| Identification | Back Directory | [Name]
2-(tert-butyldiMethylsilyloxy)ethanaMine | [CAS]
101711-55-1 | [Synonyms]
101711-55-1
Ethanamine, mono-TMS
2-(t-Butyldimethylsilyloxy)Ethanamine
2-(tert-butyldiMethylsilyloxy)ethanaMine
2-(tert-ButyldiMethylsilyloxy)ethylaMine
(2-Aminoethoxy)(tert-butyl)dimethylsilane
Ethanolamine tert-butyldimethylsilyl ether
2-(tert-butyl-dimethylsilanyloxy)ethylamine
2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethanamine
[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]amine
EthanaMine, 2-[[(1,1-diMethylethyl)diMethylsilyl]oxy]- | [Molecular Formula]
C8H21NOSi | [MDL Number]
MFCD18206132 | [MOL File]
101711-55-1.mol | [Molecular Weight]
175.344 |
| Chemical Properties | Back Directory | [Boiling point ]
178.4±13.0 °C(Predicted) | [density ]
0.849±0.06 g/cm3(Predicted) | [refractive index ]
1.43 | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [form ]
Light Brown Liquid | [pka]
8.78±0.10(Predicted) | [color ]
Colorless to Almost colorless | [InChI]
InChI=1S/C8H21NOSi/c1-8(2,3)11(4,5)10-7-6-9/h6-7,9H2,1-5H3 | [InChIKey]
XDXFUMZONWWODJ-UHFFFAOYSA-N | [SMILES]
C(N)CO[Si](C(C)(C)C)(C)C |
| Hazard Information | Back Directory | [Chemical Properties]
2-(tert-butyldiMethylsilyloxy)ethanaMine is Light Brown Liquid
| [Uses]
2-(tert-butyldiMethylsilyloxy)ethanaMine is used in the preparation of 3-substituted androsterone derivatives.
| [Synthesis]
The general procedure for the synthesis of 2-((tert-butyldimethylsilyloxy)ethylamine from 2-aminoethanol and tert-butyldimethylsilyl chloride was as follows: a solution of tert-butyldimethylsilyl chloride (3.6 g, 24 mmol) dissolved in dichloromethane (10 mL) was added slowly and dropwise over a period of 3 minutes to a stirring mixture of 2-aminoethanol (1.22 g, 20 mmol) and imidazole (2.04 g, 30 mmol) in a mixed solution. The reaction mixture was continued to be stirred at room temperature for 1 hour. Subsequently, water (20 mL) was added for quenching and the organic and aqueous phases were separated. The aqueous phase was extracted with dichloromethane (2 x 20 mL), all organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the light yellow oily product 2-((tert-butyldimethylsilyloxy)ethylamine (3.50 g, 100% yield). The product was confirmed by NMR hydrogen spectrum (400 MHz, CDCl3): δ 3.64 (t, J = 5.0 Hz, 2H), 3.05 (br s, 2H), 2.80 (t, J = 5.0 Hz, 2H), 0.90 (s, 9H), 0.06 (s, 6H); NMR carbon spectrum (100 MHz, CDCl3): δ 64.7, 44.1, 25.9, 18.3, -3.4; mass spectrum (APCI+) showing the molecular ion peak [M + H]+ = 176.6. | [References]
[1] Journal of Organic Chemistry, 2010, vol. 75, # 17, p. 6023 - 6026
[2] Patent: WO2015/100363, 2015, A1. Location in patent: Page/Page column 43
[3] Patent: US2014/194431, 2014, A1. Location in patent: Paragraph 1044-1045
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 42, p. 11356 - 11360
[5] Angew. Chem., 2014, vol. 126, # 42, p. 11538 - 11542,5 |
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