Benzoylcyanid
Benzoyl nitrile · BENZOYL CYANIDE · Benzoylcyanide98% · Benzoylcyanide 98% · Phenylglyoxynitrile · Phenylglyoxonitrile · α-oxo-α-tolunitrile · Benzoyl cyanide,95%
Identifikatoren & physikalische Daten
| CAS No. | 613-90-1 |
|---|---|
| Summenformel | C8H5NO |
| Durchschnittliche Molmasse | 131,13 g/mol |
| Monoisotopische Masse | 131,03711378 g/mol |
| SMILES | N#CC(=O)c1ccccc1 |
| InChIKey | GJQBHOAJJGIPRH-UHFFFAOYSA-N |
| PubChem CID | 11953 |
| ChEBI | CHEBI:51853 |
| EC No. | 210-359-7 |
| DTXSID | DTXSID2060626 |
| Lokaler Name | Benzoylcyanid |
Chemische & physikalische Eigenschaften
| XLogP | 1,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 171 |
| SpringerMaterials Properties | Boiling point |
| Schmelzpunkt | 28-31 °C(lit.) |
| Siedepunkt | 206 °C(lit.) |
| Dichte | 1.106 g/mL at 25 °C(lit.) |
| Brechungsindex | 1.4700 (estimate) |
| Flammpunkt | 184 °F |
| Löslichkeit | soluble in Methanolslihtly soluble, decomposes |
| Aggregatzustand | powder to lump to clear liquid |
| Farbe | White or Colorless to Light yellow |
| BRN | 1072101 |
| InChI | InChI=1S/C8H5NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H |
| InChIKey | GJQBHOAJJGIPRH-UHFFFAOYSA-N |
| SMILES | C(C1C=CC=CC=1)(=O)C#N |
| CAS Datenbank | 613-90-1(CAS DataBase Reference) |
| NIST chemische Informationen | Benzeneacetonitrile, «alpha»-oxo-(613-90-1) |
| EPA chemische Informationen | Benzeneacetonitrile, .alpha.-oxo- (613-90-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Benzeneacetonitrile, .alpha.-oxo-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Acute Tox. 2 (100%) |
| F | 10 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3439 6.1/PG 2 |
| Zollcode | 29269095 |
| R-Sätze (R) | 25-50-34-24/25-20 |
| Gefahrensymbole | T,N |
| Sicherheitshinweise (S) | 36/37/39-45-61-29-26 |
| Gefahrenklasse | 6.1(b)Acute Tox. 2 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
Anwendungen & Verwendung
Verwenden
Using benzoyl cyanide as an electrophile also gives selective acylation of the 3-position, as does levulinic acid in the presence of DCC. Benzoyl cyanide is used to study the mechanism of reduction of benzoyl cyanide in acetonitrile, N,N-dimethylformamide and acetonitrile. It undergoes hydrolysis by Rhodococcus sp. CCZU10-1 to form benzoylformic acid. Reagent for selective acylation of amino compounds.
Herstellung & Synthese
synthetische
Benzoyl cyanide is prepared by treatment of benzoyl chloride with sodium cyanide under phase-transfer catalytic conditions. This process is also used to convert 4-methyl, 4-methoxy, and 4-chlorobenzoyl chlorides into the corresponding benzoyl cyanides, and similarly cinnamoyl chloride into cinnamoyl cyanide (98%).