1-Phenyl-1-trimethylsiloxyethylene, 95%
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1-Phenyl-1-trimethylsiloxyethylene, 95%
1-Phenyl-1-trimethylsiloxyethylene, 95%
1-Phenyl-1-trimethylsiloxyethylene, 95%
Thermo Scientific Chemicals

1-Phenyl-1-trimethylsiloxyethylene, 95%

CAS: 13735-81-4 | C11H16OSi | 192.333 g/mol
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Catalog number L05308.06
also known as L05308-06
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Chemical Identifiers
CAS13735-81-4
IUPAC Nametrimethyl[(1-phenylethenyl)oxy]silane
Molecular FormulaC11H16OSi
InChI KeyAFFPCIMDERUIST-UHFFFAOYSA-N
SMILESC[Si](C)(C)OC(=C)C1=CC=CC=C1
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SpecificationsSpecification SheetSpecification Sheet
Appearance (Color)Clear colorless to yellow
Assay (GC)≥ 94.0%
FormLiquid
1-Phenyl-1-trimethylsiloxyethylene has been used in the synthesis of β-amino ketones in water via Mannich-type reaction and cis-2,6-disubstituted dihydropyrans via three-component, one-pot cascade reaction. It is also used as chemical additives and intermediates.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
1-Phenyl-1-trimethylsiloxyethylene has been used in the synthesis of β-amino ketones in water via Mannich-type reaction and cis-2,6-disubstituted dihydropyrans via three-component, one-pot cascade reaction. It is also used as chemical additives and intermediates.

Solubility
Reacts with water.

Notes
Store at 4°C. Moisture Sensitive. Store under inert gas. Incompatible materials are Oxidizing agents.
RUO – Research Use Only

General References:

  1. Teck-Peng Loh; Lin-Li Wei. Novel one-pot Mannich-type reaction in water: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters.Tetrahedron Letters. 1998,33 323-326.
  2. Yanlong Gu; Rodolphe De Sousa; Gilles Frapper; Christian Bachmann; Joël Barraulta and François Jérôme. Catalyst-free aqueous multicomponent domino reactions from formaldehyde and 1,3-dicarbonyl derivatives.Green Chem. 2009,11 1968-1972.
  3. 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-(Trimethyl siloxy) cyclohexene, A16099. For an alternative catalyst for this type of reaction, see Tetra-n-butyl ammonium fluoride, A10588.
  4. 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).
  5. For a review of the synthetic applications of silyl enol ethers, see: Synthesis, 91 (1977).