Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

1066-54-2 - (Trimethylsilyl)acetylene, 98% - Ethynyltrimethylsilane - TMS acetylene - A12856 - Alfa Aesar

A12856 (Trimethylsilyl)acetylene, 98%

CAS Number
TMS acetylene

Size Price ($) Quantity Availability
5g 36.57
25g 156.56
100g 405.82
Add to Cart Add to Quote Request View Item

(Trimethylsilyl)acetylene, 98%


Chemical Properties

Formula Weight
Boiling Point
Flash Point
Refractive Index
Miscible with organic solvents.


(Trimethylsilyl)acetylene is used in the preparation of trimethylsilanyl-propiolic acid ethyl ester by reacting with carbonochloridic acid ethyl ester as well as in the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides. It is used as a nucleophile in Friedel-Crafts type acylations and alkylations reactions, as a ligand in organometallic chemistry and an useful reagent in cycloaddition reactions. It acts as a precursor to lithium trimethylsilylacetylide It finds application in the synthesis of (±)-estrone.


Store in a cool place. Incompatible with strong oxidizing agents.

Literature 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).

Das, S.; Samanta, S.; Ray, S.; Biswas, P. 3, 6-Di (pyridin-2-yl)-1, 2, 4, 5-tetrazine capped Pd (0) nanoparticles: a catalyst for copper-free Sonogashira coupling of aryl halides in aqueous medium. 2015, 5 (92), 75263-75267.

Wang, H.; Olesik, S. V. Development of a new separation media using ultra-thin glassy carbon film modified silica. 2015, 1379, 56-64.

GHS Hazard and Precautionary Statements

Hazard Statements: H225

Highly flammable liquid and vapour.

Precautionary Statements: P210-P280-P240-P241-P233-P242-P243-P303+P361+P353-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. Use only non-sparking tools. Take precautionary measures against static discharge. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Hazard Class
Packing Group
Harmonized Tariff Code


  • A12139

    Phenylacetylene, 98+%
  • 10491

    trans-Dichlorobis(triphenylphosphine)palladium(II), Pd 14.0% min
  • A15275

    Boron trifluoride diethyl etherate, 98+%
  • A17020

    1-Bromo-2-iodobenzene, 98+%, stab. with copper
  • 43153

    Copper(I) iodide, Puratronic®, 99.998% (metals basis)

Recently Viewed


Life Science

Metals & Materials


Analytical & Labware