(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE

Bezeichnung:(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE

CAS-Nr86864-60-0

Englisch Name:(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE

CBNumberCB9489026

SummenformelC8H19BrOSi

Molgewicht239.23

MOL-Datei86864-60-0.mol

(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE physikalisch-chemischer Eigenschaften

Siedepunkt	70-75 °C2.5 mm Hg(lit.)
Dichte	1.115 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.444(lit.)
Flammpunkt	163 °F
storage temp.	2-8°C
Aggregatzustand	Liquid
Farbe	White to pale yellow
Wichte	1.115
Hydrolytic Sensitivity	7: reacts slowly with moisture/water
InChI	InChI=1S/C8H19BrOSi/c1-8(2,3)11(4,5)10-7-6-9/h6-7H2,1-5H3
InChIKey	JBKINHFZTVLNEM-UHFFFAOYSA-N
SMILES	[Si](OCCBr)(C(C)(C)C)(C)C

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-37/39
WGK Germany	3
HS Code	29319090
Speicherklasse	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
colorless liquid
Verwenden
(2-Bromoethoxy)-tert-butyldimethylsilane can be used in N-alkylation with 5-piperazin-1-yl-1H-indole to synthesize 5-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)piperazin-1-yl)-1H-indole.
Verwenden
(2-Bromoethoxy)-tert-butyldimethylsilane was used in the synthesis of 4-(3-hydroxypropyl)-4′-methyl-2,2′-bipyridine.
It may be used as a reagent for the selective N-alkylation of 5-piperazin-1-yl-1H-indole and (1H-indol-2-yl)-piperazin-1-yl-methanone and also in the synthesis of 2-[3-[(3,4,5-trimethoxyphenyl)thio]-1H-indol-5-yloxy]ethanol.
synthetische
In a round-bottom flask, TBDMSC1 (10.61 g, 70.42 mmol) and imidazole (6.23 g, 91.55 mmol) were dissolved in DMF (12.5 mL) and the solution was stirred at 30 mmat rt. Then, 2-bromoethanol (5 mL, 70.42 mmol) was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was partitioned between Et20 and water. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give 17 g of (2-Bromoethoxy)-tert-butyldimethylsilane (quantitative yield, colorless oil).
Allgemeine Beschreibung
(2-Bromoethoxy)-tert-butyldimethylsilane is a silane derivative.
Synthese

18162-48-6

540-51-2

86864-60-0

To a solution of 2-bromoethanol (3.5 mL, 49.3 mmol) in dichloromethane (DCM, 20 mL) was sequentially added tert-butyldimethylchlorosilane (TBDMSCl, 8.17 g, 54.2 mmol), triethylamine (Et3N, 13.85 mL, 98.6 mmol) and 4-dimethylaminopyridine (DMAP, 55 mg, 0.394 mmol). The reaction mixture was stirred at room temperature for 15 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was partitioned with 1N hydrochloric acid (HCl) and ethyl acetate (EtOAc). The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a yellow oily crude product. Purification by column chromatography (hexane as eluent) afforded the colorless oily product [(2-bromoethoxy)tert-butyldimethylsilane] (11.8 g, 49.3 mmol, 100% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.89 (t, 2H), 3.40 (t, 2H), 0.91 (s, 9H), 0.091 (s, 6H); GC/MS (C8H19BrOSi) showed the molecular ion peak m/z 239 (M+).
Einzelnachweise
[1] Patent: WO2005/9389, 2005, A2. Location in patent: Page/Page column 134
[2] Patent: WO2017/216293, 2017, A1. Location in patent: Page/Page column 78
[3] Patent: US2004/116475, 2004, A1. Location in patent: Page/Page column 30
[4] Patent: WO2004/60367, 2004, A1. Location in patent: Page/Page column 81

(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE Upstream-Materialien And Downstream Produkte

(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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