Trimethylsilyl fluoride
Chemical compound
From Wikipedia, the free encyclopedia
Trimethylsilyl fluoride is an organosilicon compound with the formula (CH3)3SiF. It is a colorless gas.
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| Names | |
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| IUPAC name
Fluoro(trimethyl)silane[1] | |
| Other names | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.006.362 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| (CH3)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 | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Skin burns and serious eye damage |
| GHS labelling: | |
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| Danger | |
| H224, H280, H315, H319, H335 | |
| P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P410+P403, P501 | |
| 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).
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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.
- (CH3)3SiCl + HF → (CH3)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
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]