1673-44-5

Basic information

• Product Name: 5-(3-METHOXYPHENYL)-1,3,4-OXADIAZOL-2-AMINE
• Synonyms: 5-(3-METHOXYPHENYL)-1,3,4-OXADIAZOL-2-AMINE;2-AMINE-5-(3-METHOXYPHENYL)-1,3,4-OXADIAZOLE;5-(3-METHOXYPHENYL)-1,3,4-OXADIAZOL-2-YLAMINE;OTAVA-BB 1151094;TIMTEC-BB SBB014923;UKRORGSYN-BB BBV-043032;5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-amine(SALTDATA: FREE);2-Amino-5-(3-methoxyphenyl)-1,3,4-oxadiazole
• CAS NO: 1673-44-5
• Molecular Formula: C₉H₉N₃O₂
• Molecular Weight: 191.18666
• Mol File: 1673-44-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 190-191 °C
• Boiling Point: 379.3°Cat760mmHg
• Flash Point: 183.2°C
• Appearance: /
• Density: 1.272g/cm³
• Vapor Pressure: 5.9E-06mmHg at 25°C
• Refractive Index: 1.583
• PKA: -1.22±0.26(Predicted)
• CAS DataBase Reference: 5-(3-METHOXYPHENYL)-1,3,4-OXADIAZOL-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-METHOXYPHENYL)-1,3,4-OXADIAZOL-2-AMINE(1673-44-5)
• EPA Substance Registry System: 5-(3-METHOXYPHENYL)-1,3,4-OXADIAZOL-2-AMINE(1673-44-5)

Safety Data

• Hazardous Substances Data: 1673-44-5(Hazardous Substances Data)

Usage

General Description

The chemical compound 5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-amine is an organic compound with the molecular formula C9H9N3O2. It belongs to the class of oxadiazole compounds, which are heterocyclic organic compounds containing a five-membered ring with oxygen, nitrogen, and carbon atoms. This specific compound contains a substituted phenyl group and an amine group attached to the oxadiazole ring. Oxadiazole compounds have been studied for their potential pharmaceutical and agricultural applications due to their diverse biological activities, including antimicrobial, antitumor, and anti-inflammatory properties. The presence of the methoxy substituent in this compound may also contribute to its specific biological activity or pharmacological profile. Overall, the compound 5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-amine may have potential applications in drug development and other fields of chemical research.

InChI:InChI=1/C9H9N3O2/c1-13-7-4-2-3-6(5-7)8-11-12-9(10)14-8/h2-5H,1H3,(H2,10,12)

Upstream product

• 563-41-7 semicarbazide hydrochloride 
• 591-31-1 3-methoxy-benzaldehyde 
• 5368-81-0 methyl 3-methoxybenzoate 
• 7653-41-0 2-(3-methoxybenzoyl)hydrazinecarbothioamide 

Downstream Products

• 13751-21-8 1-(3-Methoxy-benzoyl)-5-carbamoyl-diamino-guanidin 
• 36371-82-1 N'-{Imino-[N'-(3-methoxy-benzoyl)-hydrazino]-methyl}-hydrazinecarbodithioic acid methyl ester 
• 28004-30-0 2-(3-methoxy-phenyl)-7-methyl-[1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one 

Relevant articles and documents

Synthesis, telomerase inhibitory and anticancer activity of new 2-phenyl-4H-chromone derivatives containing 1,3,4-oxadiazole moiety

Based on previous studies, 66 2-phenyl-4H-chromone derivatives containing amide and 1,3,4-oxadiazole moieties were prepared as potential telomerase inhibitors. The results showed most of the title compounds exhibited significantly inhibitory activity on telomerase. Among them, some compounds demonstrated the most potent telomerase inhibitory activity (IC50 50 = 6.41 μM). In addition, clear structure–activity relationships were summarised, indicating that the substitution of the methoxy group and the position, type and number of the substituents on the phenyl ring had significant effects on telomerase activity. Among them, compound A33 showed considerable inhibition against telomerase. Flow cytometric analysis showed that compound A33 could arrest MGC-803 cell cycle at G2/M phase and induce apoptosis in a concentration-dependent way. Meanwhile, Western blotting revealed that this compound could reduce the expression of dyskerin, which is a fragment of telomerase.

Synthesis and amelioration of inflammatory paw edema by novel benzophenone appended oxadiazole derivatives by exhibiting cyclooxygenase-2 antagonist activity

Ten new 2(4-hydroxy-3-benzoyl) benzamide-5-phenyl-1,3,4-oxadiazole derivatives (10a–j) were synthesized by coupling 3-benzoyl-4-hydroxybenzoic acid (5) with 2-amino-5-phenyl-1,3,4-oxadiazoles (9a–j). The structures of these compounds were confirmed by IR, 1H, 13C NMR, and mass spectra, and also by elemental analyses. The anti-inflammatory activity of the compounds 10a–j were investigated by screening them against human red blood cells (HRBC) in-vitro. The results reveal that among this series, compound 10j with hydroxy substituent, particularly at the ortho position of the phenyl ring attached to the 5th carbon atom of the oxadiazole ring possess significant membrane stabilizing activity in comparison with the control. Further, in-vivo chick chorioallantoic membrane (CAM) and rat corneal anti-angiogenesis assays were performed to assess the effect of compound 10j on endothelial cell migration. This confirmed that compound 10j inhibits the proliferation of endothelial cells. Anti-inflammatory studies detected the amelioration of carrageen induced rat hind paw edema. Further in-vivo and in-silico approaches revealed the inhibition of inflammatory marker enzyme cyclooxygenase-2 (Cox-2) and myleoperoxidase (MPO). The study reports that the compound 10j effectively act against the inflammatory mediated anti-angiogenic disorders which could be translated into a new drug in future.

A convenient synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles from corresponding acylthiosemicarbazides using iodine and Oxone

A convenient methodology has been developed for the synthesis of substituted 2-amino-1,3,4-oxadiazoles from corresponding acylthiosemicarbazides using catalytic amount of iodine/KI in the presence of Oxone as a bulk oxidant. This offers the adv