Other grades of this product :
| 1-METHYL-1-(TRIMETHYLSILYL)ALLENE Basic information |
| 1-METHYL-1-(TRIMETHYLSILYL)ALLENE Chemical Properties |
| Boiling point | 111-112 °C(lit.) | | density | 0.759 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.444(lit.) | | Fp | 19 °F | | solubility | sol CH2Cl2, benzene, THF, Et2O, and most organic
solvents. |
| Hazard Codes | F | | Risk Statements | 11 | | Safety Statements | 16 | | RIDADR | UN 1993 3/PG 2 | | WGK Germany | 3 |
| 1-METHYL-1-(TRIMETHYLSILYL)ALLENE Usage And Synthesis |
| 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 |
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