3-(T-BUTYLDIMETHYLSILOXY)PROPANOL Chemical Properties

Boiling point:

110 °C6 mm Hg(lit.)

Density 

0.892 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4350(lit.)

Flash point:

199 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Dichloromethane, Ether, Ethyl Acetate, Hexane, Methanol

form 

Clear Colourless Liquid

pka

14.87±0.10(Predicted)

Specific Gravity

0.892

color 

Colorless to Almost colorless

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

Safety Information

WGK Germany 

3

TSCA 

No

HS Code 

2931900090

MSDS

• Language:English Provider:SigmaAldrich

3-(T-BUTYLDIMETHYLSILOXY)PROPANOL Usage And Synthesis

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

3-(T-BUTYLDIMETHYLSILOXY)PROPANOL(73842-99-6)Related Product Information

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• 3-(T-BUTYLDIMETHYLSILOXY)PROPANOL
• 5'-O-(4,4'-DIMETHOXYTRITYL)-N6-BENZOYL-R-ADENOSINE-3'-T-BUTYLDIMETHYLSILYL-2'-(2-CYANOETHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE
• N2-(ISOBUTYRYL)-5'-O-(DIMETHOXYTRITYL)-2'-O-(T-BUTYLDIMETHYLSILYL)-GUANOSINE-3'-N,N-DIISOPROPYL (CYANOETHYL) PHOSPHORAMIDITE
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• 3-FORMYL-6-(S)-T-BUTYL- DIMETHYLSILOXYMETHYL-7-(R)-TETRAHYDROPYRANYLOXY-(1S,5S)-BICYCLO-(3,3,0)-OCT-2-(E)-ENE