829-35-6

Usage

Uses

Used in Pharmaceutical Applications:
2-(4-methoxyphenyl)-1,3,4-oxadiazole is utilized as a pharmaceutical agent for its antimicrobial, anti-inflammatory, and antiviral properties, making it a candidate for the development of new drugs to combat various infections and inflammatory conditions.
Used in Agricultural Applications:
In agriculture, 2-(4-methoxyphenyl)-1,3,4-oxadiazole is employed as a bioactive compound to protect crops from microbial infections and pests, thereby enhancing crop yield and quality.
Used in Fluorescent Probes for Biological Imaging:
2-(4-methoxyphenyl)-1,3,4-oxadiazole is used as a fluorescent probe in biological imaging due to its unique optical properties, allowing for the visualization and tracking of biological processes at the molecular level.
Used in Organic Synthesis as a Building Block:
2-(4-methoxyphenyl)-1,3,4-oxadiazole serves as a key building block in organic synthesis, enabling the creation of various derivatives with diverse biological and chemical properties, which can be further explored for their potential applications in different industries.

InChI:InChI=1/C9H8N2O2/c1-12-8-4-2-7(3-5-8)9-11-10-6-13-9/h2-6H,1H3

Upstream product

• 74-83-9 methyl bromide 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 149-73-5 trimethyl orthoformate 
• 696-62-8 para-iodoanisole 
• 1895-39-2 sodium chlorodifluoroacetate 
• 68-12-2 N,N-dimethyl-formamide 
• 536-74-3 phenylacetylene 
• 100-42-5 styrene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 100-09-4 4-methoxybenzoic acid 
• 94-30-4 ethyl 4-methoxybenzoate 
• 121-98-2 methyl 4-methoxybenzoate 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 1026396-33-7 (1-{hydroxy-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-methyl}-2-methyl-propyl)-carbamic acid tert-butyl ester 
• 1181219-09-9 (E)-2-(1,2-diphenylvinyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 93986-11-9 2-(4-chlorophenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 313662-94-1 2-(4-bromo-phenyl)-5-(4-methoxy-phenyl)-1,3,4-oxadiazole 
• 847-39-2 2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole 
• 1065124-08-4 4-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)benzonitrile 
• 944672-79-1 2-benzyl-5-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 842-79-5 2-(4-methoxy-phenyl)-5-phenyl-[1,3,4]oxadiazole 
• 23767-54-6 4-[5-(4-methoxy-phenyl)-1,3,4-oxadiazol-2-yl]morpholine 
• 944907-16-8 C₁₀H₈N₂O₄ 
• 1236115-28-8 methyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate 
• 1261274-33-2 rac-N-[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]-S-methyl-S-phenylsulfoximine 
• 5306-49-0 2-(N,N-dimethylamino)-5-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 1304685-42-4 N,N-diethyl-5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-amine 

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.

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

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

Method for one-step construction of 2-(4-methoxyphenyl)-1,3,4-oxadiazole by using DMF as carbon source

The invention discloses a method for one-step construction of 2-(4-methoxyphenyl)-1,3,4-oxadiazole by using DMF (N,N-dimethylformamide) as a carbon source. According to the present invention, 2-(4-methoxyphenyl)-1,3,4-oxadiazole is subjected to one-step c

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

Synthesis of 1,3,4-Oxadiazoles via Annulation of Hydrazides and Benzene-1,3,5-triyl Triformate under Metal-Free Conditions

A new and efficient method for the synthesis of 1,3,4-oxadiazoles via the annulation of hydrazides with benzene-1,3,5-triyl triformate (TFBen) under metal-free conditions is reported. A broad range of hydrazides were transformed into the corresponding 1,3

(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.

Iodine-Mediated Domino Oxidative Cyclization: One-Pot Synthesis of 1,3,4-Oxadiazoles via Oxidative Cleavage of C(sp2)-H or C(sp)-H Bond

An I2-promoted, metal-free domino protocol for one-pot synthesis of 1,3,4-oxadiazoles has been developed via oxidative cleavage of C(sp2)-H or C(sp)-H bonds, followed by cyclization and deacylation. In this reaction, the use of K2CO3 as a base is found to be an essential factor in the cyclization and the C-C bond cleavage. This procedure proceeded smoothly in moderate to high yields with good functional group compatibility.