Benzylcarbamat
Z-NH2 · CARBAM · O-Benzylcarbamate · Benzyl aminoformate · N-CARBOBENZOXY-AMIDE · CarbaMyl Benzyl Ester · CARBAMIC ACID BENZYL ESTER · Z-AMIDE
Identifikatoren & physikalische Daten
| CAS No. | 621-84-1 |
|---|---|
| Summenformel | C8H9NO2 |
| Durchschnittliche Molmasse | 151,16 g/mol |
| Monoisotopische Masse | 151,06332853 g/mol |
| SMILES | NC(=O)OCc1ccccc1 |
| InChIKey | PUJDIJCNWFYVJX-UHFFFAOYSA-N |
| PubChem CID | 12136 |
| ChEMBL | CHEMBL2259788 |
| EC No. | 210-710-4 |
| DTXSID | DTXSID00211159 |
| Lokaler Name | Benzylcarbamat |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 130 |
| Schmelzpunkt | 86-89 °C (lit.) |
| Siedepunkt | 273.17°C (rough estimate) |
| Dichte | 1.2023 (rough estimate) |
| Brechungsindex | 1.5810 (estimate) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly)68.02g/L(37 ºC) |
| Aggregatzustand | Powder or Flakes |
| pKa (Säurekonstante) | 13.42±0.50(Predicted) |
| Farbe | Off-white to light beige |
| BRN | 1865635 |
| InChI | InChI=1S/C8H9NO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10) |
| InChIKey | PUJDIJCNWFYVJX-UHFFFAOYSA-N |
| SMILES | C(OCC1=CC=CC=C1)(=O)N |
| CAS Datenbank | 621-84-1(CAS DataBase Reference) |
| NIST chemische Informationen | Carbamic acid, benzyl ester(621-84-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (50%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29242995 |
| R-Sätze (R) | 20/21/22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 22-24/25-36-26 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Benzyl carbamate is a reagent used for the nucleophilic introduction of an amino-protected group, Benzyl carbamates can be considered as a benzyloxycarbonyl (otherwise known as carbobenzyloxy, Cbz or Z) protecting group for amino groups. It was introduced as a versatile alternative to the ethoxy carbamate group in peptide synthesis.
Herstellung & Synthese
synthetische
Benzyl carbamate is prepared by reacting benzyl chloroformate with ammonia. Benzyl chloroformate was slowly added to 5 times the volume of cold ammonia water (relative density 0.90) under vigorous stirring, the reaction mixture was placed at room temperature for 30 minutes, the precipitate was filtered out, washed with water and dried to obtain the finished product of benzyl carbamate.