Trimethylsilylacetylene
Synonym(s):Ethinyltrimethylsilane;Trimethylsilylacetylene
- CAS NO.:1066-54-2
- Empirical Formula: C5H10Si
- Molecular Weight: 98.22
- MDL number: MFCD00008569
- EINECS: 213-919-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-21 22:41:43
What is Trimethylsilylacetylene?
Chemical properties
CLEAR COLORLESS LIQUID
Physical properties
bp 53 °C; d 0.695 g cm?3.
The Uses of Trimethylsilylacetylene
Trimethylsilylacetylene is a valuable reagent used in ethynylation by palladium(0)-catalyzed coupling/condensation with aryl and vinyl halides and triflates, or by nucleophilic attack of the corresponding acetylide on electrophilic centers; reacts with alkyl iodides, tin hydrides,6 and dichloroketene in a regioselective and stereoselective manner, participating in the following synthesis reactions: Ethynylations, Palladium(0)-Catalyzed Coupling Reactions,Reaction of Trimethylsilylacetylides with Electrophiles, Radical-Initiated and Transition Metal-Catalyzed Additions, Cycloaddition Reactions, Ethynylations, Cycloaddition Reactions, Further Transformations etc.
The Uses of Trimethylsilylacetylene
Ethynyltrimethylsilane was used in: ? microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles synthesis of poly(ethynyltrimethylsilane) containing Pd (II) coordination sites pyrazole synthesis via 1,3-dipolar cycloaddition of diazo compounds to acetylenes
The Uses of Trimethylsilylacetylene
(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.
General Description
Laser-induced polymerization of gaseous ethynyltrimethylsilane was used for efficient chemical vapour deposition of polycarbosilane films. Ethynyltrimethylsilane acts as substrate for nickel-catalyzed cross-coupling with benzonitriles.
Purification Methods
Distil it through an efficient column. The IR has bands at max 2041 (CC) and 3289 (C-H) cm-1. [Kr.hnke & Goss Chem Ber 92 30 1959, Beilstein 4 IV 3937.]
Properties of Trimethylsilylacetylene
Melting point: | >0°C |
Boiling point: | 53 °C(lit.) |
Density | 0.695 g/mL at 25 °C(lit.) |
vapor pressure | 4.18 psi ( 20 °C) |
refractive index | n |
Flash point: | <−30 °F |
storage temp. | Store below +30°C. |
solubility | Miscible with organic solvents. |
form | liquid |
color | colorless |
Specific Gravity | 0.695 |
Water Solubility | reacts |
Hydrolytic Sensitivity | 4: no reaction with water under neutral conditions |
BRN | 906752 |
CAS DataBase Reference | 1066-54-2(CAS DataBase Reference) |
NIST Chemistry Reference | (Trimethylsilyl)acetylene(1066-54-2) |
EPA Substance Registry System | Trimethylsilylacetylene (1066-54-2) |
Safety information for Trimethylsilylacetylene
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H225:Flammable liquids H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P240:Ground/bond container and receiving equipment. P241:Use explosion-proof electrical/ventilating/lighting/…/equipment. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Trimethylsilylacetylene
InChIKey | CWMFRHBXRUITQE-UHFFFAOYSA-N |
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