Trimethylsilyl formate

Trimethylsilyl formate
Names
	IUPAC name Trimethylsilyl formate
	Other names Formic acid trimethylsilyl ester; TMS formate;
Identifiers
CAS Number	18243-21-5;
3D model (JSmol)	Interactive image;
ChemSpider	453173;
PubChem CID	519533;
CompTox Dashboard (EPA)	DTXSID401347568;
	InChI InChI=1S/C4H10O2Si/c1-7(2,3)6-4-5/h4H,1-3H3 Key: KBPSATXXRVXAAJ-UHFFFAOYSA-N;
	SMILES C[Si](C)(C)OC=O;
Properties
Chemical formula	C4H10O2Si
Molar mass	118.207 g·mol−1
Related compounds
Related compounds	tert-Butyl formate; Trimethylsilyl acetate;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Trimethylsilyl formate (TMS formate) is an ester of formic acid, structurally analogous to tert-butyl formate but instead bearing a trimethylsilyl group (TMS). It is useful for hydrosilylation of a range of different ketones, giving the silyl ether in good yields.^[1] For this type of reaction, its ease of handling provides a practical advantage over the more traditional trimethylsilane reagent.^[1] It can also be used for silyl transfer reactions to convert alcohols to trimethylsilyl ethers.^[2] In this context, its practival advantage over other TMS donor reagents is that the reaction has only gaseous byproducts.^[2]

References

1 2 Romero, R. Martin; Thyagarajan, Neethu; Hellou, Nora; Chauvier, Clément; Godou, Timothé; Anthore-Dalion, Lucile; Cantat, Thibault (2022). "Silyl formates as hydrosilane surrogates for the transfer hydrosilylation of ketones". Chemical Communications. 58 (43): 6308–6311. doi:10.1039/d2cc00666a. PMC 9476892. PMID 35522145.
1 2 Cantat, Thibault; Godou, Timothé; Chauvier, Clément; Thuéry, Pierre (2017). "Iron-Catalyzed Silylation of Alcohols by Transfer Hydrosilylation with Silyl Formates". Synlett. 28 (18): 2473–2477. doi:10.1055/s-0036-1591508.

[Romero_2022-1] 1 2 Romero, R. Martin; Thyagarajan, Neethu; Hellou, Nora; Chauvier, Clément; Godou, Timothé; Anthore-Dalion, Lucile; Cantat, Thibault (2022). "Silyl formates as hydrosilane surrogates for the transfer hydrosilylation of ketones". Chemical Communications. 58 (43): 6308–6311. doi:10.1039/d2cc00666a. PMC 9476892. PMID 35522145.

[Godou_2017-2] 1 2 Cantat, Thibault; Godou, Timothé; Chauvier, Clément; Thuéry, Pierre (2017). "Iron-Catalyzed Silylation of Alcohols by Transfer Hydrosilylation with Silyl Formates". Synlett. 28 (18): 2473–2477. doi:10.1055/s-0036-1591508.

[1]

[2]