93073-37-1

Basic information

• Product Name: 5-(4-METHOXYBENZYL)-1,3,4-OXADIAZOLE-2-THIOL
• Synonyms: 5-[(4-methoxyphenyl)methyl]-3H-1,3,4-oxadiazole-2-thione
• CAS NO: 93073-37-1
• Molecular Formula: C₁₀H₁₀N₂O₂S
• Molecular Weight: 222.27
• Mol File: 93073-37-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 323.6°Cat760mmHg
• Flash Point: 149.5°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 0.000259mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: 5-(4-METHOXYBENZYL)-1,3,4-OXADIAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-METHOXYBENZYL)-1,3,4-OXADIAZOLE-2-THIOL(93073-37-1)
• EPA Substance Registry System: 5-(4-METHOXYBENZYL)-1,3,4-OXADIAZOLE-2-THIOL(93073-37-1)

Safety Data

• Hazardous Substances Data: 93073-37-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H10N2O2S/c1-13-8-4-2-7(3-5-8)6-9-11-12-10(15)14-9/h2-5H,6H2,1H3,(H,12,15)

Upstream product

• 75-15-0 carbon disulfide 
• 57676-49-0 2-(4-methoxyphenyl)acetic acid hydrazide 
• 104-01-8 4-Methoxyphenylacetic acid 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 

Downstream Products

• 93073-14-4 4-amino-3-(p-methoxybenzyl)-5-mercapto-1,2,4-triazole 
• 1268161-62-1 S-(5-(4-methoxybenzyl)-4-amino-1,2,4-triazole-3-yl) naphthalene-1-carbothioate 
• 865423-59-2 S-(5-(4-methoxybenzyl)-1,3,4-oxadiazole-2-yl) naphthalene-1-carbothioate 
• 93073-23-5 6-(4-Chloro-phenyl)-3-(4-methoxy-benzyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 93073-22-4 5-(p-methoxybenzyl)-2-phenyl-s-triazolo<3,4-b>-1,3,4-thiadiazole 
• 302949-11-7 1-(4-bromo-phenyl)-2-[5-(4-methoxy-benzyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-ethanone 
• 302949-15-1 2-[5-(4-methoxy-benzyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-1-phenyl-ethanone 

Relevant articles and documents

Similarities and differences in the crystal packing of methoxybenzyl and methoxyphenylethyl-1,3,4-oxadiazole-2(3H)-thiones

This work reports the crystal and molecular structures of five 1,3,4-oxadiazol-2(3H)-thiones derived from 2, 3 and 4-methoxy substituted 2-phenylacetic acid and 2- and 4-methoxy substituted 3-phenylpropanoic acid. The methoxybenzyl-1,3,4-oxadiazol-2(3H)-thiones are V-shaped while the corresponding methoxyphenylethyl-systems are close to planar, which impacts the solid state molecular packing arrangement. For molecules 1-4, inversion related N-H...S hydrogen bonds generating R22(8) rings dominate the packing, supported by an eclectic mix of C-H...O, C-H...S, C-H...π and π...π contacts that stack the molecules into interconnected columns. In contrast, each of the two unique molecules in the asymmetric unit of 5 forms N-H...O contacts with like molecules augmented by C-H...S contacts for one molecule and C-H...O contacts for the other to generate planar layers that are interconnected though a series of π...π stacking interactions. The Royal Society of Chemistry.

Synthesis, characterization and antifungal evaluation of 5-substituted-4-amino-1,2,4-triazole-3-thioesters

A series of 5-substituted-4-amino-1,2,4-triazole-3-thioesters was synthesized by converting variously substituted organic acids successively into the corresponding esters, hydrazides, 5-substituted-1,3,4-oxadiazole-2-thiols, 5-substituted-1,2,4-triazole-2-thiols and 5-substituted-1,3,4-oxadiazole-2- thioesters. Finally the target compounds were obtained by refluxing 5-substituted-1,3,4-oxadiazole-2-thioesters in the presence of hydrazine hydrate and absolute alcohol. The structures of the synthesized compounds were established by physicochemical and spectroscopic methods. The synthesized compounds were evaluated for their in vitro antifungal activity. Some of the evaluated compounds possessed significant antifungal activity as compared to a terbinafine standard.

Synthesis, characterization and antifungal activity of some 5-substituted 4-amino-1,2,4-triazole-3-thiols

A series of 5-substituted 4-amino-1,2,4-triazole-3-thiols (4a-i) was synthesized by refluxing substituted organic acids (a-i) with methanol to the corresponding esters (1a-i). These esters were then converted to hydrazides (2a-i) by reaction with hydrazine hydrate in the presence of absolute ethanol. The hydrazides were then converted to 5-substituted 1,3,4-oxadiazole-2-thiols (3a-i) by cyclization reaction with carbon disulfide and KOH which was followed by reaction with hydrazine hydrate in the presence of absolute ethanol. Structure of the synthesized compounds was established by physico-chemical and spectral data analysis. Synthesized compounds were subjected to antifungal activity. Antifungal activity analysis was performed against Aspergillus flavus, Mucor species, Aspergillus niger and Aspergillus fumigates, with test compounds at a concentration of 200 μg/mL. Terbinafine was used as the standard drug.