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.)

Flash point:

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

Safety Information

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

MSDS

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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(17872-92-3)Related Product Information

• Methyl phenyl sulfone
• TRIMETHYLSILYLBENZENESULFONATE
• TRIMETHYLSILYLMETHANETHIOL
• (PHENYLTHIOMETHYL)TRIMETHYLSILANE
• TRIMETHYLSILYLBENZENESULFONATE
• METHYL PHENYL SULFOXIDE