Trimethylsilyl acetate
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| Names | |
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| IUPAC name
Trimethylsilyl acetate[1] | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.018.550 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| CH3COOSi(CH3)3 | |
| Molar mass | 132.234 g·mol−1 |
| Appearance | Colorless liquid[2][3][4] |
| Odor | Mild, sweet[3] |
| Density | 0.882 g/cm3, relative vapor density 4.57 (air = 1)[2][4] |
| Melting point | −32 °C (−26 °F; 241 K)[2] |
| Boiling point | 107.5 °C (225.5 °F; 380.6 K)[2] |
| Soluble[5], reacts[4][5] | |
| Solubility | Soluble in diethyl ether and ethanol |
| Vapor pressure | 47 hPa at 30 °C[2] |
Refractive index (nD) |
1.388[4] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Highly flammable[2] |
| GHS labelling: | |
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| Danger | |
| H225, H315, H319 | |
| P210, P233, P240, P241, P242, P243, P264, P280, P303+P361+P353, P370+P378, P403+P235, P501 | |
| Flash point | 19 °C (66 °F; 292 K)[5] |
| 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 acetate, also known as TMSOAc, is an organosilicon compound with the chemical formula CH3COOSi(CH3)3. It is a colorless liquid. It is the silyl ester analog of tert-butyl acetate, having a trimethylsilyl group −Si(CH3)3 in place of the tert-butyl group −C(CH3)3.
Synthesis
Trimethylsilyl acetate can be prepared by the reaction of trimethylsilyl chloride with sodium acetate in hexanes or diethyl ether in the presence of a phase-transfer catalyst to speed up the reaction.[6]
- (CH3)3SiCl + CH3COO−Na+ → CH3COOSi(CH3)3 + NaCl
Applications and reactions
A trimethylsilyl acetate and methane mixture can be used to produce a-C:H:SiOx coatings using plasma-enhanced chemical vapor deposition (PECVD), which have a hardness of up to 11 GPa.[7]
Other coatings can be produced with a trimethylsilyl acetate and oxygen mixture, again using PECVD.[8]
Trimethylsilyl acetate can also be used for acetylation of alcohols.[9]
References
- 1 2 "Silanol, 1,1,1-trimethyl-, 1-acetate". pubchem.ncbi.nlm.nih.gov.
- 1 2 3 4 5 6 https://www.sigmaaldrich.com/GB/en/sds/aldrich/284459
- 1 2 "CAS 2754-27-0: Trimethylsilyl acetate | CymitQuimica". cymitquimica.com.
- 1 2 3 4 "Trimethylsilyl acetate | 2754-27-0". ChemicalBook.
- 1 2 3 ThermoFisher. "Trimethylsilyl acetate". www.thermofisher.com. Retrieved 23 March 2026.
- ↑ https://patents.google.com/patent/CN103755734A/en
- ↑ Kelarová, Štĕpánka; Václavik, Richard; Přibyl, Roman; Stupavská, Monika; Buršíková, Vilma (2024). "Development of a-C:H coatings doped with trimethylsilyl acetate prepared using plasma enhanced chemical vapor deposition". Diamond and Related Materials. 147 111233. Elsevier BV. doi:10.1016/j.diamond.2024.111233. ISSN 0925-9635.
- ↑ Kelarová, Štěpánka; Homola, Vojtěch; Stupavká, Monika; Čermák, Martin; Vohánka, Jiří; Přibyl, Roman; Zábranský, Lukáš; Buršíková, Vilma (2020). "Deposition of organosilicon coatings from trimethylsilyl acetate and oxygen gases in capacitively coupled RF glow discharge". Progress in Organic Coatings. 149 105927. Elsevier BV. doi:10.1016/j.porgcoat.2020.105927. ISSN 0300-9440.
- ↑ Pantawane, Amit Ravindra; Thul, Mayur; Lin, Yi-Jyun; Lin, Michelle; Lin, Wesley; Julakanti, Satyanarayana Reddy; Wu, Hsin-Ru; Luo, Shun-Yuan (2021-07-07). "Mild and Efficient Tunable Brønsted Acidic Ionic Liquid Catalyzed O-Acetylation and O-Trimethylsilylation with Trimethylsilyl Acetate (TMSOAc) and Hexamethyldisilazane (HMDS)". Catalysts. 11 (7). MDPI AG: 825. doi:10.3390/catal11070825. ISSN 2073-4344.