Trimethylsilyl-N-trimethylsilyl-acetamidat
BSA · BIS(TRIMETHYLSILYL)ACETAMIDE · TMS-BA · TriMethylsilyl N-(triMethylsilyl)acetiMidate · trimethylsilyl N-trimethylsilylethanimidate · trimethylsilyl (E)-N-(trimethylsilyl)acetimidate · CB2500 · dynasylan bsa
Identifikatoren & physikalische Daten
| CAS No. | 10416-59-8 |
|---|---|
| Summenformel | C8H21NOSi2 |
| Durchschnittliche Molmasse | 203,43 g/mol |
| Monoisotopische Masse | 203,11616735 g/mol |
| SMILES | CC(=N[Si](C)(C)C)O[Si](C)(C)C |
| InChIKey | SIOVKLKJSOKLIF-UHFFFAOYSA-N |
| PubChem CID | 25248 |
| DTXSID | DTXSID5051525 |
| Lokaler Name | Trimethylsilyl-N-trimethylsilyl-acetamidat |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 21,6 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 176 |
| SpringerMaterials Properties | 29Si nuclear magnetic resonance spectrum |
| Schmelzpunkt | 24 °C |
| Siedepunkt | 71-73 °C35 mm Hg(lit.) |
| Dichte | 0.832 g/mL at 20 °C(lit.) |
| Dampfdruck | 10 hPa (50 °C) |
| Brechungsindex | n20/D 1.417(lit.) |
| Flammpunkt | 53 °F |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Miscible with many nonpolar and polar aprotic solvents. |
| Aggregatzustand | Crystalline Powder, Crystals and/or Chunks |
| pKa (Säurekonstante) | 5.82±0.50(Predicted) |
| Wichte | 0.832 |
| Farbe | Light yellow or beige to brown |
| BRN | 1306669 |
| InChI | 1S/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3/b9-8+ |
| InChIKey | SIOVKLKJSOKLIF-CMDGGOBGSA-N |
| SMILES | C\C(O[Si](C)(C)C)=N/[Si](C)(C)C |
| CAS Datenbank | 10416-59-8(CAS DataBase Reference) |
| NIST chemische Informationen | Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester(10416-59-8) |
| EPA chemische Informationen | Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester (10416-59-8) |
Sicherheit & Vorschriften
| F | 10-21 |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2920 8/PG 2 |
| Zollcode | 29310095 |
| RTECS-Nr. | AK3000000 |
| R-Sätze (R) | 10-14-22-34-40-20/21/22-11 |
| Toxizität | LD50 orally in Rabbit: 1580 mg/kg |
| Gefahrensymbole | C,Xn,F |
| Sicherheitshinweise (S) | 26-36/37/39-45-7/8-43A-36-30-23-16-7/9 |
| Gefahrenklasse | 8Acute Tox. 4 OralFlam. Liq. 3Skin Corr. 1B |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Verwenden
N,O-Bis(trimethylsilyl)acetamide is a powerful silylating agent; reacts with a wide range of functional groups.BSA was used to trimethylsilylate the hydroxyl group of 12 selectively to form in almost quantitative yield (eq 32).The presence of catalytic amounts (～0.02 equiv) of tetrabutylammonium fluoride (TBAF) significantly promoted the silylation of alcohols under mild conditions with high chemoselectivity, i.e., TBAF plays a role as a smooth silyl transfer catalyst from nitrogen to the hydroxyl group.
Herstellung & Synthese
synthetische
N,O-Bis(trimethylsilyl)acetamide is made by the reaction of acetamide with a large excess of chlorotrimethylsilane in the presence of triethylamine.