PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE
- CAS No.
- 73476-18-3
- Chemical Name:
- PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE
- Synonyms
- (2-Phenylsulfonylethyl)trimethylsilane;PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE;Trimethyl(2-(Phenylsulfonyl)Ethyl)Silane;1-(phenylsulfonyl)-2-(trimethylsilyl)ethane;PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE, 99+%;Benzene, [[2-(trimethylsilyl)ethyl]sulfonyl]-;1-(Phenylsulfonyl)-2-(trimethylsilyl)ethane, 2-(Phenylsulfonyl)ethyltrimethylsilane, 2-(Trimethylsilyl)ethyl phenyl sulfone
- CBNumber:
- CB1284168
- Molecular Formula:
- C11H18O2SSi
- Molecular Weight:
- 242.41
- MDL Number:
- MFCD00015929
- MOL File:
- 73476-18-3.mol
Melting point | 51-52 °C(lit.) |
---|---|
Boiling point | 347.4±34.0 °C(Predicted) |
Density | 1.040±0.06 g/cm3(Predicted) |
Flash point | >230 °F |
solubility | sol all common ethereal, halocarbon, and hydrocarbon solvents. |
form | solid |
CAS DataBase Reference | 73476-18-3 |
SAFETY
Risk and Safety Statements
Safety Statements | 22-24/25 |
---|---|
WGK Germany | 3 |
HS Code | 29310099 |
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE Chemical Properties,Uses,Production
Chemical Properties
white fine crystalline powder
Physical properties
mp 52 °C.
Uses
(2-Phenylsulfonylethyl)trimethylsilane is widely used as reagent for the synthesis of mono- and 1,1-disubstituted alkenes via sulfone metalation, alkylation, and fluoride-induced elimination.
A sequence involving metalation, alkylation, and fluoride-induced elimination of benzenesulfinate allows the conversion of (2) to a terminal alkene. An analogous sequence involving a double alkylation of (2) provides a 1,1-disubstituted alkene (eq 2). The lithio derivative of (2) has also been used to prepare cyclopropylidene derivatives, homoallylic alcohols, and allyl silanes via the Julia alkenation.
Preparation
(2-phenylsulfonylethyl)trimethylsilane (2) is prepared by radical addition of thiophenol to vinyltrimethylsilane to give (2-phenylthioethyl)trimethylsilane (1), which is then oxidized with hydrogen peroxide).
Purification Methods
Dissolve it in Et2O, wash it with saturated HCO 3 followed by saturated NaCl, H2O and dried (MgSO4). Evaporation leaves residual crystals with m 52o. [Hsiao & Shechter Tetrahedron Lett 23 1963 1982, Bortolini et al. J Org Chem 53 2688 1985.]
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE Preparation Products And Raw materials
Raw materials
Preparation Products
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