85533-19-3

Basic information

• Product Name: Silane, trimethyl[2-(phenylsulfinyl)ethyl]-
• CAS NO: 85533-19-3
• Molecular Formula: C11H18OSSi
• Molecular Weight: 226.415
• Mol File: 85533-19-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Silane, trimethyl[2-(phenylsulfinyl)ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, trimethyl[2-(phenylsulfinyl)ethyl]-(85533-19-3)
• EPA Substance Registry System: Silane, trimethyl[2-(phenylsulfinyl)ethyl]-(85533-19-3)

Safety Data

• Hazardous Substances Data: 85533-19-3(Hazardous Substances Data)

Upstream product

• 754-05-2 ethenyltrimethylsilane 
• 108-98-5 thiophenol 
• 17988-59-9 phenyl 2-(trimethylsilyl)ethyl sulfide 
• 4206-67-1 iodo(trimethylsilyl)methane 
• 1193-82-4 racemic methyl phenyl sulfoxide 

Downstream Products

• 945-51-7 1,1'-sulfinylbisbenzene 
• 65085-80-5 1-(4-(phenylsulfinyl)phenyl)ethanone 

Relevant articles and documents

Oxidative fragmentations of 2-(trimethylsilyl)ethyl sulfoxides - Routes to alkane-, arene-, and highly substituted 1-alkenesulfinyl chlorides

The preparation of a collection of alkyl, aryl, and 1-alkenyl 2-(trimethylsilyl)ethyl sulfoxides is outlined, using mostly vinyltrimethylsilane or 2-(trimethylsilyl)ethanesulfenyl chloride (5) as key starting materials. The 2-(trimethylsilyl)ethyl group can be cleaved from many of the sulfoxides under oxidative fragmentation conditions using sulfuryl chloride and the reaction represents a new protocol for sulfinyl chloride synthesis. The method is suitable for most alkane- and arenesulfinyl chlorides (3), but is limited to highly substituted vinylic sulfinyl chlorides. 1-Alkenyl 2-(trimethylsilyl)ethyl sulfoxides with reduced double bond substitution (6, 7, 11) succumb to reactions involving chlorination of the double bond. The β-effect of silicon is invoked to explain the ability of the 2-(trimethylsilyl)ethyl group to induce C-S bond scission under the oxidative cleavage reaction conditions. A mechanism is offered to account for the role played by the β-silicon atom of the 2-(trimethylsilyl)ethyl group. Indeed, the silicon atom is self-sacrificial in that it diverts the course of the reaction from the usual α-carbon chlorination mode to one of oxidative cleavage, whereby the 2-(trimethylsilyl)ethyl group is lost. The overall reaction calls upon the ability of silicon atoms to donate electron density by hyperconjugation.

1-LITHIO-1-BENZENESULFINYL-2-TRIMETHYLSILYLETHANE AS A 2-TRIMETHYLSILYLVINYL ANION EQUIVALENT IN REACTIONS WITH ALHEDYDES, KETONES AND EPOXIDES

Aldehydes, ketones and epoxides give adducts with 1-lithio-1-benzenesulfinyl-2-trimethylsilylethane which upon neutralization eliminate benezenesulfenic acid efficiently at 76 deg C to yield trans-3-(trimethylsilyl)allyl alcohols and trans-4-(trimethylsilyl)-3-alken-1-ols.