ethyl 2-(trimethylsilyl)acetate

• ChemBase ID: 146761
• Molecular Formular: C7H16O2Si
• Molecular Mass: 160.28624
• Monoisotopic Mass: 160.09195628
• SMILES: CCOC(=O)C[Si](C)(C)C
• Canonical SMILES: CCOC(=O)C[Si](C)(C)C
• InChI: InChI=1S/C7H16O2Si/c1-5-9-7(8)6-10(2,3)4/h5-6H2,1-4H3
• InChIKey: QQFBQBDINHJDMN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(trimethylsilyl)acetate
• IUPAC Traditional name: ethyl 2-(trimethylsilyl)acetate
• Synonyms: ETSA; Ethyl trimethylsilylacetate; (Trimethylsilyl)acetic acid ethyl ester; Ethyl (trimethylsilyl)acetate; Ethyl (trimethylsilyl)acetate; (三甲基硅基)乙酸乙酯; (三甲基硅基)醋酸乙酯

Database IDs

• CAS Number: 4071-88-9
• EC Number: 223-783-2
• MDL Number: MFCD00009172
• Beilstein Number: 1755902
• PubChem SID: 162240953; 24852542
• PubChem CID: 77687

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.8655
• LogD (pH = 7.4): 1.8655
• Log P: 1.8655
• Molar Refractivity: 37.9463 cm^3
• Polarizability: 17.328793 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 156-158°C; 156-159 °C(lit.)
• Flash Point: 118.4 °F; 35°C(95°F); 48 °C
• Density: 0.876; 0.876 g/mL at 25 °C(lit.)
• Refractive Index: 1.4150; n20/D 1.415(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• UN Number: 3272; UN3272
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10
• Safety Statements: 7-33-43-60
• TSCA Listed: 否
• GHS Pictograms: GHS02
• GHS Signal Word: Warning
• GHS Hazard statements: H226
• GHS Precautionary statements: 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 3

Product Information

• Purity: 97%; 98+%; 99%
• Linear Formula: (CH3)3SiCH2CO2C2H5

DETAILS

Sigma Aldrich - 209120

Packaging
25 g in glass bottle

REFERENCES

• Reagent for silylation, under nucleophilic catalysis by TBAF, particularly of sensitive substrates, since the by-product (ethyl acetate) is neutral and filtration is avoided: J. Am. Chem. Soc., 98, 2346 (1976).Alcohols, phenols, ketones, thiols, carboxylic acids and terminal alkynes can be silylated: Bull. Chem. Soc. Jpn., 54, 805 (1981). For conversion of ketones to silyl enol ethers, see: Org. Synth. Coll., 7, 512 (1990).
• Aromatic aldehydes undergo F^- promoted Reformatsky-like addition: Tetrahedron Lett., 1699 (1976). Further heating results in Peterson-type elimination to give the ɑ?-unsaturated ester: J. Org. Chem., 60, 6582 (1995):
  
• Grignard reagents give tertiary carbinols which give 1,1-disubstituted ethylenes by Peterson elimination: Tetrahedron Lett., 23, 1035 (1982). See Appendix 4.