Iodotrimethylsilane

• Catalog No.: A12902
• CAS Number: 16029-98-4
• M. F.: C3H9ISi
• M. W.: 200.09353
• Purity: 97%, stab. with copper

SYNONYMS

• Title: 三甲基碘硅烷
• IUPAC name: iodotrimethylsilane
• IUPAC Traditional name: trimethylsilyl iodide
• Synonyms: Trimethyliodosilane; TMS iodide

DATABASE IDS

• CAS Number: 16029-98-4
• MDL Number: MFCD00001028
• EC Number: 240-171-0
• Beilstein Number: 1731136

PROPERTIES

• Purity: 97%, stab. with copper
• Boiling Point: 105-106°C
• Density: 1.440
• Flash Point: -2°C(28°F)
• Refractive Index: 1.4760
• GHS Hazard statements: H225-H314-H318
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-14-34
• Safety Statements: 8-9-16-23-26-36/37/39-45-60
• Storage Warning: Moisture & Light Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2924
• Packing Group: II

REFERENCES

• Valuable reagent for the mild cleavage of dialkyl and aralkyl ethers: J. Org. Chem., 42, 3761 (1977).
• Catalyzes the transesterification of esters, even those of hindered acids: Synthesis, 142 (1981).
• 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).
• 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).
• 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).