Iodotrimethylsilan
TRIMETHYLSILYL IODIDE · TMIS · TRIMETHYLIODOSILANE · TMS iodide · CT3610 · IodotrimethyL · Trimethylsilyl io · Iodotrmethylsilane
Identifikatoren & physikalische Daten
| CAS No. | 16029-98-4 |
|---|---|
| Summenformel | C3H9ISi |
| Durchschnittliche Molmasse | 200,09 g/mol |
| Monoisotopische Masse | 199,95182482 g/mol |
| SMILES | C[Si](C)(C)I |
| InChIKey | CSRZQMIRAZTJOY-UHFFFAOYSA-N |
| PubChem CID | 85247 |
| EC No. | 240-171-0 |
| DTXSID | DTXSID4065997 |
| Lokaler Name | Iodotrimethylsilan |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 0 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 28,4 |
| Stoffklassen | Metals -> Metalloid Compounds (Silicon) |
| SpringerMaterials Properties | 29Si nuclear magnetic resonance spectrum |
| Physical Description | Clear light brown liquid[Sigma-Aldrich MSDS] |
| Schmelzpunkt | <0°C |
| Siedepunkt | 106 °C(lit.) |
| Dichte | 1.406 g/mL at 25 °C(lit.) |
| Brechungsindex | n20/D 1.471(lit.) |
| Flammpunkt | −25 °F |
| Lagerbedingungen | -20°C |
| Löslichkeit | reacts |
| Aggregatzustand | Liquid |
| Wichte | 1.47 |
| Farbe | Clear colorless to reddish |
| BRN | 1731136 |
| Stabilität | Moisture Sensitive (Reactive) |
| InChI | 1S/C3H9ISi/c1-5(2,3)4/h1-3H3 |
| InChIKey | CSRZQMIRAZTJOY-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)I |
| CAS Datenbank | 16029-98-4(CAS DataBase Reference) |
| NIST chemische Informationen | Iodotrimethylsilane(16029-98-4) |
| EPA chemische Informationen | Silane, iodotrimethyl- (16029-98-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (98.4%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Silane, iodotrimethyl-Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24465Iodotrimethylsilane: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Reacts violently with waterCauses burnsInhalation may cause corrosive injuries to upper respiratory tract and lungs[Sigma-Aldrich MSDS] See Silicon tetraiodide. |
| Hazard Classes and Categories | Flam. Liq. 2 (98.4%) |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| F | 8-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2924 3/PG 2 |
| Zollcode | 29310095 |
| R-Sätze (R) | 11-14-34 |
| Gefahrensymbole | F,C |
| Sicherheitshinweise (S) | 16-26-36/37/39-43-45-25 |
| Gefahrenklasse | 3Eye Dam. 1Flam. Liq. 2Skin Corr. 1B |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Verwenden
Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.Iodotrimethylsilane is a highly efficient reagent for the cleavage of ethers, esters, carbamates, ketals, and lactones. It is also used for the introduction of TMS groups, such as TMS enol ethers, and is a key reagent for the selective removal of N-Cbz groups in the presence of a trimethyltin moiety.This reagent has recently been reported to convert allyl and benzyl phosphotriesters to the corresponding iodides.
Herstellung & Synthese
synthetische
Iodotrimethylsilane is prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes. Other have been reported for the preparation of Trimethylsilyl Iodide(TMS-I): chlorotrimethylsilane undergoes halogen exchange with either lithium iodide in CHCl3 or sodium iodide in MeCN, which allows in situ reagent formation. Alternatively, hexamethyldisilane reacts with iodine at 25–61°C to afford TMS-I with no byproducts.