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Thermo Scientific Chemicals
Iodotrimethylsilane, 97%, stab. with copper
CAS: 16029-98-4 | C3H9ISi | 200.094 g/mol
化学物質識別子
CAS16029-98-4
IUPAC Nameiodotrimethylsilane
Molecular FormulaC3H9ISi
InChI KeyCSRZQMIRAZTJOY-UHFFFAOYSA-N
SMILESC[Si](C)(C)I
さらに表示
仕様
スペックシート
スペックシートAppearance (Color)Clear colorless to red or brown
FormLiquid
Assay (unspecified)≥96.0%
CommentMaterial Sourced in the U.S. and in other countries
CommentStabilised with Copper powder. Assay performed by Titration or GC.
さらに表示
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Miscible with water.
Notes
Moisture and light Sensitive. Incompatible withstrong acids, strong bases, strong oxidizing agents and reacts violently with water.
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.
Solubility
Miscible with water.
Notes
Moisture and light Sensitive. Incompatible withstrong acids, strong bases, strong oxidizing agents and reacts violently with water.
RUO – Research Use Only
General References:
- 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 Hexamethyl disilazane, 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).