Azidotrimethylsilan
TMSN3 · TRIMETHYLSILYL AZIDE · TMSiA · decomposes · (CH3)3SiN3 · AzidotrimethyL · Trimethylazidosilane · Three methyl azide silane
Identifikatoren & physikalische Daten
| CAS No. | 4648-54-8 |
|---|---|
| Summenformel | C3H9N3Si |
| Durchschnittliche Molmasse | 115,21 g/mol |
| SMILES | C[Si](C)(C)N=[N+]=[N-] |
| InChIKey | SEDZOYHHAIAQIW-UHFFFAOYSA-N |
| PubChem CID | 78378 |
| EC No. | 225-078-5 |
| DTXSID | DTXSID3063542 |
| Lokaler Name | Azidotrimethylsilan |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 14,4 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 97,2 |
| Stoffklassen | Metals -> Metalloid Compounds (Silicon) |
| Physical Description | Colorless liquid[Alfa Aesar MSDS] |
| Schmelzpunkt | -95°C |
| Siedepunkt | 92-95 °C(lit.) |
| Dichte | 0.876 g/mL at 20 °C(lit.) |
| Brechungsindex | n20/D 1.415(lit.) |
| Flammpunkt | 74 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Miscible with toluene, dichloromethane, diethyl ether and most organic solvents.decomposes |
| Aggregatzustand | Liquid |
| Wichte | 0.868 |
| Farbe | Clear colorless to slightly yellow |
| BRN | 1903730 |
| InChI | 1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 |
| InChIKey | SEDZOYHHAIAQIW-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)N=[N+]=[N-] |
| CAS Datenbank | 4648-54-8(CAS DataBase Reference) |
| NIST chemische Informationen | Azidotrimethylsilane(4648-54-8) |
| EPA chemische Informationen | Azidotrimethylsilane (4648-54-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P316, P321, P330, P361+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 52 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Silane, azidotrimethyl-Status: Active Update: 09-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23688Trimethylsilyl azide: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Reacts with water evolving toxic gasesMay cause irritationToxic by ingestion, inhalation, and skin absorption[Alfa Aesar MSDS] See Hexamethyldisilazane. See Sodium azide. |
| Hazard Classes and Categories | Flam. Liq. 2 (100%) |
| CSL Reaction Information | CSL00010BORON TRIFLUORIDE + AZIDOTRIMETHYLSILANECombinations of TMSN3 and Lewis acids can detonate, presumably due to formation of HN3 from residual water. Avoid Lewis acids.ExplosiveCycloadditionUser-Reported |
| F | 10-33 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1992 3/PG 2 |
| Zollcode | 29310095 |
| R-Sätze (R) | 11-23/24/25-50/53-29 |
| Gefahrensymbole | F,T,N |
| Sicherheitshinweise (S) |
Anwendungen & Verwendung
Verwenden
Many applications of TMSA in organic synthesis have been reported but only representative examples are described herein.Substitution Reactions. Benzyl,allyl,and substituted alkyl halides are converted to the corresponding azides in 60–100% yields via reactions with TMSA under neutral conditions in a nonaqueous solvent (eq 1).By using tin(IV) chloride as a catalyst, secondary and tertiary cyclic and polycyclic halides are similarly transformed into the corresponding azides in 50–92% yields (eq 1).
Herstellung & Synthese
synthetische
Azidotrimethylsilane may be synthesised by reacting trimethylchlorosilane with sodium azide in hexamethylphosphoramidic triamide. several methods for the synthesis of this azide have been reported.The procedure involving aluminum chloride is not recommended, since an explosive product is formed.Azidotrimethylsilane is now commercially available, and a representative synthetic procedure is as follows. A mixture of sodium azide and chlorotrimethylsilane is refluxed in di-n-butyl ether for 2 days and the azide is safely distilled directly from the reaction vessel. Purer compound (99% content) is obtained by redistillation of the product. Several improved conditions have been reported for the preparation of this azide.In these procedures, trimethylsilyl chloride is reacted with sodium azide either neat or in a high boiling point solvent, such as a mixture of silicone oil and polyethylene glycol. Distillation of the crude product usually provides trimethylsilyl azide (TMSA) in high purity (97.9%) and yield (97%).