Trimethylsilyl iodide
| Trimethylsilyl iodide | |
|---|---|
 | |
| IUPAC name Iodo(trimethyl)silane | |
| Identifiers | |
| CAS number | 16029-98-4 |
| PubChem | 85247 |
| ChemSpider | 76879 |
| Jmol-3D images | {{#if:I[Si](C)(C)C|Image 1 |
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| Properties | |
| Molecular formula | C3H9ISi |
| Molar mass | 200.09 g mol−1 |
| Density | 1.406 g/mL at 25 °C |
| Boiling point | 106 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Trimethylsilyl iodide, (CH3)3SiI, or iodotrimethylsilane, 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.[2][1]
- 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.
References
- ↑ 1.0 1.1 Olah, G.; Narang, S.C. (1982). "Iodotrimethylsilane—a versatile synthetic reagent". Tetrahedron 38 (15): 2225. doi:10.1016/0040-4020(82)87002-6.
- ↑ Michael E. Jung; Mark A. Lyster (1988), "Cleavage of Methyl Ethers with Iodotrimethylsilane: Cyclohexanol from Cyclohexyl Methyl Ether", Org. Synth.; Coll. Vol. 6: 353
- ↑ http://www.chem.agilent.com/Library/applications/gcms59_opiates_urine.pdf