3-Phenylpropiononitril
3-Phenylpropanenitrile · benzenepropanenitrile · HYDROCINNAMONITRILE · Benzenepropionitrile · NSC 16936 · phenethylcyanide · Phenethyl cyanide · Benzylacetonitrile
Identifikatoren & physikalische Daten
| CAS No. | 645-59-0 |
|---|---|
| Summenformel | C9H9N |
| Durchschnittliche Molmasse | 131,17 g/mol |
| Monoisotopische Masse | 131,07349929 g/mol |
| SMILES | N#CCCc1ccccc1 |
| InChIKey | ACRWYXSKEHUQDB-UHFFFAOYSA-N |
| PubChem CID | 12581 |
| ChEBI | CHEBI:85426 |
| EC No. | 211-447-8 |
| DTXSID | DTXSID4060949 |
| Lokaler Name | 3-Phenylpropiononitril |
Chemische & physikalische Eigenschaften
| XLogP | 1,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 23,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 125 |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | 1.72 |
| Siedepunkt | 261.00 °C. @ 760.00 mm Hg113 °C9 mm Hg(lit.) |
| Schmelzpunkt | -1 °C−2-−1 °C(lit.) |
| Physical Description | Liquid |
| Dichte | 1.001 g/mL at 25 °C(lit.) |
| Brechungsindex | n20/D 1.521(lit.) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | 1.68g/l (calculated) |
| Aggregatzustand | Liquid |
| Wichte | 1 |
| Farbe | Clear colorless to light yellow |
| Geruch | powerful nasturtium |
| BRN | 636348 |
| InChI | 1S/C9H9N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7H2 |
| InChIKey | ACRWYXSKEHUQDB-UHFFFAOYSA-N |
| SMILES | N#CCCc1ccccc1 |
| CAS Datenbank | 645-59-0(CAS DataBase Reference) |
| EPA chemische Informationen | Benzenepropanenitrile (645-59-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (80.7%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 57 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (80.7%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3276 6.1/PG 3 |
| Zollcode | 29269095 |
| RTECS-Nr. | MW5604750 |
| R-Sätze (R) | 23/24/25-36-34 |
| Gefahrensymbole | T,C |
| Sicherheitshinweise (S) | 36/37/39-45-27-26 |
| Gefahrenklasse | 6.1Acute Tox. 3 Oral |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Verwenden
3-Phenylpropionitrile was used to study the free enzyme activity of nitrilase AtNIT1.
Herstellung & Synthese
synthetische
To a stirred solution of 3-phenylpropanamide (50 mg, 0.34 mmol) in acetonitrile (0.8 mL) at room temperature were successively added formic acid (0.2 mL) and paraformaldehyde (50 mg, 1.67 mmol). The reaction mixture was then refluxed for 12 h, and the solution obtained was cooled to room temperature. Work-up A: The crude mixture was concentrated under reduced pressure, and the residue was subjected to flash chromatography on silica gel (230–240 mesh) eluting with hexane/ethyl acetate (7:3) to yield 3-phenylpropanonitrile (37 mg, 85%). Work-up B: The reaction mixture was diluted with ethyl acetate (10 mL) and washed successively with saturated sodium hydrogen carbonate solution (5 mL) and water (5 mL). The combined aqueous layers were extracted with ethyl acetate (2 × 10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude 3-phenylpropanonitrile was purified as described above (Work-up A).