ChemicalBook Product Catalog Chemical Reagents Organic reagents Silane (2-Bromoethoxy)-tert-butyldimethylsilane

(2-Bromoethoxy)-tert-butyldimethylsilane

Product Name(2-Bromoethoxy)-tert-butyldimethylsilane
CAS86864-60-0
MFC8H19BrOSi
MW239.23
EINECS
MOL File86864-60-0.mol

Chemical Properties

Boiling point	70-75 °C2.5 mm Hg(lit.)
Density	1.115 g/mL at 25 °C(lit.)
refractive index	n20/D 1.444(lit.)
Flash point	163 °F
storage temp.	2-8°C
form	Liquid
Specific Gravity	1.115
color	White to pale yellow
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

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36-37/39
WGK Germany	3
HS Code	29319090
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

colorless liquid

Uses

(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.

Uses

(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.

Preparation

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).

General Description

(2-Bromoethoxy)-tert-butyldimethylsilane is a silane derivative.

Synthesis

18162-48-6

540-51-2

(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE

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+).

References

[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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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