17872-92-3

Basic information

• Product Name: TRIMETHYLSILYLBENZENESULFONATE
• Synonyms: (PHENYLSULFONYLMETHYL)TRIMETHYLSILANE;PHENYL TRIMETHYLSILYLMETHYL SULFONE;TRIMETHYLSILYLBENZENESULPHONATE;TRIMETHYLSILYLBENZENESULFONATE;Trimethylsilybenzenesulfonate;(Phenylsulfonylmethyl)trimethylsilane, (Trimethylsilyl)methyl phenyl sulfone
• CAS NO: 17872-92-3
• Molecular Formula: C₁₀H₁₆O₂SSi
• Molecular Weight: 228.39
• EINECS: 241-833-1
• Product Categories: Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 17872-92-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 28-32 °C
• Boiling Point: 154-156 °C(lit.)
• Flash Point: 48 °F
• Appearance: /
• Density: 1.138 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.53E-07mmHg at 25°C
• Refractive Index: n20/D 1.493(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TRIMETHYLSILYLBENZENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLSILYLBENZENESULFONATE(17872-92-3)
• EPA Substance Registry System: TRIMETHYLSILYLBENZENESULFONATE(17872-92-3)

Safety Data

• Hazard Codes: F,Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3272 3/PG 2
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 17872-92-3(Hazardous Substances Data)

Usage

Purification Methods

Fractionate it at high vacuum and recrystallise it from pentane at -80o. If too impure (cf IR), dissolve it in CH2Cl2 (ca 800mL for 100g), wash this with 2M aqueous NaOH (2 x 200mL), brine, dry, evaporate and distil it. [Craig et al. J Chem Soc, Perkin Trans 1 1949 1985, IR and NMR: Cooper J Am Chem Soc 76 3713 1954.]

InChI:InChI=1/C10H16O2SSi/c1-14(2,3)9-13(11,12)10-7-5-4-6-8-10/h4-8H,9H2,1-3H3

Upstream product

• 930-69-8 sodium thiophenolate 
• 3112-85-4 methylphenylsulfonate 
• 100-68-5 methyl-phenyl-thioether 
• 75-77-4 chloro-trimethyl-silane 
• 18789-72-5 Phenyl trimethylsilylmethyl sulfoxide 
• 17873-08-4 (phenylsulfanylmethyl)trimethylsilane 

Downstream Products

• 82751-28-8 1-((E)-2-Benzenesulfonyl-vinyl)-piperidine 
• 100289-50-7 (E)-(4'S)-2-(2',2'-dimethyl-1',3'-dioxalan-4'-yl)vinyl phenyl sulphone 
• 100289-51-8 (Z)-(4'S)-2-(2',2'-dimethyl-1',3'-dioxalan-4'-yl)vinyl phenyl sulphone 
• 97399-03-6 benzenesulfonylmethane 
• 82895-42-9 6-methyl-2-phenylsulfonylmethyl-1,5-heptadiene 
• 1338565-58-4 (Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone 
• 1338565-59-5 (E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone 
• 1338565-61-9 (1S,2R)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone 
• 1338565-60-8 (1R,2S)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone 
• 1338566-17-8 3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone 
• 1338566-17-8 3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone 
• 1338566-15-6 (Z)-3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)prop-1-en-1-yl phenyl sulfone 

Relevant articles and documents

Azetidine derivatives, their preparation and pharmaceutical compositions containing them

Compounds of formula: in which R represents a CR1R2, C═C(R5)SO2R6 or C═C(R7)SO2alk radical, their preparation and the pharmaceutical compositions containing them.

Reagents for rapid peptide synthesis

This invention relates to compounds of the formula: STR1 wherein R is an electron withdrawing group; R1 is H or COZ; X1 and X2 are independently H, lower alkyl, aryl, aryl lower-alkyl or polystyrene or R and X1 taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; and Z is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.

Preparation of Vinylic Sulphones by Peterson Olefination using Phenyl Trimethylsilylmethyl Sulphone

The anion generated from phenyl trimethylsilylmethyl sulphone using butyl-lithium in dimethoxyethane, readily reacts at -78 deg C with various carbonyl compounds to afford vinylic sulphones on work-up at room temperature.The reaction conditions are tolera