1-METHYL-1-(TRIMETHYLSILYL)ALLENE
- Product Name
- 1-METHYL-1-(TRIMETHYLSILYL)ALLENE
- CAS No.
- 74542-82-8
- Chemical Name
- 1-METHYL-1-(TRIMETHYLSILYL)ALLENE
- Synonyms
- 3-(Trimethylsilyl)-1,2-butadiene;1-METHYL-1-(TRIMETHYLSILYL)ALLENE;Buta-2,3-Dien-2-Yl(Trimethyl)Silane;3-(Trimethylsilyl)-1,2-butadiene 98%;Silane, trimethyl(1-methyl-1,2-propadien-1-yl)-
- CBNumber
- CB7184217
- Molecular Formula
- C7H14Si
- Formula Weight
- 126.27
- MOL File
- 74542-82-8.mol
1-METHYL-1-(TRIMETHYLSILYL)ALLENE Property
- Boiling point:
- 111-112 °C(lit.)
- Density
- 0.759 g/mL at 25 °C(lit.)
- refractive index
- n20/D 1.444(lit.)
- Flash point:
- 19 °F
- solubility
- sol CH2Cl2, benzene, THF, Et2O, and most organic solvents.
1-METHYL-1-(TRIMETHYLSILYL)ALLENE Chemical Properties,Usage,Production
Physical properties
bp 111 °C; bp 54–56 °C/90 mmHg
Uses
It is widely used as propargylic anion equivalents; three-carbon synthons for [3 + 2] annulations leading to five-membered compounds including cyclopentenes,4 dihydrofurans, pyrrolines, isoxazoles, furans, and azulenes.
Uses
3-(Trimethylsilyl)-1,2-butadiene may be used for the synthesis of γ-(trimethylsilyl)allylborane.
Preparation
1-methyl-1-(trialkylsilyl)allenes can be conveniently prepared by the method of Vermeer. Silylsubstituted propargyl mesylates thus undergo SN2 displacement by the organocopper reagent generated from methylmagnesium chloride, copper(I) bromide, and lithium bromide 1-Methyl-1-(trimethylsilyl)allene is produced in 52% yield from commercially available (trimethylsilyl)propargyl alcohol in this fashion (eq 1). The t-butyldimethylsilyl and triisopropylsilyl analogs are synthesized by the same method in 90% and 58% yield, respectively. Propargyl alcohols bearing these and other trialkylsilyl groups can be prepared by treatment of propargyl alcohol with n-butyllithium and the appropriate trialkylsilyl chloride. Allenylsilanes bearing other C-1 substituents can be prepared in an analogous manner by using the appropriate Grignard reagents.
1-METHYL-1-(TRIMETHYLSILYL)ALLENE Preparation Products And Raw materials
Raw materials
Preparation Products
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