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31469-15-5 - 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene, 97% - 1-Methoxy-1-trimethylsiloxy-2-methyl-1-propene - Methyl trimethylsilyl dimethylketene acetal - L06931 - Alfa Aesar

L06931 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene, 97%

CAS Number
31469-15-5
Synonyms
1-Methoxy-1-trimethylsiloxy-2-methyl-1-propene
Methyl trimethylsilyl dimethylketene acetal

Size Price ($) Quantity Availability
5g 64.50
25g 223.00
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1-Methoxy-2-methyl-1-(trimethylsiloxy)propene, 97%

MDL
MFCD00010232
EINECS
000-000-0

Chemical Properties

Formula
C8H18O2Si
Formula Weight
174.32
Boiling Point
35-36°/15mm
Flash Point
30°(86°F)
Density
0.858
Refractive Index
1.4150
Sensitivity
Moisture Sensitive
Solubility
Hydrolyzes in water.

Applications

1-Methoxy-2-methyl-1-(trimethylsiloxy)propene is used in the synthesis of chiral β-lactams by reacting with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride. It acts as a catalyst or initiator in the group-transfer polymerization. It is also used as a versatile reagent in conjugate addition4 and aldol reactions.

Notes

Moisture Sensitive. Incompatible materials are Strong oxidizing agents and Strong acids. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

Literature References

Masahiro Yamanaka; Junji Itoh, Kohei Fuchibe; Takahiko Akiyama. Chiral Brønsted acid catalyzed enantioselective Mannich-type reaction.Journal of the American Chemical Society.2007,129 (21), 6756-6764.

.

Silyl ketene acetal. The silyl enol ether of methyl isobutyrate. Catalyst for the initiation of group transfer polymerization, for controlled polymerization of ɑß-unsaturated esters, ketones, nitriles and amides, in which the ketene acetal function is transferred along the growing polymer chain: J. Am. Chem. Soc., 105, 5706 (1983); Science, 222, 39 (1983).

In the presence of a Lewis acid e.g. TiCl4 or TMS-OTf, undergoes the Mukaiyama aldol reaction with aldehydes to give methyl ɑɑ-dimethyl-ß-hydroxy esters: Chem. Lett., 989 (1975); Synth. Commun., 13, 449 (1983). Excellent results are obtained in these reactions with lanthanide triflates, e.g. Yb(OTf)3, as catalysts: Synthesis, 371 (1993).

With imines, gives ß-amino esters or ß-lactams according to conditions: Tetrahedron Lett., 3643 (1977); Chem. Lett., 1397 (1989); Tetrahedron, 44, 4157 (1988).

Michael additions to enones, catalyzed by Yb(OTf)3, have also been reported: Tetrahedron Lett., 33, 6815 (1992).

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H315-H319-H335

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. 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.

Other References

Beilstein
1362893
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
No

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