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

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

Downstream Products

• 82751-28-8 1-((E)-2-Benzenesulfonyl-vinyl)-piperidine 
• 26189-62-8 phenyl 2,2-diphenylethenyl sulfone 
• 100289-46-1 cycloprop-1-enyl phenyl sulphone 
• 100289-52-9 (ZE,E)-3-dimethylpent-1,3-dienyl phenyl sulphone 
• 61242-29-3 4-phenylsulphonyl-3-methylbut-2-enal 
• 90020-47-6 4,4-dimethoxy-2-methylbut-1-enyl phenyl sulphone 
• 90020-44-3 (cyclohexylidene)methyl phenyl sulfone 
• 16212-06-9 phenyl styryl sulfone 
• 100289-55-2 1-acetoxy-1-phenyl-2-trimethylsilylethyl phenyl sulphone 
• 91787-37-0 1-phenylsulphonyl-1-trimethylsilylpropane 
• 105494-81-3 1-phenylsulphonyl-1-trimethylsilylbutane 
• 74858-07-4 (E)-1-dimethylamino-2-phenylsulfonylethylene 
• 91787-26-7 1-phenylsulfonyl methylidenecyclopentane 
• 91787-27-8 1-phenylsulphonyl-2-phenylprop-1-ene 

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.

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.