ChemicalBook Product Catalog Chemical Reagents Silane reagent 3-(t-Butyldimethylsiloxy)propanol

3-(t-Butyldimethylsiloxy)propanol

Product Name3-(t-Butyldimethylsiloxy)propanol
CAS73842-99-6
MFC9H22O2Si
MW190.36
EINECS
MOL File73842-99-6.mol

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
Storage Class	10 - Combustible liquids

MSDS

Provider	Language
SigmaAldrich	English

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

18162-48-6

504-63-2

73842-99-6

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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