1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE manufacturers
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| | 1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE Basic information |
| | 1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE Chemical Properties |
| Boiling point | 52 °C / 27mmHg | | density | 0.87 | | refractive index | 1.4130-1.4160 | | storage temp. | 0-10°C | | form | clear liquid | | color | Colorless to Almost colorless | | Specific Gravity | 0.87 | | CAS DataBase Reference | 34880-70-1 |
| RIDADR | 1993 | | HazardClass | 3 | | PackingGroup | III | | HS Code | 2931900090 |
| | 1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE Usage And Synthesis |
| Uses | 1-Methoxy-1-(trimethylsilyloxy)propene is used to reactive nucleophile in Mukaiyama-type aldol reactions with aldehydes, imines, acetals,
dialkoxycarbenium ions, and orthoesters; Michael-type additions to α,β-unsaturated carbonyl compounds; substitution reactions with allylic alcohols and esters; acylations; aminations; hydroxylations; and
pericyclic reactions; silylating agent. | | Preparation | since the first preparation of a ketene trialkylsilyl acetal by Petrov in 1959 by the reaction
of triethylsilane and methyl acrylate, several alternative pathways have been explored. Ainsworth and coworkers prepared 1-methoxy-1-(trimethylsilyloxy)propene in 90% yield by deprotonation of methyl propionate
with Lithium Diisopropylamide at -78 °C followed by addition of Chlorotrimethylsilane. Reaction of the
lithium enolate of methyl acetate with TMS-Cl provides 65% O-silylated and 35% C-silylated products (eq 1).
Substitution on the alcohol portion of the ester favors C-silylation while substitution on the α-carbon favors O-silylation. An increase in the steric bulk of the silylating agent (e.g. use of t-Butyldimethylchlorosilane) results
in significantly more O-silylation.
 | | storage |
1-Methoxy-1-(trimethylsilyloxy)propene is easily hydrolyzed and oxidized by exposure to air. Storage is possible in
sealed tubes at rt. Use in a fume hood.
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| | 1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE Preparation Products And Raw materials |
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