trimethylsilyl acetate

• ChemBase ID: 147672
• Molecular Formular: C5H12O2Si
• Molecular Mass: 132.23308
• Monoisotopic Mass: 132.06065616
• SMILES: CC(=O)O[Si](C)(C)C
• Canonical SMILES: CC(=O)O[Si](C)(C)C
• InChI: InChI=1S/C5H12O2Si/c1-5(6)7-8(2,3)4/h1-4H3
• InChIKey: QHUNJMXHQHHWQP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethylsilyl acetate
• IUPAC Traditional name: trimethylsilyl acetate
• Synonyms: Trimethylsilyl acetate; Acetic acid trimethylsilyl ester; Acetoxytrimethylsilane; 三甲基硅乙酸酯; 乙酸三甲基硅酯

Database IDs

• CAS Number: 2754-27-0
• EC Number: 220-404-2
• MDL Number: MFCD00008695
• Beilstein Number: 1744463
• PubChem SID: 162241859; 24857157
• PubChem CID: 75988

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.3216
• LogD (pH = 7.4): 1.3216
• Log P: 1.3216
• Molar Refractivity: 29.0564 cm^3
• Polarizability: 13.661113 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -32 °C(lit.); -32°C
• Boiling Point: 107.5 °C(lit.); 107°C
• Flash Point: 19 °C; 4°C(39°F); 66.2 °F
• Density: 0.882 g/mL at 25 °C(lit.); 0.884
• Refractive Index: 1.3880; n20/D 1.388(lit.); n20/D 1.389
• Vapor Pressure: 35 mmHg ( 30 °C)
• Vapor Density: 1 (vs air)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Flammable (F)
• UN Number: 3272; UN3272
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11
• Safety Statements: 16-23; 16-33
• TSCA Listed: 是
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• GHS Precautionary statements: P210; P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3272 3/PG 2

Product Information

• Purity: ≥97.0% (GC); 97%
• Grade: purum
• Linear Formula: CH3CO2Si(CH3)3

DETAILS

Sigma Aldrich - 284459

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 46053

Other Notes
The lithium enolate adds to ketones1,2; Reaction with activated derivatives of acids to β-keto esters3,4

REFERENCES

• Lithiation and acylation give the TMS esters of ?-keto acids, which can be converted to the unstable ?-keto acids themselves, or directly to methyl ketones: Synth. Commun., 13, 183 (1983).
• Has been used in a 2-carbon homologation sequence for the synthesis of (E)-alkenoic acids via silyl ketene acetals: J. Org. Chem., 63, 8785 (1998):