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Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.
Reactive silylating agent for conversion of ketones to silyl enol ethers (see Appendix 4). In triethylamine, the rate of silyl enol ether formation by TMS iodide is 7x109 times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980). In combination with Hexamethyldisilazane, A15139, unsymmetrical ketones give the thermodynamically more stable isomer: Synthesis, 730 (1979).
Valuable reagent for the mild cleavage of dialkyl and aralkyl ethers: J. Org. Chem., 42, 3761 (1977).
Alcohols are converted to alkyl iodides: Tetrahedron Lett., 2659 (1977). ɑɑ-Diaryl alcohols are reduced to the corresponding alkanes: Tetrahedron, 51, 11043 (1995); Synth. Commun., 26, 101 (1996).
Effective reagent for the O-alkyl cleavage of carboxylic esters: J. Am. Chem. Soc., 99, 968 (1977). The reaction can be catalyzed by iodine: J. Org. Chem., 44, 2185 (1979).
Catalyzes the transesterification of esters, even those of hindered acids: Synthesis, 142 (1981).
Alkyl carbamates are cleaved to amines, via the TMS esters: J. Chem. Soc., Chem. Commun., 315 (1978); for application to cleavage of N-Cbz and N-Boc groups, see: J. Chem. Soc., Chem. Commun., 495 (1979).
Catalyst for the protection of alcohols, under mild neutral conditions, as MOM ethers by trans-acetalization with Dimethoxymethane, A12055: Synthesis, 896 (1983), and as THP ethers by acetalization with dihydropyran: Synthesis, 703 (1985).
Catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives, effective at lower temperatures than bromotrimethylsilane: Org. Lett., 5, 1661 (2003).
For reviews of the use of iodotrimethylsilane in organic synthesis, see: Synthesis, 861 (1980); Tetrahedron, 38, 2225 (1982); Adv. Silicon Chem., 1, 1 (1991).
Sato, A. H.; Ohashi, K.; Iwasawa, T. Regio-and stereospecific synthesis of (E)-alpha-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation. Tetrahedron Lett. 2013, 54 (10), 1309-1311.
Sato, A. H.; Mihara, S.; Iwasawa, T. One-step synthesis of (1-iodovinyl) arenes from trimethylsilyl ethynylarene through iodotrimethylsilane-mediated hydroiodation. Tetrahedron Lett. 2012, 53 (28), 3585-3589.
Hazard Statements: H225-H314-H318
Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.