52596-94-8

Basic information

• Product Name: methyl 4-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl ether
• Synonyms: 2-(4-methoxyphenyl)-5-(4-methylphenyl)-1,3,4-oxadiazole;methyl 4-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl ether
• CAS NO: 52596-94-8
• Molecular Formula: C₁₆H₁₄N₂O₂
• Molecular Weight: 266.29456
• Mol File: 52596-94-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 4-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl ether(52596-94-8)
• EPA Substance Registry System: methyl 4-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl ether(52596-94-8)

Safety Data

• Hazardous Substances Data: 52596-94-8(Hazardous Substances Data)

Upstream product

• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 874-60-2 4-methyl-benzoyl chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 3619-22-5 p-toluic hydrazide 
• 6926-51-8 5-(4-methoxyphenyl)-2H-tetrazole 
• 67-66-3 chloroform 
• 624-31-7 4-tolyl iodide 
• 874-90-8 4-methoxybenzonitrile 
• 24994-04-5 5-(p-tolyl)-1H-tetrazole 
• 100-09-4 4-methoxybenzoic acid 
• 7163-50-0 (4-methylphenyl)(oxo)acetic acid 
• 827-58-7 2-p-tolyl-1,3,4-oxadiazole 
• 141339-54-0 bis(4-anisyl)iodonium triflate 
• 829-35-6 2-(4-methoxyphenyl)-1,3,4-oxadiazole 

Downstream Products

• 59136-19-5 2-(4-methoxy-phenyl)-5-{4-[2-(5-methyl-2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-[1,3,4]oxadiazole 
• 59098-55-4 2-(4-methoxy-phenyl)-5-{4-[2-(2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-[1,3,4]oxadiazole 
• 52822-97-6 2-[4-(trans-2-dibenzofuran-2-yl-vinyl)-phenyl]-5-(4-methoxy-phenyl)-[1,3,4]oxadiazole 
• 52822-24-9 2-[4-(trans-2-dibenzofuran-3-yl-vinyl)-phenyl]-5-(4-methoxy-phenyl)-[1,3,4]oxadiazole 
• 72094-05-4 5-(4-methoxy-phenyl)-3-(4-{4-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-trans-styryl}-phenyl)-[1,2,4]oxadiazole 
• 65965-75-5 2-(4-{4-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-styryl}-phenyl)-[1,2,4]triazolo[1,5-a]pyridine 
• 59151-79-0 2-(4-methoxy-phenyl)-5-{4-[4-(4-phenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 
• 59151-71-2 2-(4-methoxy-phenyl)-5-{4-[4-(2-phenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 
• 37430-91-4 2-(4-{4-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-trans-styryl}-phenyl)-2H-naphtho[1,2-d][1,2,3]triazole 
• 71944-65-5 2-(4-methoxy-phenyl)-5-{4-[4-(3-phenyl-pyrazol-1-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 
• 71944-80-4 2-{4-[4-(2,5-diphenyl-2H-pyrazol-3-yl)-styryl]-phenyl}-5-(4-methoxy-phenyl)-[1,3,4]oxadiazole 
• 71944-69-9 2-(4-methoxy-phenyl)-5-{4-[4-(1-phenyl-1H-pyrazol-3-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 
• 71944-72-4 2-(4-{4-[1-(4-chloro-phenyl)-1H-pyrazol-3-yl]-styryl}-phenyl)-5-(4-methoxy-phenyl)-[1,3,4]oxadiazole 

Relevant articles and documents

UV-Induced 1,3,4-Oxadiazole Formation from 5-Substituted Tetrazoles and Carboxylic Acids in Flow

A range of 1,3,4-oxadiazoles have been synthesized using a UV-B activated flow approach starting from carboxylic acids and 5-substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino acids.

Columnar self-assembly, gelation and electrochemical behavior of cone-shaped luminescent supramolecular calix[4]arene LCs based on oxadiazole and thiadiazole derivatives

