(Trimethylsilyl)acetylene

• Catalog No.: A12856
• CAS Number: 1066-54-2
• M. F.: C5H10Si
• M. W.: 98.2184
• Purity: 98%

SYNONYMS

• Title: (三甲基硅烷基)乙炔
• IUPAC name: ethynyltrimethylsilane
• IUPAC Traditional name: trimethylsilylacetylene
• Synonyms: TMS acetylene; Ethynyltrimethylsilane

DATABASE IDS

• EC Number: 213-919-9
• Beilstein Number: 906752
• MDL Number: MFCD00008569
• CAS Number: 1066-54-2

PROPERTIES

• Purity: 98%
• Boiling Point: 52-53°C
• Density: 0.710
• Flash Point: <-34°C(-29°F)
• Refractive Index: 1.3900
• GHS Hazard statements: H225
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Risk Statements: 11
• Safety Statements: 9-16-29-33
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1993
• Packing Group: II

REFERENCES

• Pd catalyzed coupling with aryl bromides or iodides gives aryl TMS alkynes, from which the TMS group is readily cleaved by K₂CO₃ in MeOH: Synthesis, 627 (1980); J. Org. Chem., 46, 2280 (1981). Coupling with 1-bromo-2-nitrobenzene or ethyl 2-bromocarbanilate gives indole precursors. Other terminal alkynes lead to 2-substituted indoles: Heterocycles, 24, 31 (1986):
  
• Cross-coupling with aryl halides can also be catalyzed by Pd-C in the presence of Ph₃P, CuI and Et₃N: Synth. Commun., 20, 2059 (1990); for an example, see 2-Bromonaphthalene, A15300. Pd catalyzed coupling with quinolinol and isoquinolinol triflates has also been reported: Tetrahedron, 51, 3737 (1995). For coupling with vinyl halides catalyzed by Tetrakis(triphenylphosphine)palladium(0), 10548 in the presence of CuI as an example of a route to enynes, see: Tetrahedron Lett., 30, 6997 (1989); Org. Synth. Coll., 9, 117 (1998). CuCl-TMEDA catalyzed oxidative (Hay) coupling gives bis(TMS)-1,3-butadiyne: Org. Synth. Coll., 8, 63 (1993).
• For the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides, see: J. Org. Chem., 47, 2251 (1982).