32501-93-2

Basic information

• Product Name: PHENYL 2-(TRIMETHYLSILYLETHYNYL) SULFONE
• Synonyms: PHENYL 2-(TRIMETHYLSILYLETHYNYL) SULFONE;(Trimethylsilylethynyl)phenyl sulfone;Phenyl[(trimethylsilyl)ethynyl] sulfone;TriMethyl((phenylsulfonyl)ethynyl)silane;1-Phenylsulfonyl-2-(trimethylsilyl)acetylene
• CAS NO: 32501-93-2
• Molecular Formula: C₁₁H₁₄O₂SSi
• Molecular Weight: 238.38
• Mol File: 32501-93-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 65-66 °C
• Boiling Point: 315.1°C at 760 mmHg
• Flash Point: 144.3°C
• Appearance: /
• Density: 1.102g/cm³
• Vapor Pressure: 0.000828mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: PHENYL 2-(TRIMETHYLSILYLETHYNYL) SULFONE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL 2-(TRIMETHYLSILYLETHYNYL) SULFONE(32501-93-2)
• EPA Substance Registry System: PHENYL 2-(TRIMETHYLSILYLETHYNYL) SULFONE(32501-93-2)

Safety Data

• Hazardous Substances Data: 32501-93-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H14O2SSi/c1-15(2,3)10-9-14(12,13)11-7-5-4-6-8-11/h4-8H,1-3H3

Upstream product

• 882-33-7 diphenyldisulfane 
• 1066-54-2 trimethylsilylacetylene 
• 63139-23-1 phenylthioethynyl trimethylsilane 
• 98-09-9 benzenesulfonyl chloride 
• 14630-40-1 Bis(trimethylsilyl)ethyne 

Downstream Products

• 83219-88-9 Δ²,Δ²⁰-N-tosyl-4,8-dioxo-21-(phenylsulfonyl)aspidospermidine 
• 64489-07-2 cis-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene 
• 64489-06-1 trans-1-(benzylsulfonyl)-2-(trimethylsilyl)ethylene 
• 82201-53-4 (E)-1,2-dideuterio-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene 
• 158812-81-8 C₂₅H₂₄O₂SSi 
• 158812-80-7 (3-Benzenesulfonyl-1-methoxy-bicyclo[2.2.2]octa-2,5-dien-2-yl)-trimethyl-silane 
• 4192-77-2 ethyl cinnamate 
• 32501-95-4 1,1-dimethoxy-2-phenylsulphonylethane 
• 82201-49-8 C₃₀H₃₄O₂SSi 
• 82201-47-6 C₂₅H₂₅⁽²⁾HO₂SSi 
• 82201-45-4 C₂₅H₂₆O₂SSi 
• 82201-48-7 C₂₆H₂₈O₂SSi 
• 83219-96-9 ethyl 3-cyano-2-methyl-2-<(Z)-2-(phenylsulfonyl)vinyl>-3-(trimethylsiloxy)butanoate 
• 82209-55-0 C₃₆H₃₆O₃SSi 

Relevant articles and documents

A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.

Oxidative addition of Pd(0) to Ar-SO2R bonds: Heck-type reactions of sulfones

Phenyl vinyl sulfones and sulfoxides react with Pd(OAc)2 to form styryl sulfoxides and sulfones according to the first Mizoroki-Heck reaction reported for these thio derivatives. Only sulfones are able to react by using catalytic amounts of Pd

Sulfone reagents in organic synthesis. VI. Sulfonyl- and silyl-substituted hydrocarbons as versatile carbanion precursors in organic synthesis

The basic organometallic chemistry of β-silyl-substituted acetylenic, vinylic and alkyl sulfones has been investigated, with attention being given to metallation, carbometallation and the chemical reduction of carbon-carbon unsaturation. 2-Trimethylsilylvinyl and 2-trimethylsilylalkyl sulfones underwent smooth and stereoselective lithiation with RLi on the carbon α to the sulfonyl group. Carbometallation of vinyl sulfones could be achieved with RMgX or LiCuR2, but acetylenic sulfones carbometallated smoothly only with LiCuR2; with RMgX or RLi, these acetylenes underwent alkyldesulfonylation. The utility in synthesis of these metallo derivatives of sulfonyl-silyl-hydrocarbons is discussed and their value in elaborating carbon skeletons is illustrated for the preparation of alkenes, allenes, carbocycles and stereo-defined vinyl sulfones.