Diazoacetophenone
α-Diazoacetophenone · Nsc25280 · Diazoacetylbenzene · 2-Diazoacetophenone · Benzoyldiazomethane · a-Diazoacetophenone · Acetophenone, 2-diazo- · 2-Diazo-1-phenylethanone
Identifikatoren & physikalische Daten
| CAS No. | 3282-32-4 |
|---|---|
| Summenformel | C8H6N2O |
| Durchschnittliche Molmasse | 146,15 g/mol |
| SMILES | [N-]=[N+]=CC(=O)c1ccccc1 |
| InChIKey | ZSTBZBURMWJKSQ-UHFFFAOYSA-N |
| PubChem CID | 18667 |
| DTXSID | DTXSID80954476 |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 19,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 188 |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Schmelzpunkt | 49 °C |
| Siedepunkt | 265.75°C (rough estimate) |
| Dichte | 1.2312 (rough estimate) |
| Brechungsindex | 1.4900 (estimate) |
| Löslichkeit | sol ether, THFslightly sol pentane. |
| Aggregatzustand | rods |
| Farbe | pale yellow |
Anwendungen & Verwendung
Verwenden
α-Diazoacetophenone is used as a precursor to carbenes and carbenoids; reagent for preparation of sulfonium, oxonium, and pyridinium ylides; 1,3 dipole for heterocycle synthesis; reagent for Lewis acid or transition metal-mediated insertion reactions; reagent for cyclopropanation of alkenes and for aromatic annulation.
Herstellung & Synthese
synthetische
Preparative Methods of α-Diazoacetophenone: an improved method of synthesis of diazo ketones has been recently published, via acylation of the lithium enolate of the ketone with 2,2,2-Trifluoroethyl Trifluoroacetate and subsequent reaction with Methanesulfonyl Azide. [1] Alternatively, acylation of diazomethane with aroyl chlorides in the presence of triethylamine provides a general method for the synthesis of aromatic diazo ketones.[2]