| Identification | Back Directory | [Name]
TRIMETHYLSILYLBENZENESULFONATE | [CAS]
17872-92-3 | [Synonyms]
Trimethylsilybenzenesulfonate
TRIMETHYLSILYLBENZENESULFONATE
TRIMETHYLSILYLBENZENESULPHONATE
PHENYL TRIMETHYLSILYLMETHYL SULFONE
PhenylTrimethylsilylmethylSulfone>
(PHENYLSULFONYLMETHYL)TRIMETHYLSILANE
benzenesulfonylmethyl(trimethyl)silane
(Phenylsulfonylmethyl)trimethylsilane, (Trimethylsilyl)methyl phenyl sulfone | [EINECS(EC#)]
679-678-0 | [Molecular Formula]
C10H16O2SSi | [MDL Number]
MFCD00042814 | [MOL File]
17872-92-3.mol | [Molecular Weight]
228.39 |
| Chemical Properties | Back Directory | [Melting point ]
28-32 °C
| [Boiling point ]
154-156 °C(lit.)
| [density ]
1.138 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.493(lit.)
| [Fp ]
48 °F
| [storage temp. ]
2-8°C
| [solubility ]
readily sol THF, DME, ether | [form ]
powder to lump to clear liquid | [color ]
White or Colorless to Almost white or Almost colorless |
| Hazard Information | Back Directory | [Uses]
TRIMETHYLSILYLBENZENESULFONATE is used for the lithio anion reacts with carbonyl compounds to afford vinyl sulfones via a modified Peterson alkenation procedure; double alkylation, reduction, and sila-Pummerer rearrangement provides ketones.
| [Synthesis Reference(s)]
1. Craig, D.; Ley, S. V.; Simpkins, N. S.; Whitham, G. H.; Prior, M. J. JCS(P1) 1985, 1949.
2. Cooper, G. D. JACS 1954, 76, 3713.
| [Synthesis]
Trimethylsilylbenzenesulfonate can be readily synthesized via several routes,1of which the most suitable for large-scale preparation involves the reaction of sodium thiophenolate with (Chloromethyl)trimethylsilane, the sulfide obtained then being oxidized to the sulfone with buffered Peracetic Acid.2
| [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.] |
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TCI AMERICA
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