Diazoacetophenone
Grundinformationen
- CAS
3282-32-4- Standard-SMILES
[N-]=[N+]=CC(=O)c1ccccc1- InChIKey
ZSTBZBURMWJKSQ-UHFFFAOYSA-N- Summenformel
- C8H6N2O
- Durchschnittliche Molmasse
- 146,15 g/mol
Namen und Bezeichner
- Bevorzugter Name
- Diazoacetophenone
- IUPAC
- 2-diazo-1-phenylethanone
- Englischer Name
- Diazoacetylbenzene
- Summenformel
- C8H6N2O
- Molmasse
- 146.15
Namen und Synonyme
Diazoacetophenone2-Diazo-1-phenylethanone3282-32-4Phenyl diazomethyl ketone2-DiazoacetophenoneDiazomethyl phenyl ketoneEthanone, 2-diazo-1-phenyl-ACETOPHENONE, 2-DIAZO-NSC 25280BRN 16361224-07-00-02133 (Beilstein Handbook Reference)RefChem:132758
Weitere Namen anzeigen
α-DiazoacetophenoneNsc25280Benzoyldiazomethanea-Diazoacetophenone
Ethanone, 2-diazo-1-phenyl-(9CI)ZSTBZBURMWJKSQ-UHFFFAOYSA-NDiazoacetylbenzene2-Diazo-1-phenylethan-1-onealpha-Diazoacetophenone.alpha.-Diazoacetophenone.omega.-Diazoacetophenone2-diazo-1-phenyl-ethanone
Datenbank-Bezeichner
- CAS
3282-32-4- PubChem CID
- 18667
- DTXSID
DTXSID80954476- Nikkaji
- J2.294.264F、J80.679J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,6
- Polarare Oberfläche (TPSA)
- 19,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 188
Experimentelle und physikochemische Eigenschaften
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Physikochemische Eigenschaften
- Schmelzpunkt
- 49 °C · 49 °C
- Siedepunkt
- 265.75 °C · 265.75°C (rough estimate)
- Dichte
- 1.2312 · 1.2312 (rough estimate)
- Brechungsindex
- 1.49 · 1.4900 (estimate)
- Löslichkeit
- sol ether, THF; slightly sol pentane.
- Aggregatzustand
- rods
- Farbe
- pale yellow
Chemie und Industrie
Anwendungen
Verwendenα-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.
Darstellung
synthetischePreparative 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]
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