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(Trimethylsilyl)acetylene

Catalog No. A12856 Name Alfa Aesar
CAS Number 1066-54-2 Website
M. F. C5H10Si Telephone
M. W. 98.2184 Fax
Purity 98% Email
Storage Chembase ID: 8579

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 Pictograms GHS02
GHS Hazard statements H225
European Hazard Symbols Flammable 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
Hazard Class 3
UN Number UN1993
Packing Group II

DETAILS

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).