-di-iodo analogue with reducing agents and certain nucleophiles

The azines CF3CR=NN=CRCF3 (R = F, I, PhO, 2,4-Cl2C6H3O, PhS and EtO) are formed by treatment of the title dichloroazine 1 with an excess of the appropriate nucleophile, while reaction with phosphorus (V) sulphide at 180 deg C gives 2,5-bis(trifluoromethyl-1,3,4-thiadiazole in quantitative yield.In the reaction with NaOEt, the compound CF3C(OEt)=NN=C(ONa)CF3 is also produced from the NaOH impurity present.Di-iodoazine 3b undergoes ready reaction with aniline (1:2 molar ratio) and potassium diethyl phenylmalonate (1:1 molar ratio) to afford the monosubstituted compounds PhN=C(CF3)NHN=CICF3 and (EtO2C)2PhC(CF3)=NN=CICF3, respectively.Azine 1 is not reduced by the reagents NaH, LiAlH4 and NaBH4, but di-iodoazine 3b is reduced by tri-n-butyltin hydride at c. 90 deg C to give mainly the compounds CF3CH=NN=CHCF3, CF3CH=NN=CICF3, CFCH2NHN=CICF3 and possibly CF3CH=NNHCH2CF3; with hydrogen iodide at 200 deg C, the major products are the hydroazines CF3CH=NN=CHCF3 and CF3CH=NN=CICF3 and 2,4,6-tris(trifluoromethyl)-1,3,5-triazene.

Reaction of 2,5-Bis(trifluoromethyl)-1,3,4-oxadiazole with Primary Amines. Synthesis of 4-Substituted-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles

Reaction of 3,5-bis(trifluoromethyl)-1,3,4-oxadiazole (1a) with primary amines under a variety of conditions conveniently produced 4-substituted-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles 4a in 26-85percent yield.Alkyl amines reacted with 1a in methanol