A new class of blue light-emitting supramolecular liquid crystalline cone or bowl-shaped compounds were synthesized from substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles inbuilt with ester groups containing substituted alkoxy side chains (-OC4H9,-OC8H17) at the lower rim of calix[4]arene. These supramolecular compounds were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), high-temperature X-ray diffraction (XRD), cyclic voltammetry (CV) and photophysical behavior studies. It was observed that the 1,3,4-thiadizole calix[4]arene-based derivatives are more capable of stabilizing the hexagonal columnar phase over a broad thermal range compared to the 1,3,4-oxadiazole calix[4]arene derivatives. The cone-shaped calixarene-based LCs with terminally substituted alkyl chains are packed into columns with enhanced intermolecular interactions. Moreover, the 1,3,4-oxadiazole calix[4]arene derivatives show deeper blue emissions compared to the 1,3,4-thidiazole calix[4]arene derivatives in solution as well as in thin films. The thermal and photophysical behaviors of the synthesized bowl-shaped supramolecular derivatives are extremely dependent on the terminal substituted alkoxy chains on the lower rim of calix[4]arene. Due to their hexagonal columnar phases and the emissive nature of their supramolecular liquid crystal and xerogel states, these molecules are favourable for application in emissive electronic displays. The 1,3,4-thiadiazole calix[4]arene derivatives display lower band gaps than the 1,3,4-oxadiazole calix[4]arene derivatives and are considered to be promising entities for applications in organic light emitting diodes (OLEDs).

Photocatalyzed facile synthesis of 2,5-diaryl 1,3,4-oxadiazoles with polyaniline-?g-C3N4-TiO2 composite under visible light

PANI (polyaniline)-g-C3N4-TiO2 composite was prepared and found to be efficient for the synthesis of 2,5-diaryl 1,3,4-oxadiazoles under visible light. This reaction involved decarboxylation and cyclization from α-keto acids with acylhydrazines, and a broad scope of substrates were tolerated to provide the desired products in moderate to good yields. Control experiments indicated that a radical pathway was involved in the present photocatalytic reaction and a synergistic effect may exist in the ternary composite. Moreover, this semiconductor photocatalyst could be readily recovered and showed good reusability with only slight decrease in the catalytic activity after six consecutive runs.

One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted N-Acylation of Aryl Tetrazoles with Aldehydes

A metal- and base-free protocol for one-pot synthesis of 2,5-diaryl 1,3,4-oxadiazoles via a radical-promoted cross-dehydrogenative coupling strategy was developed. This reaction involved the N-acylation of aryl tetrazoles with aryl aldehydes, followed by thermal rearrangement. A wide range of aryl tetrazoles and aryl aldehydes survived the reaction conditions to deliver the corresponding products in moderate to good yields. (Chemical Equation Presented).

Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,3,4-Oxadiazoles using Chloroform as the Carbon Monoxide Source

A palladium-catalyzed aminocarbonylation reaction of aryl halides with chloroform and tetrazoles has been developed, where chloroform was employed as the carbon monoxide (CO) source in the presence of cesium hydroxide. The in situ generated N-acylated tetrazoles were unstable and easily decomposed to afford 2,5-disubstituted 1,3,4-oxadiazoles. A wide range of tetrazoles and aryl halides reacted smoothly under the optimized reaction conditions to give the corresponding products in moderate to good yields.

Iodine-catalysed oxidative cyclisation of acylhydrazones to 2,5-substituted 1,3,4-oxadiazoles

An environmentally benign synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed starting from N-aroylhydrazones and N-acetylhydrazones at room or ambient temperature using a catalytic quantity of iodine in the presence of an aqueous hydrogen peroxide oxidant.

C-H arylation of azaheterocycles: A direct ligand-free and Cu-catalyzed approach using diaryliodonium salts

An efficient and high yielding Cu-catalyzed direct C-H arylation of azaheterocycles including oxadiazoles, thiadiazoles, benzoxazoles and benzothiazoles has been achieved by employing easily accessible diaryliodonium salts. the Partner Organisations 2014.

Palladium-catalyzed deamidative arylation of azoles with arylamides through a tandem decarbonylation-C-H functionalization

A highly chemo-, regio-selective, and efficient palladium-catalyzed deamidative arylation of azoles with arylamides, as an aryl metal equivalent, has been developed. The reaction proceeds smoothly to generate the corresponding products in good yields via a tandem decarbonylation-C-H activation.

Cu(II) catalyzed imine C-H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles

A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C-H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-catalyzed oxidative coupling of an imine C-H bond. These reactions can be performed in air atmosphere and moisture making it exceptionally practical for application in organic synthesis.

17O NMR studies of substituted 1,3,4-oxadiazoles

Three series of substituted 1,3,4-oxadiazoles were studied by 17O NMR spectroscopy. Chemical shifts values were correlated with empirical Hammett parameters as well as calculated bond lengths and chemical shielding values.