1-METHYL-1-(TRIMETHYLSILYL)ALLENE

1-METHYL-1-(TRIMETHYLSILYL)ALLENE Structure
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
Molecular Weight:
126.27
MOL File:
74542-82-8.mol
MSDS File:
SDS
Modify Date:
2023/6/1 8:28:59

1-METHYL-1-(TRIMETHYLSILYL)ALLENE Properties

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.

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS02
Signal word  Danger
Hazard statements  H225
Precautionary statements  P210
Hazard Codes  F
Risk Statements  11
Safety Statements  16
RIDADR  UN 1993 3/PG 2
WGK Germany  3

1-METHYL-1-(TRIMETHYLSILYL)ALLENE Chemical Properties,Uses,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.

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.

74542-82-8 synthesis

1-METHYL-1-(TRIMETHYLSILYL)ALLENE Preparation Products And Raw materials

Raw materials

Preparation Products

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