477886-85-4

Usage

General Description

1,3,4-Oxadiazole, 2-[4-(trifluoromethyl)phenyl]- is a chemical compound with the molecular formula C9H5F3N2O. It is a white to yellow crystalline solid with a molecular weight of 208.1 g/mol. 1,3,4-Oxadiazole, 2-[4-(trifluoromethyl)phenyl]- is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential applications in materials science, particularly as a building block for the construction of organic semiconductors and optoelectronic devices. Additionally, 1,3,4-Oxadiazole, 2-[4-(trifluoromethyl)phenyl]- has been investigated for its biological and pharmacological properties, with potential applications in the development of new drugs and therapeutic agents.

Upstream product

• 339-59-3 4-(trifluoromethyl)benzoic acid hydrazide 
• 1895-39-2 sodium chlorodifluoroacetate 
• 455-13-0 4-Iodobenzotrifluoride 
• 68-12-2 N,N-dimethyl-formamide 
• 43100-38-5 4-tert-butylbenzoic acid hydrazide 
• 122-51-0 orthoformic acid triethyl ester 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1218811-71-2 2-[(4-methylphenyl)ethynyl]-5-(4-trifluoromethylphenyl)-1,3,4-oxadiazole 
• 724434-37-1 2-phenyl-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole 
• 1236115-27-7 methyl 5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazole-2-carboxylate 
• 455-18-5 4-CF₃C₆H₄CN 
• 1261274-34-3 rac-S-methyl-S-phenyl-N-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]sulfoximine 
• 1207551-78-7 2-(phenylethynyl)-5-(4-trifluoromethylphenyl)-1,3,4-oxadiazole 
• 1350919-95-7 2-[(E)-2-phenylvinyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole 
• 1374348-21-6 2-(naphthalen-1-ylethynyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazole 

Relevant academic research and scientific papers

[4u202f+u202f1] Cyclization of benzohydrazide and ClCF2COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5

A facile synthesis of 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5 via [4 + 1] cyclization of ClCF2COONa with non-amine compounds containing amino groups is developed. Of note, this is the first time that halofluorinated compounds are used as C1 synthon to construct deuterated nitrogen-heterocyclic compounds. The current protocol features simple operation, readily accessible raw materials, wide substrate scope and valuable products

Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds

The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.

Functionalization of 1,3,4-Oxadiazoles and 1,2,4-Triazoles via Selective Zincation or Magnesiation Using 2,2,6,6-Tetramethylpiperidyl Bases

We report the metalation of the 1,3,4-oxadiazole and 1,2,4-triazole scaffolds via regioselective zincation or magnesiation using the TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) TMP2Zn·2LiCl, TMP2Zn·2MgCl2·2LiCl, TMPMgCl

Ligand-Enabled Palladium-Catalyzed Through-Space C?H Bond Activation via a Carbopalladation/1,4-Pd Migration/C?H Functionalization Sequence

We report, herein, a palladium-catalyzed cascade comprising carbopalladation, 1,4-Pd-migration and C(sp2)?C(sp2) bond formation to construct a variety of bis-heterocyclic frameworks in a single operational step. The methodology provi

Method for one-step construction of 2-(4-trifluoromethyl phenyl)-1,3,4-oxadiazole by taking DMF (dimethyl formamide) as carbon source

The invention discloses a method for one-step construction of 2-(4-trifluoromethyl phenyl)-1,3,4-oxadiazole by taking DMF (dimethyl formamide) as a carbon source. In the method, p-trifluoromethyl benzoyl hydrazine is used as a reaction raw material, and t

DMF as Methine Source: Copper-Catalyzed Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles

An unprecedented Cu-catalyzed direct annulation of hydrazides with N,N-dimethylformamide (DMF) was developed, providing an efficient synthesis of valuable 1,3,4-oxadiazoles. This process features the short reaction time and can be safely conducted on gram scale. The reaction also facilitated the convenient synthesis of 1,3,4-oxadiazole-2(3H)-ones. Moreover, the mechanistic studies suggest that the source of CH is from the N-methyl group of DMF. (Figure presented.).

Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues

Palladium-catalyzed intramolecular carbopalladation onto allenamides completed by direct C-H allylation of heterocycles is studied. The domino construction/heteroarylation of isoquinolone process is first achieved. A general three-step one-pot strategy, i

(NHC)Cu-Catalyzed Mild C-H Amidation of (Hetero)arenes with Deprotectable Carbamates: Scope and Mechanistic Studies

Primary arylamines are an important unit broadly found in synthetic, biological, and materials science. Herein we describe the development of a (NHC)Cu system that mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A facile stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of tBuONa base made this transformation catalytic under mild conditions. The present (NHC)Cu-catalyzed C-H amidation works efficiently and selectively on a large scale over a range of arenes including polyfluorobenzenes, azoles, and quinoline N-oxides. Deprotection of the newly installed carbamate groups such as Boc and Cbz was readily performed to afford the corresponding primary arylamines.

Pd(OAc)2 catalyzed C-H activation of 1,3,4-oxadiazoles and their direct oxidative coupling with benzothiazoles and aryl boronic acids using Cu(OAc)2 as an oxidant

The first direct oxidative coupling of 1,3,4-oxadiazoles with benzothiazoles has been accomplished using Pd(OAc)2 as a catalyst and Cu(OAc)2 as an oxidant. The similar combination of the catalyst and the oxidant has also been applied for direct arylation of 1,3,4-oxadiazoles with aryl boronic acids. Several novel oxadiazole derivatives have been prepared in high yields following both the methods.

Transition metal-free direct C-H bond thiolation of 1,3,4-oxadiazoles and related heteroarenes

A convenient transition metal-free procedure for the direct thiolation of 1,3,4-oxadiazole C-H bonds using diaryl disulfides has been developed. Other substrates including indole, benzothiazole, N-phenylbenzimidazole, and caffeine were also thiolated in this manner, providing the corresponding products in good to excellent yields. This journal is