(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE 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

MSDS

• Language:English Provider:SigmaAldrich

(2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE Usage And Synthesis

Chemical Properties

colorless liquid

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.

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.

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

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: WO2005/9389, 2005, A2. Location in patent: Page/Page column 134
[4] Patent: US2004/116475, 2004, A1. Location in patent: Page/Page column 30
[5] Patent: WO2004/60367, 2004, A1. Location in patent: Page/Page column 81

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