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
UNSPSC Code:
12352101
NACRES:
NA.22
Recommended Products
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
Precautionary Statements
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
Target Organs
Central nervous system
Supplementary Hazards
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)
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)
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