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748854

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
NACRES:
NA.22
UNSPSC Code:
12352101
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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.

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.

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

-23.8 °F

flash_point_c

-31 °C

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3104
MKCV4304
MKCV6894
MKCQ8317
MKCP8384

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

Global Trade Item Number

SKUGTIN
748854-100ML04061837791062