| Identification | Back Directory | [Name]
3-(T-BUTYLDIMETHYLSILOXY)PROPANOL | [CAS]
73842-99-6 | [Synonyms]
AKOS 90371
3-(T-BUTYLDIMETHYLSILOXY)PROPANOL
3-(TERT-BUTYLDIMETHYLSILOXY)PROPANOL
3-(T-Butyldimethylsiloxy)propan-1-ol
3-[(TERT-BUTYLDIMETHYLSILYL)OXY]PROPANOL
3-(tert-ButyldiMethylsilanyloxy)propan-1-ol
3-[(TERT-BUTYLDIMETHYLSILYL)OXY]-1-PROPANOL
3-((tert-ButyldiMethylsilyl)oxy)propan-1-ol
3-((tert-ButyldiMethylsilyl)oxy)-propanol 97%
3-[Dimethyl(1,1-dimethylethyl)siloxy]propanol
3-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-1-propanol
1-Propanol, 3-[[(1,1-diMethylethyl)diMethylsilyl]oxy]- | [Molecular Formula]
C9H22O2Si | [MDL Number]
MFCD00187968 | [MOL File]
73842-99-6.mol | [Molecular Weight]
190.36 |
| Chemical Properties | Back Directory | [Appearance]
Clear Colourless Liquid | [Boiling point ]
110 °C6 mm Hg(lit.)
| [density ]
0.892 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4350(lit.)
| [Fp ]
199 °F
| [storage temp. ]
Refrigerator | [solubility ]
Dichloromethane, Ether, Ethyl Acetate, Hexane, Methanol | [form ]
Clear Colourless Liquid | [pka]
14.87±0.10(Predicted) | [color ]
Colorless to Almost colorless | [Specific Gravity]
0.892 | [Hydrolytic Sensitivity]
7: reacts slowly with moisture/water | [InChI]
InChI=1S/C9H22O2Si/c1-9(2,3)12(4,5)11-8-6-7-10/h10H,6-8H2,1-5H3 | [InChIKey]
NETUFVYVNJNFMU-UHFFFAOYSA-N | [SMILES]
C(O)CCO[Si](C(C)(C)C)(C)C |
| Hazard Information | Back Directory | [Chemical Properties]
Clear Colourless Liquid | [Uses]
3-(T-butyldimethylsiloxy)propanol is primarily used as a protective group in organic synthesis, specifically for protecting alcohol or phenol functional groups. It can also act as a coupling agent, adhesion promoter, and forms periodic mesoporous silicas. | [General Description]
3-((tert-Butyldimethylsilyl)oxy)-propanol (3-[(tert-butyldimethylsilyl)oxy]-1-propanol) is formed as an intermediate during the synthesis of 3-(tert-butyldimethylsilyl)oxy]propanal. | [Synthesis]
The general procedure for the synthesis of 3-(tert-butyldimethylsilyloxy)propanol from tert-butyldimethylchlorosilane and 1,3-propanediol is as follows: this synthesis has been reported in the literature as part of the exemplary "bottom fragment "15 for the preparation of dictyostatin and its analogs. Specifically, 1,3-propanediol is converted in nine steps to the known bis-TBS-protected Homer-Wadsworth-Emmons product by an Evans chirality-assisted method.10 For related literature, see Phukan, P.; Sasmal, S.; Maier, M. E. Eur. J. Org. Chem. 2003, 1733 and Andrus, S., S., S., S., S., S., S., S., S., and S.. 2003, 1733 and Andrus, M. B.; Argade, A. B. Tetrahedron Lett. 1996, 37, 5049. | [References]
[1] Patent: WO2005/117588, 2005, A2. Location in patent: Page/Page column 31
[2] Journal of the American Chemical Society, 2004, vol. 126, # 37, p. 11440 - 11441
[3] Organic Letters, 2007, vol. 9, # 16, p. 3105 - 3108
[4] Patent: WO2014/145302, 2014, A2. Location in patent: Page/Page column 34; 35; 38; 39
[5] Patent: WO2016/44558, 2016, A1. Location in patent: Page/Page column 51; 52; 54; 55 |
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