1,3,4-Oxadiazole
oxdiazole · 1,3,4-oxadiazole · 1,3,4-furodiazole
Identifikatoren & physikalische Daten
| CAS No. | 288-99-3 |
|---|---|
| Summenformel | C2H2N2O |
| Durchschnittliche Molmasse | 70,05 g/mol |
| Monoisotopische Masse | 70,01671268 g/mol |
| SMILES | c1nnco1 |
| InChIKey | FKASFBLJDCHBNZ-UHFFFAOYSA-N |
| PubChem CID | 97428 |
| EC No. | 873-098-3 |
| DTXSID | DTXSID10182987 |
Chemische & physikalische Eigenschaften
| XLogP | -0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 26,8 |
| Stoffklassen | Nitrogen Compounds -> Other Nitrogen Compounds |
| SpringerMaterials Properties | Schoenflies notation |
| Physical Description | Liquid[Merck Index] |
| Siedepunkt | 121.44°C (rough estimate) |
| Dichte | 1.2619 (rough estimate) |
| Brechungsindex | 1.4300 (estimate) |
| Lagerbedingungen | Refrigerator, Under inert atmosphere |
| Löslichkeit | Chloroform (Soluble), Methanol (Slightly) |
| Aggregatzustand | Oil |
| pKa (Säurekonstante) | -3.82±0.22(Predicted) |
| Farbe | Colourless |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Gefahrenübersicht | An irritant[Matrix Scientific MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Alarmwort | Warnung |
| Gefahrenhinweise | Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H315 |
Anwendungen & Verwendung
Beschreibung
1,3,4-Oxadiazole is a five-membered, conjugated, planar, stable heteroaromatic, comprised of two adjacent nitrogen atoms at the 3,4-positions with one oxygen atom and two vicinal carbon atoms. Each nitrogen atom in the ring is one carbon apart from the oxygen heteroatom. The 1,3,4-oxadiazole ring is electron deficient due to the presence of two pyridine-like nitrogen atoms in the ring and as a result its chemical properties are unlike those of furan as evidenced from the downfield chemical shift of C2(5)H at δ 8.73 ppm (CDCl3) of the parent 1,3,4-oxadiazole. The presence of two electronegative nitrogen atoms deactivates the ring, making electrophilic substitution difficult in the ring at the C2- and C5-positions. From a medicinal chemistry point of view, it is a very important molecule because it is a surrogate of carboxylic acids, esters, and carboxamides and displays a wide spectrum of pharmacological activities.
Verwenden
1,3,4-Oxadiazole has therapeutic potential with antibacterial, anti-mycobacterial, antitumor, anti-viral and antioxidant activity.
Herstellung & Synthese
synthetische
A solution of potassium hydroxide (4 pellets) was made in absolute ethanol (40ml) & poured into a round bottom flask. 10g of prepared hydrazide and 10ml of carbon disulphide was added in the round bottom flask. Condenser was adjusted and allowed to reflux for 6-8 hours. Reaction progress was checked at regular intervals by using TLC procedure with the use of varying ratio of n-hexane & ethyl acetate. As the reaction got completed, 20ml of chilled distilled water and a very small amount of dil. Sulfuric acid (H2SO4) to maintain the pH 2-3 in order to remove un-reacted base. Solid precipitates were obtained on vigorous shaking and filtered. Product was dried, collected &calculated.