73476-18-3 Usage
Description
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE, also known as (2-Phenylsulfonylethyl)trimethylsilane, is a white fine crystalline powder with a melting point of 52 °C. It is a chemical compound that is widely used in the synthesis of various alkene derivatives due to its unique chemical properties.
Uses
Used in Chemical Synthesis:
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE is used as a reagent for the synthesis of monoand 1,1-disubstituted alkenes via sulfone metalation, alkylation, and fluoride-induced elimination. PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE plays a crucial role in the conversion of specific precursors to terminal alkenes and 1,1-disubstituted alkenes through a series of chemical reactions, including metalation, alkylation, and fluoride-induced elimination.
Used in Organic Chemistry:
In the field of organic chemistry, PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE is used as a key intermediate in the preparation of various complex organic molecules. The lithio derivative of this compound has been employed to synthesize cyclopropylidene derivatives, homoallylic alcohols, and allyl silanes via the Julia alkenation, which are important building blocks in the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Industry:
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE may also find applications in the pharmaceutical industry, where it can be used as a starting material or intermediate for the synthesis of various drug candidates. Its unique chemical properties and reactivity make it a valuable tool in the development of new medications and therapeutic agents.
Used in Material Science:
In material science, PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE could potentially be utilized in the development of novel materials with specific properties, such as improved stability, reactivity, or selectivity. Its unique structure and chemical properties may contribute to the creation of advanced materials for various applications, including electronics, coatings, and adhesives.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 73476-18-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,4,7 and 6 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 73476-18:
(7*7)+(6*3)+(5*4)+(4*7)+(3*6)+(2*1)+(1*8)=143
143 % 10 = 3
So 73476-18-3 is a valid CAS Registry Number.
InChI:InChI=1/C11H18O2SSi/c1-15(2,3)10-9-14(12,13)11-7-5-4-6-8-11/h4-8H,9-10H2,1-3H3
73476-18-3Relevant articles and documents
A general approach to iridoids by applying a new Julia olefination and a tandem anion-radical-carbocation crossover reaction
?ehová, Lucie,Dra?ínsky, Martin,Jahn, Ullrich
supporting information, p. 9612 - 9621 (2016/10/22)
A unified, asymmetric approach to the total synthesis of naturally occurring iridoids is presented. The synthesis features a recently discovered ortho → α transmetalation of alkyl aryl sulfone carbanions, thus enabling Julia reactions, by which so far har
β,β-disilylated sulfones as versatile building blocks in organic chemistry - A new sulfonyl carbanion transmetalation
Puget, Bertrand,Jahn, Ullrich
supporting information; experimental part, p. 2579 - 2582 (2010/12/20)
1,3-Bis(trimethylsilyl)propyl phenyl sulfone undergoes, in contrast to all reported sulfones bearing α-hydrogen atoms, an initial ortho metalation to an aryllithium at low temperature, which transmetalates quantitatively to the corresponding α-sulfonyl or
A new silicon-mediated elimination-rearrangement
Menichetti, Stefano,Stirling, Charles J. M.
, p. 1511 - 1515 (2007/10/03)
Treatment of trimethylsilylethanes bearing α-phenyl groups and β-phenylthio, phenylsulfonyl or cyano groups with LDA causes elimination-rearrangement mediated by the β-carbanionic species. Mechanistic conclusions are based on isotopic labelling experiment
