Trimethylsilyl iodide

Trimethylsilyl iodide
Names
IUPAC name
Iodo(trimethyl)silane
Identifiers
16029-98-4
ChemSpider 76879
Jmol 3D model Interactive image
PubChem 85247
Properties
C3H9ISi
Molar mass 200.09 g·mol−1
Density 1.406 g/mL at 25 °C
Boiling point 106 °C (223 °F; 379 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethylsilyl iodide, (CH3)3SiI, iodotrimethylsilane or TMSI, is an organosilicon compound. It is a colorless, volatile liquid at room temperature.

Preparation

Trimethylsilyl iodide may be prepared by the oxidative cleavage of hexamethyldisilane by iodine,[1] or by the cleavage of hexamethyldisiloxane with aluminium triiodide.[1][2]

TMS-TMS + I2 2 TMSI (TMS = (CH3)3Si)
TMS-O-TMS + AlI3 2 TMSI + "AlIO"

Applications

Trimethylsilyl iodide is used to introduce the trimethylsilyl group onto alcohols (ROH):

ROH + TMSI RO(TMS) + HI

This type of reaction may be useful for gas chromatography analysis; the resultant silyl ether is more volatile than the underivatized original materials.[3]

For the preparation of bulk trimethylsilylated material, trimethylsilyl chloride may be preferred due to its lower cost.

Trimethylsilyl iodide is also used for the removal of the Boc protecting group,[4][5][1] especially where other deprotection methods are too harsh for the substrate.[6]

References

  1. 1 2 3 Olah, G; Narang, S. C. (1982). "Iodotrimethylsilane—a versatile synthetic reagent". Tetrahedron 38 (15): 2225. doi:10.1016/0040-4020(82)87002-6.
  2. Michael E. Jung; Mark A. Lyster (1988). "Cleavage of Methyl Ethers with Iodotrimethylsilane: Cyclohexanol from Cyclohexyl Methyl Ether". Org. Synth.; Coll. Vol. 6, p. 353
  3. http://www.chem.agilent.com/Library/applications/gcms59_opiates_urine.pdf
  4. Michael E. Jung, Mark A. Lyster (1978). "Conversion of alkyl carbamates into amines via treatment with trimethylsilyl iodide". J. Chem. Soc., Chem. Commun.: 315–316. doi:10.1039/C39780000315.
  5. Richard S. Lott, Virander S. Chauhan, Charles H. Stammer (1979). "Trimethylsilyl iodide as a peptide deblocking agent". J. Chem. Soc., Chem. Commun.: 495–496. doi:10.1039/C39790000495.
  6. Zhijian Liu, Nobuyoshi Yasuda, Michael Simeone, Robert A. Reamer (2014). "N-Boc Deprotection and Isolation Method for Water-Soluble Zwitterionic Compounds". J. Org. Chem. 79: 11792–11796. doi:10.1021/jo502319z.
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