| Identification | Back Directory | [Name]
1-METHYL-1-(TRIMETHYLSILYL)ALLENE | [CAS]
74542-82-8 | [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)- | [Molecular Formula]
C7H14Si | [MDL Number]
MFCD01321223 | [MOL File]
74542-82-8.mol | [Molecular Weight]
126.27 |
| Chemical Properties | Back Directory | [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 Information | Back Directory | [Physical properties]
bp 111 °C; bp 54–56 °C/90 mmHg | [Uses]
3-(Trimethylsilyl)-1,2-butadiene may be used for the synthesis of γ-(trimethylsilyl)allylborane. | [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. | [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.
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