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L05308 1-Phenyl-1-trimethylsiloxyethylene, 97%

Numéro de CAS
13735-81-4
Synonymes
alpha-(Trimethylsiloxy)styrene

Stock No. Conditionnement Prix ($) Quantité Disponibilité
L05308-03 1g 18,40
L05308-06 5g 63,90
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1-Phenyl-1-trimethylsiloxyethylene, 97%

MDL
MFCD00008582
EINECS
237-308-1

Propriétés chimiques

Formule
C11H16OSi
Poids moleculaire
192.34
Point d'ébullition
53-54°/1mm
Point d'éclair
78°(172°F)
Densité
0.938
Indice de réfraction
1.5020
Storage & Sensitivity
Keep Cold. Moisture Sensitive. Store under Nitrogen.
Solubilité
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.

Références bibliographiques

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).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H227-H315-H319-H335

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

Mentions de prudence: P210u-P261-P280a-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
1306914
Code tarifaire harmonisé
2931.90
TSCA
Yes

Recommandé

Consulté récemment

Produits chimiques

Sciences de la vie

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Catalyseurs

Analytique et matériel de laboratoire