Iodotrimethylsilane

Structural formula
General
Surname	Iodotrimethylsilane
other names	Iodotrimethylsilyl iodide
Molecular formula	C 3 H 9 ISi
Brief description	Orange to brownish liquid with a pungent odor
External identifiers / databases
CAS number 16029-98-4 EC number 240-171-0 ECHA InfoCard 100.036.503 PubChem 85247 ChemSpider 76879 Wikidata Q1191741
properties
Molar mass	200.09 g mol −1
Physical state	liquid
density	1.47 g cm −3
boiling point	107 ° C
solubility	Decomposes with water
Refractive index	1.471
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 225-314 P: 210-280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Iodotrimethylsilane is a chemical compound . It consists of a central silicon atom, which is surrounded in an almost tetrahedral manner by three methyl groups and one iodine substituent.

Manufacturing

Iodotrimethylsilane can be obtained in a Finkelstein- like reaction by reacting chlorotrimethylsilane with sodium iodide or magnesium iodide .

${\displaystyle \mathrm {(CH_{3})_{3}Si{-}Cl\ +\ NaI\longrightarrow \ (CH_{3})_{3}Si{-}I\ +\ NaCl} }$

Another possibility is the cleavage of hexamethyldisilane or hexamethyldisiloxane by iodine .

${\displaystyle \mathrm {(CH_{3})_{3}{-}Si{-}Si{-}(CH_{3})_{3}\ +\ I_{2}\longrightarrow \ 2(CH_{3})_{3}Si{-}I} }$

properties

Iodotrimethylsilane is an orange to brownish liquid that boils at 107 ° C.

use

Iodotrimethylsilane can be used for the synthesis of Eschenmoser salt . To do this, it is reacted with tetra- N- methyl methanediamine.

Due to its Lewis acidic properties, it can also be used to open oxygen-containing heterocycles . An example of this is the opening of epoxies .

Individual evidence

1. ↑ ^{a b c d e} data sheet iodotrimethylsilane (PDF) from Merck , accessed on February 27, 2010.
2. ↑ ^{a b c} data sheet iodotrimethylsilane from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
3. ↑ C. Paolucci, L. Mattioli: Stereoisomeric Sugar-Derived Indolizines as Versatile Building Blocks: Synthesis of Enantiopure Di- and Tetrahydroxyindolizidines , in: J. Org. Chem. , 2001 , 66 , pp. 4787-4794; doi : 10.1021 / jo0016428 .
4. ↑ U. Krüerke: Halogen exchange on chlorosilanes and the tetrahydrofuran cleavage by bromo- and iodosilanes , in: Chem. Ber. , 1962 , 95 , pp. 174-182; doi : 10.1002 / cber.19620950128 .
5. ↑ EC Frederick, CB Abma, PF Vartanian: Metal-halogen bonding studies with group IV A trialkylmetal Halides , in: J. Organomet. Chem. , 1980 , 187 , pp. 203-211; doi : 10.1016 / S0022-328X (00) 81789-1 .
6. ↑ ME Jung, MA Lyster: Quantitative dealkylation of alkyl ethers via treatment with trimethylsilyl iodide. A new method for ether hydrolysis , in: J. Org. Chem. , 1977 , 42 , pp. 3761-3764; doi : 10.1021 / jo00443a033 .
7. ^ TA Bryson, GH Bonitz, CJ Reichel, RE Dardis: Performed Mannich salts: a facile preparation of dimethyl (methylene) ammonium iodide , in: J. Org. Chem. , 1980 , 45 , pp. 524-525; doi : 10.1021 / jo01291a032 .
8. ↑ H. Poleschner, M. Heydenreich, D. Martin: Cyclic ethers as educts for the synthesis of butterfly pheromones , in: Synthesis , 1991 , 12 , pp. 1231-1235; doi : 10.1055 / s-1991-28425 .