TRIMETHYLSILYLBENZENESULFONATE manufacturers
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| | TRIMETHYLSILYLBENZENESULFONATE Basic information |
| | TRIMETHYLSILYLBENZENESULFONATE Chemical Properties |
| 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 Codes | F,Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | RIDADR | UN 3272 3/PG 2 | | WGK Germany | 3 | | F | 10-21 | | HS Code | 2931.90.9010 |
| | TRIMETHYLSILYLBENZENESULFONATE Usage And Synthesis |
| 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.] |
| | TRIMETHYLSILYLBENZENESULFONATE Preparation Products And Raw materials |
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