bp 91–93 °C/760 mmHg; 40 °C/140 mmHg;
d 0.753 g mL?1; nD
20 1.4140.
3-Trimethylsilyl-1-propyne is used as propargylation agent; allenylation agent; can give addition
reactions on the triple bond. It takes part in the following reactions: Propargylation Reactions, Alkylation Reactions, Reactions with Epoxides,Reactions with Aldehydes and Ketones, Reactions with Chloroformates, Reactions with Polyoxymethylene and Amines, Allenylation Reactions, Substitution Reactions, Reactions with Acetals and Hemiacetals, Reactions with Aldehydes and Ketones, Reactions with in situ Generated Iminium and α-Acyl
Iminium Ions, Reactions with Acid Chlorides, Reactions with Conjugated Heteroatomic Systems, Reactions of the Triple Bond etc.
Trimethyl(propargyl)silane is suitable for use in the synthesis of diverse end-functionalized (ω-carboxyl, ω-hydroxy, ω-methyl-vinyl, ω-trimethylsilane, and ω-glycidyl-ether) via ′′click′′ reaction. It may be used in the synthesis of γ-allenyl-GABA (γ-aminobutyric acid), via Lewis acid mediated reaction with ω-ethoxy lactams.
The main method of preparation is shown
in eq 1. The title reagent can be obtained by other methods, but in poor yields.
Trimethyl(propargyl)silane (2-Propynyl-trimethylsilane) is a clear colorless liquid and contains 500ppm of butylated hydroxytoluene (BHT) as stabilizer. It undergoes GaCl3-catalyzed dehydrogenation reaction with aldimines to afford 4-methylquinoline.
Fractionally distil it and add 2,6-di-tert-butyl-p-cresol (~0.5%) to stabilise it. [Petrov et al. Doklady Acad Nauk USSR 93 293 1953, cf Chem Abstr 48 13616 1954, Beilstein 4 IV 3938.]
