Bromtrimethylsilan
TMSBR · TRIMETHYLSILYL BROMIDE · TRIMETHYLBROMOSILANE · TMBS · (CH3)3SiBr · Silane, bromotrimethyl- · Trimethylsilicon bromide · CT2928
Identifikatoren & physikalische Daten
| CAS No. | 2857-97-8 |
|---|---|
| Summenformel | C3H9BrSi |
| Durchschnittliche Molmasse | 153,09 g/mol |
| Monoisotopische Masse | 151,96568892 g/mol |
| SMILES | C[Si](C)(C)Br |
| InChIKey | IYYIVELXUANFED-UHFFFAOYSA-N |
| PubChem CID | 76113 |
| EC No. | 220-672-0 |
| DTXSID | DTXSID1062671 |
| Lokaler Name | Bromtrimethylsilan |
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 |
| SpringerMaterials Properties | 29Si nuclear magnetic resonance spectrum |
| Dichte | 1.16 @25 °C1.16 g/mL at 25 °C(lit.) |
| Siedepunkt | 79 °C @760 [mm Hg]79 °C(lit.) |
| Schmelzpunkt | -43 °C |
| Brechungsindex | n20/D 1.424(lit.) |
| Flammpunkt | 90 °F |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | DECOMPOSES |
| Aggregatzustand | Liquid |
| Wichte | 1.1725 |
| Farbe | Clear colorless to yellow |
| BRN | 1731135 |
| Stabilität | Stable. Flammable. Incompatible with strong acids, strong oxidizing agents. May decompose on exposure to water or moist air. |
| InChI | 1S/C3H9BrSi/c1-5(2,3)4/h1-3H3 |
| InChIKey | IYYIVELXUANFED-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)Br |
| CAS Datenbank | 2857-97-8(CAS DataBase Reference) |
| NIST chemische Informationen | Bromotrimethylsilane(2857-97-8) |
| EPA chemische Informationen | Silane, bromotrimethyl- (2857-97-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (15.1%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 53 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24353Bromotrimethylsilane: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Flam. Liq. 2 (15.1%) |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2920 8/PG 2 |
| Zollcode | 29310095 |
| R-Sätze (R) | 10-34-29-14 |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 16-26-36/37/39-45-8 |
| Gefahrenklasse | 3Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSTOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Verwenden
Bromotrimethylsilane is a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers; effective reagent for formation of silyl enol ethers; can function as brominating agent.Amines react with TMS-Br to form isolable adducts, which react readily with ketones to form enamines under mild conditions (eq 15).
Herstellung & Synthese
synthetische
although many methods are reported, only a few are provided here: chlorotrimethylsilane undergoes halogen exchange with either magnesium bromide in Et2O or sodium bromide in MeCN, which allows in situ reagent formation (eq 1); alternatively, hexamethyldisilane reacts with bromine in benzene solution or neat, to afford only TMS-Br with no byproducts (eq 2).4 TMS-Br may also be generated by reaction of hexamethyldisiloxane and aluminum bromide (eq 3).However, it should be noted that the reactivity of in situ generated reagent appears to depend upon the method of preparation.