Trimethylsilyl fluoride is an organosilicon compound with the formula (CH3)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.

(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

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. ^ abcde"Fluorotrimethylsilane". pubchem.ncbi.nlm.nih.gov. Retrieved 25 February 2026.
  2. ^Wilson, W. W.; Haiges, R.; Christe, K. O. (1 August 2023). "High resolution NMR spectra of fluorotrimethylsilane". Journal of Fluorine Chemistry. 270 110166. doi:10.1016/j.jfluchem.2023.110166. Retrieved 25 February 2026 – via ScienceDirect.
  3. ^ abcdehttps://www.sigmaaldrich.com/GB/en/sds/aldrich/364533
  4. ^ abcd"Trimethylfluorosilane | 420-56-4". ChemicalBook. Retrieved 25 February 2026.
  5. ^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. Retrieved 25 February 2026 – via www.thieme-connect.com.
  6. ^Della, Ernest W.; Tsanaktsidis, John (25 May 1988). "A Convenient Synthesis of Trimethylsilyl Fluoride". Synthesis. 5 (5): 407. doi:10.1055/s-1988-27596. Retrieved 25 February 2026 – via www.thieme-connect.com.
  7. ^Bull, Chemical. "Trimethylsilyl Fluoride | 420-56-4 | Chemical Bull Pvt. Ltd". www.chemicalbull.com. Retrieved 25 February 2026.
  8. ^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. Retrieved 25 February 2026 – via ACS Publications.