| Identification | Back Directory | [Name]
PROPARGYLTRIMETHYLSILANE | [CAS]
13361-64-3 | [Synonyms]
PROPARGYLTRIMETHYLSILANE
3-(TRIMETHYLSILYL)PROPYNE
2-PROPYNYL-TRIMETHYLSILANE
TRIMETHYL(PROPARGYL)SILANE
trimethyl-2-propynyl-silan
3-TRIMETHYLSILYL-1-PROPYNE
Trimethyl(2-propynyl)silane
1-(Trimethylsilyl)-2-propyne
trimethyl(prop-2-ynyl)silane
Propargyltrimethylsilane,97%
Propargyltrimethylsilanestab
Silane, trimethyl-2-propynyl-
triMethyl(prop-2-yn-1-yl)silane
Silane,trimethyl-2-propyn-1-yl-
PropargyltriMethylsilane, stabilized, 8
Propargyltrimethylsilane, 90%, stabilized
Propargyltrimethylsilane, stabilized, 90%
Propargyltrimethylsilane,80-90%,stabilized
Propargyltrimethylsilane, stabilized, 80-90%
2-Propynyl-trimethylsilane, 3-(Trimethylsilyl)propyne
TriMethyl(propargyl)silane contains 500 ppM BHT as stabilizer | [EINECS(EC#)]
236-427-6 | [Molecular Formula]
C6H12Si | [MDL Number]
MFCD00042922 | [MOL File]
13361-64-3.mol | [Molecular Weight]
112.24 |
| Chemical Properties | Back Directory | [Appearance]
Clear yellow liquid | [Melting point ]
148-151 °C(Solv: ethyl ether (60-29-7)) | [Boiling point ]
91-93 °C(lit.)
| [density ]
0.753 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.413(lit.)
| [Fp ]
13 °F
| [storage temp. ]
−20°C
| [solubility ]
sol ether, THF, CH2Cl2. | [form ]
Liquid | [color ]
Clear yellow | [BRN ]
2036316 | [InChI]
InChI=1S/C6H12Si/c1-5-6-7(2,3)4/h1H,6H2,2-4H3 | [InChIKey]
ULYLMHUHFUQKOE-UHFFFAOYSA-N | [SMILES]
[Si](C)(C)(C)CC#C | [CAS DataBase Reference]
13361-64-3 | [EPA Substance Registry System]
Silane, trimethyl-2-propynyl- (13361-64-3) |
| Hazard Information | Back Directory | [Chemical Properties]
Clear yellow liquid | [Physical properties]
bp 91–93 °C/760 mmHg; 40 °C/140 mmHg;
d 0.753 g mL?1; nD
20 1.4140. | [Uses]
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. | [Uses]
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. | [Preparation]
The main method of preparation is shown
in eq 1. The title reagent can be obtained by other methods, but in poor yields. 
| [Purification Methods]
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.] | [General Description]
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. |
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