(PHENYLTHIOMETHYL)TRIMETHYLSILANE Chemical Properties

Boiling point:

158-159 °C52 mm Hg(lit.)

Density 

0.967 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.539(lit.)

Flash point:

103 °F

solubility 

sol most common organic solvents.

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

0.97

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

BRN 

1932375

NIST Chemistry Reference

Silane, trimethyl[(phenylthio)methyl]-(17873-08-4)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20-38

Safety Statements 

23-28

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HS Code 

2931.90.6000

HazardClass 

3.2

PackingGroup 

III

MSDS

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(PHENYLTHIOMETHYL)TRIMETHYLSILANE Usage And Synthesis

Physical properties

bp 158–159 °C/52 mmHg; d20 0.967 g cm?3; n20 D 1.5390.

Uses

lithio derivative is a one-carbon homologating agent leading to aldehydes via sila-Pummerer rearrangement, vinyl sulfides via Peterson alkenation, and vinylsilanes from silyl epoxides.

Preparation

(Phenylthiomethyl)trimethylsilane is abtained by reaction of Phenylthiomethyllithium with Chlorotrimethylsilane.^[1]

storage

(Phenylthiomethyl)trimethylsilane is irriting; foul smelling; use in a fume hood.

Purification Methods

If the sample is suspect, then add H2O, wash it with 10% aqueous NaOH, H2O again, dry (anhydrous CaCl2) and fractionally distil it through a 2ft column packed with glass helices. [Cooper J Am Chem Soc 76 3713 1954.]

References

1. (a) Gilman, H.; Webb, F. J. JACS 1940, 62, 987. (b) Cooper, G. D. JACS 1954, 76, 3713. (c) Carey, F. A.; Court, A. S. JOC 1972, 37, 939.

(PHENYLTHIOMETHYL)TRIMETHYLSILANE(17873-08-4)Related Product Information

• Silicon tetrahydride
• TRIMETHYLSILYLBENZENESULFONATE
• TRIMETHYLSILYLMETHANETHIOL
• (PHENYLTHIOMETHYL)TRIMETHYLSILANE