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L05308 1-Phenyl-1-trimethylsiloxyethylene, 97%

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

Stock No. Size Price ($) Quantity Availability
L05308-03 1g 19.00
L05308-06 5g 69.10
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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
Storage & Sensitivity
Keep Cold. Moisture Sensitive. Store under Nitrogen.
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: H227-H315-H319-H335

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

Precautionary Statements: P210-P235-P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1306914
Harmonized Tariff Code
2931.90
TSCA
Yes

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