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13735-81-4 - 1-Phenyl-1-trimethylsiloxyethylene, 97% - alpha-(Trimethylsiloxy)styrene - L05308 - Alfa Aesar

L05308 1-Phenyl-1-trimethylsiloxyethylene, 97%

CAS Number
13735-81-4
Synonyms
alpha-(Trimethylsiloxy)styrene

Size Price ($) Quantity Availability
1g 18.33
5g 63.96
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1-Phenyl-1-trimethylsiloxyethylene, 97%

MDL
MFCD00008582
EINECS
237-308-1

Chemical Properties

Formula
C11H16OSi
Formula Weight
192.34
Boiling Point
53-54°/1mm
Flash Point
78°(172°F)
Density
0.938
Refractive Index
1.5020
Sensitivity
Moisture Sensitive
Solubility
Reacts with water.

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.

Notes

Store at 4°C. Moisture Sensitive. Store under inert gas. Incompatible materials are Oxidizing agents.

Literature References

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.

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.

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335-H227

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Combustible liquid.

Precautionary Statements: P210-P261-P280-P305+P351+P338-P304+P340-P362-P312-P405-P403+P233-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1306914
Harmonized Tariff Code
2931.90
TSCA
Yes

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