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748854

Sigma-Aldrich

Iodotrimethylsilane solution

1 M in dichloromethane

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Synonym(s):
Iodotrimethylsilane solution, TMS iodine, TMS-I, TMSI, Trimethyliodosilane
Empirical Formula (Hill Notation):
C3H9ISi
Molecular Weight:
200.09
UNSPSC Code:
12352101
NACRES:
NA.22

form

liquid

Quality Level

100

concentration

1 M in dichloromethane

refractive index

n20/D 1.433

density

1.334 g/mL at 25 °C

storage temp.

2-8°C

Related Categories

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

WGK

WGK 3

Flash Point(F)

-23.8 °F

Flash Point(C)

-31 °C

Regulatory Information

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  5. What is known of the mechanism of reactions involving product 195529, Iodotrimethylsilane?

    The mechanism for cleavage of esters is described in PNAS, 75(1), 4-6 (1978).The authors go on to explain that the data do not support a previously published mechanism via a carbenium iodide.The paper also discusses the cleavage of ethers using iodotrimethylsilane. It appears that this is not as efficient as cleavage of esters, and a couple of mechanisms (pages 5 and 6) are proposed.Olah also described the cleavage of the phosphate esters in peptides that contain phosphate esters, using iodotrimethylsilane (Tetrahedron, 38, 2225 (1982)). The amide linkages in the peptide backbone are not cleaved.

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Iodotrimethylsilane
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2005)
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)
Regio-and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation
Sato AH, et al.
Tetrahedron Letters, 54(10), 1309-1311 (2013)

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