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748854

Sigma-Aldrich

Iodotrimethylsilane solution

1 M in dichloromethane

Synonym(s):

Iodotrimethylsilane solution, TMS iodine, TMS-I, TMSI, Trimethyliodosilane

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About This Item

Empirical Formula (Hill Notation):
C3H9ISi
Molecular Weight:
200.09
UNSPSC Code:
12352101
NACRES:
NA.22

form

liquid

concentration

1 M in dichloromethane

refractive index

n20/D 1.433

density

1.334 g/mL at 25 °C

storage temp.

2-8°C

General description

Iodotrimethylsilane [(CH3)3SiI] is an important and versatile organosilicon reagent with wide applications in organic synthesis. It is used as a neutral nucleophilic reagent, trimethylsilylating agent, Lewis acid catalyst, reducing agent and dehydrating agent in many organic reactions.

Application

Iodotrimethylsilane can be used as:
  • A reagent in the hydroiodation of ynamides to yield the important building blocks (E)-α-iodoenamides.
  • A reagent in the synthesis of (1-iodovinyl) arenes by hydroiodation of trimethylsilyl ethynylarenes.

Signal Word

Danger

Hazard Statements

H225,H314,H336,H351

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Central nervous system

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-23.8 °F

Flash Point(C)

-31 °C

Certificates of Analysis (COA)

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One-step synthesis of (1-iodovinyl) arenes from trimethylsilyl ethynylarene through iodotrimethylsilane-mediated hydroiodation
Sato AH, et al.
Tetrahedron Letters, 53(28), 3585-3589 (2012)

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