Chemistry:Trimethylsilyl fluoride
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| IUPAC name
Fluoro(trimethyl)silane[1]
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| Other names | |
| Identifiers | |
3D model (JSmol)
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CompTox Dashboard (EPA)
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| Properties | |
| (CH 3) 3SiF | |
| Molar mass | 92.188 g·mol−1 |
| Appearance | Colorless gas[3] |
| Density | 0.793 g/cm3 at 0 °C |
| Melting point | −74 °C (−101 °F; 199 K)[3] |
| Boiling point | 16 °C (61 °F; 289 K)[3] |
| Reacts[4] | |
| Solubility | Soluble in most organic solvents, except the protic ones with which it reacts.[4] |
| Hazards | |
| Main hazards | Skin burns and serious eye damage |
| GHS pictograms |   
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| GHS Signal word | Danger |
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| Flash point | -30 °C[3] |
| Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Trimethylsilyl fluoride is an organosilicon compound with the formula (CH
3)
3SiF. It is a colorless gas.
Synthesis
Trimethylsilyl fluoride can be synthesized from trimethylsilyl chloride and potassium fluoride in the presence of a phase-transfer catalyst and a few drops of water.[5] It can also be synthesized by the reaction of trimethylsilyl trifluoromethanesulfonate with potassium fluoride in dimethylformamide containing 18-crown-6 ether.[6] It can be synthesized from trimethylsilyl chloride by treatment with hydrogen fluoride.
- (CH
3)
3SiCl + HF → (CH
3)
3SiF + HCl
It can also be generated in situ by reaction of ethyl trimethylsilylacetate and tetra-n-butylammonium fluoride.[4]
Uses
Trimethylsilyl fluoride is used as a protecting group during synthesis of certain chemicals and during certain reactions (e.g. silylation). Its applications are in pharmaceutical industry and organic synthesis.[7]
Reactions
Trimethylsilyl fluoride reacts with norbornyllithium to give trimethylsilylnorbornane.[8] Trimethylsilyl fluoride can silylate ketones, alcohols, and terminal alkynes.[4]
Safety
Trimethylsilyl fluoride is a dermatotoxin. Cause skin, eye and respiratory system irritation. It causes skin burns and serious eye damage. It can cause chemical pneumonitis.[1] It is extremely flammable and its vapors can form explosive mixtures with air.[3]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 "Fluorotrimethylsilane". https://pubchem.ncbi.nlm.nih.gov/compound/9869. Retrieved 25 February 2026.
- ↑ Wilson, W. W.; Haiges, R.; Christe, K. O. (1 August 2023). "High resolution NMR spectra of fluorotrimethylsilane". Journal of Fluorine Chemistry 270. doi:10.1016/j.jfluchem.2023.110166. https://www.sciencedirect.com/science/article/pii/S0022113923000817. Retrieved 25 February 2026.
- ↑ 3.0 3.1 3.2 3.3 3.4 https://www.sigmaaldrich.com/GB/en/sds/aldrich/364533
- ↑ 4.0 4.1 4.2 4.3 "Trimethylfluorosilane | 420-56-4". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8756495.htm. Retrieved 25 February 2026.
- ↑ Dehmlow, E. V.; Fastabend, U.; Keßler, M. (25 February 1988). "A One-Pot Synthesis of Trimethylsilyl Fluoride". Synthesis 1988 (12): 996–997. doi:10.1055/s-1988-27783. http://www.thieme-connect.de/DOI/DOI?10.1055/s-1988-27783. Retrieved 25 February 2026.
- ↑ Della, Ernest W.; Tsanaktsidis, John (25 May 1988). "A Convenient Synthesis of Trimethylsilyl Fluoride". Synthesis 5 (5): 407. doi:10.1055/s-1988-27596. http://www.thieme-connect.de/DOI/DOI?10.1055/s-1988-27596. Retrieved 25 February 2026.
- ↑ Bull, Chemical. "Trimethylsilyl Fluoride | 420-56-4 | Chemical Bull Pvt. Ltd.". https://www.chemicalbull.com/products/trimethylsilyl-fluoride. Retrieved 25 February 2026.
- ↑ Della, Ernest W.; Tsanaktsidis, John. (1 May 1988). "Synthesis of some bridgehead (trimethylsilyl)polycycloalkanes. Silicon-29 NMR chemical shifts and silicon-29-carbon-13 coupling constants". Organometallics 7 (5): 1178–1182. doi:10.1021/om00095a025. https://doi.org/10.1021/om00095a025. Retrieved 25 February 2026.
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