trimethyl[(1-phenylethenyl)oxy]silane

• ChemBase ID: 146743
• Molecular Formular: C11H16OSi
• Molecular Mass: 192.32964
• Monoisotopic Mass: 192.09704166
• SMILES: C[Si](C)(C)OC(=C)c1ccccc1
• Canonical SMILES: C=C(c1ccccc1)O[Si](C)(C)C
• InChI: InChI=1S/C11H16OSi/c1-10(12-13(2,3)4)11-8-6-5-7-9-11/h5-9H,1H2,2-4H3
• InChIKey: AFFPCIMDERUIST-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethyl[(1-phenylethenyl)oxy]silane
• IUPAC Traditional name: trimethyl[(1-phenylethenyl)oxy]silane
• Synonyms: α-(Trimethylsiloxy)styrene; Acetophenone enol trimethylsilyl ether; 1-Phenyl-1-trimethylsiloxyethylene; alpha-(Trimethylsiloxy)styrene; Trimethyl((1-phenylvinyl)oxy)silane; α-(三甲基硅氧基)苯乙烯; 1-苯基-1-三甲硅氧基乙烯; 1-苯基-1-三甲基硅氧乙烯; 1-苯基-1-三甲基甲硅氧基乙烯

Database IDs

• CAS Number: 13735-81-4
• EC Number: 237-308-1
• MDL Number: MFCD00008582
• Beilstein Number: 1306914
• PubChem SID: 24854075; 162240935
• PubChem CID: 117406

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.1595
• LogD (pH = 7.4): 3.1595
• Log P: 3.1595
• Molar Refractivity: 53.7625 cm^3
• Polarizability: 23.007662 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 53-54°C/1mm; 88-89 °C/11 mmHg(lit.)
• Flash Point: 168.8 °F; 76 °C; 78°C(172°F)
• Density: 0.938; 0.938 g/mL at 25 °C(lit.)
• Refractive Index: 1.5020; n20/D 1.502(lit.); n20/D 1.503
• Vapor Density: >1 (vs air)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H227; H315-H319-H335
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98.0% (GC); 95+%; 97%; 98%
• Grade: purum
• Shipped in: wet ice
• Linear Formula: C6H5C(=CH2)OSi(CH3)3

DETAILS

Sigma Aldrich - 235040

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 79270

Other Notes
Versatile intermediate1,2,3,4

REFERENCES

• The TiCl₄ promoted crossed aldol condensation with acetone illustrates the reaction of silyl enol ethers with aldehydes and ketones: Org. Synth. Coll., 8, 323 (1993). For a further example and reaction scheme, see 1-(Trimethylsiloxy)cyclohexene, A16099. For an alternative catalyst for this type of reaction, see Tetra-n-butylammonium fluoride, A10588.
• ɑ-Arylation with diazonium fluoroborates to give ɑ-arylacetophenones (deoxybenzoins) occurs in pyridine, and also in other solvents in the presence of a Pd catalyst: J. Chem. Soc. Perkin 1, 283 (1994).
• For a review of the synthetic applications of silyl enol ethers, see: Synthesis, 91 (1977).