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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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100 ML
$427.00

$427.00

Estimated to ship on25 March 2025

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100 ML
$427.00

About This Item

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

$427.00

Estimated to ship on25 March 2025

Request a Bulk Order

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

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.[1]

Application

Iodotrimethylsilane can be used as:
  • A reagent in the hydroiodation of ynamides to yield the important building blocks (E)-α-iodoenamides.[2]
  • A reagent in the synthesis of (1-iodovinyl) arenes by hydroiodation of trimethylsilyl ethynylarenes.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV4304
MKCV6894
MKCQ8317
MKCP8384
MKCH5333

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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)
Iodotrimethylsilane
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2005)
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)

Questions

1–2 of 2 Questions  

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

    1 answer

    1. 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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  2. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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